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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:31 UTC

Update Date

2022-03-07 02:49:12 UTC

HMDB ID

HMDB0001993

Secondary Accession Numbers

HMDB0001331
HMDB01331
HMDB01993

Metabolite Identification

Common Name

7a-Hydroxy-cholestene-3-one

Description

7a-Hydroxy-cholestene-3-one, also known as cholest-4-en-7alpha-ol-3-one, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 7a-hydroxy-cholestene-3-one is considered to be a bile acid. Based on a literature review a significant number of articles have been published on 7a-Hydroxy-cholestene-3-one.

Structure

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

  Mrv0541 02231219182D          

 33 36  0  0  1  0            999 V2000
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    7.7016   -6.5193    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2742   -6.5193    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0038   -6.9158    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5605   -6.9158    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.4867   -5.4567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0038   -5.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 26 23  1  0  0  0  0
 27 24  1  0  0  0  0
 11 32  1  6  0  0  0
 33 27  2  0  0  0  0
M  END

HMDB0001993
     RDKit          3D
7a-Hydroxy-cholestene-3-one
 73 76  0  0  0  0  0  0  0  0999 V2000
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M  END

  Mrv0541 02231219182D          

 33 36  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
HMDB0001993

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)CC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h15,17-18,21-25,29H,6-14,16H2,1-5H3/t18-,21-,22+,23+,24-,25+,26+,27-/m1/s1

> <INCHI_KEY>
IOIZWEJGGCZDOL-RQDYSCIWSA-N

> <FORMULA>
C27H44O2

> <MOLECULAR_WEIGHT>
400.6371

> <EXACT_MASS>
400.334130652

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
50.60210025081398

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,9R,10S,11S,14R,15R)-9-hydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

> <ALOGPS_LOGP>
5.46

> <JCHEM_LOGP>
6.371370181666665

> <ALOGPS_LOGS>
-6.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.946034043249984

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.14119467931331

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6353871697001251

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
121.15759999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.69e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7α-hydroxy-4-cholesten-3-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0001993
     RDKit          3D
7a-Hydroxy-cholestene-3-one
 73 76  0  0  0  0  0  0  0  0999 V2000
    6.7965    2.0760   -0.7491 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8958    0.9376   -0.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7602    0.0231    0.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3018    0.2958   -1.4624 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3864   -0.8460   -1.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1929   -0.4076   -0.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3536   -1.5977   -0.0838 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1473   -2.7021    0.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0773   -1.4546    0.6354 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2234   -0.8933    2.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3173    0.3481    1.9431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8106   -0.2357    1.1872 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8819    0.6479    0.6997 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9352   -0.2942    0.1137 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3893   -1.2197   -0.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0677   -1.8281   -0.6026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0813   -0.8316   -0.0286 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1648    0.2074   -1.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1605    0.3884   -0.3686 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0061    0.7391   -1.8518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2902   -0.6446   -0.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6201   -0.0705   -0.6628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6883    1.4066   -0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5576    2.0367   -1.2472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7301    2.1049    0.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5128    1.6108    0.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5421    2.3259    1.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5965    1.3446    1.8705 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2892    0.4463    2.6457 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2225    2.7821   -1.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1661    2.6671    0.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6894    1.6803   -1.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1206    1.4224    0.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8259    0.3443    0.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4108    0.0306    1.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7607   -1.0195    0.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0848   -0.0458   -2.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7299    1.0867   -2.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9491   -1.6526   -0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9477   -1.1801   -2.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7550    0.4325   -0.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6463    0.0310    0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1331   -2.0578   -1.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4187   -3.4728    0.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8115   -3.2315   -0.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6652   -2.3205    1.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7361   -2.5358    0.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2347   -0.6540    2.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7613   -1.5230    2.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8362    1.1650    1.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0681    0.7158    2.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2660   -1.0457    1.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5980    1.4483    0.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2419   -0.9296    0.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4464   -0.7698   -1.9284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1125   -2.0903   -0.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6370   -2.2295   -1.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1568   -2.6940    0.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5188    1.1744   -0.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8372    0.4029   -1.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7432   -0.2455   -1.8884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0259    1.1793   -2.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7491    1.5544   -2.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2770   -0.1076   -2.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0574   -1.5101   -0.9581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3582   -1.0644    0.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4130   -0.4764    0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8856   -0.4341   -1.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0230    3.0189    0.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8987    2.9417    0.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0466    2.9781    1.9471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8600    1.9581    2.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8031    0.3624    3.5187 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  1  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  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 17  9  1  0
 26 19  1  0
 17 12  1  0
 28 13  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  6
  8 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  1
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  1
 13 53  1  6
 14 54  1  1
 15 55  1  0
 15 56  1  0
 16 57  1  0
 16 58  1  0
 18 59  1  0
 18 60  1  0
 18 61  1  0
 20 62  1  0
 20 63  1  0
 20 64  1  0
 21 65  1  0
 21 66  1  0
 22 67  1  0
 22 68  1  0
 25 69  1  0
 27 70  1  0
 27 71  1  0
 28 72  1  1
 29 73  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      14.376 -10.659   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.376 -12.169   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.712 -12.169   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.074 -12.910   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.380 -12.910   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.842 -10.186   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.074  -9.875   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.712 -10.659   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.842 -12.643   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.715 -11.414   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.074 -14.464   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.380 -14.464   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.712 -15.234   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.842  -8.617   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.376  -9.076   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.380 -11.400   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.077 -12.169   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.521  -8.572   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.219  -7.803   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.077 -15.234   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.436  -7.921   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.853  -7.773   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.186  -8.484   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.715 -12.910   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      21.186 -10.023   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      22.518  -7.655   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.715 -14.464   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0      11.712 -13.709   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0      13.074 -11.370   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      14.376 -13.709   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      15.842 -11.725   0.000  0.00  0.00           H+0
HETATM   32  O   UNK     0      14.263 -15.246   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       6.492 -15.246   0.000  0.00  0.00           O+0
CONECT    1    2    6    7   15                                             
CONECT    2    1    4    9   30                                             
CONECT    3    8    5    4   28                                             
CONECT    4    2    3   11   29                                             
CONECT    5    3   12   16   17                                             
CONECT    6    1   10   14   31                                             
CONECT    7    1    8                                                       
CONECT    8    3    7                                                       
CONECT    9    2   10                                                       
CONECT   10    6    9                                                       
CONECT   11    4   13   32                                                  
CONECT   12    5   20   13                                                  
CONECT   13   11   12                                                       
CONECT   14    6   19   21                                                  
CONECT   15    1                                                            
CONECT   16    5                                                            
CONECT   17    5   24                                                       
CONECT   18   19   22                                                       
CONECT   19   14   18                                                       
CONECT   20   12   27                                                       
CONECT   21   14                                                            
CONECT   22   18   23                                                       
CONECT   23   22   25   26                                                  
CONECT   24   17   27                                                       
CONECT   25   23                                                            
CONECT   26   23                                                            
CONECT   27   20   24   33                                                  
CONECT   28    3                                                            
CONECT   29    4                                                            
CONECT   30    2                                                            
CONECT   31    6                                                            
CONECT   32   11                                                            
CONECT   33   27                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0001993
HETATM    1  C1  UNL     1       6.797   2.076  -0.749  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.896   0.938  -0.250  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.760   0.023   0.556  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.302   0.296  -1.462  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.386  -0.846  -1.175  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.193  -0.408  -0.310  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.354  -1.598  -0.084  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.147  -2.702   0.639  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.077  -1.455   0.635  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.223  -0.893   2.034  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.317   0.348   1.943  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.811  -0.236   1.187  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.882   0.648   0.700  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.935  -0.294   0.114  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.389  -1.220  -0.904  1.00  0.00           C  
HETATM   16  C16 UNL     1      -1.068  -1.828  -0.603  1.00  0.00           C  
HETATM   17  C17 UNL     1      -0.081  -0.832  -0.029  1.00  0.00           C  
HETATM   18  C18 UNL     1       0.165   0.207  -1.051  1.00  0.00           C  
HETATM   19  C19 UNL     1      -4.160   0.388  -0.369  1.00  0.00           C  
HETATM   20  C20 UNL     1      -4.006   0.739  -1.852  1.00  0.00           C  
HETATM   21  C21 UNL     1      -5.290  -0.645  -0.307  1.00  0.00           C  
HETATM   22  C22 UNL     1      -6.620  -0.070  -0.663  1.00  0.00           C  
HETATM   23  C23 UNL     1      -6.688   1.407  -0.592  1.00  0.00           C  
HETATM   24  O1  UNL     1      -7.558   2.037  -1.247  1.00  0.00           O  
HETATM   25  C24 UNL     1      -5.730   2.105   0.250  1.00  0.00           C  
HETATM   26  C25 UNL     1      -4.513   1.611   0.355  1.00  0.00           C  
HETATM   27  C26 UNL     1      -3.542   2.326   1.211  1.00  0.00           C  
HETATM   28  C27 UNL     1      -2.597   1.345   1.871  1.00  0.00           C  
HETATM   29  O2  UNL     1      -3.289   0.446   2.646  1.00  0.00           O  
HETATM   30  H1  UNL     1       6.222   2.782  -1.377  1.00  0.00           H  
HETATM   31  H2  UNL     1       7.166   2.667   0.122  1.00  0.00           H  
HETATM   32  H3  UNL     1       7.689   1.680  -1.275  1.00  0.00           H  
HETATM   33  H4  UNL     1       5.121   1.422   0.383  1.00  0.00           H  
HETATM   34  H5  UNL     1       7.826   0.344   0.593  1.00  0.00           H  
HETATM   35  H6  UNL     1       6.411   0.031   1.622  1.00  0.00           H  
HETATM   36  H7  UNL     1       6.761  -1.019   0.198  1.00  0.00           H  
HETATM   37  H8  UNL     1       6.085  -0.046  -2.142  1.00  0.00           H  
HETATM   38  H9  UNL     1       4.730   1.087  -2.008  1.00  0.00           H  
HETATM   39  H10 UNL     1       4.949  -1.653  -0.697  1.00  0.00           H  
HETATM   40  H11 UNL     1       3.948  -1.180  -2.137  1.00  0.00           H  
HETATM   41  H12 UNL     1       2.755   0.433  -0.865  1.00  0.00           H  
HETATM   42  H13 UNL     1       3.646   0.031   0.600  1.00  0.00           H  
HETATM   43  H14 UNL     1       2.133  -2.058  -1.087  1.00  0.00           H  
HETATM   44  H15 UNL     1       2.419  -3.473   0.994  1.00  0.00           H  
HETATM   45  H16 UNL     1       3.812  -3.231  -0.080  1.00  0.00           H  
HETATM   46  H17 UNL     1       3.665  -2.321   1.521  1.00  0.00           H  
HETATM   47  H18 UNL     1       0.736  -2.536   0.837  1.00  0.00           H  
HETATM   48  H19 UNL     1       2.235  -0.654   2.322  1.00  0.00           H  
HETATM   49  H20 UNL     1       0.761  -1.523   2.820  1.00  0.00           H  
HETATM   50  H21 UNL     1       0.836   1.165   1.402  1.00  0.00           H  
HETATM   51  H22 UNL     1       0.068   0.716   2.949  1.00  0.00           H  
HETATM   52  H23 UNL     1      -1.266  -1.046   1.791  1.00  0.00           H  
HETATM   53  H24 UNL     1      -1.598   1.448   0.018  1.00  0.00           H  
HETATM   54  H25 UNL     1      -3.242  -0.930   0.997  1.00  0.00           H  
HETATM   55  H26 UNL     1      -2.446  -0.770  -1.928  1.00  0.00           H  
HETATM   56  H27 UNL     1      -3.112  -2.090  -0.974  1.00  0.00           H  
HETATM   57  H28 UNL     1      -0.637  -2.230  -1.548  1.00  0.00           H  
HETATM   58  H29 UNL     1      -1.157  -2.694   0.081  1.00  0.00           H  
HETATM   59  H30 UNL     1       0.519   1.174  -0.700  1.00  0.00           H  
HETATM   60  H31 UNL     1      -0.837   0.403  -1.550  1.00  0.00           H  
HETATM   61  H32 UNL     1       0.743  -0.245  -1.888  1.00  0.00           H  
HETATM   62  H33 UNL     1      -3.026   1.179  -2.084  1.00  0.00           H  
HETATM   63  H34 UNL     1      -4.749   1.554  -2.100  1.00  0.00           H  
HETATM   64  H35 UNL     1      -4.277  -0.108  -2.507  1.00  0.00           H  
HETATM   65  H36 UNL     1      -5.057  -1.510  -0.958  1.00  0.00           H  
HETATM   66  H37 UNL     1      -5.358  -1.064   0.729  1.00  0.00           H  
HETATM   67  H38 UNL     1      -7.413  -0.476   0.032  1.00  0.00           H  
HETATM   68  H39 UNL     1      -6.886  -0.434  -1.696  1.00  0.00           H  
HETATM   69  H40 UNL     1      -6.023   3.019   0.777  1.00  0.00           H  
HETATM   70  H41 UNL     1      -2.899   2.942   0.516  1.00  0.00           H  
HETATM   71  H42 UNL     1      -4.047   2.978   1.947  1.00  0.00           H  
HETATM   72  H43 UNL     1      -1.860   1.958   2.448  1.00  0.00           H  
HETATM   73  H44 UNL     1      -2.803   0.362   3.519  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    4   33
CONECT    3   34   35   36
CONECT    4    5   37   38
CONECT    5    6   39   40
CONECT    6    7   41   42
CONECT    7    8    9   43
CONECT    8   44   45   46
CONECT    9   10   17   47
CONECT   10   11   48   49
CONECT   11   12   50   51
CONECT   12   13   17   52
CONECT   13   14   28   53
CONECT   14   15   19   54
CONECT   15   16   55   56
CONECT   16   17   57   58
CONECT   17   18
CONECT   18   59   60   61
CONECT   19   20   21   26
CONECT   20   62   63   64
CONECT   21   22   65   66
CONECT   22   23   67   68
CONECT   23   24   24   25
CONECT   25   26   26   69
CONECT   26   27
CONECT   27   28   70   71
CONECT   28   29   72
CONECT   29   73
END

HMDB0001993
     RDKit          3D
7a-Hydroxy-cholestene-3-one
 73 76  0  0  0  0  0  0  0  0999 V2000
    6.7965    2.0760   -0.7491 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8958    0.9376   -0.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7602    0.0231    0.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3018    0.2958   -1.4624 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3864   -0.8460   -1.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1929   -0.4076   -0.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3536   -1.5977   -0.0838 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1473   -2.7021    0.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0773   -1.4546    0.6354 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2234   -0.8933    2.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3173    0.3481    1.9431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8106   -0.2357    1.1872 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8819    0.6479    0.6997 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9352   -0.2942    0.1137 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3893   -1.2197   -0.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0677   -1.8281   -0.6026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0813   -0.8316   -0.0286 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1648    0.2074   -1.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1605    0.3884   -0.3686 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0061    0.7391   -1.8518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2902   -0.6446   -0.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6201   -0.0705   -0.6628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6883    1.4066   -0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5576    2.0367   -1.2472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7301    2.1049    0.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5128    1.6108    0.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5421    2.3259    1.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5965    1.3446    1.8705 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2892    0.4463    2.6457 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2225    2.7821   -1.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1661    2.6671    0.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6894    1.6803   -1.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1206    1.4224    0.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8259    0.3443    0.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4108    0.0306    1.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7607   -1.0195    0.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0848   -0.0458   -2.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7299    1.0867   -2.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9491   -1.6526   -0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9477   -1.1801   -2.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7550    0.4325   -0.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6463    0.0310    0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1331   -2.0578   -1.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4187   -3.4728    0.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8115   -3.2315   -0.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6652   -2.3205    1.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7361   -2.5358    0.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2347   -0.6540    2.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7613   -1.5230    2.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8362    1.1650    1.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0681    0.7158    2.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2660   -1.0457    1.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5980    1.4483    0.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2419   -0.9296    0.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4464   -0.7698   -1.9284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1125   -2.0903   -0.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6370   -2.2295   -1.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1568   -2.6940    0.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5188    1.1744   -0.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8372    0.4029   -1.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7432   -0.2455   -1.8884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0259    1.1793   -2.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7491    1.5544   -2.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2770   -0.1076   -2.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0574   -1.5101   -0.9581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3582   -1.0644    0.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4130   -0.4764    0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8856   -0.4341   -1.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0230    3.0189    0.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8987    2.9417    0.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0466    2.9781    1.9471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8600    1.9581    2.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8031    0.3624    3.5187 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  1  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  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 17  9  1  0
 26 19  1  0
 17 12  1  0
 28 13  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  6
  8 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  1
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  1
 13 53  1  6
 14 54  1  1
 15 55  1  0
 15 56  1  0
 16 57  1  0
 16 58  1  0
 18 59  1  0
 18 60  1  0
 18 61  1  0
 20 62  1  0
 20 63  1  0
 20 64  1  0
 21 65  1  0
 21 66  1  0
 22 67  1  0
 22 68  1  0
 25 69  1  0
 27 70  1  0
 27 71  1  0
 28 72  1  1
 29 73  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7alpha-Hydroxy-4-cholesten-3-one	ChEBI
Cholest-4-en-7alpha-ol-3-one	ChEBI
7a-Hydroxy-4-cholesten-3-one	Generator
7Α-hydroxy-4-cholesten-3-one	Generator
Cholest-4-en-7a-ol-3-one	Generator
Cholest-4-en-7α-ol-3-one	Generator
7-Hydroxy-4-cholesten-3-one	MeSH
Cholest-4-en-7 alpha-ol-3-one	MeSH
7 alpha-Hydroxy-4-cholesten-3-one	MeSH
7 alpha-3Ox-C	HMDB
7-a-Hydroxy-4-cholesten-3-one	HMDB
7-a-Hydroxycholest-4-en-3-one	HMDB
7-alpha-Hydroxy-4-cholesten-3-one	HMDB
7-alpha-Hydroxycholest-4-en-3-one	HMDB
7-Hydroxycholest-4-en-3-one	HMDB
7a-Hydroxy-4-cholesten-3-one-12alpha	HMDB
7alpha-Hydroxycholest-4-en-3-one	HMDB
HCO	HMDB

Chemical Formula

C₂₇H₄₄O₂

Average Molecular Weight

400.6371

Monoisotopic Molecular Weight

400.334130652

IUPAC Name

(1S,2R,9R,10S,11S,14R,15R)-9-hydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

Traditional Name

7α-hydroxy-4-cholesten-3-one

CAS Registry Number

3862-25-7

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)CC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

InChI Identifier

InChI=1S/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h15,17-18,21-25,29H,6-14,16H2,1-5H3/t18-,21-,22+,23+,24-,25+,26+,27-/m1/s1

InChI Key

IOIZWEJGGCZDOL-RQDYSCIWSA-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-oxo-delta-4-steroid
3-oxosteroid
7-hydroxysteroid
Oxosteroid
Hydroxysteroid
Delta-4-steroid
Cyclohexenone
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo steroid (CHEBI:17899 )
7alpha-hydroxy steroid (CHEBI:17899 )
cholestanoid (CHEBI:17899 )
Cholesterol and derivatives (C05455 )
C27 bile acids, alcohols, and derivatives (LMST04030123 )

Ontology

Not Available

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	0.00017 g/L	ALOGPS
logP	5.46	ALOGPS
logP	6.37	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	17.14	ChemAxon
pKa (Strongest Basic)	-0.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	121.16 m³·mol⁻¹	ChemAxon
Polarizability	50.6 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]+	198.502	31661259
DarkChem	[M-H]-	193.992	31661259
DeepCCS	[M-2H]-	238.21	30932474
DeepCCS	[M+Na]+	212.234	30932474
AllCCS	[M+H]+	205.2	32859911
AllCCS	[M+H-H2O]+	203.1	32859911
AllCCS	[M+NH4]+	207.2	32859911
AllCCS	[M+Na]+	207.7	32859911
AllCCS	[M-H]-	204.5	32859911
AllCCS	[M+Na-2H]-	206.3	32859911
AllCCS	[M+HCOO]-	208.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
7a-Hydroxy-cholestene-3-one	[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)CC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C	3289.8	Standard polar	33892256
7a-Hydroxy-cholestene-3-one	[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)CC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C	3329.0	Standard non polar	33892256
7a-Hydroxy-cholestene-3-one	[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)CC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C	3498.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
7a-Hydroxy-cholestene-3-one,1TMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O[Si](C)(C)C	3366.5	Semi standard non polar	33892256
7a-Hydroxy-cholestene-3-one,1TMS,isomer #2	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C=C1C[C@H]3O	3298.0	Semi standard non polar	33892256
7a-Hydroxy-cholestene-3-one,2TMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C=C1C[C@H]3O[Si](C)(C)C	3175.6	Semi standard non polar	33892256
7a-Hydroxy-cholestene-3-one,2TMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C=C1C[C@H]3O[Si](C)(C)C	3322.7	Standard non polar	33892256
7a-Hydroxy-cholestene-3-one,2TMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C=C1C[C@H]3O[Si](C)(C)C	3462.2	Standard polar	33892256
7a-Hydroxy-cholestene-3-one,1TBDMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O[Si](C)(C)C(C)(C)C	3597.5	Semi standard non polar	33892256
7a-Hydroxy-cholestene-3-one,1TBDMS,isomer #2	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C=C1C[C@H]3O	3531.9	Semi standard non polar	33892256
7a-Hydroxy-cholestene-3-one,2TBDMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C=C1C[C@H]3O[Si](C)(C)C(C)(C)C	3648.7	Semi standard non polar	33892256
7a-Hydroxy-cholestene-3-one,2TBDMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C=C1C[C@H]3O[Si](C)(C)C(C)(C)C	3721.8	Standard non polar	33892256
7a-Hydroxy-cholestene-3-one,2TBDMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C=C1C[C@H]3O[Si](C)(C)C(C)(C)C	3662.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 7a-Hydroxy-cholestene-3-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-1339000000-8b87f8914863b4c7e8e7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a-Hydroxy-cholestene-3-one GC-MS (1 TMS) - 70eV, Positive	splash10-0a6r-4672900000-f5cd21522bdf7607c5cb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a-Hydroxy-cholestene-3-one 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 - 7a-Hydroxy-cholestene-3-one 10V, Positive-QTOF	splash10-0f89-0019500000-764a74c3942ad452aa8e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxy-cholestene-3-one 20V, Positive-QTOF	splash10-0f89-3339100000-87e6e598932d57a6274e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxy-cholestene-3-one 40V, Positive-QTOF	splash10-0ab9-8469000000-b55e4f0de6f6dbfbe093	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxy-cholestene-3-one 10V, Negative-QTOF	splash10-0002-0009000000-b03a7cbfe5ca7374d51f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxy-cholestene-3-one 20V, Negative-QTOF	splash10-0002-0009000000-903f15d46f6bf7449623	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxy-cholestene-3-one 40V, Negative-QTOF	splash10-00lr-1009000000-fd9c44e4f27a3c62b7e8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxy-cholestene-3-one 10V, Positive-QTOF	splash10-0udi-0001900000-7ee7f5ca27c449403c35	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxy-cholestene-3-one 20V, Positive-QTOF	splash10-0pvl-9246300000-d08ac46b391d42697238	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxy-cholestene-3-one 40V, Positive-QTOF	splash10-0a4l-9620000000-e3dea04967eb9e6421c1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxy-cholestene-3-one 10V, Negative-QTOF	splash10-0002-0009000000-dc23ba87137530d83f68	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxy-cholestene-3-one 20V, Negative-QTOF	splash10-0002-0009000000-dc23ba87137530d83f68	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxy-cholestene-3-one 40V, Negative-QTOF	splash10-0002-0009000000-75e53e521203e582561b	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Liver

Pathways

Name	SMPDB/PathBank	KEGG
Primary bile acid biosynthesis	Not Available
Congenital Bile Acid Synthesis Defect Type II		Not Available
Congenital Bile Acid Synthesis Defect Type III		Not Available
Familial Hypercholanemia (FHCA)		Not Available
Zellweger Syndrome		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	109.8 +/- 16.44 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16544968	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.18 (0.102-0.28) uM	Adult (>18 years old)	Both	Irritable bowel syndrome (IBS)	8723414	details
Blood	Detected and Quantified	0.13 (0.09-0.17) uM	Adult (>18 years old)	Both	Diverticular disease	8723414	details
Blood	Detected and Quantified	0.15 uM	Adult (>18 years old)	Both	Ileocysoiplasty	8723414	details
Blood	Detected and Quantified	0.132 uM	Adult (>18 years old)	Both	Meckels diverticulum	8723414	details
Blood	Detected and Quantified	0.127 uM	Adult (>18 years old)	Both	Atrophic gastritis	8723414	details
Blood	Detected and Quantified	0.12 uM	Adult (>18 years old)	Both	Cronh's ileitis	8723414	details
Blood	Detected and Quantified	0.0999 uM	Adult (>18 years old)	Both	Chronic pancreatitis	8723414	details
Blood	Detected and Quantified	0.16 (0.09-0.25) uM	Adult (>18 years old)	Both	Alcohol abuse	8723414	details
Blood	Detected and Quantified	0.033 +/- 0.011 uM	Adult (>18 years old)	Both	Gallstone disease	9615912	details

Associated Disorders and Diseases

Disease References

Gallbladder disease
Hillebrant CG, Axelson M, Bjorkhem I, Wang FH, Nyberg B, Einarsson C: Effects of short-term treatment with pravastatin on the hepatic synthesis of cholesterol and bile acids in gallstone patients. Eur J Clin Invest. 1998 Apr;28(4):324-8. [PubMed:9615912 ]
Irritable bowel syndrome
Brydon WG, Nyhlin H, Eastwood MA, Merrick MV: Serum 7 alpha-hydroxy-4-cholesten-3-one and selenohomocholyltaurine (SeHCAT) whole body retention in the assessment of bile acid induced diarrhoea. Eur J Gastroenterol Hepatol. 1996 Feb;8(2):117-23. [PubMed:8723414 ]
Diverticular disease
Brydon WG, Nyhlin H, Eastwood MA, Merrick MV: Serum 7 alpha-hydroxy-4-cholesten-3-one and selenohomocholyltaurine (SeHCAT) whole body retention in the assessment of bile acid induced diarrhoea. Eur J Gastroenterol Hepatol. 1996 Feb;8(2):117-23. [PubMed:8723414 ]
Ileocystoplasty
Brydon WG, Nyhlin H, Eastwood MA, Merrick MV: Serum 7 alpha-hydroxy-4-cholesten-3-one and selenohomocholyltaurine (SeHCAT) whole body retention in the assessment of bile acid induced diarrhoea. Eur J Gastroenterol Hepatol. 1996 Feb;8(2):117-23. [PubMed:8723414 ]
Meckels diverticulum
Brydon WG, Nyhlin H, Eastwood MA, Merrick MV: Serum 7 alpha-hydroxy-4-cholesten-3-one and selenohomocholyltaurine (SeHCAT) whole body retention in the assessment of bile acid induced diarrhoea. Eur J Gastroenterol Hepatol. 1996 Feb;8(2):117-23. [PubMed:8723414 ]
Atrophic gastritis
Brydon WG, Nyhlin H, Eastwood MA, Merrick MV: Serum 7 alpha-hydroxy-4-cholesten-3-one and selenohomocholyltaurine (SeHCAT) whole body retention in the assessment of bile acid induced diarrhoea. Eur J Gastroenterol Hepatol. 1996 Feb;8(2):117-23. [PubMed:8723414 ]
Crohn's disease
Brydon WG, Nyhlin H, Eastwood MA, Merrick MV: Serum 7 alpha-hydroxy-4-cholesten-3-one and selenohomocholyltaurine (SeHCAT) whole body retention in the assessment of bile acid induced diarrhoea. Eur J Gastroenterol Hepatol. 1996 Feb;8(2):117-23. [PubMed:8723414 ]
Chronic pancreatitis
Brydon WG, Nyhlin H, Eastwood MA, Merrick MV: Serum 7 alpha-hydroxy-4-cholesten-3-one and selenohomocholyltaurine (SeHCAT) whole body retention in the assessment of bile acid induced diarrhoea. Eur J Gastroenterol Hepatol. 1996 Feb;8(2):117-23. [PubMed:8723414 ]
Alcoholism
Brydon WG, Nyhlin H, Eastwood MA, Merrick MV: Serum 7 alpha-hydroxy-4-cholesten-3-one and selenohomocholyltaurine (SeHCAT) whole body retention in the assessment of bile acid induced diarrhoea. Eur J Gastroenterol Hepatol. 1996 Feb;8(2):117-23. [PubMed:8723414 ]

Associated OMIM IDs

1551 (Meckels diverticulum)
266600 (Crohn's disease)
1678 (Chronic pancreatitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022786

KNApSAcK ID

Not Available

Chemspider ID

110306

KEGG Compound ID

C05455

BioCyc ID

Not Available

BiGG ID

45848

Wikipedia Link

Not Available

METLIN ID

6419

PubChem Compound

123743

PDB ID

Not Available

ChEBI ID

17899

Food Biomarker Ontology

Not Available

VMH ID

XOL7AONE

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Alexander, David L.; Fisher, Jed F. A convenient synthesis of 7a-hydroxycholest-4-en-3-one by the hydroxypropyl-b-cyclodextrin-facilitated cholesterol oxidase oxidation of 3b,7a-cholest-5-ene-3,7-diol. Steroids (1995), 60(3), 290-4.

Material Safety Data Sheet (MSDS)

Not Available

General References

Skrede S, Bjorkhem I, Buchmann MS, Hopen G, Fausa O: A novel pathway for biosynthesis of cholestanol with 7 alpha-hydroxylated C27-steroids as intermediates, and its importance for the accumulation of cholestanol in cerebrotendinous xanthomatosis. J Clin Invest. 1985 Feb;75(2):448-55. [PubMed:3919058 ]
Lin RC, Fillenwarth MJ, Du X: Cytotoxic effect of 7alpha-hydroxy-4-cholesten-3-one on HepG2 cells: hypothetical role of acetaldehyde-modified delta4-3-ketosteroid-5beta-reductase (the 37-kd-liver protein) in the pathogenesis of alcoholic liver injury in the rat. Hepatology. 1998 Jan;27(1):100-7. [PubMed:9425924 ]
Axelson M, Bjorkhem I, Reihner E, Einarsson K: The plasma level of 7 alpha-hydroxy-4-cholesten-3-one reflects the activity of hepatic cholesterol 7 alpha-hydroxylase in man. FEBS Lett. 1991 Jun 24;284(2):216-8. [PubMed:2060639 ]
Skrede S, Bjorkhem I: A novel route for the biosynthesis of cholestanol, and its significance for the pathogenesis of cerebrotendinous xanthomatosis. Scand J Clin Lab Invest Suppl. 1985;177:15-21. [PubMed:3865344 ]
Skrede S, Buchmann MS, Bjorkhem I: Hepatic 7 alpha-dehydroxylation of bile acid intermediates, and its significance for the pathogenesis of cerebrotendinous xanthomatosis. J Lipid Res. 1988 Feb;29(2):157-64. [PubMed:3367085 ]
Sauter GH, Munzing W, von Ritter C, Paumgartner G: Bile acid malabsorption as a cause of chronic diarrhea: diagnostic value of 7alpha-hydroxy-4-cholesten-3-one in serum. Dig Dis Sci. 1999 Jan;44(1):14-9. [PubMed:9952217 ]
Brydon WG, Nyhlin H, Eastwood MA, Merrick MV: Serum 7 alpha-hydroxy-4-cholesten-3-one and selenohomocholyltaurine (SeHCAT) whole body retention in the assessment of bile acid induced diarrhoea. Eur J Gastroenterol Hepatol. 1996 Feb;8(2):117-23. [PubMed:8723414 ]

Enzymes

Enzyme Details

1. 3-oxo-5-beta-steroid 4-dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4-cholesten-3-one can also act as substrates.
Gene Name:: AKR1D1
Uniprot ID:: P51857
Molecular weight:: 32889.38

Reactions

7a-Hydroxy-5b-cholestan-3-one + NADP → 7a-Hydroxy-cholestene-3-one + NADPH + Hydrogen Ion	details

Enzyme Details

2. 3 beta-hydroxysteroid dehydrogenase type 7

General function:: Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:: The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids. HSD VII is active against four 7-alpha-hydroxylated sterols. Does not metabolize several different C(19/21) steroids as substrates. Involved in bile acid synthesis.
Gene Name:: HSD3B7
Uniprot ID:: Q9H2F3
Molecular weight:: 21322.265

Reactions

Cholest-5-ene-3-beta,7-alpha-diol + NAD → 7a-Hydroxy-cholestene-3-one + NADH	details
7alpha-Hydroxycholesterol + NAD → 7a-Hydroxy-cholestene-3-one + NADH + Hydrogen Ion	details

Enzyme Details

3. 7-alpha-hydroxycholest-4-en-3-one 12-alpha-hydroxylase

General function:: Involved in monooxygenase activity
Specific function:: Involved in bile acid synthesis and is responsible for the conversion of 7 alpha-hydroxy-4-cholesten-3-one into 7 alpha, 12 alpha-dihydroxy-4-cholesten-3-one. Responsible for the balance between formation of cholic acid and chenodeoxycholic acid. Has a rather broad substrate specificity including a number of 7-alpha-hydroxylated C27 steroids.
Gene Name:: CYP8B1
Uniprot ID:: Q9UNU6
Molecular weight:: 58068.01

Reactions

7a-Hydroxy-cholestene-3-one + NADPH + Oxygen → 7a,12a-Dihydroxy-cholestene-3-one + NADP + Water	details
7a-Hydroxy-cholestene-3-one + Hydrogen Ion + Oxygen + NADPH → 7a,12a-Dihydroxy-cholestene-3-one + NADP + Water	details

Showing metabocard for 7a-Hydroxy-cholestene-3-one (HMDB0001993)

MOL for HMDB0001993 (7a-Hydroxy-cholestene-3-one)

3D MOL for HMDB0001993 (7a-Hydroxy-cholestene-3-one)

3D SDF for HMDB0001993 (7a-Hydroxy-cholestene-3-one)

3D-SDF for HMDB0001993 (7a-Hydroxy-cholestene-3-one)

PDB for HMDB0001993 (7a-Hydroxy-cholestene-3-one)

3D PDB for HMDB0001993 (7a-Hydroxy-cholestene-3-one)

SMILES for HMDB0001993 (7a-Hydroxy-cholestene-3-one)

INCHI for HMDB0001993 (7a-Hydroxy-cholestene-3-one)

Structure for HMDB0001993 (7a-Hydroxy-cholestene-3-one)

3D Structure for HMDB0001993 (7a-Hydroxy-cholestene-3-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions

Reactions