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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2009-04-06 16:20:19 UTC

Update Date

2022-03-07 02:51:21 UTC

HMDB ID

HMDB0012166

Secondary Accession Numbers

HMDB12166

Metabolite Identification

Common Name

4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol

Description

4alpha-carboxy-5alpha-cholesta-8-en-3beta-ol is a 3-beta-hydroxysterol that is an intermediate in cholesterol biosynthesis II (via 24,25-dihydrolanosterol). It is a substrate for NAD(P)-dependent steroid dehydrogenase (H105E3) and it can be generated from the enzymatic carboxylation of 5alpha-cholesta-8-en-3-one. It is also a substrate for C-4 methyl sterol oxidase (SC4MOL) and can be generated from the enzymatic oxidation of 4alpha-formyl-5alpha-cholesta-8-en-3beta-ol. The sequence of reactions and the types of intermediates in cholesterol biosynthesis may vary. Alternate routes exist because reduction of the carbon 24,25 double bond on the hydrocarbon side chain of the sterol ring structure by sterol delta24-reductase can occur at multiple points in the pathway, giving rise to different intermediates. These intermediates, with or without a double bond in the hydrocarbon side chain, can serve as substrates for the other enzymes in the pathway.

Structure

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


  Mrv0541 02241203482D          

 31 34  0  0  1  0            999 V2000
   16.6729  -10.6821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6109  -11.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5959   -9.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2528  -10.1978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9650  -11.4225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5069  -10.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3139  -10.2405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9549   -9.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3939  -13.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3779  -11.4225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8930  -12.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6794  -13.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6794  -11.0101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5360  -12.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3939  -10.5975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2505  -11.8350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8659  -10.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1479   -9.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3939  -12.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8930  -10.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1083  -11.8350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6794  -11.8350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9650  -13.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5360  -13.0725    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2505  -14.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1083  -11.0101    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.9650  -12.2475    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2505  -13.4850    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8216  -13.4850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9650  -14.7225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5360  -14.7225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0  0  0  0
  2 17  1  0  0  0  0
  3 18  1  0  0  0  0
 26  4  1  1  0  0  0
 27  5  1  1  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7 17  1  0  0  0  0
  8 18  1  0  0  0  0
  9 19  1  0  0  0  0
  9 12  1  0  0  0  0
 10 20  1  0  0  0  0
 10 11  1  0  0  0  0
 11 21  1  0  0  0  0
 12 23  1  0  0  0  0
 13 22  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 24  1  0  0  0  0
 15 26  1  0  0  0  0
 16 27  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  2  0  0  0  0
 20 26  1  0  0  0  0
 21 26  1  0  0  0  0
 22 27  1  0  0  0  0
 23 27  1  0  0  0  0
 23 28  1  0  0  0  0
 24 29  1  1  0  0  0
 24 28  1  0  0  0  0
 28 25  1  6  0  0  0
 25 30  1  0  0  0  0
 25 31  2  0  0  0  0
M  END

HMDB0012166
     RDKit          3D
4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol
 77 80  0  0  0  0  0  0  0  0999 V2000
   -7.8633   -0.5969    0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4758   -0.1052   -0.7026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9658    1.2930   -0.8913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9596   -0.2017   -0.9277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2116    0.5993    0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7265    0.6792   -0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9464   -0.5906    0.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2260   -1.9570   -0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1745    0.6371    1.5835 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1522    1.3225    0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5679    0.3389   -0.2243 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0195    1.1878   -1.3780 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7018    0.1467    1.0300 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7893    0.8969    2.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1931   -1.2329    1.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2249   -1.7451    0.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2915   -0.7714   -0.0132 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4947   -1.0265    0.6844 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9495    0.6608    0.1811 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7429    1.4894   -0.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5454    0.9213   -1.5374 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6059    2.8716   -0.7827 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4764    0.9452    0.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0380    0.8354   -1.3718 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8860   -0.0507   -1.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.9592   -0.7516   -1.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9036    1.3502   -1.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2143    1.7527    0.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.4438    0.2879    1.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6268    1.6670    0.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5378    1.2034   -1.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3428    1.3513    0.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4313   -1.0934    1.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7228   -2.4732   -0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6153   -2.0971    1.6527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7332   -2.6479    0.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0640   -2.7089   -1.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1424   -2.3364    0.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3795   -0.6650   -1.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6753    2.0803    0.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0534    1.4556   -1.9297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5693    0.6364   -2.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4135    2.1697   -1.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5683    1.9575    2.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8247    0.7901    2.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5605   -1.3904    2.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3067   -1.9302    1.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3104    0.9508    1.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4093    3.2974   -1.6810 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3609    2.0326    0.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9128    0.4738   -1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8078    1.8394   -1.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3251    0.3156   -2.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2069   -1.0875   -1.9634 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
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 11 12  1  0
 12 13  1  0
 13 14  2  0
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 17 18  1  6
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 17  9  1  0
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 17 12  1  0
 31 13  1  0
  1 32  1  0
  1 33  1  0
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  2 35  1  0
  3 36  1  0
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 30 74  1  0
 30 75  1  0
 31 76  1  0
 31 77  1  0
M  END


  Mrv0541 02241203482D          

 31 34  0  0  1  0            999 V2000
   16.6729  -10.6821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6109  -11.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5959   -9.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2528  -10.1978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9650  -11.4225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5069  -10.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3139  -10.2405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9549   -9.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3939  -13.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3779  -11.4225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8930  -12.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6794  -13.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.1083  -11.8350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.1083  -11.0101    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    9.2505  -13.4850    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8216  -13.4850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  2 17  1  0  0  0  0
  3 18  1  0  0  0  0
 26  4  1  1  0  0  0
 27  5  1  1  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7 17  1  0  0  0  0
  8 18  1  0  0  0  0
  9 19  1  0  0  0  0
  9 12  1  0  0  0  0
 10 20  1  0  0  0  0
 10 11  1  0  0  0  0
 11 21  1  0  0  0  0
 12 23  1  0  0  0  0
 13 22  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 24  1  0  0  0  0
 15 26  1  0  0  0  0
 16 27  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  2  0  0  0  0
 20 26  1  0  0  0  0
 21 26  1  0  0  0  0
 22 27  1  0  0  0  0
 23 27  1  0  0  0  0
 23 28  1  0  0  0  0
 24 29  1  1  0  0  0
 24 28  1  0  0  0  0
 28 25  1  6  0  0  0
 25 30  1  0  0  0  0
 25 31  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012166

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@H](C1CC3)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H46O3/c1-17(2)7-6-8-18(3)20-11-12-21-19-9-10-23-25(26(30)31)24(29)14-16-28(23,5)22(19)13-15-27(20,21)4/h17-18,20-21,23-25,29H,6-16H2,1-5H3,(H,30,31)/t18?,20?,21?,23?,24-,25-,27+,28+/m0/s1

> <INCHI_KEY>
RODBXVVNKJCWQR-KLZNZPMLSA-N

> <FORMULA>
C28H46O3

> <MOLECULAR_WEIGHT>
430.663

> <EXACT_MASS>
430.344695338

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
53.15866025503658

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5S,6S,15R)-5-hydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carboxylic acid

> <ALOGPS_LOGP>
6.20

> <JCHEM_LOGP>
6.447883179333331

> <ALOGPS_LOGS>
-5.16

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.95987356799279

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.599002345072687

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9369127811123397

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
126.43579999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5S,6S,15R)-5-hydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012166
     RDKit          3D
4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol
 77 80  0  0  0  0  0  0  0  0999 V2000
   -7.8633   -0.5969    0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4758   -0.1052   -0.7026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9658    1.2930   -0.8913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9596   -0.2017   -0.9277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2116    0.5993    0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7265    0.6792   -0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9464   -0.5906    0.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1767   -1.5752   -1.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5283   -0.4494    0.5240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9629   -1.8781    0.6133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2260   -1.9570   -0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4998   -0.5744   -0.7963 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8768   -0.1338   -0.5739 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2575    0.2044    0.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1745    0.6371    1.5835 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1522    1.3225    0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5679    0.3389   -0.2243 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0195    1.1878   -1.3780 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7018    0.1467    1.0300 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7893    0.8969    2.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1931   -1.2329    1.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2249   -1.7451    0.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2915   -0.7714   -0.0132 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4947   -1.0265    0.6844 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9495    0.6608    0.1811 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7429    1.4894   -0.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5454    0.9213   -1.5374 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6059    2.8716   -0.7827 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4764    0.9452    0.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0380    0.8354   -1.3718 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8860   -0.0507   -1.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8785   -1.0552    0.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1946   -1.3815    1.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9667    0.2668    1.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9592   -0.7516   -1.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9036    1.3502   -1.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2143    1.7527    0.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1464    1.9092   -1.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7664    0.0515   -1.9572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7092   -1.2963   -0.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4438    0.2879    1.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6268    1.6670    0.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5378    1.2034   -1.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3428    1.3513    0.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4313   -1.0934    1.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1886   -1.9812   -1.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7323   -1.1481   -1.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7228   -2.4732   -0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5677   -0.0867    1.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6153   -2.0971    1.6527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7332   -2.6479    0.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0640   -2.7089   -1.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1424   -2.3364    0.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3795   -0.6650   -1.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5399    1.4202    2.2881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7650   -0.2155    2.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6116    1.7710    1.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6753    2.0803    0.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0534    1.4556   -1.9297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5693    0.6364   -2.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4135    2.1697   -1.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5683    1.9575    2.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1257    0.3566    3.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8247    0.7901    2.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5605   -1.3904    2.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3067   -1.9302    1.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7403   -2.6134    0.8593 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7959   -2.2260   -0.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5696   -0.9376   -1.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2163   -1.4046    1.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3104    0.9508    1.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4093    3.2974   -1.6810 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3609    2.0326    0.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9128    0.4738   -1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8078    1.8394   -1.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3251    0.3156   -2.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2069   -1.0875   -1.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 14 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 25 29  1  0
 29 30  1  0
 30 31  1  0
 17  9  1  0
 29 19  1  0
 17 12  1  0
 31 13  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  0
  8 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
 10 50  1  0
 10 51  1  0
 11 52  1  0
 11 53  1  0
 12 54  1  0
 15 55  1  0
 15 56  1  0
 16 57  1  0
 16 58  1  0
 18 59  1  0
 18 60  1  0
 18 61  1  0
 20 62  1  0
 20 63  1  0
 20 64  1  0
 21 65  1  0
 21 66  1  0
 22 67  1  0
 22 68  1  0
 23 69  1  6
 24 70  1  0
 25 71  1  1
 28 72  1  0
 29 73  1  0
 30 74  1  0
 30 75  1  0
 31 76  1  0
 31 77  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      31.123 -19.940   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      29.140 -21.725   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.512 -17.467   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.872 -19.036   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.601 -21.322   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.080 -19.436   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.586 -19.116   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.049 -18.291   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.269 -24.402   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.972 -21.322   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.067 -22.568   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.935 -25.172   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.935 -20.552   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.934 -22.862   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.269 -19.782   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.268 -22.092   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.616 -20.260   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.543 -18.612   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.269 -22.862   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.067 -20.076   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      22.602 -22.092   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.935 -22.092   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.601 -24.402   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.934 -24.402   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.268 -26.712   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      22.602 -20.552   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.601 -22.862   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.268 -25.172   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      14.600 -25.172   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      18.601 -27.482   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      15.934 -27.482   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2   17                                                            
CONECT    3   18                                                            
CONECT    4   26                                                            
CONECT    5   27                                                            
CONECT    6    7    8                                                       
CONECT    7    6   17                                                       
CONECT    8    6   18                                                       
CONECT    9   19   12                                                       
CONECT   10   20   11                                                       
CONECT   11   10   21                                                       
CONECT   12    9   23                                                       
CONECT   13   22   15                                                       
CONECT   14   16   24                                                       
CONECT   15   13   26                                                       
CONECT   16   14   27                                                       
CONECT   17    1    2    7                                                  
CONECT   18    3    8   20                                                  
CONECT   19    9   21   22                                                  
CONECT   20   10   18   26                                                  
CONECT   21   11   19   26                                                  
CONECT   22   13   19   27                                                  
CONECT   23   12   27   28                                                  
CONECT   24   14   29   28                                                  
CONECT   25   28   30   31                                                  
CONECT   26    4   15   20   21                                             
CONECT   27    5   16   22   23                                             
CONECT   28   23   24   25                                                  
CONECT   29   24                                                            
CONECT   30   25                                                            
CONECT   31   25                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

COMPND    HMDB0012166
HETATM    1  C1  UNL     1      -7.863  -0.597   0.654  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.476  -0.105  -0.703  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.966   1.293  -0.891  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.960  -0.202  -0.928  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.212   0.599   0.056  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.726   0.679  -0.030  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.946  -0.591   0.078  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.177  -1.575  -1.007  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.528  -0.449   0.524  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.963  -1.878   0.613  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.226  -1.957  -0.267  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.500  -0.574  -0.796  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.877  -0.134  -0.574  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.257   0.204   0.650  1.00  0.00           C  
HETATM   15  C15 UNL     1       1.174   0.637   1.584  1.00  0.00           C  
HETATM   16  C16 UNL     1       0.152   1.322   0.713  1.00  0.00           C  
HETATM   17  C17 UNL     1      -0.568   0.339  -0.224  1.00  0.00           C  
HETATM   18  C18 UNL     1      -1.020   1.188  -1.378  1.00  0.00           C  
HETATM   19  C19 UNL     1       3.702   0.147   1.030  1.00  0.00           C  
HETATM   20  C20 UNL     1       3.789   0.897   2.370  1.00  0.00           C  
HETATM   21  C21 UNL     1       4.193  -1.233   1.281  1.00  0.00           C  
HETATM   22  C22 UNL     1       5.225  -1.745   0.348  1.00  0.00           C  
HETATM   23  C23 UNL     1       6.291  -0.771  -0.013  1.00  0.00           C  
HETATM   24  O1  UNL     1       7.495  -1.026   0.684  1.00  0.00           O  
HETATM   25  C24 UNL     1       5.950   0.661   0.181  1.00  0.00           C  
HETATM   26  C25 UNL     1       6.743   1.489  -0.759  1.00  0.00           C  
HETATM   27  O2  UNL     1       7.545   0.921  -1.537  1.00  0.00           O  
HETATM   28  O3  UNL     1       6.606   2.872  -0.783  1.00  0.00           O  
HETATM   29  C26 UNL     1       4.476   0.945   0.035  1.00  0.00           C  
HETATM   30  C27 UNL     1       4.038   0.835  -1.372  1.00  0.00           C  
HETATM   31  C28 UNL     1       2.886  -0.051  -1.664  1.00  0.00           C  
HETATM   32  H1  UNL     1      -8.879  -1.055   0.583  1.00  0.00           H  
HETATM   33  H2  UNL     1      -7.195  -1.381   1.061  1.00  0.00           H  
HETATM   34  H3  UNL     1      -7.967   0.267   1.341  1.00  0.00           H  
HETATM   35  H4  UNL     1      -7.959  -0.752  -1.463  1.00  0.00           H  
HETATM   36  H5  UNL     1      -8.904   1.350  -1.479  1.00  0.00           H  
HETATM   37  H6  UNL     1      -8.214   1.753   0.103  1.00  0.00           H  
HETATM   38  H7  UNL     1      -7.146   1.909  -1.319  1.00  0.00           H  
HETATM   39  H8  UNL     1      -5.766   0.051  -1.957  1.00  0.00           H  
HETATM   40  H9  UNL     1      -5.709  -1.296  -0.778  1.00  0.00           H  
HETATM   41  H10 UNL     1      -5.444   0.288   1.123  1.00  0.00           H  
HETATM   42  H11 UNL     1      -5.627   1.667   0.053  1.00  0.00           H  
HETATM   43  H12 UNL     1      -3.538   1.203  -1.013  1.00  0.00           H  
HETATM   44  H13 UNL     1      -3.343   1.351   0.803  1.00  0.00           H  
HETATM   45  H14 UNL     1      -3.431  -1.093   1.000  1.00  0.00           H  
HETATM   46  H15 UNL     1      -2.189  -1.981  -1.378  1.00  0.00           H  
HETATM   47  H16 UNL     1      -3.732  -1.148  -1.882  1.00  0.00           H  
HETATM   48  H17 UNL     1      -3.723  -2.473  -0.694  1.00  0.00           H  
HETATM   49  H18 UNL     1      -1.568  -0.087   1.581  1.00  0.00           H  
HETATM   50  H19 UNL     1      -0.615  -2.097   1.653  1.00  0.00           H  
HETATM   51  H20 UNL     1      -1.733  -2.648   0.418  1.00  0.00           H  
HETATM   52  H21 UNL     1       0.064  -2.709  -1.066  1.00  0.00           H  
HETATM   53  H22 UNL     1       1.142  -2.336   0.275  1.00  0.00           H  
HETATM   54  H23 UNL     1       0.380  -0.665  -1.921  1.00  0.00           H  
HETATM   55  H24 UNL     1       1.540   1.420   2.288  1.00  0.00           H  
HETATM   56  H25 UNL     1       0.765  -0.216   2.124  1.00  0.00           H  
HETATM   57  H26 UNL     1      -0.612   1.771   1.356  1.00  0.00           H  
HETATM   58  H27 UNL     1       0.675   2.080   0.079  1.00  0.00           H  
HETATM   59  H28 UNL     1      -0.053   1.456  -1.930  1.00  0.00           H  
HETATM   60  H29 UNL     1      -1.569   0.636  -2.166  1.00  0.00           H  
HETATM   61  H30 UNL     1      -1.413   2.170  -1.112  1.00  0.00           H  
HETATM   62  H31 UNL     1       3.568   1.958   2.258  1.00  0.00           H  
HETATM   63  H32 UNL     1       3.126   0.357   3.073  1.00  0.00           H  
HETATM   64  H33 UNL     1       4.825   0.790   2.787  1.00  0.00           H  
HETATM   65  H34 UNL     1       4.561  -1.390   2.333  1.00  0.00           H  
HETATM   66  H35 UNL     1       3.307  -1.930   1.214  1.00  0.00           H  
HETATM   67  H36 UNL     1       5.740  -2.613   0.859  1.00  0.00           H  
HETATM   68  H37 UNL     1       4.796  -2.226  -0.580  1.00  0.00           H  
HETATM   69  H38 UNL     1       6.570  -0.938  -1.096  1.00  0.00           H  
HETATM   70  H39 UNL     1       7.216  -1.405   1.573  1.00  0.00           H  
HETATM   71  H40 UNL     1       6.310   0.951   1.203  1.00  0.00           H  
HETATM   72  H41 UNL     1       6.409   3.297  -1.681  1.00  0.00           H  
HETATM   73  H42 UNL     1       4.361   2.033   0.329  1.00  0.00           H  
HETATM   74  H43 UNL     1       4.913   0.474  -1.987  1.00  0.00           H  
HETATM   75  H44 UNL     1       3.808   1.839  -1.839  1.00  0.00           H  
HETATM   76  H45 UNL     1       2.325   0.316  -2.575  1.00  0.00           H  
HETATM   77  H46 UNL     1       3.207  -1.088  -1.963  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3    4   35
CONECT    3   36   37   38
CONECT    4    5   39   40
CONECT    5    6   41   42
CONECT    6    7   43   44
CONECT    7    8    9   45
CONECT    8   46   47   48
CONECT    9   10   17   49
CONECT   10   11   50   51
CONECT   11   12   52   53
CONECT   12   13   17   54
CONECT   13   14   14   31
CONECT   14   15   19
CONECT   15   16   55   56
CONECT   16   17   57   58
CONECT   17   18
CONECT   18   59   60   61
CONECT   19   20   21   29
CONECT   20   62   63   64
CONECT   21   22   65   66
CONECT   22   23   67   68
CONECT   23   24   25   69
CONECT   24   70
CONECT   25   26   29   71
CONECT   26   27   27   28
CONECT   28   72
CONECT   29   30   73
CONECT   30   31   74   75
CONECT   31   76   77
END

HMDB0012166
     RDKit          3D
4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol
 77 80  0  0  0  0  0  0  0  0999 V2000
   -7.8633   -0.5969    0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4758   -0.1052   -0.7026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9658    1.2930   -0.8913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9596   -0.2017   -0.9277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2116    0.5993    0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7265    0.6792   -0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9464   -0.5906    0.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1767   -1.5752   -1.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5283   -0.4494    0.5240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9629   -1.8781    0.6133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2260   -1.9570   -0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4998   -0.5744   -0.7963 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8768   -0.1338   -0.5739 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2575    0.2044    0.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1745    0.6371    1.5835 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1522    1.3225    0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5679    0.3389   -0.2243 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0195    1.1878   -1.3780 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7018    0.1467    1.0300 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7893    0.8969    2.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1931   -1.2329    1.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2249   -1.7451    0.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2915   -0.7714   -0.0132 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4947   -1.0265    0.6844 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9495    0.6608    0.1811 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7429    1.4894   -0.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5454    0.9213   -1.5374 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6059    2.8716   -0.7827 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4764    0.9452    0.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0380    0.8354   -1.3718 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8860   -0.0507   -1.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8785   -1.0552    0.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1946   -1.3815    1.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9667    0.2668    1.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9592   -0.7516   -1.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9036    1.3502   -1.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2143    1.7527    0.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1464    1.9092   -1.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7664    0.0515   -1.9572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7092   -1.2963   -0.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4438    0.2879    1.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6268    1.6670    0.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5378    1.2034   -1.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3428    1.3513    0.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4313   -1.0934    1.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1886   -1.9812   -1.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7323   -1.1481   -1.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7228   -2.4732   -0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5677   -0.0867    1.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6153   -2.0971    1.6527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7332   -2.6479    0.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0640   -2.7089   -1.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1424   -2.3364    0.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3795   -0.6650   -1.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5399    1.4202    2.2881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7650   -0.2155    2.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6116    1.7710    1.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6753    2.0803    0.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0534    1.4556   -1.9297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5693    0.6364   -2.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4135    2.1697   -1.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5683    1.9575    2.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1257    0.3566    3.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8247    0.7901    2.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5605   -1.3904    2.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3067   -1.9302    1.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7403   -2.6134    0.8593 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7959   -2.2260   -0.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5696   -0.9376   -1.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2163   -1.4046    1.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3104    0.9508    1.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4093    3.2974   -1.6810 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3609    2.0326    0.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9128    0.4738   -1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8078    1.8394   -1.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3251    0.3156   -2.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2069   -1.0875   -1.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 14 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 25 29  1  0
 29 30  1  0
 30 31  1  0
 17  9  1  0
 29 19  1  0
 17 12  1  0
 31 13  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  0
  8 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
 10 50  1  0
 10 51  1  0
 11 52  1  0
 11 53  1  0
 12 54  1  0
 15 55  1  0
 15 56  1  0
 16 57  1  0
 16 58  1  0
 18 59  1  0
 18 60  1  0
 18 61  1  0
 20 62  1  0
 20 63  1  0
 20 64  1  0
 21 65  1  0
 21 66  1  0
 22 67  1  0
 22 68  1  0
 23 69  1  6
 24 70  1  0
 25 71  1  1
 28 72  1  0
 29 73  1  0
 30 74  1  0
 30 75  1  0
 31 76  1  0
 31 77  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4a-Carboxy-5a-cholesta-8-en-3b-ol	Generator
4Α-carboxy-5α-cholesta-8-en-3β-ol	Generator
4a-Carboxy-5a-cholesta-8-en-3beta-ol	HMDB
4alpha-Carboxy-5alpha-cholesta-8-en-3b-ol	HMDB
(2S,5S,6S,15R)-5-Hydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carboxylate	Generator

Chemical Formula

C₂₈H₄₆O₃

Average Molecular Weight

430.663

Monoisotopic Molecular Weight

430.344695338

IUPAC Name

(2S,5S,6S,15R)-5-hydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carboxylic acid

Traditional Name

(2S,5S,6S,15R)-5-hydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@H](C1CC3)C(O)=O

InChI Identifier

InChI=1S/C28H46O3/c1-17(2)7-6-8-18(3)20-11-12-21-19-9-10-23-25(26(30)31)24(29)14-16-28(23,5)22(19)13-15-27(20,21)4/h17-18,20-21,23-25,29H,6-16H2,1-5H3,(H,30,31)/t18?,20?,21?,23?,24-,25-,27+,28+/m0/s1

InChI Key

RODBXVVNKJCWQR-KLZNZPMLSA-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
Steroid acid
4-carboxy steroid
3-hydroxysteroid
15-hydroxysteroid
Hydroxysteroid
3-beta-hydroxysteroid
Beta-hydroxy acid
Hydroxy acid
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Alcohol
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Metabolic syndrome (HMDB: HMDB0012166)

Disposition

Biological location

Cytoplasm (HMDB: HMDB0012166)
Cell membrane (HMDB: HMDB0012166)

Biofluid or Excreta

Feces (HMDB: HMDB0012166)
Urine (HMDB: HMDB0012166)

Tissue substructure

Excreta

Biofluid or Excreta

Feces (PMID: 26848182)

Cellular substructure

Extracellular (HMDB: HMDB0012166)
Membrane (HMDB: HMDB0012166)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012166)

Source

Endogenous

Endogenous (HMDB: HMDB0012166)

Animal

Animal (HMDB: HMDB0012166)

Exogenous

Food

Food (HMDB: HMDB0012166)

Animal origin

Poultry

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0012166)

Molecular messenger

Signaling molecule (HMDB: HMDB0012166)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012166)

Emulsifier (HMDB: HMDB0012166)

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	0.003 g/L	ALOGPS
logP	6.2	ALOGPS
logP	6.45	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	4.6	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	126.44 m³·mol⁻¹	ChemAxon
Polarizability	53.16 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	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	203.505	31661259
DarkChem	[M-H]-	200.001	31661259
DeepCCS	[M-2H]-	241.978	30932474
DeepCCS	[M+Na]+	217.609	30932474
AllCCS	[M+H]+	210.2	32859911
AllCCS	[M+H-H2O]+	208.3	32859911
AllCCS	[M+NH4]+	212.0	32859911
AllCCS	[M+Na]+	212.5	32859911
AllCCS	[M-H]-	207.7	32859911
AllCCS	[M+Na-2H]-	209.8	32859911
AllCCS	[M+HCOO]-	212.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol	CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@H](C1CC3)C(O)=O	3392.8	Standard polar	33892256
4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol	CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@H](C1CC3)C(O)=O	3292.4	Standard non polar	33892256
4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol	CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@H](C1CC3)C(O)=O	3465.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol,1TMS,isomer #1	CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)[C@@H](C(=O)O)C1CC3	3520.0	Semi standard non polar	33892256
4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol,1TMS,isomer #2	CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O)[C@@H](C(=O)O[Si](C)(C)C)C1CC3	3462.2	Semi standard non polar	33892256
4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol,2TMS,isomer #1	CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)[C@@H](C(=O)O[Si](C)(C)C)C1CC3	3461.6	Semi standard non polar	33892256
4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol,1TBDMS,isomer #1	CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C(=O)O)C1CC3	3749.5	Semi standard non polar	33892256
4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol,1TBDMS,isomer #2	CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)C1CC3	3721.6	Semi standard non polar	33892256
4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol,2TBDMS,isomer #1	CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)C1CC3	3940.3	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 - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0j4i-1009500000-d0500fdc254a799c072d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol GC-MS (2 TMS) - 70eV, Positive	splash10-08fr-3101390000-46cdde9e4e8648d63301	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 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 - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 10V, Positive-QTOF	splash10-03e9-0004900000-3407ec9be563d9b7ca26	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 20V, Positive-QTOF	splash10-03xs-3019400000-d27da2a126830b00ff9d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 40V, Positive-QTOF	splash10-066u-6239200000-f3726ed20f097b0424ea	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 10V, Negative-QTOF	splash10-004i-0004900000-77d8d1520aaeaa4fd388	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 20V, Negative-QTOF	splash10-00n0-0009500000-1fbb5a29da673f0e742a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 40V, Negative-QTOF	splash10-014i-1009100000-5ad9f534d16a48a405c1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 10V, Negative-QTOF	splash10-004r-0008900000-250dce703c733254dfb5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 20V, Negative-QTOF	splash10-000i-0009000000-eddf0611bb25b50405f8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 40V, Negative-QTOF	splash10-014r-0009000000-8175a5e0027417e0b0ce	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 10V, Positive-QTOF	splash10-001i-0005900000-f3b4f582c48804094069	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 20V, Positive-QTOF	splash10-06a3-6259400000-4c8ff808d75df1d51209	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 40V, Positive-QTOF	splash10-0aov-9213000000-7b6183a193d666f727d2	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Inflammatory bowel disease	26848182	details

Associated Disorders and Diseases

Disease References

Inflammatory bowel disease
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028820

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25200718

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Dietschy JM, Turley SD: Thematic review series: brain Lipids. Cholesterol metabolism in the central nervous system during early development and in the mature animal. J Lipid Res. 2004 Aug;45(8):1375-97. [PubMed:15254070 ]
O'Byrne SM, Blaner WS: Retinol and retinyl esters: biochemistry and physiology. J Lipid Res. 2013 Jul;54(7):1731-43. doi: 10.1194/jlr.R037648. Epub 2013 Apr 26. [PubMed:23625372 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
Linda T. Welson (2006). Triglycerides and Cholesterol Research. Nova Science Publishers Inc..

Showing metabocard for 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol (HMDB0012166)

MOL for HMDB0012166 (4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol)

3D MOL for HMDB0012166 (4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol)

3D SDF for HMDB0012166 (4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol)

3D-SDF for HMDB0012166 (4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol)

PDB for HMDB0012166 (4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol)

3D PDB for HMDB0012166 (4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol)

SMILES for HMDB0012166 (4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol)

INCHI for HMDB0012166 (4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol)

Structure for HMDB0012166 (4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol)

3D Structure for HMDB0012166 (4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra