Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:32 UTC

Update Date

2022-03-07 02:49:12 UTC

HMDB ID

HMDB0002027

Secondary Accession Numbers

HMDB02027

Metabolite Identification

Common Name

8-Dehydrocholesterol

Description

8-Dehydrocholesterol (8-DHC) elevated concentration is one of the diagnostic biochemical hallmarks of classical Smith-Lemli-Opitz syndrome (SLOS). Plasma 8-DHC could be only marginally elevated. (PMID: 16435228 ). Smith-Lemli-Opitz syndrome (SLOS) is an autosomal recessive condition caused by a defect in cholesterol synthesis (caused by a deficit of 3beta-hydroxysterol-Delta7 reductase). Affected children often have malformations and mental retardation. Autistic behaviors also are evident. In children, the baseline cholesterol, 8-DHC levels, and cholesterol levels following supplementation does not correlate with the presence or severity of autistic symptoms. (PMID: 16761297 ). Accumulation of 8-dehydrocholesterol in Amniotic fluid is diagnostic for SLOS. (PMID 16231320 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv0541 02231219192D          

 30 33  0  0  1  0            999 V2000
   14.6941  -11.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6941  -12.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.4085  -12.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1230  -12.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1230  -11.2557    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.4085  -10.8431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8374  -12.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5519  -12.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5519  -11.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8374  -10.8431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2664  -10.8431    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.2664  -10.0181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.5519   -9.6056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8374  -10.0181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0511  -11.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5361  -10.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0511   -9.7632    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9795  -12.4932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3527   -9.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3061   -8.9785    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.1230  -10.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3527  -11.6636    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.7540   -8.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1130   -8.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3679   -8.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1750   -7.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4299   -7.0663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2369   -6.8947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8778   -6.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8275   -9.6250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
  2 18  1  1  0  0  0
 12 19  1  1  0  0  0
 17 20  1  1  0  0  0
  5 21  1  1  0  0  0
 11 22  1  6  0  0  0
 20 23  1  6  0  0  0
 24 20  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
 28 27  1  0  0  0  0
 29 27  1  0  0  0  0
 17 30  1  6  0  0  0
M  END

HMDB0002027
     RDKit          3D
8-Dehydrocholesterol
 72 75  0  0  0  0  0  0  0  0999 V2000
    5.7224   -1.4873    1.5963 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5030   -0.0882    1.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6367    0.7857    1.6058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5575   -0.0058   -0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4908   -0.8834   -1.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0968   -0.5078   -0.6462 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6986    0.8956   -1.0103 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7362    1.1981   -2.4644 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4864    1.3342   -0.2688 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0953    2.7535   -0.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3769    2.6141   -1.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8005    1.5807   -0.0731 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1043    0.9518   -0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3325   -0.1312    0.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2875   -0.5100    1.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1175   -0.4148    0.9208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2711    0.4955   -0.2988 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0073   -0.3153   -1.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5729   -0.9348    0.3088 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3506   -2.0265   -0.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8148   -1.6207    1.6145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2354   -1.9276    1.9295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1369   -0.7629    1.6561 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.4138   -0.9306    2.1228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0942   -0.5478    0.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7102   -0.1239   -0.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5104    0.9623   -0.8715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1431    1.4262   -1.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2245   -2.1387    0.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3015   -1.5002    2.5431 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7069   -1.8852    1.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5461    0.3532    1.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6974    1.7534    1.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5199    1.0129    2.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6210    0.2928    1.4642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4961    1.0460   -0.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5389   -0.4707   -0.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6228   -1.0186   -2.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6620   -1.9102   -0.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0281   -0.6859    0.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4229   -1.2581   -1.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5294    1.5370   -0.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9009    1.8308   -2.8293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7621    0.3093   -3.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6571    1.7778   -2.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7894    1.4002    0.8239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7194    3.2276   -1.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0704    3.4404    0.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9275    3.5423   -0.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4714    2.3090   -2.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6311    1.9794    0.9427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4223    0.0575    2.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5037   -1.5741    1.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7381    0.0070    1.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4652   -1.4419    0.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5037   -0.0500   -2.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0433   -1.4011   -1.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1052   -0.1636   -1.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3757   -2.4798   -0.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0306   -1.5871   -1.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7197   -2.8317   -0.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2527   -2.6001    1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3385   -1.0526    2.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2984   -2.1305    3.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6208   -2.8035    1.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6355    0.1428    2.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0665   -0.9113    1.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8443    0.2293   -0.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3615   -1.4701   -0.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3432    1.5590   -1.2268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9771    1.2252   -2.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1623    2.5527   -1.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 14 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 17  9  1  0
 26 19  1  0
 17 12  1  0
 28 13  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  1
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  1
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  1
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 18 56  1  0
 18 57  1  0
 18 58  1  0
 20 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 22 64  1  0
 22 65  1  0
 23 66  1  1
 24 67  1  0
 25 68  1  0
 25 69  1  0
 27 70  1  0
 28 71  1  0
 28 72  1  0
M  END

  Mrv0541 02231219192D          

 30 33  0  0  1  0            999 V2000
   14.6941  -11.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6941  -12.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.4085  -12.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1230  -12.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1230  -11.2557    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.4085  -10.8431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8374  -12.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5519  -12.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5519  -11.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8374  -10.8431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2664  -10.8431    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.2664  -10.0181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.5519   -9.6056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8374  -10.0181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0511  -11.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5361  -10.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0511   -9.7632    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9795  -12.4932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3527   -9.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3061   -8.9785    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.1230  -10.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3527  -11.6636    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.7540   -8.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1130   -8.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3679   -8.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1750   -7.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4299   -7.0663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2369   -6.8947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8778   -6.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8275   -9.6250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
  2 18  1  1  0  0  0
 12 19  1  1  0  0  0
 17 20  1  1  0  0  0
  5 21  1  1  0  0  0
 11 22  1  6  0  0  0
 20 23  1  6  0  0  0
 24 20  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
 28 27  1  0  0  0  0
 29 27  1  0  0  0  0
 17 30  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0002027

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3)[C@H](C)CCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21,23-24,28H,6-8,10-17H2,1-5H3/t19-,21+,23-,24+,26+,27-/m1/s1

> <INCHI_KEY>
VUKORTMHZDZZFR-BXAZICILSA-N

> <FORMULA>
C27H44O

> <MOLECULAR_WEIGHT>
384.6377

> <EXACT_MASS>
384.33921603

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
50.1424205903791

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),7-dien-5-ol

> <ALOGPS_LOGP>
6.91

> <JCHEM_LOGP>
6.663651724666668

> <ALOGPS_LOGS>
-5.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.27040487190894

> <JCHEM_PKA_STRONGEST_BASIC>
-1.368324909027029

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
121.19989999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.14e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-dehydrocholesterol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0002027
     RDKit          3D
8-Dehydrocholesterol
 72 75  0  0  0  0  0  0  0  0999 V2000
    5.7224   -1.4873    1.5963 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5030   -0.0882    1.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6367    0.7857    1.6058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5575   -0.0058   -0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4908   -0.8834   -1.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0968   -0.5078   -0.6462 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6986    0.8956   -1.0103 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7362    1.1981   -2.4644 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4864    1.3342   -0.2688 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0953    2.7535   -0.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3769    2.6141   -1.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8005    1.5807   -0.0731 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1043    0.9518   -0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3325   -0.1312    0.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2875   -0.5100    1.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1175   -0.4148    0.9208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2711    0.4955   -0.2988 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0073   -0.3153   -1.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5729   -0.9348    0.3088 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3506   -2.0265   -0.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8148   -1.6207    1.6145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2354   -1.9276    1.9295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1369   -0.7629    1.6561 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.4138   -0.9306    2.1228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0942   -0.5478    0.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7102   -0.1239   -0.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5104    0.9623   -0.8715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1431    1.4262   -1.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2245   -2.1387    0.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3015   -1.5002    2.5431 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7069   -1.8852    1.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5461    0.3532    1.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6974    1.7534    1.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5199    1.0129    2.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6210    0.2928    1.4642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4961    1.0460   -0.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5389   -0.4707   -0.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6228   -1.0186   -2.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6620   -1.9102   -0.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0281   -0.6859    0.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4229   -1.2581   -1.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5294    1.5370   -0.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9009    1.8308   -2.8293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7621    0.3093   -3.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6571    1.7778   -2.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7894    1.4002    0.8239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7194    3.2276   -1.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0704    3.4404    0.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9275    3.5423   -0.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4714    2.3090   -2.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6311    1.9794    0.9427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4223    0.0575    2.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5037   -1.5741    1.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7381    0.0070    1.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4652   -1.4419    0.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5037   -0.0500   -2.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0433   -1.4011   -1.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1052   -0.1636   -1.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3757   -2.4798   -0.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0306   -1.5871   -1.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7197   -2.8317   -0.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2527   -2.6001    1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3385   -1.0526    2.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2984   -2.1305    3.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6208   -2.8035    1.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6355    0.1428    2.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0665   -0.9113    1.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8443    0.2293   -0.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3615   -1.4701   -0.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3432    1.5590   -1.2268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9771    1.2252   -2.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1623    2.5527   -1.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 14 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 17  9  1  0
 26 19  1  0
 17 12  1  0
 28 13  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  1
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  1
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  1
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 18 56  1  0
 18 57  1  0
 18 58  1  0
 20 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 22 64  1  0
 22 65  1  0
 23 66  1  1
 24 67  1  0
 25 68  1  0
 25 69  1  0
 27 70  1  0
 28 71  1  0
 28 72  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      27.429 -21.011   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.429 -22.551   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      28.763 -23.321   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.096 -22.551   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.096 -21.011   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.763 -20.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.430 -23.321   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.764 -22.551   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      32.764 -21.011   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      31.430 -20.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      34.097 -20.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      34.097 -18.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      32.764 -17.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      31.430 -18.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      35.562 -20.716   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      36.467 -19.470   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      35.562 -18.225   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      26.095 -23.321   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      34.258 -17.169   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      36.038 -16.760   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      30.096 -19.470   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0      34.258 -21.772   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0      35.007 -15.615   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      37.544 -16.440   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      38.020 -14.975   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      39.527 -14.655   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      40.002 -13.190   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      41.509 -12.870   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      38.972 -12.046   0.000  0.00  0.00           C+0
HETATM   30  H   UNK     0      37.011 -17.967   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   21                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    5   14                                                  
CONECT   11    9   12   15   22                                             
CONECT   12   11   13   17   19                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   20   30                                             
CONECT   18    2                                                            
CONECT   19   12                                                            
CONECT   20   17   23   24                                                  
CONECT   21    5                                                            
CONECT   22   11                                                            
CONECT   23   20                                                            
CONECT   24   20   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   17                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

COMPND    HMDB0002027
HETATM    1  C1  UNL     1       5.722  -1.487   1.596  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.503  -0.088   1.079  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.637   0.786   1.606  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.557  -0.006  -0.432  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.491  -0.883  -1.054  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.097  -0.508  -0.646  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.699   0.896  -1.010  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.736   1.198  -2.464  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.486   1.334  -0.269  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.095   2.754  -0.641  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.377   2.614  -1.062  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.801   1.581  -0.073  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.104   0.952  -0.281  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.332  -0.131   0.447  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.288  -0.510   1.425  1.00  0.00           C  
HETATM   16  C16 UNL     1       0.118  -0.415   0.921  1.00  0.00           C  
HETATM   17  C17 UNL     1       0.271   0.495  -0.299  1.00  0.00           C  
HETATM   18  C18 UNL     1      -0.007  -0.315  -1.501  1.00  0.00           C  
HETATM   19  C19 UNL     1      -3.573  -0.935   0.309  1.00  0.00           C  
HETATM   20  C20 UNL     1      -3.351  -2.027  -0.747  1.00  0.00           C  
HETATM   21  C21 UNL     1      -3.815  -1.621   1.614  1.00  0.00           C  
HETATM   22  C22 UNL     1      -5.235  -1.928   1.930  1.00  0.00           C  
HETATM   23  C23 UNL     1      -6.137  -0.763   1.656  1.00  0.00           C  
HETATM   24  O1  UNL     1      -7.414  -0.931   2.123  1.00  0.00           O  
HETATM   25  C24 UNL     1      -6.094  -0.548   0.137  1.00  0.00           C  
HETATM   26  C25 UNL     1      -4.710  -0.124  -0.174  1.00  0.00           C  
HETATM   27  C26 UNL     1      -4.510   0.962  -0.871  1.00  0.00           C  
HETATM   28  C27 UNL     1      -3.143   1.426  -1.207  1.00  0.00           C  
HETATM   29  H1  UNL     1       6.224  -2.139   0.866  1.00  0.00           H  
HETATM   30  H2  UNL     1       6.302  -1.500   2.543  1.00  0.00           H  
HETATM   31  H3  UNL     1       4.707  -1.885   1.866  1.00  0.00           H  
HETATM   32  H4  UNL     1       4.546   0.353   1.404  1.00  0.00           H  
HETATM   33  H5  UNL     1       6.697   1.753   1.061  1.00  0.00           H  
HETATM   34  H6  UNL     1       6.520   1.013   2.682  1.00  0.00           H  
HETATM   35  H7  UNL     1       7.621   0.293   1.464  1.00  0.00           H  
HETATM   36  H8  UNL     1       5.496   1.046  -0.707  1.00  0.00           H  
HETATM   37  H9  UNL     1       6.539  -0.471  -0.742  1.00  0.00           H  
HETATM   38  H10 UNL     1       4.623  -1.019  -2.130  1.00  0.00           H  
HETATM   39  H11 UNL     1       4.662  -1.910  -0.609  1.00  0.00           H  
HETATM   40  H12 UNL     1       3.028  -0.686   0.448  1.00  0.00           H  
HETATM   41  H13 UNL     1       2.423  -1.258  -1.109  1.00  0.00           H  
HETATM   42  H14 UNL     1       3.529   1.537  -0.562  1.00  0.00           H  
HETATM   43  H15 UNL     1       1.901   1.831  -2.829  1.00  0.00           H  
HETATM   44  H16 UNL     1       2.762   0.309  -3.122  1.00  0.00           H  
HETATM   45  H17 UNL     1       3.657   1.778  -2.785  1.00  0.00           H  
HETATM   46  H18 UNL     1       1.789   1.400   0.824  1.00  0.00           H  
HETATM   47  H19 UNL     1       1.719   3.228  -1.385  1.00  0.00           H  
HETATM   48  H20 UNL     1       1.070   3.440   0.238  1.00  0.00           H  
HETATM   49  H21 UNL     1      -0.927   3.542  -0.890  1.00  0.00           H  
HETATM   50  H22 UNL     1      -0.471   2.309  -2.106  1.00  0.00           H  
HETATM   51  H23 UNL     1      -0.631   1.979   0.943  1.00  0.00           H  
HETATM   52  H24 UNL     1      -1.422   0.058   2.394  1.00  0.00           H  
HETATM   53  H25 UNL     1      -1.504  -1.574   1.739  1.00  0.00           H  
HETATM   54  H26 UNL     1       0.738   0.007   1.764  1.00  0.00           H  
HETATM   55  H27 UNL     1       0.465  -1.442   0.692  1.00  0.00           H  
HETATM   56  H28 UNL     1       0.504  -0.050  -2.425  1.00  0.00           H  
HETATM   57  H29 UNL     1       0.043  -1.401  -1.272  1.00  0.00           H  
HETATM   58  H30 UNL     1      -1.105  -0.164  -1.743  1.00  0.00           H  
HETATM   59  H31 UNL     1      -4.376  -2.480  -0.889  1.00  0.00           H  
HETATM   60  H32 UNL     1      -3.031  -1.587  -1.698  1.00  0.00           H  
HETATM   61  H33 UNL     1      -2.720  -2.832  -0.358  1.00  0.00           H  
HETATM   62  H34 UNL     1      -3.253  -2.600   1.597  1.00  0.00           H  
HETATM   63  H35 UNL     1      -3.339  -1.053   2.462  1.00  0.00           H  
HETATM   64  H36 UNL     1      -5.298  -2.131   3.035  1.00  0.00           H  
HETATM   65  H37 UNL     1      -5.621  -2.803   1.374  1.00  0.00           H  
HETATM   66  H38 UNL     1      -5.635   0.143   2.095  1.00  0.00           H  
HETATM   67  H39 UNL     1      -8.067  -0.911   1.386  1.00  0.00           H  
HETATM   68  H40 UNL     1      -6.844   0.229  -0.151  1.00  0.00           H  
HETATM   69  H41 UNL     1      -6.361  -1.470  -0.412  1.00  0.00           H  
HETATM   70  H42 UNL     1      -5.343   1.559  -1.227  1.00  0.00           H  
HETATM   71  H43 UNL     1      -2.977   1.225  -2.266  1.00  0.00           H  
HETATM   72  H44 UNL     1      -3.162   2.553  -1.115  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    4   32
CONECT    3   33   34   35
CONECT    4    5   36   37
CONECT    5    6   38   39
CONECT    6    7   40   41
CONECT    7    8    9   42
CONECT    8   43   44   45
CONECT    9   10   17   46
CONECT   10   11   47   48
CONECT   11   12   49   50
CONECT   12   13   17   51
CONECT   13   14   14   28
CONECT   14   15   19
CONECT   15   16   52   53
CONECT   16   17   54   55
CONECT   17   18
CONECT   18   56   57   58
CONECT   19   20   21   26
CONECT   20   59   60   61
CONECT   21   22   62   63
CONECT   22   23   64   65
CONECT   23   24   25   66
CONECT   24   67
CONECT   25   26   68   69
CONECT   26   27   27
CONECT   27   28   70
CONECT   28   71   72
END

HMDB0002027
     RDKit          3D
8-Dehydrocholesterol
 72 75  0  0  0  0  0  0  0  0999 V2000
    5.7224   -1.4873    1.5963 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5030   -0.0882    1.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6367    0.7857    1.6058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5575   -0.0058   -0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4908   -0.8834   -1.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0968   -0.5078   -0.6462 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6986    0.8956   -1.0103 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7362    1.1981   -2.4644 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4864    1.3342   -0.2688 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0953    2.7535   -0.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3769    2.6141   -1.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8005    1.5807   -0.0731 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1043    0.9518   -0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3325   -0.1312    0.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2875   -0.5100    1.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1175   -0.4148    0.9208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2711    0.4955   -0.2988 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0073   -0.3153   -1.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5729   -0.9348    0.3088 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3506   -2.0265   -0.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8148   -1.6207    1.6145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2354   -1.9276    1.9295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1369   -0.7629    1.6561 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.4138   -0.9306    2.1228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0942   -0.5478    0.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7102   -0.1239   -0.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5104    0.9623   -0.8715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1431    1.4262   -1.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2245   -2.1387    0.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3015   -1.5002    2.5431 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7069   -1.8852    1.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5461    0.3532    1.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6974    1.7534    1.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5199    1.0129    2.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6210    0.2928    1.4642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4961    1.0460   -0.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5389   -0.4707   -0.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6228   -1.0186   -2.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6620   -1.9102   -0.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0281   -0.6859    0.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4229   -1.2581   -1.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5294    1.5370   -0.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9009    1.8308   -2.8293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7621    0.3093   -3.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6571    1.7778   -2.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7894    1.4002    0.8239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7194    3.2276   -1.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0704    3.4404    0.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9275    3.5423   -0.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4714    2.3090   -2.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6311    1.9794    0.9427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4223    0.0575    2.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5037   -1.5741    1.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7381    0.0070    1.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4652   -1.4419    0.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5037   -0.0500   -2.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0433   -1.4011   -1.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1052   -0.1636   -1.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3757   -2.4798   -0.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0306   -1.5871   -1.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7197   -2.8317   -0.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2527   -2.6001    1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3385   -1.0526    2.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2984   -2.1305    3.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6208   -2.8035    1.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6355    0.1428    2.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0665   -0.9113    1.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8443    0.2293   -0.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3615   -1.4701   -0.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3432    1.5590   -1.2268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9771    1.2252   -2.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1623    2.5527   -1.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 14 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 17  9  1  0
 26 19  1  0
 17 12  1  0
 28 13  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  1
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  1
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  1
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 18 56  1  0
 18 57  1  0
 18 58  1  0
 20 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 22 64  1  0
 22 65  1  0
 23 66  1  1
 24 67  1  0
 25 68  1  0
 25 69  1  0
 27 70  1  0
 28 71  1  0
 28 72  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3b-Cholesta-5,8-dien-3-ol	HMDB
Cholesta-5,8-dien-3 beta-ol	MeSH, HMDB

Chemical Formula

C₂₇H₄₄O

Average Molecular Weight

384.6377

Monoisotopic Molecular Weight

384.33921603

IUPAC Name

(2S,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),7-dien-5-ol

Traditional Name

8-dehydrocholesterol

CAS Registry Number

70741-38-7

SMILES

[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3)[C@H](C)CCCC(C)C

InChI Identifier

InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21,23-24,28H,6-8,10-17H2,1-5H3/t19-,21+,23-,24+,26+,27-/m1/s1

InChI Key

VUKORTMHZDZZFR-BXAZICILSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol-skeleton
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-5-steroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Cholesterol and derivatives (LMST01010242 )

Ontology

Physiological effect

Health effect

Metabolic disorder

Metabolic syndrome (HMDB: HMDB0002027)

Genetic disorder

Inborn errors of metabolism

Smith-Lemli-Opitz syndrome (HMDB: HMDB0002027)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 10947201)
Cerebrospinal Fluid (CSF) (PMID: 9266395)
Cerebrospinal fluid (HMDB: HMDB0002027)

Cellular substructure

Tissue

All Tissues (HMDB: HMDB0002027)

Connective tissue

Adipose tissue (HMDB: HMDB0002027)

Nervous tissue

Hepatic tissue (HMDB: HMDB0002027)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0002027)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002027)

Source

Endogenous

Endogenous (HMDB: HMDB0002027)

Animal

Animal (HMDB: HMDB0002027)

Exogenous

Food

Food (HMDB: HMDB0002027)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0002027)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Steroid Biosynthesis (HMDB: HMDB0002027)
Fatty Acid Metabolism (HMDB: HMDB0002027)

Disease pathway

CHILD Syndrome (HMDB: HMDB0002027)
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2) (HMDB: HMDB0002027)
Smith-Lemli-Opitz Syndrome (SLOS) (HMDB: HMDB0002027)
Desmosterolosis (PathBank: SMP0120692)
Mevalonic Aciduria (PathBank: SMP0120794)
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2) (HMDB: HMDB0002027)
Lysosomal Acid Lipase Deficiency (Wolman Disease) (PathBank: SMP0120512)
Cholesteryl Ester Storage Disease (PathBank: SMP0120573)
Wolman Disease (PathBank: SMP0120576)
Hypercholesterolemia (PathBank: SMP0120769)
Hyper-IgD Syndrome (PathBank: SMP0120574)

Drug action pathway

Alendronate Action Pathway (HMDB: HMDB0002027)
Ibandronate Action Pathway (PathBank: SMP0000079)
Simvastatin Action Pathway (PathBank: SMP0000082)
Pravastatin Action Pathway (PathBank: SMP0000089)
Rosuvastatin Action Pathway (PathBank: SMP0000092)
Alendronate Action Pathway (PathBank: SMP0000095)
Lovastatin Action Pathway (PathBank: SMP0000099)
Zoledronate Action Pathway (PathBank: SMP0000107)
Cerivastatin Action Pathway (PathBank: SMP0000111)
Risedronate Action Pathway (PathBank: SMP0000112)
Pamidronate Action Pathway (PathBank: SMP0000117)
Fluvastatin Action Pathway (PathBank: SMP0000119)
Atorvastatin Action Pathway (PathBank: SMP0000131)

Lipid metabolism pathway (HMDB: HMDB0002027)

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0002027)

Cellular process

Cell signaling (HMDB: HMDB0002027)

Biochemical process

Lipid transport (HMDB: HMDB0002027)

Multicellular process

Inflammatory response (HMDB: HMDB0002027)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0002027)

Molecular messenger

Hormone (HMDB: HMDB0002027)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0002027)

Pharmaceutical industry

Biomarker

Smith-Lemli-Opitz syndrome (MarkerDB: MDB00000367)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00091 g/L	ALOGPS
logP	6.91	ALOGPS
logP	6.66	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	18.27	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	121.2 m³·mol⁻¹	ChemAxon
Polarizability	50.14 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	195.273	31661259
DarkChem	[M-H]-	194.142	31661259
DeepCCS	[M-2H]-	243.229	30932474
DeepCCS	[M+Na]+	217.906	30932474
AllCCS	[M+H]+	203.7	32859911
AllCCS	[M+H-H2O]+	201.6	32859911
AllCCS	[M+NH4]+	205.8	32859911
AllCCS	[M+Na]+	206.3	32859911
AllCCS	[M-H]-	203.2	32859911
AllCCS	[M+Na-2H]-	204.9	32859911
AllCCS	[M+HCOO]-	206.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Dehydrocholesterol	[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3)[C@H](C)CCCC(C)C	2541.0	Standard polar	33892256
8-Dehydrocholesterol	[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3)[C@H](C)CCCC(C)C	3146.1	Standard non polar	33892256
8-Dehydrocholesterol	[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3)[C@H](C)CCCC(C)C	3087.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-Dehydrocholesterol,1TMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)CC1=CC3	3211.4	Semi standard non polar	33892256
8-Dehydrocholesterol,1TBDMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)CC1=CC3	3424.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Dehydrocholesterol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ar0-1019000000-8455a6c27493f97ebe56	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Dehydrocholesterol GC-MS (1 TMS) - 70eV, Positive	splash10-002f-3104900000-efe703ec411e4c08c1ab	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Dehydrocholesterol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Dehydrocholesterol 10V, Positive-QTOF	splash10-014r-0009000000-8f5b8c3c66952dc51dc0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Dehydrocholesterol 20V, Positive-QTOF	splash10-05p9-3239000000-83a847e9f50d75c56b64	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Dehydrocholesterol 40V, Positive-QTOF	splash10-0a4i-5249000000-d434b4187b0bc28431c4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Dehydrocholesterol 10V, Negative-QTOF	splash10-001i-0009000000-e7c8524cf153f94d3913	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Dehydrocholesterol 20V, Negative-QTOF	splash10-001i-0009000000-484d145862cff531746a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Dehydrocholesterol 40V, Negative-QTOF	splash10-0gb9-1009000000-9618317ed2447b79a252	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Dehydrocholesterol 10V, Negative-QTOF	splash10-001i-0009000000-4d7a5f3b63c0fb62f1d7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Dehydrocholesterol 20V, Negative-QTOF	splash10-001i-0009000000-4d7a5f3b63c0fb62f1d7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Dehydrocholesterol 40V, Negative-QTOF	splash10-001i-0009000000-5f56c8ce69939caba813	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Dehydrocholesterol 10V, Positive-QTOF	splash10-00kr-0009000000-76127d016864d5ef3d22	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Dehydrocholesterol 20V, Positive-QTOF	splash10-05g0-8469000000-301b48e0bb654ed1e226	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Dehydrocholesterol 40V, Positive-QTOF	splash10-0a4l-9860000000-09ecca53ca89272c952c	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Steroid Biosynthesis
Smith-Lemli-Opitz Syndrome (SLOS)		Not Available
CHILD Syndrome		Not Available
Desmosterolosis		Not Available
Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.65 (0.0-1.3) uM	Adult (>18 years old)	Both	Normal	10947201	details
Blood	Detected and Quantified	<0.000260 uM	Children (1-13 years old)	Not Specified	Normal	12503102	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	312.0 +/- 52.0 uM	Adult (>18 years old)	Both	Smith-Lemli-Opitz syndrome	10947201	details
Blood	Detected and Quantified	0.0754 uM	Children (1-13 years old)	Male	Chondrodysplasia punctata, X-linked dominant	12503102	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.3 +/- 0.1 (0.2 - 0.5) uM	Infant (0-1 year old)	Not Specified	Smith-Lemli-Opitz syndrome	9266395	details

Associated Disorders and Diseases

Disease References

Chondrodysplasia punctata, X-linked dominant
Aughton DJ, Kelley RI, Metzenberg A, Pureza V, Pauli RM: X-linked dominant chondrodysplasia punctata (CDPX2) caused by single gene mosaicism in a male. Am J Med Genet A. 2003 Jan 30;116A(3):255-60. doi: 10.1002/ajmg.a.10852. [PubMed:12503102 ]
Smith-Lemli-Opitz syndrome
van Rooij A, Nijenhuis AA, Wijburg FA, Schutgens RB: Highly increased CSF concentrations of cholesterol precursors in Smith-Lemli-Opitz syndrome. J Inherit Metab Dis. 1997 Aug;20(4):578-80. [PubMed:9266395 ] Honda M, Tint GS, Honda A, Salen G, Shefer S, Batta AK, Matsuzaki Y, Tanaka N: Regulation of cholesterol biosynthetic pathway in patients with the Smith-Lemli-Opitz syndrome. J Inherit Metab Dis. 2000 Jul;23(5):464-74. [PubMed:10947201 ]

Associated OMIM IDs

302960 (Chondrodysplasia punctata, X-linked dominant)
270400 (Smith-Lemli-Opitz syndrome)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022805

KNApSAcK ID

Not Available

Chemspider ID

114943

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

129846

PDB ID

Not Available

ChEBI ID

89982

Food Biomarker Ontology

Not Available

VMH ID

CE1297

MarkerDB ID

MDB00000367

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

van Rooij A, Nijenhuis AA, Wijburg FA, Schutgens RB: Highly increased CSF concentrations of cholesterol precursors in Smith-Lemli-Opitz syndrome. J Inherit Metab Dis. 1997 Aug;20(4):578-80. [PubMed:9266395 ]
Haas D, Armbrust S, Haas JP, Zschocke J, Muhlmann K, Fusch C, Neumann LM: Smith-Lemli-Opitz syndrome with a classical phenotype, oesophageal achalasia and borderline plasma sterol concentrations. J Inherit Metab Dis. 2005;28(6):1191-6. [PubMed:16435228 ]
Sikora DM, Pettit-Kekel K, Penfield J, Merkens LS, Steiner RD: The near universal presence of autism spectrum disorders in children with Smith-Lemli-Opitz syndrome. Am J Med Genet A. 2006 Jul 15;140(14):1511-8. [PubMed:16761297 ]
Chevy F, Humbert L, Wolf C: Sterol profiling of amniotic fluid: a routine method for the detection of distal cholesterol synthesis deficit. Prenat Diagn. 2005 Nov;25(11):1000-6. [PubMed:16231320 ]

Showing metabocard for 8-Dehydrocholesterol (HMDB0002027)

MOL for HMDB0002027 (8-Dehydrocholesterol)

3D MOL for HMDB0002027 (8-Dehydrocholesterol)

3D SDF for HMDB0002027 (8-Dehydrocholesterol)

3D-SDF for HMDB0002027 (8-Dehydrocholesterol)

PDB for HMDB0002027 (8-Dehydrocholesterol)

3D PDB for HMDB0002027 (8-Dehydrocholesterol)

SMILES for HMDB0002027 (8-Dehydrocholesterol)

INCHI for HMDB0002027 (8-Dehydrocholesterol)

Structure for HMDB0002027 (8-Dehydrocholesterol)

3D Structure for HMDB0002027 (8-Dehydrocholesterol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra