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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:41 UTC

Update Date

2022-03-07 02:49:13 UTC

HMDB ID

HMDB0002197

Secondary Accession Numbers

HMDB02197

Metabolite Identification

Common Name

7a,12a-Dihydroxy-cholestene-3-one

Description

7a,12a-Dihydroxy-cholestene-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. Based on a literature review very few articles have been published on 7a,12a-Dihydroxy-cholestene-3-one.

Structure

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

2-trans,4-trans-Octadienoyl-CoA.mol
  Mrv0541 02231219252D          

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M  END

HMDB0002197
     RDKit          3D
7a,12a-Dihydroxy-cholestene-3-one
 74 77  0  0  0  0  0  0  0  0999 V2000
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M  END

2-trans,4-trans-Octadienoyl-CoA.mol
  Mrv0541 02231219252D          

 33 36  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
HMDB0002197

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2CC(=O)C=C[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O3/c1-16(2)7-6-8-17(3)20-9-10-21-25-22(15-24(30)27(20,21)5)26(4)12-11-19(28)13-18(26)14-23(25)29/h11-12,16-18,20-25,29-30H,6-10,13-15H2,1-5H3/t17-,18?,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
VJGNBLOGSXHTLR-JFXJTJEYSA-N

> <FORMULA>
C27H44O3

> <MOLECULAR_WEIGHT>
416.6365

> <EXACT_MASS>
416.329045274

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
50.91866258272553

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-en-5-one

> <ALOGPS_LOGP>
4.69

> <JCHEM_LOGP>
5.184216939333334

> <ALOGPS_LOGS>
-5.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.1535227164545213

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
122.93969999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.86e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-en-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002197
     RDKit          3D
7a,12a-Dihydroxy-cholestene-3-one
 74 77  0  0  0  0  0  0  0  0999 V2000
    7.0364   -1.5737    1.9211 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6519   -0.9004    1.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7223   -2.0698    1.3462 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8200    0.0537    0.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6636    0.8699    0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4421    0.1468   -0.3901 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4631    1.2245   -0.8035 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1442    2.0370   -1.8991 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1735    0.8008   -1.2855 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1085   -0.0687   -2.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3365   -0.6036   -2.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9443    0.0500   -1.3015 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1418   -0.4855   -0.6660 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5578    0.5879    0.3617 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4813    0.5510    1.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1376    0.8402    0.8559 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0337    2.2119    0.5807 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2584    0.0629   -0.3404 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6443   -1.3494   -0.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9232    0.3807    0.8818 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0922    0.7498    2.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8678    1.2264    0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1648    0.9101    0.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6750   -0.2534    0.7597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9027   -0.4166    0.9617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7291   -1.2818    1.2531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3406   -1.0695    0.6435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4419   -1.3574   -0.8199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2852   -0.7550   -1.6087 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6610    0.3373   -2.3545 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6519   -0.9047    2.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8663   -2.5593    2.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5595   -1.7182    0.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2958   -0.3908    2.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5193   -2.1322    0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1934   -3.0318    1.7174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7707   -2.0237    1.8989 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7226    0.7058    0.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1712   -0.5587   -0.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0439    1.5905   -0.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4160    1.5558    0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7225   -0.4772   -1.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0133   -0.3766    0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3515    1.9008    0.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8789    1.4576   -2.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6440    2.9444   -1.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3976    2.4222   -2.6237 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5969    1.7395   -1.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2747    0.5224   -3.4453 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8449   -0.8762   -2.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3487   -1.7021   -2.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8340   -0.2494   -3.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1503    1.1276   -1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0352   -1.4017   -0.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4802    1.5735   -0.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4644   -0.4866    1.8315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6735    1.2274    2.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6183    0.6239    1.6669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8138    2.7061    0.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1545   -2.1045   -0.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9285   -1.4533    0.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4840   -1.7281   -0.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    0.8621    2.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6354    1.7550    2.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7343   -0.0052    3.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5146    2.1115   -0.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8724    1.5044   -0.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1067   -2.2715    0.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6386   -1.1686    2.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6743   -1.7749    1.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3982   -1.0205   -1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4562   -2.4819   -0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9444   -1.5435   -2.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3149    0.2953   -3.2768 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
 16 18  1  0
 18 19  1  1
 14 20  1  0
 20 21  1  1
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 18  9  1  0
 27 20  1  0
 18 12  1  0
 29 13  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  6 42  1  0
  6 43  1  0
  7 44  1  1
  8 45  1  0
  8 46  1  0
  8 47  1  0
  9 48  1  6
 10 49  1  0
 10 50  1  0
 11 51  1  0
 11 52  1  0
 12 53  1  6
 13 54  1  1
 14 55  1  6
 15 56  1  0
 15 57  1  0
 16 58  1  1
 17 59  1  0
 19 60  1  0
 19 61  1  0
 19 62  1  0
 21 63  1  0
 21 64  1  0
 21 65  1  0
 22 66  1  0
 23 67  1  0
 26 68  1  0
 26 69  1  0
 27 70  1  0
 28 71  1  0
 28 72  1  0
 29 73  1  6
 30 74  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 2-trans,4-trans-Octadienoyl-CoA.mol               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.391  -5.743   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.391  -4.203   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.057  -3.433   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.057  -6.513   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.723  -5.743   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.390  -6.513   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.944  -5.743   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.944  -4.203   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.278  -3.433   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.742  -3.909   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.647  -2.663   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.742  -1.417   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.218   0.047   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.249   1.244   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.801   2.682   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.832   3.879   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.384   5.316   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.414   6.513   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.905   5.557   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.725   0.368   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.278  -1.893   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.278  -0.353   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.944  -1.123   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.390  -1.893   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.390  -3.433   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.723  -4.203   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.723  -2.663   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -5.725  -6.513   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.944   0.417   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.278  -6.513   0.000  0.00  0.00           O+0
HETATM   31  H   UNK     0      -0.390  -4.973   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.944  -2.663   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.278  -4.973   0.000  0.00  0.00           H+0
CONECT    1    2    4   28                                                  
CONECT    2    1    3                                                       
CONECT    3    2   26                                                       
CONECT    4    1    5                                                       
CONECT    5    4    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   30                                                  
CONECT    8    7    9   25   32                                             
CONECT    9    8   10   21   33                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   13                                                            
CONECT   21   12    9   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24    8   26   31                                             
CONECT   26   25    3    5   27                                             
CONECT   27   26                                                            
CONECT   28    1                                                            
CONECT   29   23                                                            
CONECT   30    7                                                            
CONECT   31   25                                                            
CONECT   32    8                                                            
CONECT   33    9                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0002197
HETATM    1  C1  UNL     1       7.036  -1.574   1.921  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.652  -0.900   1.652  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.722  -2.070   1.346  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.820   0.054   0.533  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.664   0.870   0.101  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.442   0.147  -0.390  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.463   1.224  -0.804  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.144   2.037  -1.899  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.174   0.801  -1.285  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.109  -0.069  -2.495  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.337  -0.604  -2.466  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.944   0.050  -1.301  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.142  -0.486  -0.666  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.558   0.588   0.362  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.481   0.551   1.422  1.00  0.00           C  
HETATM   16  C16 UNL     1      -0.138   0.840   0.856  1.00  0.00           C  
HETATM   17  O1  UNL     1       0.034   2.212   0.581  1.00  0.00           O  
HETATM   18  C17 UNL     1       0.258   0.063  -0.340  1.00  0.00           C  
HETATM   19  C18 UNL     1       0.644  -1.349  -0.097  1.00  0.00           C  
HETATM   20  C19 UNL     1      -3.923   0.381   0.882  1.00  0.00           C  
HETATM   21  C20 UNL     1      -4.092   0.750   2.336  1.00  0.00           C  
HETATM   22  C21 UNL     1      -4.868   1.226   0.105  1.00  0.00           C  
HETATM   23  C22 UNL     1      -6.165   0.910   0.059  1.00  0.00           C  
HETATM   24  C23 UNL     1      -6.675  -0.253   0.760  1.00  0.00           C  
HETATM   25  O2  UNL     1      -7.903  -0.417   0.962  1.00  0.00           O  
HETATM   26  C24 UNL     1      -5.729  -1.282   1.253  1.00  0.00           C  
HETATM   27  C25 UNL     1      -4.341  -1.069   0.643  1.00  0.00           C  
HETATM   28  C26 UNL     1      -4.442  -1.357  -0.820  1.00  0.00           C  
HETATM   29  C27 UNL     1      -3.285  -0.755  -1.609  1.00  0.00           C  
HETATM   30  O3  UNL     1      -3.661   0.337  -2.354  1.00  0.00           O  
HETATM   31  H1  UNL     1       7.652  -0.905   2.551  1.00  0.00           H  
HETATM   32  H2  UNL     1       6.866  -2.559   2.378  1.00  0.00           H  
HETATM   33  H3  UNL     1       7.559  -1.718   0.955  1.00  0.00           H  
HETATM   34  H4  UNL     1       5.296  -0.391   2.555  1.00  0.00           H  
HETATM   35  H5  UNL     1       4.519  -2.132   0.277  1.00  0.00           H  
HETATM   36  H6  UNL     1       5.193  -3.032   1.717  1.00  0.00           H  
HETATM   37  H7  UNL     1       3.771  -2.024   1.899  1.00  0.00           H  
HETATM   38  H8  UNL     1       6.723   0.706   0.735  1.00  0.00           H  
HETATM   39  H9  UNL     1       6.171  -0.559  -0.370  1.00  0.00           H  
HETATM   40  H10 UNL     1       5.044   1.591  -0.683  1.00  0.00           H  
HETATM   41  H11 UNL     1       4.416   1.556   0.957  1.00  0.00           H  
HETATM   42  H12 UNL     1       3.722  -0.477  -1.232  1.00  0.00           H  
HETATM   43  H13 UNL     1       3.013  -0.377   0.492  1.00  0.00           H  
HETATM   44  H14 UNL     1       2.351   1.901   0.066  1.00  0.00           H  
HETATM   45  H15 UNL     1       3.879   1.458  -2.464  1.00  0.00           H  
HETATM   46  H16 UNL     1       3.644   2.944  -1.470  1.00  0.00           H  
HETATM   47  H17 UNL     1       2.398   2.422  -2.624  1.00  0.00           H  
HETATM   48  H18 UNL     1       0.597   1.740  -1.559  1.00  0.00           H  
HETATM   49  H19 UNL     1       1.275   0.522  -3.445  1.00  0.00           H  
HETATM   50  H20 UNL     1       1.845  -0.876  -2.545  1.00  0.00           H  
HETATM   51  H21 UNL     1      -0.349  -1.702  -2.471  1.00  0.00           H  
HETATM   52  H22 UNL     1      -0.834  -0.249  -3.392  1.00  0.00           H  
HETATM   53  H23 UNL     1      -1.150   1.128  -1.576  1.00  0.00           H  
HETATM   54  H24 UNL     1      -2.035  -1.402  -0.049  1.00  0.00           H  
HETATM   55  H25 UNL     1      -2.480   1.574  -0.144  1.00  0.00           H  
HETATM   56  H26 UNL     1      -1.464  -0.487   1.831  1.00  0.00           H  
HETATM   57  H27 UNL     1      -1.674   1.227   2.257  1.00  0.00           H  
HETATM   58  H28 UNL     1       0.618   0.624   1.667  1.00  0.00           H  
HETATM   59  H29 UNL     1      -0.814   2.706   0.697  1.00  0.00           H  
HETATM   60  H30 UNL     1      -0.154  -2.105  -0.249  1.00  0.00           H  
HETATM   61  H31 UNL     1       0.929  -1.453   0.989  1.00  0.00           H  
HETATM   62  H32 UNL     1       1.484  -1.728  -0.741  1.00  0.00           H  
HETATM   63  H33 UNL     1      -5.200   0.862   2.511  1.00  0.00           H  
HETATM   64  H34 UNL     1      -3.635   1.755   2.469  1.00  0.00           H  
HETATM   65  H35 UNL     1      -3.734  -0.005   3.034  1.00  0.00           H  
HETATM   66  H36 UNL     1      -4.515   2.112  -0.435  1.00  0.00           H  
HETATM   67  H37 UNL     1      -6.872   1.504  -0.495  1.00  0.00           H  
HETATM   68  H38 UNL     1      -6.107  -2.271   0.939  1.00  0.00           H  
HETATM   69  H39 UNL     1      -5.639  -1.169   2.339  1.00  0.00           H  
HETATM   70  H40 UNL     1      -3.674  -1.775   1.165  1.00  0.00           H  
HETATM   71  H41 UNL     1      -5.398  -1.020  -1.268  1.00  0.00           H  
HETATM   72  H42 UNL     1      -4.456  -2.482  -0.927  1.00  0.00           H  
HETATM   73  H43 UNL     1      -2.944  -1.543  -2.311  1.00  0.00           H  
HETATM   74  H44 UNL     1      -3.315   0.295  -3.277  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3    4   34
CONECT    3   35   36   37
CONECT    4    5   38   39
CONECT    5    6   40   41
CONECT    6    7   42   43
CONECT    7    8    9   44
CONECT    8   45   46   47
CONECT    9   10   18   48
CONECT   10   11   49   50
CONECT   11   12   51   52
CONECT   12   13   18   53
CONECT   13   14   29   54
CONECT   14   15   20   55
CONECT   15   16   56   57
CONECT   16   17   18   58
CONECT   17   59
CONECT   18   19
CONECT   19   60   61   62
CONECT   20   21   22   27
CONECT   21   63   64   65
CONECT   22   23   23   66
CONECT   23   24   67
CONECT   24   25   25   26
CONECT   26   27   68   69
CONECT   27   28   70
CONECT   28   29   71   72
CONECT   29   30   73
CONECT   30   74
END

HMDB0002197
     RDKit          3D
7a,12a-Dihydroxy-cholestene-3-one
 74 77  0  0  0  0  0  0  0  0999 V2000
    7.0364   -1.5737    1.9211 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6519   -0.9004    1.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7223   -2.0698    1.3462 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8200    0.0537    0.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6636    0.8699    0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4421    0.1468   -0.3901 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4631    1.2245   -0.8035 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1442    2.0370   -1.8991 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1735    0.8008   -1.2855 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1085   -0.0687   -2.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3365   -0.6036   -2.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9443    0.0500   -1.3015 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1418   -0.4855   -0.6660 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5578    0.5879    0.3617 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4813    0.5510    1.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1376    0.8402    0.8559 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0337    2.2119    0.5807 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2584    0.0629   -0.3404 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6443   -1.3494   -0.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9232    0.3807    0.8818 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0922    0.7498    2.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8678    1.2264    0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1648    0.9101    0.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6750   -0.2534    0.7597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9027   -0.4166    0.9617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7291   -1.2818    1.2531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3406   -1.0695    0.6435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4419   -1.3574   -0.8199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2852   -0.7550   -1.6087 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6610    0.3373   -2.3545 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6519   -0.9047    2.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8663   -2.5593    2.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5595   -1.7182    0.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2958   -0.3908    2.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5193   -2.1322    0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1934   -3.0318    1.7174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7707   -2.0237    1.8989 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7226    0.7058    0.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1712   -0.5587   -0.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0439    1.5905   -0.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4160    1.5558    0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7225   -0.4772   -1.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0133   -0.3766    0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3515    1.9008    0.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8789    1.4576   -2.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6440    2.9444   -1.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3976    2.4222   -2.6237 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5969    1.7395   -1.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2747    0.5224   -3.4453 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8449   -0.8762   -2.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3487   -1.7021   -2.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8340   -0.2494   -3.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1503    1.1276   -1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0352   -1.4017   -0.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4802    1.5735   -0.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4644   -0.4866    1.8315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6735    1.2274    2.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6183    0.6239    1.6669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8138    2.7061    0.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1545   -2.1045   -0.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9285   -1.4533    0.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4840   -1.7281   -0.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    0.8621    2.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6354    1.7550    2.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7343   -0.0052    3.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5146    2.1115   -0.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8724    1.5044   -0.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1067   -2.2715    0.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6386   -1.1686    2.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6743   -1.7749    1.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3982   -1.0205   -1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4562   -2.4819   -0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9444   -1.5435   -2.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3149    0.2953   -3.2768 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
 16 18  1  0
 18 19  1  1
 14 20  1  0
 20 21  1  1
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 18  9  1  0
 27 20  1  0
 18 12  1  0
 29 13  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  6 42  1  0
  6 43  1  0
  7 44  1  1
  8 45  1  0
  8 46  1  0
  8 47  1  0
  9 48  1  6
 10 49  1  0
 10 50  1  0
 11 51  1  0
 11 52  1  0
 12 53  1  6
 13 54  1  1
 14 55  1  6
 15 56  1  0
 15 57  1  0
 16 58  1  1
 17 59  1  0
 19 60  1  0
 19 61  1  0
 19 62  1  0
 21 63  1  0
 21 64  1  0
 21 65  1  0
 22 66  1  0
 23 67  1  0
 26 68  1  0
 26 69  1  0
 27 70  1  0
 28 71  1  0
 28 72  1  0
 29 73  1  6
 30 74  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7-a,12-a-Dihydroxy-4-cholesten-3-one	HMDB
7-a,12-a-Dihydroxycholest-4-en-3-one	HMDB
7-a,12-alpha-Dihydroxy-4-cholesten-3-one	HMDB
7-a,12-alpha-Dihydroxycholest-4-en-3-one	HMDB
7-alpha,12-alpha-Dihydroxy-4-cholesten-3-one	HMDB
7-alpha,12-alpha-Dihydroxycholest-4-en-3-one	HMDB
7alpha,12alpha-Dihydroxy-cholestene-3-one	HMDB

Chemical Formula

C₂₇H₄₄O₃

Average Molecular Weight

416.6365

Monoisotopic Molecular Weight

416.329045274

IUPAC Name

(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-en-5-one

Traditional Name

(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-en-5-one

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2CC(=O)C=C[C@]12C

InChI Identifier

InChI=1S/C27H44O3/c1-16(2)7-6-8-17(3)20-9-10-21-25-22(15-24(30)27(20,21)5)26(4)12-11-19(28)13-18(26)14-23(25)29/h11-12,16-18,20-25,29-30H,6-10,13-15H2,1-5H3/t17-,18?,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1

InChI Key

VJGNBLOGSXHTLR-JFXJTJEYSA-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-1-steroid
3-oxosteroid
7-hydroxysteroid
Oxosteroid
12-hydroxysteroid
Hydroxysteroid
Delta-1-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

Not Available

Ontology

Physiological effect

Health effect

Metabolic disorder

Metabolic syndrome (HMDB: HMDB0002197)

Disposition

Biological location

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0002197)

Tissue

All Tissues (HMDB: HMDB0002197)

Connective tissue

Adipose tissue (HMDB: HMDB0002197)

Nervous tissue

Hepatic tissue (HMDB: HMDB0002197)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0002197)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002197)

Source

Endogenous

Endogenous (HMDB: HMDB0002197)

Animal

Animal (HMDB: HMDB0002197)

Exogenous

Food

Food (HMDB: HMDB0002197)

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: HMDB0002197)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0002197)

Biochemical pathway

Disease pathway

Congenital Bile Acid Synthesis Defect Type II (HMDB: HMDB0002197)
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: HMDB0002197)
Bile Acid Biosynthesis (PathBank: SMP0087329)

Lipid metabolism pathway (HMDB: HMDB0002197)

Cellular process

Cell signaling (HMDB: HMDB0002197)

Biochemical process

Lipid transport (HMDB: HMDB0002197)

Multicellular process

Inflammatory response (HMDB: HMDB0002197)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0002197)

Molecular messenger

Hormone (HMDB: HMDB0002197)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0002197)

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	0.0029 g/L	ALOGPS
logP	4.69	ALOGPS
logP	5.18	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Basic)	-0.15	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	122.94 m³·mol⁻¹	ChemAxon
Polarizability	50.92 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	203.948	31661259
DarkChem	[M-H]-	199.724	31661259
DeepCCS	[M-2H]-	250.421	30932474
DeepCCS	[M+Na]+	225.733	30932474
AllCCS	[M+H]+	207.2	32859911
AllCCS	[M+H-H2O]+	205.1	32859911
AllCCS	[M+NH4]+	209.0	32859911
AllCCS	[M+Na]+	209.6	32859911
AllCCS	[M-H]-	205.9	32859911
AllCCS	[M+Na-2H]-	207.8	32859911
AllCCS	[M+HCOO]-	210.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	7.89 minutes	32390414
Predicted by Siyang on May 30, 2022	19.3781 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.59 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3451.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	363.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	248.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	185.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	515.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	934.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	870.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	90.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1554.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	675.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1990.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	500.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	544.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	179.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	367.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
7a,12a-Dihydroxy-cholestene-3-one	[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2CC(=O)C=C[C@]12C	3336.1	Standard polar	33892256
7a,12a-Dihydroxy-cholestene-3-one	[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2CC(=O)C=C[C@]12C	3399.9	Standard non polar	33892256
7a,12a-Dihydroxy-cholestene-3-one	[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2CC(=O)C=C[C@]12C	3625.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
7a,12a-Dihydroxy-cholestene-3-one,1TMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)C=CC(=O)CC1C[C@H]3O	3441.3	Semi standard non polar	33892256
7a,12a-Dihydroxy-cholestene-3-one,1TMS,isomer #2	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)C=CC(=O)CC1C[C@H]3O[Si](C)(C)C	3401.9	Semi standard non polar	33892256
7a,12a-Dihydroxy-cholestene-3-one,1TMS,isomer #3	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)C=CC(O[Si](C)(C)C)=CC1C[C@H]3O	3308.5	Semi standard non polar	33892256
7a,12a-Dihydroxy-cholestene-3-one,2TMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)C=CC(=O)CC1C[C@H]3O[Si](C)(C)C	3353.1	Semi standard non polar	33892256
7a,12a-Dihydroxy-cholestene-3-one,2TMS,isomer #2	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)C=CC(O[Si](C)(C)C)=CC1C[C@H]3O	3289.9	Semi standard non polar	33892256
7a,12a-Dihydroxy-cholestene-3-one,2TMS,isomer #3	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)C=CC(O[Si](C)(C)C)=CC1C[C@H]3O[Si](C)(C)C	3232.7	Semi standard non polar	33892256
7a,12a-Dihydroxy-cholestene-3-one,3TMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)C=CC(O[Si](C)(C)C)=CC1C[C@H]3O[Si](C)(C)C	3242.6	Semi standard non polar	33892256
7a,12a-Dihydroxy-cholestene-3-one,3TMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)C=CC(O[Si](C)(C)C)=CC1C[C@H]3O[Si](C)(C)C	3251.3	Standard non polar	33892256
7a,12a-Dihydroxy-cholestene-3-one,3TMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)C=CC(O[Si](C)(C)C)=CC1C[C@H]3O[Si](C)(C)C	3370.3	Standard polar	33892256
7a,12a-Dihydroxy-cholestene-3-one,1TBDMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)C=CC(=O)CC1C[C@H]3O	3660.7	Semi standard non polar	33892256
7a,12a-Dihydroxy-cholestene-3-one,1TBDMS,isomer #2	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)C=CC(=O)CC1C[C@H]3O[Si](C)(C)C(C)(C)C	3610.9	Semi standard non polar	33892256
7a,12a-Dihydroxy-cholestene-3-one,1TBDMS,isomer #3	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)C=CC(O[Si](C)(C)C(C)(C)C)=CC1C[C@H]3O	3552.6	Semi standard non polar	33892256
7a,12a-Dihydroxy-cholestene-3-one,2TBDMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)C=CC(=O)CC1C[C@H]3O[Si](C)(C)C(C)(C)C	3778.5	Semi standard non polar	33892256
7a,12a-Dihydroxy-cholestene-3-one,2TBDMS,isomer #2	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)C=CC(O[Si](C)(C)C(C)(C)C)=CC1C[C@H]3O	3745.1	Semi standard non polar	33892256
7a,12a-Dihydroxy-cholestene-3-one,2TBDMS,isomer #3	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)C=CC(O[Si](C)(C)C(C)(C)C)=CC1C[C@H]3O[Si](C)(C)C(C)(C)C	3678.9	Semi standard non polar	33892256
7a,12a-Dihydroxy-cholestene-3-one,3TBDMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)C=CC(O[Si](C)(C)C(C)(C)C)=CC1C[C@H]3O[Si](C)(C)C(C)(C)C	3900.7	Semi standard non polar	33892256
7a,12a-Dihydroxy-cholestene-3-one,3TBDMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)C=CC(O[Si](C)(C)C(C)(C)C)=CC1C[C@H]3O[Si](C)(C)C(C)(C)C	3830.7	Standard non polar	33892256
7a,12a-Dihydroxy-cholestene-3-one,3TBDMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)C=CC(O[Si](C)(C)C(C)(C)C)=CC1C[C@H]3O[Si](C)(C)C(C)(C)C	3596.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0957100000-f9ca360b20be30aee5cd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one GC-MS (2 TMS) - 70eV, Positive	splash10-0002-6421590000-060d19b9863c108036ea	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a,12a-Dihydroxy-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,12a-Dihydroxy-cholestene-3-one 10V, Positive-QTOF	splash10-00kb-0009200000-ca011752a678df923d91	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one 20V, Positive-QTOF	splash10-007k-2109000000-fe2eac67f433d8e5ffd6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one 40V, Positive-QTOF	splash10-0avi-7209000000-dd9edd2da2f8a7cfa3b7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one 10V, Negative-QTOF	splash10-014i-0004900000-9a4838827d7cc0003b0c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one 20V, Negative-QTOF	splash10-014j-0009800000-d99dd5a2761313bbd19c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one 40V, Negative-QTOF	splash10-0012-1109000000-12f6e81d23b56a07105c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one 10V, Positive-QTOF	splash10-014i-0005900000-6e10002b2e4a4ff63704	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one 20V, Positive-QTOF	splash10-052r-6369100000-1f4ae070beee131b40ce	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one 40V, Positive-QTOF	splash10-0a6u-9530000000-59dfe5c229199b50616d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one 10V, Negative-QTOF	splash10-014i-0000900000-67ea14fb7a26b9b2d929	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one 20V, Negative-QTOF	splash10-014i-0001900000-949821f2e2f9dbbe8632	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one 40V, Negative-QTOF	splash10-0udr-0079200000-cad453714d3d5275e24b	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane
Mitochondria

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

FDB022899

KNApSAcK ID

Not Available

Chemspider ID

13628315

KEGG Compound ID

C05457

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6539

PubChem Compound

21252277

PDB ID

Not Available

ChEBI ID

28477

Food Biomarker Ontology

Not Available

VMH ID

XOLDIOLONE

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Bjorkhem I, Oftebro H, Skrede S, Pedersen JI: Assay of intermediates in bile acid biosynthesis using isotope dilution--mass spectrometry: hepatic levels in the normal state and in cerebrotendinous xanthomatosis. J Lipid Res. 1981 Feb;22(2):191-200. [PubMed:7017048 ]

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,12a-Dihydroxy-5b-cholestan-3-one + NADP → 7a,12a-Dihydroxy-cholestene-3-one + NADPH + Hydrogen Ion	details

Enzyme Details

2. 3-oxo-5-alpha-steroid 4-dehydrogenase 2

General function:: Involved in 3-oxo-5-alpha-steroid 4-dehydrogenase activity
Specific function:: Converts testosterone (T) into 5-alpha-dihydrotestosterone (DHT) and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and androgen physiology.
Gene Name:: SRD5A2
Uniprot ID:: P31213
Molecular weight:: 28407.035

Enzyme Details

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

General function:: Involved in 3-oxo-5-alpha-steroid 4-dehydrogenase activity
Specific function:: Converts testosterone into 5-alpha-dihydrotestosterone and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and androgen physiology.
Gene Name:: SRD5A1
Uniprot ID:: P18405
Molecular weight:: 29458.18

Enzyme Details

4. 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,12a-Dihydroxy-cholestene-3-one (HMDB0002197)

MOL for HMDB0002197 (7a,12a-Dihydroxy-cholestene-3-one)

3D MOL for HMDB0002197 (7a,12a-Dihydroxy-cholestene-3-one)

3D SDF for HMDB0002197 (7a,12a-Dihydroxy-cholestene-3-one)

3D-SDF for HMDB0002197 (7a,12a-Dihydroxy-cholestene-3-one)

PDB for HMDB0002197 (7a,12a-Dihydroxy-cholestene-3-one)

3D PDB for HMDB0002197 (7a,12a-Dihydroxy-cholestene-3-one)

SMILES for HMDB0002197 (7a,12a-Dihydroxy-cholestene-3-one)

INCHI for HMDB0002197 (7a,12a-Dihydroxy-cholestene-3-one)

Structure for HMDB0002197 (7a,12a-Dihydroxy-cholestene-3-one)

3D Structure for HMDB0002197 (7a,12a-Dihydroxy-cholestene-3-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions