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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2008-08-14 18:10:28 UTC

Update Date

2022-03-07 02:49:34 UTC

HMDB ID

HMDB0006892

Secondary Accession Numbers

HMDB06892

Metabolite Identification

Common Name

7a-Hydroxy-5b-cholestan-3-one

Description

7alpha-Hydroxy-5beta-cholestan-3-one is an intermediate in bile acid synthesis. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g. membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487 , 16037564 , 12576301 , 11907135 ).

Structure

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

  Mrv0541 02231220552D          

 29 32  0  0  1  0            999 V2000
   14.8360   -6.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4770   -6.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3532   -8.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7223  -10.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8212   -9.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9671   -7.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7741   -7.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7122   -8.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1352  -10.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6503  -10.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2933  -11.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4367   -9.9047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0078  -10.7297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1512   -9.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0078  -12.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4367  -12.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0291   -6.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9052   -8.8652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7223  -11.9672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2933  -11.9672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6503   -9.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8656  -10.7297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4367  -10.7297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1512  -11.9672    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1512  -11.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.8656   -9.9047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5788  -12.3797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8656  -12.3797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0  0  0  0
  2 17  1  0  0  0  0
  3 18  1  0  0  0  0
 26  4  1  1  0  0  0
 27  5  1  1  0  0  0
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 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 24 25  1  0  0  0  0
 24 29  1  1  0  0  0
M  END

HMDB0006892
     RDKit          3D
7a-Hydroxy-5b-cholestan-3-one
 75 78  0  0  0  0  0  0  0  0999 V2000
    7.3331   -1.0040    0.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

  Mrv0541 02231220552D          

 29 32  0  0  1  0            999 V2000
   14.8360   -6.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4770   -6.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7223  -10.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8212   -9.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9671   -7.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7741   -7.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.6503  -10.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2933  -11.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4367   -9.9047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0006892

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CCCC(C)C1CCC2C3[C@@H](O)CC4CC(=O)CC[C@]4(C)C3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O2/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/h17-19,21-25,29H,6-16H2,1-5H3/t18?,19?,21?,22?,23?,24-,25?,26-,27+/m0/s1

> <INCHI_KEY>
HWOOALPDOJHOPO-SENDYOAPSA-N

> <FORMULA>
C27H46O2

> <MOLECULAR_WEIGHT>
402.6529

> <EXACT_MASS>
402.349780716

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
50.43250477637848

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
5.53

> <JCHEM_LOGP>
6.417204516666668

> <ALOGPS_LOGS>
-6.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.987846456178296

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5821703787037896

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
120.33089999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.77e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,9S,15R)-9-hydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0006892
     RDKit          3D
7a-Hydroxy-5b-cholestan-3-one
 75 78  0  0  0  0  0  0  0  0999 V2000
    7.3331   -1.0040    0.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2396    0.0218    0.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9350    1.3618   -0.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4421    0.1139    1.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3180    1.0607    1.3786 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1657    0.8821    0.4960 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2608   -0.3078    0.7230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0122   -1.5802    0.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1162   -0.1527   -0.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3967   -0.1618   -1.6708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0210    0.1639   -2.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9684   -0.3892   -1.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9404    0.6541   -0.6476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8429    0.1202    0.4028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2275   -0.9852    1.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7511   -0.7109    1.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0984   -0.9630   -0.0480 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0134   -2.4378   -0.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2148   -0.2851   -0.0824 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2114   -1.3340   -1.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0143   -0.8076    1.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3431    0.1782    2.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3797    1.5828    1.6907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8728    2.3971    2.4796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8837    2.0884    0.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8414    0.9728   -0.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0774    1.4668   -1.7942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6101    1.4048   -1.7402 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1820    0.8397   -2.9715 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8958   -1.1905   -0.6383 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0883   -0.6254    1.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9108   -1.9692    0.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6904   -0.2191   -0.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7223    1.1222   -0.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1553    2.0165   -0.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3758    1.7745    0.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1950    0.5352    2.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2663   -0.8984    1.7498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7703    2.0813    1.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0212    1.2218    2.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4278    0.8508   -0.5879 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4753    1.7765    0.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053   -0.2909    1.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2379   -2.0504    1.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4087   -2.4001    0.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8984   -1.5121   -0.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7270    0.9440   -0.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7118   -1.1571   -2.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0992    0.6010   -1.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0270    1.2923   -2.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0665   -0.2880   -3.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4909   -1.2380   -1.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2430    1.3778   -0.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0460    0.9572    1.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6048   -0.9298    2.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4886   -1.9886    0.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2297   -1.3823    2.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6141    0.3264    1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1014   -2.7743   -0.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4747   -2.7894   -1.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2583   -2.9513    0.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5399   -2.1975   -0.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2395   -1.8063   -1.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0580   -0.9928   -2.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4881   -1.6962    1.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9577   -1.2372    0.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6702    0.0536    3.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3727   -0.0560    2.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6517    2.8232    0.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9445    2.6616    0.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8800    0.7534   -0.8958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4498    2.5249   -1.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5190    0.9218   -2.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126    2.4634   -1.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5459    1.3717   -3.7308 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  1  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  0
  8 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  0
 13 53  1  0
 14 54  1  0
 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
 25 70  1  0
 26 71  1  0
 27 72  1  0
 27 73  1  0
 28 74  1  6
 29 75  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      27.694 -12.659   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.157 -11.834   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.193 -15.404   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.282 -19.259   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.200 -16.917   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.205 -14.763   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.712 -14.443   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.729 -16.228   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.652 -19.259   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.747 -20.505   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.614 -20.799   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.615 -18.489   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.948 -20.029   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.949 -17.719   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.948 -23.109   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.615 -23.109   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.188 -12.979   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      22.223 -16.548   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.282 -22.339   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.614 -22.339   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      21.747 -18.013   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.282 -20.029   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.615 -20.029   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.949 -22.339   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.949 -20.799   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.282 -20.799   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      20.282 -18.489   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      12.280 -23.109   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      20.282 -23.109   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2   17                                                            
CONECT    3   18                                                            
CONECT    4   26                                                            
CONECT    5   27                                                            
CONECT    6    7    8                                                       
CONECT    7    6   17                                                       
CONECT    8    6   18                                                       
CONECT    9   21   10                                                       
CONECT   10    9   22                                                       
CONECT   11   13   20                                                       
CONECT   12   23   14                                                       
CONECT   13   11   26                                                       
CONECT   14   12   27                                                       
CONECT   15   20   19                                                       
CONECT   16   19   24                                                       
CONECT   17    1    2    7                                                  
CONECT   18    3    8   21                                                  
CONECT   19   15   16   26                                                  
CONECT   20   11   15   28                                                  
CONECT   21    9   18   27                                                  
CONECT   22   10   25   27                                                  
CONECT   23   12   25   26                                                  
CONECT   24   16   25   29                                                  
CONECT   25   22   23   24                                                  
CONECT   26    4   13   19   23                                             
CONECT   27    5   14   21   22                                             
CONECT   28   20                                                            
CONECT   29   24                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

COMPND    HMDB0006892
HETATM    1  C1  UNL     1       7.333  -1.004   0.321  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.240   0.022   0.106  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.935   1.362  -0.182  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.442   0.114   1.387  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.318   1.061   1.379  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.166   0.882   0.496  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.261  -0.308   0.723  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.012  -1.580   0.551  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.116  -0.153  -0.200  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.397  -0.162  -1.671  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.021   0.164  -2.196  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.968  -0.389  -1.192  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.940   0.654  -0.648  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.843   0.120   0.403  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.228  -0.985   1.220  1.00  0.00           C  
HETATM   16  C16 UNL     1      -0.751  -0.711   1.300  1.00  0.00           C  
HETATM   17  C17 UNL     1      -0.098  -0.963  -0.048  1.00  0.00           C  
HETATM   18  C18 UNL     1      -0.013  -2.438  -0.220  1.00  0.00           C  
HETATM   19  C19 UNL     1      -4.215  -0.285  -0.082  1.00  0.00           C  
HETATM   20  C20 UNL     1      -4.211  -1.334  -1.140  1.00  0.00           C  
HETATM   21  C21 UNL     1      -5.014  -0.808   1.082  1.00  0.00           C  
HETATM   22  C22 UNL     1      -5.343   0.178   2.128  1.00  0.00           C  
HETATM   23  C23 UNL     1      -5.380   1.583   1.691  1.00  0.00           C  
HETATM   24  O1  UNL     1      -5.873   2.397   2.480  1.00  0.00           O  
HETATM   25  C24 UNL     1      -4.884   2.088   0.408  1.00  0.00           C  
HETATM   26  C25 UNL     1      -4.841   0.973  -0.608  1.00  0.00           C  
HETATM   27  C26 UNL     1      -4.077   1.467  -1.794  1.00  0.00           C  
HETATM   28  C27 UNL     1      -2.610   1.405  -1.740  1.00  0.00           C  
HETATM   29  O2  UNL     1      -2.182   0.840  -2.971  1.00  0.00           O  
HETATM   30  H1  UNL     1       7.896  -1.191  -0.638  1.00  0.00           H  
HETATM   31  H2  UNL     1       8.088  -0.625   1.046  1.00  0.00           H  
HETATM   32  H3  UNL     1       6.911  -1.969   0.675  1.00  0.00           H  
HETATM   33  H4  UNL     1       5.690  -0.219  -0.789  1.00  0.00           H  
HETATM   34  H5  UNL     1       7.722   1.122  -0.941  1.00  0.00           H  
HETATM   35  H6  UNL     1       6.155   2.017  -0.641  1.00  0.00           H  
HETATM   36  H7  UNL     1       7.376   1.774   0.729  1.00  0.00           H  
HETATM   37  H8  UNL     1       6.195   0.535   2.140  1.00  0.00           H  
HETATM   38  H9  UNL     1       5.266  -0.898   1.750  1.00  0.00           H  
HETATM   39  H10 UNL     1       4.770   2.081   1.125  1.00  0.00           H  
HETATM   40  H11 UNL     1       4.021   1.222   2.458  1.00  0.00           H  
HETATM   41  H12 UNL     1       3.428   0.851  -0.588  1.00  0.00           H  
HETATM   42  H13 UNL     1       2.475   1.777   0.569  1.00  0.00           H  
HETATM   43  H14 UNL     1       1.905  -0.291   1.806  1.00  0.00           H  
HETATM   44  H15 UNL     1       3.238  -2.050   1.553  1.00  0.00           H  
HETATM   45  H16 UNL     1       2.409  -2.400   0.051  1.00  0.00           H  
HETATM   46  H17 UNL     1       3.898  -1.512  -0.101  1.00  0.00           H  
HETATM   47  H18 UNL     1       0.727   0.944  -0.043  1.00  0.00           H  
HETATM   48  H19 UNL     1       1.712  -1.157  -2.047  1.00  0.00           H  
HETATM   49  H20 UNL     1       2.099   0.601  -1.996  1.00  0.00           H  
HETATM   50  H21 UNL     1      -0.027   1.292  -2.226  1.00  0.00           H  
HETATM   51  H22 UNL     1      -0.067  -0.288  -3.191  1.00  0.00           H  
HETATM   52  H23 UNL     1      -1.491  -1.238  -1.650  1.00  0.00           H  
HETATM   53  H24 UNL     1      -1.243   1.378  -0.121  1.00  0.00           H  
HETATM   54  H25 UNL     1      -3.046   0.957   1.140  1.00  0.00           H  
HETATM   55  H26 UNL     1      -2.605  -0.930   2.285  1.00  0.00           H  
HETATM   56  H27 UNL     1      -2.489  -1.989   0.876  1.00  0.00           H  
HETATM   57  H28 UNL     1      -0.230  -1.382   2.019  1.00  0.00           H  
HETATM   58  H29 UNL     1      -0.614   0.326   1.618  1.00  0.00           H  
HETATM   59  H30 UNL     1      -1.101  -2.774  -0.388  1.00  0.00           H  
HETATM   60  H31 UNL     1       0.475  -2.789  -1.147  1.00  0.00           H  
HETATM   61  H32 UNL     1       0.258  -2.951   0.702  1.00  0.00           H  
HETATM   62  H33 UNL     1      -3.540  -2.198  -0.857  1.00  0.00           H  
HETATM   63  H34 UNL     1      -5.239  -1.806  -1.128  1.00  0.00           H  
HETATM   64  H35 UNL     1      -4.058  -0.993  -2.160  1.00  0.00           H  
HETATM   65  H36 UNL     1      -4.488  -1.696   1.531  1.00  0.00           H  
HETATM   66  H37 UNL     1      -5.958  -1.237   0.652  1.00  0.00           H  
HETATM   67  H38 UNL     1      -4.670   0.054   3.007  1.00  0.00           H  
HETATM   68  H39 UNL     1      -6.373  -0.056   2.532  1.00  0.00           H  
HETATM   69  H40 UNL     1      -5.652   2.823   0.025  1.00  0.00           H  
HETATM   70  H41 UNL     1      -3.945   2.662   0.471  1.00  0.00           H  
HETATM   71  H42 UNL     1      -5.880   0.753  -0.896  1.00  0.00           H  
HETATM   72  H43 UNL     1      -4.450   2.525  -1.967  1.00  0.00           H  
HETATM   73  H44 UNL     1      -4.519   0.922  -2.685  1.00  0.00           H  
HETATM   74  H45 UNL     1      -2.213   2.463  -1.810  1.00  0.00           H  
HETATM   75  H46 UNL     1      -2.546   1.372  -3.731  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   69   70
CONECT   26   27   71
CONECT   27   28   72   73
CONECT   28   29   74
CONECT   29   75
END

HMDB0006892
     RDKit          3D
7a-Hydroxy-5b-cholestan-3-one
 75 78  0  0  0  0  0  0  0  0999 V2000
    7.3331   -1.0040    0.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2396    0.0218    0.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9350    1.3618   -0.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4421    0.1139    1.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3180    1.0607    1.3786 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1657    0.8821    0.4960 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2608   -0.3078    0.7230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0122   -1.5802    0.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1162   -0.1527   -0.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3967   -0.1618   -1.6708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0210    0.1639   -2.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9684   -0.3892   -1.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9404    0.6541   -0.6476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8429    0.1202    0.4028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2275   -0.9852    1.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7511   -0.7109    1.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0984   -0.9630   -0.0480 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0134   -2.4378   -0.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2148   -0.2851   -0.0824 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2114   -1.3340   -1.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0143   -0.8076    1.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3431    0.1782    2.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3797    1.5828    1.6907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8728    2.3971    2.4796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8837    2.0884    0.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8414    0.9728   -0.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0774    1.4668   -1.7942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6101    1.4048   -1.7402 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1820    0.8397   -2.9715 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8958   -1.1905   -0.6383 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0883   -0.6254    1.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9108   -1.9692    0.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6904   -0.2191   -0.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7223    1.1222   -0.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1553    2.0165   -0.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3758    1.7745    0.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1950    0.5352    2.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2663   -0.8984    1.7498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7703    2.0813    1.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0212    1.2218    2.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4278    0.8508   -0.5879 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4753    1.7765    0.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053   -0.2909    1.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2379   -2.0504    1.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4087   -2.4001    0.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8984   -1.5121   -0.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7270    0.9440   -0.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7118   -1.1571   -2.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0992    0.6010   -1.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0270    1.2923   -2.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0665   -0.2880   -3.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4909   -1.2380   -1.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2430    1.3778   -0.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0460    0.9572    1.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6048   -0.9298    2.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4886   -1.9886    0.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2297   -1.3823    2.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6141    0.3264    1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1014   -2.7743   -0.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4747   -2.7894   -1.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2583   -2.9513    0.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5399   -2.1975   -0.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2395   -1.8063   -1.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0580   -0.9928   -2.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4881   -1.6962    1.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9577   -1.2372    0.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6702    0.0536    3.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3727   -0.0560    2.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6517    2.8232    0.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9445    2.6616    0.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8800    0.7534   -0.8958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4498    2.5249   -1.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5190    0.9218   -2.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126    2.4634   -1.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5459    1.3717   -3.7308 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  1  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  0
  8 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  0
 13 53  1  0
 14 54  1  0
 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
 25 70  1  0
 26 71  1  0
 27 72  1  0
 27 73  1  0
 28 74  1  6
 29 75  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5b-Cholestan-7a-ol-3-one	HMDB
5beta-Cholestan-7alpha-ol-3-one	HMDB
7alpha-Hydroxy-5beta-cholestan-3-one	HMDB

Chemical Formula

C₂₇H₄₆O₂

Average Molecular Weight

402.6529

Monoisotopic Molecular Weight

402.349780716

IUPAC Name

(2S,9S,15R)-9-hydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one

Traditional Name

(2S,9S,15R)-9-hydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one

CAS Registry Number

Not Available

SMILES

CC(C)CCCC(C)C1CCC2C3[C@@H](O)CC4CC(=O)CC[C@]4(C)C3CC[C@]12C

InChI Identifier

InChI=1S/C27H46O2/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/h17-19,21-25,29H,6-16H2,1-5H3/t18?,19?,21?,22?,23?,24-,25?,26-,27+/m0/s1

InChI Key

HWOOALPDOJHOPO-SENDYOAPSA-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-oxosteroid
Hydroxysteroid
Oxosteroid
7-alpha-hydroxysteroid
7-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Ketone
Cyclic ketone
Organooxygen compound
Alcohol
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Metabolic disorder

Metabolic syndrome (HMDB: HMDB0006892)

Disposition

Biological location

Cellular substructure

Tissue

All Tissues (HMDB: HMDB0006892)

Connective tissue

Adipose tissue (HMDB: HMDB0006892)

Nervous tissue

Hepatic tissue (HMDB: HMDB0006892)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0006892)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006892)

Source

Endogenous

Endogenous (HMDB: HMDB0006892)

Animal

Animal (HMDB: HMDB0006892)

Exogenous

Food

Food (HMDB: HMDB0006892)

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: HMDB0006892)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0006892)

Biochemical pathway

Disease pathway

Congenital Bile Acid Synthesis Defect Type II (HMDB: HMDB0006892)
27-Hydroxylase Deficiency (PathBank: SMP0120652)
Cerebrotendinous Xanthomatosis (CTX) (PathBank: SMP0120683)
Familial Hypercholanemia (FHCA) (PathBank: SMP0120697)
Zellweger Syndrome (PathBank: SMP0120715)
Congenital Bile Acid Synthesis Defect Type II (PathBank: SMP0120687)
Congenital Bile Acid Synthesis Defect Type III (PathBank: SMP0120688)

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0006892)
Bile Acid Biosynthesis (PathBank: SMP0087329)

Lipid metabolism pathway (HMDB: HMDB0006892)

Cellular process

Cell signaling (HMDB: HMDB0006892)

Biochemical process

Lipid transport (HMDB: HMDB0006892)

Multicellular process

Inflammatory response (HMDB: HMDB0006892)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0006892)

Molecular messenger

Signaling molecule (HMDB: HMDB0006892)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006892)

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	8.8e-05 g/L	ALOGPS
logP	5.53	ALOGPS
logP	6.42	ChemAxon
logS	-6.7	ALOGPS
pKa (Strongest Acidic)	19.99	ChemAxon
pKa (Strongest Basic)	-0.58	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	120.33 m³·mol⁻¹	ChemAxon
Polarizability	50.43 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]+	197.876	31661259
DarkChem	[M-H]-	194.431	31661259
DeepCCS	[M-2H]-	237.537	30932474
DeepCCS	[M+Na]+	213.703	30932474
AllCCS	[M+H]+	205.9	32859911
AllCCS	[M+H-H2O]+	203.8	32859911
AllCCS	[M+NH4]+	207.8	32859911
AllCCS	[M+Na]+	208.3	32859911
AllCCS	[M-H]-	203.8	32859911
AllCCS	[M+Na-2H]-	205.7	32859911
AllCCS	[M+HCOO]-	207.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
7a-Hydroxy-5b-cholestan-3-one	CC(C)CCCC(C)C1CCC2C3[C@@H](O)CC4CC(=O)CC[C@]4(C)C3CC[C@]12C	2575.9	Standard polar	33892256
7a-Hydroxy-5b-cholestan-3-one	CC(C)CCCC(C)C1CCC2C3[C@@H](O)CC4CC(=O)CC[C@]4(C)C3CC[C@]12C	3329.6	Standard non polar	33892256
7a-Hydroxy-5b-cholestan-3-one	CC(C)CCCC(C)C1CCC2C3[C@@H](O)CC4CC(=O)CC[C@]4(C)C3CC[C@]12C	3377.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
7a-Hydroxy-5b-cholestan-3-one,1TMS,isomer #1	CC(C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CCC(=O)CC1C[C@@H]3O[Si](C)(C)C	3383.1	Semi standard non polar	33892256
7a-Hydroxy-5b-cholestan-3-one,1TMS,isomer #2	CC(C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC=C(O[Si](C)(C)C)CC1C[C@@H]3O	3363.8	Semi standard non polar	33892256
7a-Hydroxy-5b-cholestan-3-one,1TMS,isomer #3	CC(C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CCC(O[Si](C)(C)C)=CC1C[C@@H]3O	3371.4	Semi standard non polar	33892256
7a-Hydroxy-5b-cholestan-3-one,2TMS,isomer #1	CC(C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CCC(O[Si](C)(C)C)=CC1C[C@@H]3O[Si](C)(C)C	3315.4	Semi standard non polar	33892256
7a-Hydroxy-5b-cholestan-3-one,2TMS,isomer #1	CC(C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CCC(O[Si](C)(C)C)=CC1C[C@@H]3O[Si](C)(C)C	3237.2	Standard non polar	33892256
7a-Hydroxy-5b-cholestan-3-one,2TMS,isomer #1	CC(C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CCC(O[Si](C)(C)C)=CC1C[C@@H]3O[Si](C)(C)C	3415.2	Standard polar	33892256
7a-Hydroxy-5b-cholestan-3-one,2TMS,isomer #2	CC(C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC=C(O[Si](C)(C)C)CC1C[C@@H]3O[Si](C)(C)C	3311.2	Semi standard non polar	33892256
7a-Hydroxy-5b-cholestan-3-one,2TMS,isomer #2	CC(C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC=C(O[Si](C)(C)C)CC1C[C@@H]3O[Si](C)(C)C	3204.5	Standard non polar	33892256
7a-Hydroxy-5b-cholestan-3-one,2TMS,isomer #2	CC(C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC=C(O[Si](C)(C)C)CC1C[C@@H]3O[Si](C)(C)C	3419.1	Standard polar	33892256
7a-Hydroxy-5b-cholestan-3-one,1TBDMS,isomer #1	CC(C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CCC(=O)CC1C[C@@H]3O[Si](C)(C)C(C)(C)C	3572.5	Semi standard non polar	33892256
7a-Hydroxy-5b-cholestan-3-one,1TBDMS,isomer #2	CC(C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)CC1C[C@@H]3O	3592.0	Semi standard non polar	33892256
7a-Hydroxy-5b-cholestan-3-one,1TBDMS,isomer #3	CC(C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=CC1C[C@@H]3O	3595.9	Semi standard non polar	33892256
7a-Hydroxy-5b-cholestan-3-one,2TBDMS,isomer #1	CC(C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=CC1C[C@@H]3O[Si](C)(C)C(C)(C)C	3750.2	Semi standard non polar	33892256
7a-Hydroxy-5b-cholestan-3-one,2TBDMS,isomer #1	CC(C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=CC1C[C@@H]3O[Si](C)(C)C(C)(C)C	3657.7	Standard non polar	33892256
7a-Hydroxy-5b-cholestan-3-one,2TBDMS,isomer #1	CC(C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=CC1C[C@@H]3O[Si](C)(C)C(C)(C)C	3615.1	Standard polar	33892256
7a-Hydroxy-5b-cholestan-3-one,2TBDMS,isomer #2	CC(C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)CC1C[C@@H]3O[Si](C)(C)C(C)(C)C	3742.1	Semi standard non polar	33892256
7a-Hydroxy-5b-cholestan-3-one,2TBDMS,isomer #2	CC(C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)CC1C[C@@H]3O[Si](C)(C)C(C)(C)C	3578.4	Standard non polar	33892256
7a-Hydroxy-5b-cholestan-3-one,2TBDMS,isomer #2	CC(C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)CC1C[C@@H]3O[Si](C)(C)C(C)(C)C	3617.8	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-5b-cholestan-3-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-059l-1429000000-36dd7661988002ae7048	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a-Hydroxy-5b-cholestan-3-one GC-MS (1 TMS) - 70eV, Positive	splash10-0a4l-4553900000-095eadc0e820bc80b096	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a-Hydroxy-5b-cholestan-3-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a-Hydroxy-5b-cholestan-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-5b-cholestan-3-one 10V, Positive-QTOF	splash10-0f79-0019400000-4dd1a559cbcc4562e70d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxy-5b-cholestan-3-one 20V, Positive-QTOF	splash10-0550-3119100000-f5ee2373268e16d7dfa9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxy-5b-cholestan-3-one 40V, Positive-QTOF	splash10-0a4i-3139000000-8871a8cc4f848fcb3ea7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxy-5b-cholestan-3-one 10V, Negative-QTOF	splash10-0udi-0002900000-36cc7f2c2ca5297e94f2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxy-5b-cholestan-3-one 20V, Negative-QTOF	splash10-0udi-0004900000-2cf478d98ec9f18cfc00	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxy-5b-cholestan-3-one 40V, Negative-QTOF	splash10-00y0-2009000000-56c5e620409babd7e456	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxy-5b-cholestan-3-one 10V, Positive-QTOF	splash10-0udi-0002900000-f9057318f9e096ddd572	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxy-5b-cholestan-3-one 20V, Positive-QTOF	splash10-052o-9036200000-04613e200ca6b799ca70	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxy-5b-cholestan-3-one 40V, Positive-QTOF	splash10-052g-9520000000-58169fe3ab060f15e0e6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxy-5b-cholestan-3-one 10V, Negative-QTOF	splash10-0udi-0000900000-079f76b4d985e4b92c9d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxy-5b-cholestan-3-one 20V, Negative-QTOF	splash10-0udi-0000900000-079f76b4d985e4b92c9d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxy-5b-cholestan-3-one 40V, Negative-QTOF	splash10-0udi-0006900000-07c8001378695cbb19a4	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

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

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024139

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C05451

BioCyc ID

Not Available

BiGG ID

45839

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477905

PDB ID

Not Available

ChEBI ID

2290

Food Biomarker Ontology

Not Available

VMH ID

XOL7AH

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. [PubMed:11316487 ]
Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21. [PubMed:16037564 ]
Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. [PubMed:12576301 ]
Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. [PubMed:11907135 ]

Enzymes

Enzyme Details

1. Aldo-keto reductase family 1 member C4

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
Gene Name:: AKR1C4
Uniprot ID:: P17516
Molecular weight:: 37094.57

Reactions

3a,7a-Dihydroxy-5b-cholestane + NAD → 7a-Hydroxy-5b-cholestan-3-one + NADH + Hydrogen Ion	details
3a,7a-Dihydroxy-5b-cholestane + NADP → 7a-Hydroxy-5b-cholestan-3-one + NADPH + Hydrogen Ion	details

Enzyme Details

2. 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

Showing metabocard for 7a-Hydroxy-5b-cholestan-3-one (HMDB0006892)

MOL for HMDB0006892 (7a-Hydroxy-5b-cholestan-3-one)

3D MOL for HMDB0006892 (7a-Hydroxy-5b-cholestan-3-one)

3D SDF for HMDB0006892 (7a-Hydroxy-5b-cholestan-3-one)

3D-SDF for HMDB0006892 (7a-Hydroxy-5b-cholestan-3-one)

PDB for HMDB0006892 (7a-Hydroxy-5b-cholestan-3-one)

3D PDB for HMDB0006892 (7a-Hydroxy-5b-cholestan-3-one)

SMILES for HMDB0006892 (7a-Hydroxy-5b-cholestan-3-one)

INCHI for HMDB0006892 (7a-Hydroxy-5b-cholestan-3-one)

Structure for HMDB0006892 (7a-Hydroxy-5b-cholestan-3-one)

3D Structure for HMDB0006892 (7a-Hydroxy-5b-cholestan-3-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions