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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:10 UTC

HMDB ID

HMDB0001457

Secondary Accession Numbers

HMDB01457

Metabolite Identification

Common Name

5beta-Cholestane-3alpha,7alpha,12alpha-triol

Description

5beta-Cholestane-3alpha,7alpha,12alpha-triol is an intermediate in bile acid biosynthesis. 5beta-Cholestane-3alpha,7alpha,12alpha-triol is the second to last step in the synthesis of 5beta-cyprinolsulfate. It is converted from 7alpha,12alpha-dihydroxy-5beta-cholestan-3-one via enzymatic reaction, and then it is converted into 3alpha,7alpha,12alpha,26-tetrahydroxy-5beta-cholestane via the enzyme cytochrome P450 (EC 1.14.13.15). This compound inhibits la-hydroxylation (PMID: 7937829 ). It is the byproduct of cholestanetetraol 26-dehydrogenase (EC 1.1.1.161) and the reaction that catalyzes it is classified as a small molecule reaction (BioCyc).

Structure

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


  Mrv1652308121918502D          

 35 38  0  0  0  0            999 V2000
 9999.9783 9998.1488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.976210001.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7004 9998.1488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8404 9997.7376    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.840410000.2166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5523 9998.9836    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.264310001.8801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9762 9998.9836    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.264310000.2166    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8384 9999.3899    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.8384 9998.5648    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.5529 9998.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2674 9998.5648    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.264910001.0474    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.550410000.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5504 9999.8098    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.2649 9999.3974    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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 9996.4132 9999.3900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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10000.7640 9999.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.248910000.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.764010000.8899    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.764010001.7149    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.479710002.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.193310001.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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10004.338310002.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.624710000.8899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.050410002.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.479710001.3024    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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 14  7  1  6  0  0  0
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 16  6  1  6  0  0  0
 13 17  1  0  0  0  0
 17  9  1  1  0  0  0
 22 23  1  0  0  0  0
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 17 23  1  0  0  0  0
 23  8  1  6  0  0  0
 14 22  1  0  0  0  0
 22  2  1  1  0  0  0
M  END

HMDB0001457
     RDKit          3D
5beta-Cholestane-3alpha,7alpha,12alpha-triol
 78 81  0  0  0  0  0  0  0  0999 V2000
    4.9153   -1.9723    0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9859   -1.2865   -0.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3207    0.4924   -0.9910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0066    1.1967    0.2995 C   0  0  1  0  0  0  0  0  0  0  0  0
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 30 78  1  0
M  END


  Mrv1652308121918502D          

 35 38  0  0  0  0            999 V2000
 9999.9783 9998.1488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.976210001.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 9999.264310001.8801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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10001.479710001.3024    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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 10  5  1  1  0  0  0
 14  7  1  6  0  0  0
 16 10  1  0  0  0  0
 16  6  1  6  0  0  0
 13 17  1  0  0  0  0
 17  9  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 27  1  0  0  0  0
 26 35  1  6  0  0  0
 27 28  1  0  0  0  0
 27 34  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 26 22  1  0  0  0  0
 26 25  1  0  0  0  0
 17 23  1  0  0  0  0
 23  8  1  6  0  0  0
 14 22  1  0  0  0  0
 22  2  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0001457

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H48O3/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/h16-25,28-30H,6-15H2,1-5H3/t17-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
RIVQQZVHIVNQFH-XJZYBRFWSA-N

> <FORMULA>
C27H48O3

> <MOLECULAR_WEIGHT>
420.6682

> <EXACT_MASS>
420.360345402

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
52.39617308315909

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol

> <ALOGPS_LOGP>
4.78

> <JCHEM_LOGP>
4.978892648000002

> <ALOGPS_LOGS>
-4.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.2963399055959

> <JCHEM_PKA_STRONGEST_BASIC>
-0.1594347148409706

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
122.87449999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.34e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001457
     RDKit          3D
5beta-Cholestane-3alpha,7alpha,12alpha-triol
 78 81  0  0  0  0  0  0  0  0999 V2000
    4.9153   -1.9723    0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9859   -1.2865   -0.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3330   -2.0156   -1.8310 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8471    0.1838   -0.7718 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6853    0.6576   -1.5230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3207    0.4924   -0.9910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0066    1.1967    0.2995 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1853    2.6725    0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7852    0.6967    0.9000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5214    1.4398    2.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0602    1.3455    2.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4103    0.3926    1.4734 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8707    0.4257    1.1881 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2694   -0.1127   -0.1345 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3288    0.2235   -1.2540 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0750   -0.1910   -0.7708 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1371   -1.4517   -0.1593 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4650    0.7906    0.2664 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0442    2.2028   -0.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6948    0.2636   -0.3917 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9029    1.7626   -0.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1685   -0.1338   -1.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4958   -1.5720   -1.9188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5384   -1.9803   -0.8721 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9299   -3.2747   -1.1085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8046   -1.8340    0.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5675   -0.3631    0.6668 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0476   -0.1588    2.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5961   -0.4613    2.2192 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3388   -1.8007    2.0031 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3705   -2.7364    0.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3453   -1.3074    0.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1925   -2.5104   -0.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9399   -1.4034    0.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0076   -1.3558   -2.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4224   -2.2449   -2.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8417   -2.9497   -1.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7688    0.4724   -1.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0259    0.6770    0.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6842    0.0530   -2.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8313    1.7016   -1.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9735   -0.5528   -0.9336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6357    0.9914   -1.7511 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8581    0.9354    1.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3183    3.2219    1.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5127    3.1374   -0.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2142    2.7874   -0.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9157   -0.3727    1.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8255    2.4980    2.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1352    0.9921    3.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4693    2.3086    2.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0721    0.8576    3.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1054   -0.6416    1.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2299    1.4461    1.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2678   -1.2463   -0.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3660    1.2443   -1.6192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5447   -0.4616   -2.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7349   -0.3833   -1.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6609   -2.0017   -0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0454    2.3609    0.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2639    2.4776   -1.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5124    2.8978    0.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9044    2.0374   -0.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9672    2.1576    0.7075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1829    2.3209   -0.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4234    0.1837   -2.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0997    0.4684   -1.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6014   -2.2118   -1.8581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9665   -1.7173   -2.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3573   -1.2400   -0.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8522   -3.2314   -1.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4908   -2.1739    1.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8879   -2.4359    0.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5569    0.1381    0.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1974    0.9160    2.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6632   -0.7638    2.7439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3002   -0.1478    3.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5679   -2.1331    2.5241 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  6
 14 20  1  0
 20 21  1  6
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  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  1
 10 49  1  0
 10 50  1  0
 11 51  1  0
 11 52  1  0
 12 53  1  1
 13 54  1  6
 14 55  1  1
 15 56  1  0
 15 57  1  0
 16 58  1  6
 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
 22 67  1  0
 23 68  1  0
 23 69  1  0
 24 70  1  1
 25 71  1  0
 26 72  1  0
 26 73  1  0
 27 74  1  1
 28 75  1  0
 28 76  1  0
 29 77  1  1
 30 78  1  0
M  END

HEADER    PROTEIN                                 12-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-AUG-19         0                                  
HETATM    1  O   UNK     0    8666.6268663.211   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8666.6228669.399   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8658.6418663.211   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0    8662.6358662.444   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0    8662.6358667.071   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0    8663.9648664.769   0.000  0.00  0.00           H+0
HETATM    7  O   UNK     0    8665.2938670.176   0.000  0.00  0.00           O+0
HETATM    8  H   UNK     0    8666.6228664.769   0.000  0.00  0.00           H+0
HETATM    9  H   UNK     0    8665.2938667.071   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0    8662.6328665.528   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8662.6328663.988   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8663.9658663.218   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.2998663.988   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8665.2948668.622   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.9618667.852   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8663.9618666.312   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8665.2948665.542   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8661.3058666.298   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8659.9718665.528   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8659.9718663.988   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8661.3058663.218   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8666.6288667.852   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8666.6288666.312   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8668.0938665.836   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8668.9988667.082   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8668.0938668.328   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8668.0938669.868   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8669.4298670.638   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8670.7618669.868   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8672.0978670.638   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8673.4338669.868   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8674.7658670.638   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8673.4338668.328   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0    8666.7618670.638   0.000  0.00  0.00           C+0
HETATM   35  H   UNK     0    8669.4298669.098   0.000  0.00  0.00           H+0
CONECT    1   13                                                            
CONECT    2   22                                                            
CONECT    3   20                                                            
CONECT    4   11                                                            
CONECT    5   10                                                            
CONECT    6   16                                                            
CONECT    7   14                                                            
CONECT    8   23                                                            
CONECT    9   17                                                            
CONECT   10   11   18    5   16                                             
CONECT   11   10   12   21    4                                             
CONECT   12   11   13                                                       
CONECT   13   12    1   17                                                  
CONECT   14   15    7   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   10    6                                             
CONECT   17   16   13    9   23                                             
CONECT   18   19   10                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21    3                                                  
CONECT   21   20   11                                                       
CONECT   22   23   26   14    2                                             
CONECT   23   22   24   17    8                                             
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   27   35   22   25                                             
CONECT   27   26   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   27                                                            
CONECT   35   26                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

COMPND    HMDB0001457
HETATM    1  C1  UNL     1       4.915  -1.972   0.220  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.986  -1.286  -0.531  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.333  -2.016  -1.831  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.847   0.184  -0.772  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.685   0.658  -1.523  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.321   0.492  -0.991  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.007   1.197   0.300  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.185   2.673   0.098  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.785   0.697   0.900  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.521   1.440   2.230  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.060   1.346   2.505  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.410   0.393   1.473  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.871   0.426   1.188  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.269  -0.113  -0.135  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.329   0.224  -1.254  1.00  0.00           C  
HETATM   16  C16 UNL     1       0.075  -0.191  -0.771  1.00  0.00           C  
HETATM   17  O1  UNL     1      -0.137  -1.452  -0.159  1.00  0.00           O  
HETATM   18  C17 UNL     1       0.465   0.791   0.266  1.00  0.00           C  
HETATM   19  C18 UNL     1       0.044   2.203  -0.078  1.00  0.00           C  
HETATM   20  C19 UNL     1      -3.695   0.264  -0.392  1.00  0.00           C  
HETATM   21  C20 UNL     1      -3.903   1.763  -0.312  1.00  0.00           C  
HETATM   22  C21 UNL     1      -4.169  -0.134  -1.765  1.00  0.00           C  
HETATM   23  C22 UNL     1      -4.496  -1.572  -1.919  1.00  0.00           C  
HETATM   24  C23 UNL     1      -5.538  -1.980  -0.872  1.00  0.00           C  
HETATM   25  O2  UNL     1      -5.930  -3.275  -1.108  1.00  0.00           O  
HETATM   26  C24 UNL     1      -4.805  -1.834   0.468  1.00  0.00           C  
HETATM   27  C25 UNL     1      -4.567  -0.363   0.667  1.00  0.00           C  
HETATM   28  C26 UNL     1      -4.048  -0.159   2.055  1.00  0.00           C  
HETATM   29  C27 UNL     1      -2.596  -0.461   2.219  1.00  0.00           C  
HETATM   30  O3  UNL     1      -2.339  -1.801   2.003  1.00  0.00           O  
HETATM   31  H1  UNL     1       5.371  -2.736   0.917  1.00  0.00           H  
HETATM   32  H2  UNL     1       4.345  -1.307   0.872  1.00  0.00           H  
HETATM   33  H3  UNL     1       4.193  -2.510  -0.456  1.00  0.00           H  
HETATM   34  H4  UNL     1       6.940  -1.403   0.084  1.00  0.00           H  
HETATM   35  H5  UNL     1       7.008  -1.356  -2.392  1.00  0.00           H  
HETATM   36  H6  UNL     1       5.422  -2.245  -2.420  1.00  0.00           H  
HETATM   37  H7  UNL     1       6.842  -2.950  -1.554  1.00  0.00           H  
HETATM   38  H8  UNL     1       6.769   0.472  -1.371  1.00  0.00           H  
HETATM   39  H9  UNL     1       6.026   0.677   0.207  1.00  0.00           H  
HETATM   40  H10 UNL     1       4.684   0.053  -2.497  1.00  0.00           H  
HETATM   41  H11 UNL     1       4.831   1.702  -1.935  1.00  0.00           H  
HETATM   42  H12 UNL     1       2.974  -0.553  -0.934  1.00  0.00           H  
HETATM   43  H13 UNL     1       2.636   0.991  -1.751  1.00  0.00           H  
HETATM   44  H14 UNL     1       3.858   0.935   1.002  1.00  0.00           H  
HETATM   45  H15 UNL     1       3.318   3.222   1.058  1.00  0.00           H  
HETATM   46  H16 UNL     1       2.513   3.137  -0.616  1.00  0.00           H  
HETATM   47  H17 UNL     1       4.214   2.787  -0.370  1.00  0.00           H  
HETATM   48  H18 UNL     1       1.916  -0.373   1.245  1.00  0.00           H  
HETATM   49  H19 UNL     1       1.826   2.498   2.155  1.00  0.00           H  
HETATM   50  H20 UNL     1       2.135   0.992   3.036  1.00  0.00           H  
HETATM   51  H21 UNL     1      -0.469   2.309   2.520  1.00  0.00           H  
HETATM   52  H22 UNL     1      -0.072   0.858   3.509  1.00  0.00           H  
HETATM   53  H23 UNL     1      -0.105  -0.642   1.768  1.00  0.00           H  
HETATM   54  H24 UNL     1      -2.230   1.446   1.427  1.00  0.00           H  
HETATM   55  H25 UNL     1      -2.268  -1.246  -0.091  1.00  0.00           H  
HETATM   56  H26 UNL     1      -1.366   1.244  -1.619  1.00  0.00           H  
HETATM   57  H27 UNL     1      -1.545  -0.462  -2.103  1.00  0.00           H  
HETATM   58  H28 UNL     1       0.735  -0.383  -1.598  1.00  0.00           H  
HETATM   59  H29 UNL     1       0.661  -2.002  -0.244  1.00  0.00           H  
HETATM   60  H30 UNL     1      -1.045   2.361   0.055  1.00  0.00           H  
HETATM   61  H31 UNL     1       0.264   2.478  -1.127  1.00  0.00           H  
HETATM   62  H32 UNL     1       0.512   2.898   0.663  1.00  0.00           H  
HETATM   63  H33 UNL     1      -4.904   2.037  -0.773  1.00  0.00           H  
HETATM   64  H34 UNL     1      -3.967   2.158   0.707  1.00  0.00           H  
HETATM   65  H35 UNL     1      -3.183   2.321  -0.975  1.00  0.00           H  
HETATM   66  H36 UNL     1      -3.423   0.184  -2.502  1.00  0.00           H  
HETATM   67  H37 UNL     1      -5.100   0.468  -1.965  1.00  0.00           H  
HETATM   68  H38 UNL     1      -3.601  -2.212  -1.858  1.00  0.00           H  
HETATM   69  H39 UNL     1      -4.967  -1.717  -2.908  1.00  0.00           H  
HETATM   70  H40 UNL     1      -6.357  -1.240  -0.930  1.00  0.00           H  
HETATM   71  H41 UNL     1      -6.852  -3.231  -1.513  1.00  0.00           H  
HETATM   72  H42 UNL     1      -5.491  -2.174   1.246  1.00  0.00           H  
HETATM   73  H43 UNL     1      -3.888  -2.436   0.385  1.00  0.00           H  
HETATM   74  H44 UNL     1      -5.557   0.138   0.603  1.00  0.00           H  
HETATM   75  H45 UNL     1      -4.197   0.916   2.353  1.00  0.00           H  
HETATM   76  H46 UNL     1      -4.663  -0.764   2.744  1.00  0.00           H  
HETATM   77  H47 UNL     1      -2.300  -0.148   3.244  1.00  0.00           H  
HETATM   78  H48 UNL     1      -1.568  -2.133   2.524  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   66   67
CONECT   23   24   68   69
CONECT   24   25   26   70
CONECT   25   71
CONECT   26   27   72   73
CONECT   27   28   74
CONECT   28   29   75   76
CONECT   29   30   77
CONECT   30   78
END

HMDB0001457
     RDKit          3D
5beta-Cholestane-3alpha,7alpha,12alpha-triol
 78 81  0  0  0  0  0  0  0  0999 V2000
    4.9153   -1.9723    0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9859   -1.2865   -0.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3330   -2.0156   -1.8310 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8471    0.1838   -0.7718 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6853    0.6576   -1.5230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3207    0.4924   -0.9910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0066    1.1967    0.2995 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1853    2.6725    0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7852    0.6967    0.9000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5214    1.4398    2.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0602    1.3455    2.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4103    0.3926    1.4734 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8707    0.4257    1.1881 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2694   -0.1127   -0.1345 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3288    0.2235   -1.2540 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0750   -0.1910   -0.7708 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1371   -1.4517   -0.1593 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4650    0.7906    0.2664 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0442    2.2028   -0.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6948    0.2636   -0.3917 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9029    1.7626   -0.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1685   -0.1338   -1.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4958   -1.5720   -1.9188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5384   -1.9803   -0.8721 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9299   -3.2747   -1.1085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8046   -1.8340    0.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5675   -0.3631    0.6668 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0476   -0.1588    2.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5961   -0.4613    2.2192 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3388   -1.8007    2.0031 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3705   -2.7364    0.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3453   -1.3074    0.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1925   -2.5104   -0.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9399   -1.4034    0.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0076   -1.3558   -2.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4224   -2.2449   -2.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8417   -2.9497   -1.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7688    0.4724   -1.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0259    0.6770    0.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6842    0.0530   -2.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8313    1.7016   -1.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9735   -0.5528   -0.9336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6357    0.9914   -1.7511 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8581    0.9354    1.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3183    3.2219    1.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5127    3.1374   -0.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2142    2.7874   -0.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9157   -0.3727    1.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8255    2.4980    2.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1352    0.9921    3.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4693    2.3086    2.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0721    0.8576    3.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1054   -0.6416    1.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2299    1.4461    1.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2678   -1.2463   -0.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3660    1.2443   -1.6192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5447   -0.4616   -2.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7349   -0.3833   -1.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6609   -2.0017   -0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0454    2.3609    0.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2639    2.4776   -1.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5124    2.8978    0.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9044    2.0374   -0.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9672    2.1576    0.7075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1829    2.3209   -0.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4234    0.1837   -2.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0997    0.4684   -1.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6014   -2.2118   -1.8581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9665   -1.7173   -2.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3573   -1.2400   -0.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8522   -3.2314   -1.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4908   -2.1739    1.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8879   -2.4359    0.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5569    0.1381    0.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1974    0.9160    2.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6632   -0.7638    2.7439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3002   -0.1478    3.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5679   -2.1331    2.5241 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  6
 14 20  1  0
 20 21  1  6
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  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  1
 10 49  1  0
 10 50  1  0
 11 51  1  0
 11 52  1  0
 12 53  1  1
 13 54  1  6
 14 55  1  1
 15 56  1  0
 15 57  1  0
 16 58  1  6
 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
 22 67  1  0
 23 68  1  0
 23 69  1  0
 24 70  1  1
 25 71  1  0
 26 72  1  0
 26 73  1  0
 27 74  1  1
 28 75  1  0
 28 76  1  0
 29 77  1  1
 30 78  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestane	ChEBI
3alpha,7alpha,12alpha-Trihydroxycoprostane	ChEBI
3a,7a,12a-Trihydroxy-5b-cholestane	Generator
3Α,7α,12α-trihydroxy-5β-cholestane	Generator
3a,7a,12a-Trihydroxycoprostane	Generator
3Α,7α,12α-trihydroxycoprostane	Generator
5b-Cholestane-3a,7a,12a-triol	Generator
5Β-cholestane-3α,7α,12α-triol	Generator
5-beta-Cholestane-3-alpha,7-alpha,12-alpha-triol	HMDB
3,7,12-Trihydroxycholestane	MeSH, HMDB
3,7,12-Trihydroxycoprostane	MeSH, HMDB
3,7,12-Trihydroxycoprostane, (3alpha,5alpha,7alpha,12alpha)-isomer	MeSH, HMDB
3,7,12-Trihydroxycoprostane, (3beta,5alpha,7alpha,12alpha)-isomer	MeSH, HMDB
3,7,12-Trihydroxycoprostane, (3beta,5beta,7alpha,12alpha)-isomer	MeSH, HMDB
3alpha, 7alpha,12alpha-Trihydroxy-5beta-cholestane	MeSH, HMDB
5 beta-Cholestane-3 alpha,7 alpha,12 alpha-triol	MeSH, HMDB
5beta-Cholestane-3alpha,7alpha,12alpha-triol	MeSH, KEGG
Chtriol	MeSH, HMDB
Trihydroxycoprostane	MeSH, HMDB
(3alpha,5beta,7alpha,12alpha)-Cholestane-3,7,12-triol	HMDB
(3α,5β,7α,12α)-Cholestane-3,7,12-triol	HMDB
5beta-Cholestan-3alpha,7alpha,12alpha-triol	HMDB
5β-Cholestan-3α,7α,12α-triol	HMDB

Chemical Formula

C₂₇H₄₈O₃

Average Molecular Weight

420.6682

Monoisotopic Molecular Weight

420.360345402

IUPAC Name

(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol

Traditional Name

(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol

CAS Registry Number

547-96-6

SMILES

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

InChI Identifier

InChI=1S/C27H48O3/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/h16-25,28-30H,6-15H2,1-5H3/t17-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1

InChI Key

RIVQQZVHIVNQFH-XJZYBRFWSA-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
Cholesterol
7-hydroxysteroid
3-alpha-hydroxysteroid
Hydroxysteroid
12-hydroxysteroid
3-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3alpha-hydroxy steroid (CHEBI:16496 )
7alpha-hydroxy steroid (CHEBI:16496 )
12alpha-hydroxy steroid (CHEBI:16496 )
C27 bile acids, alcohols, and derivatives (C05454 )
C27 bile acids, alcohols, and derivatives (LMST04030035 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0053 g/L	ALOGPS
logP	4.78	ALOGPS
logP	4.98	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	-0.16	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	122.87 m³·mol⁻¹	ChemAxon
Polarizability	52.4 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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]+	205.726	31661259
DarkChem	[M-H]-	202.878	31661259
AllCCS	[M+H]+	209.593	32859911
AllCCS	[M-H]-	204.456	32859911
DeepCCS	[M-2H]-	242.971	30932474
DeepCCS	[M+Na]+	216.989	30932474
AllCCS	[M+H]+	209.6	32859911
AllCCS	[M+H-H2O]+	207.7	32859911
AllCCS	[M+NH4]+	211.4	32859911
AllCCS	[M+Na]+	211.9	32859911
AllCCS	[M-H]-	204.5	32859911
AllCCS	[M+Na-2H]-	206.6	32859911
AllCCS	[M+HCOO]-	209.1	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.	7.6 minutes	32390414
Predicted by Siyang on May 30, 2022	18.1972 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.43 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	54.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3363.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	301.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	243.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	177.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	538.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	923.0 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	793.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	92.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1404.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	656.3 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	2013.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	460.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	538.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	170.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	315.5 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	9.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5beta-Cholestane-3alpha,7alpha,12alpha-triol	[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)C	3122.0	Standard polar	33892256
5beta-Cholestane-3alpha,7alpha,12alpha-triol	[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)C	3335.8	Standard non polar	33892256
5beta-Cholestane-3alpha,7alpha,12alpha-triol	[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)C	3633.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5beta-Cholestane-3alpha,7alpha,12alpha-triol,1TMS,isomer #1	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)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3231.6	Semi standard non polar	33892256
5beta-Cholestane-3alpha,7alpha,12alpha-triol,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)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3291.0	Semi standard non polar	33892256
5beta-Cholestane-3alpha,7alpha,12alpha-triol,1TMS,isomer #3	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)CC[C@@H](O)C[C@H]1C[C@H]3O	3292.1	Semi standard non polar	33892256
5beta-Cholestane-3alpha,7alpha,12alpha-triol,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)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3242.8	Semi standard non polar	33892256
5beta-Cholestane-3alpha,7alpha,12alpha-triol,2TMS,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)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3222.0	Semi standard non polar	33892256
5beta-Cholestane-3alpha,7alpha,12alpha-triol,2TMS,isomer #3	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)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3242.3	Semi standard non polar	33892256
5beta-Cholestane-3alpha,7alpha,12alpha-triol,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)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3252.2	Semi standard non polar	33892256
5beta-Cholestane-3alpha,7alpha,12alpha-triol,1TBDMS,isomer #1	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)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3465.3	Semi standard non polar	33892256
5beta-Cholestane-3alpha,7alpha,12alpha-triol,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)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	3528.7	Semi standard non polar	33892256
5beta-Cholestane-3alpha,7alpha,12alpha-triol,1TBDMS,isomer #3	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)CC[C@@H](O)C[C@H]1C[C@H]3O	3531.8	Semi standard non polar	33892256
5beta-Cholestane-3alpha,7alpha,12alpha-triol,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)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3701.5	Semi standard non polar	33892256
5beta-Cholestane-3alpha,7alpha,12alpha-triol,2TBDMS,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)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3668.3	Semi standard non polar	33892256
5beta-Cholestane-3alpha,7alpha,12alpha-triol,2TBDMS,isomer #3	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)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	3706.5	Semi standard non polar	33892256
5beta-Cholestane-3alpha,7alpha,12alpha-triol,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)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3930.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kkc-0349300000-7324287f0b234066bd64	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol GC-MS (3 TMS) - 70eV, Positive	splash10-00di-3210079000-e1f273aa178918c83174	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol 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 - 5beta-Cholestane-3alpha,7alpha,12alpha-triol 10V, Positive-QTOF	splash10-0udr-0007900000-f9ed4dff04df44d2af49	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol 20V, Positive-QTOF	splash10-0f79-2209400000-84e3ed6130fdfe17578f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol 40V, Positive-QTOF	splash10-00di-5209000000-1166d5a4d66dea526dfc	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol 10V, Negative-QTOF	splash10-014i-0001900000-766e9dee4a7aba343c98	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol 20V, Negative-QTOF	splash10-0uxr-0001900000-90680fd53f8266be1ace	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol 40V, Negative-QTOF	splash10-0f79-2209400000-a1dd0a941d753b0d75e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol 10V, Negative-QTOF	splash10-014i-0000900000-722417cd9cab9945ab4a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol 20V, Negative-QTOF	splash10-014i-0000900000-722417cd9cab9945ab4a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol 40V, Negative-QTOF	splash10-014i-0010900000-aeb99a2e383b60fbc744	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol 10V, Positive-QTOF	splash10-00di-0001900000-f143819ead264249729e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol 20V, Positive-QTOF	splash10-0abi-9122200000-2f2c0b60a02fc711aa0c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol 40V, Positive-QTOF	splash10-0a4i-9721000000-6687d50233adfbaf7604	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

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

FDB022635

KNApSAcK ID

Not Available

Chemspider ID

141053

KEGG Compound ID

C05454

BioCyc ID

Not Available

BiGG ID

45846

Wikipedia Link

Not Available

METLIN ID

6254

PubChem Compound

160520

PDB ID

Not Available

ChEBI ID

16496

Food Biomarker Ontology

Not Available

VMH ID

XOLTRIOL

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Shimazu K, Kuwabara M, Yoshii M, Kihira K, Takeuchi H, Nakano I, Ozawa S, Onuki M, Hatta Y, Hoshita T: Bile alcohol profiles in bile, urine, and feces of a patient with cerebrotendinous xanthomatosis. J Biochem. 1986 Feb;99(2):477-83. [PubMed:3700361 ]
Oftebro H, Bjorkhem I, Skrede S, Schreiner A, Pederson JI: Cerebrotendinous xanthomatosis: a defect in mitochondrial 26-hydroxylation required for normal biosynthesis of cholic acid. J Clin Invest. 1980 Jun;65(6):1418-30. [PubMed:7410549 ]
Axen E, Postlind H, Sjoberg H, Wikvall K: Liver mitochondrial cytochrome P450 CYP27 and recombinant-expressed human CYP27 catalyze 1 alpha-hydroxylation of 25-hydroxyvitamin D3. Proc Natl Acad Sci U S A. 1994 Oct 11;91(21):10014-8. [PubMed:7937829 ]

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

5beta-Cholestane-3alpha,7alpha,12alpha-triol + NAD → 7a,12a-Dihydroxy-5b-cholestan-3-one + NADH + Hydrogen Ion	details
5beta-Cholestane-3alpha,7alpha,12alpha-triol + NADP → 7a,12a-Dihydroxy-5b-cholestan-3-one + NADPH + Hydrogen Ion	details

Enzyme Details

2. Sterol 26-hydroxylase, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the first step in the oxidation of the side chain of sterol intermediates; the 27-hydroxylation of 5-beta-cholestane-3-alpha,7-alpha,12-alpha-triol. Has also a vitamin D3-25-hydroxylase activity.
Gene Name:: CYP27A1
Uniprot ID:: Q02318
Molecular weight:: 60234.28

Reactions

5beta-Cholestane-3alpha,7alpha,12alpha-triol + NADPH + Oxygen → Coprocholic acid + NADP + Water	details
5beta-Cholestane-3alpha,7alpha,12alpha-triol + Oxygen + NADPH → 27-Deoxy-5b-cyprinol + NADP + Water	details

Showing metabocard for 5beta-Cholestane-3alpha,7alpha,12alpha-triol (HMDB0001457)

MOL for HMDB0001457 (5beta-Cholestane-3alpha,7alpha,12alpha-triol)

3D MOL for HMDB0001457 (5beta-Cholestane-3alpha,7alpha,12alpha-triol)

3D SDF for HMDB0001457 (5beta-Cholestane-3alpha,7alpha,12alpha-triol)

3D-SDF for HMDB0001457 (5beta-Cholestane-3alpha,7alpha,12alpha-triol)

PDB for HMDB0001457 (5beta-Cholestane-3alpha,7alpha,12alpha-triol)

3D PDB for HMDB0001457 (5beta-Cholestane-3alpha,7alpha,12alpha-triol)

SMILES for HMDB0001457 (5beta-Cholestane-3alpha,7alpha,12alpha-triol)

INCHI for HMDB0001457 (5beta-Cholestane-3alpha,7alpha,12alpha-triol)

Structure for HMDB0001457 (5beta-Cholestane-3alpha,7alpha,12alpha-triol)

3D Structure for HMDB0001457 (5beta-Cholestane-3alpha,7alpha,12alpha-triol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions