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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-04-06 16:20:18 UTC

Update Date

2022-03-07 02:51:21 UTC

HMDB ID

HMDB0012165

Secondary Accession Numbers

HMDB12165

Metabolite Identification

Common Name

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

Description

4alpha-carboxy-4beta-methyl-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 C-4 methyl sterol oxidase (SC4MOL) and can be generated from the enzymatic oxidation of 4alpha-formyl-4beta-methyl-5alpha-cholesta-8-en-3beta-ol. It is also a substrate for NAD(P)-dependent steroid dehydrogenase (H105E3) and can be generated from the enzymatic carboxylation of 4alpha-methyl-5alpha-cholesta-8-en-3-one. 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          

 32 35  0  0  1  0            999 V2000
   17.8018   -7.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5025   -6.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0999  -10.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3100  -10.5217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0221  -11.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7201  -14.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1370   -8.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6521   -8.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8005   -9.6577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4510  -13.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4351  -11.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9501  -12.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7366  -13.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7366  -11.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5931  -12.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4510  -10.9215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3076  -12.1590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9875   -7.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2855  -10.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4510  -12.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9501  -11.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1655  -12.1590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7366  -12.1590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0221  -13.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5931  -13.3965    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.8951  -14.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1655  -11.3340    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.0221  -12.5715    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.3076  -13.8090    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8787  -13.8090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3076  -15.2380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0701  -14.5235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2 18  1  0  0  0  0
  3 19  1  0  0  0  0
 27  4  1  1  0  0  0
 28  5  1  1  0  0  0
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  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 18  1  0  0  0  0
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 15 25  1  0  0  0  0
 16 27  1  0  0  0  0
 17 28  1  0  0  0  0
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 24 29  1  0  0  0  0
 25 30  1  1  0  0  0
 25 29  1  0  0  0  0
 26 29  1  0  0  0  0
 26 31  1  0  0  0  0
 26 32  2  0  0  0  0
M  END

HMDB0012165
     RDKit          3D
4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol
 80 83  0  0  0  0  0  0  0  0999 V2000
    6.1175    2.3504    0.8555 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9076    1.1032    1.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3664    1.3913    0.8949 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4626   -0.4831    1.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
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 17  9  1  0
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 26 74  1  0
 29 75  1  0
 30 76  1  0
 31 77  1  0
 31 78  1  0
 32 79  1  0
 32 80  1  0
M  END


  Mrv0541 02241203482D          

 32 35  0  0  1  0            999 V2000
   17.8018   -7.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5025   -6.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0999  -10.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3100  -10.5217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0221  -11.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 13 24  1  0  0  0  0
 14 23  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 25  1  0  0  0  0
 16 27  1  0  0  0  0
 17 28  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  2  0  0  0  0
 21 27  1  0  0  0  0
 22 27  1  0  0  0  0
 23 28  1  0  0  0  0
 24 28  1  0  0  0  0
 24 29  1  0  0  0  0
 25 30  1  1  0  0  0
 25 29  1  0  0  0  0
 26 29  1  0  0  0  0
 26 31  1  0  0  0  0
 26 32  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012165

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C29H48O3/c1-18(2)8-7-9-19(3)21-11-12-22-20-10-13-24-28(5,23(20)14-16-27(21,22)4)17-15-25(30)29(24,6)26(31)32/h18-19,21-22,24-25,30H,7-17H2,1-6H3,(H,31,32)/t19?,21?,22?,24?,25-,27+,28+,29-/m0/s1

> <INCHI_KEY>
GLCDBDRQLZKKOJ-XQTRBMGCSA-N

> <FORMULA>
C29H48O3

> <MOLECULAR_WEIGHT>
444.6896

> <EXACT_MASS>
444.360345402

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
55.13699367783912

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
6.82

> <JCHEM_LOGP>
7.0038974813333335

> <ALOGPS_LOGS>
-5.52

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.716008813949259

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.590055980466473

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0380298101870595

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
130.93679999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.33e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012165
     RDKit          3D
4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol
 80 83  0  0  0  0  0  0  0  0999 V2000
    6.1175    2.3504    0.8555 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9076    1.1032    1.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3664    1.3913    0.8949 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4277   -0.0554    0.2893 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9476   -0.3257    0.5548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5586   -1.4688   -0.3390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1037   -1.8675   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8745   -3.0089   -1.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1885   -0.7429   -0.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2170    0.0594   -1.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8498    0.7676   -1.6322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2841    0.4906   -0.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1545    0.6481   -0.1060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8734   -0.3193    0.3877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2632   -1.4456    1.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2453   -1.3427    1.2466 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7371   -0.9753   -0.0975 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0883   -1.7465   -1.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3466   -0.3954    0.1951 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5750   -1.4879   -0.8673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9145   -0.9040    1.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4093   -0.9519    1.3959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8747    0.4726    1.2049 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2665    0.4668    1.2465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3882    1.0640   -0.0850 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2448    0.4870   -1.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6835    2.5176   -0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1330    3.0527    0.9866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4753    3.3260   -1.1765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9308    0.8750   -0.3273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1167    2.0071    0.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7741    1.9361   -0.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3552    2.5145    1.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7762    3.2667    0.8564 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6528    2.3031   -0.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7228    0.7958    2.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5390    2.4764    1.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6203    1.0907   -0.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0009    0.7712    1.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0509   -0.9535    0.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5875    0.2731   -0.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4279    0.6155    0.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792   -0.5781    1.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8369   -1.2747   -1.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1715   -2.3479   -0.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0281   -2.3128    0.8407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9935   -2.7525   -2.2035 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542   -3.5963   -0.9158 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7120   -3.7455   -0.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4918    0.0046    0.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9821    0.8602   -1.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2896   -0.5641   -2.4589 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9821    1.8701   -1.7536 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2134    0.3647   -2.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8735    1.0425    0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5864   -2.4267    0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7013   -1.3558    2.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6320   -2.2714    1.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4626   -0.4831    1.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2929   -2.7076   -0.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7734   -1.8681   -2.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7914   -1.2134   -1.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6565   -1.5897   -1.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1564   -1.1366   -1.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1850   -2.4542   -0.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5587   -0.2788    2.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5352   -1.9637    1.5847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8425   -1.2774    2.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7751   -1.5597    0.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5223    1.0553    2.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6428   -0.4549    1.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0890    1.1639   -1.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7487   -0.4680   -0.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6562    0.2974   -2.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2577    4.2988   -1.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7493    0.9198   -1.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9438    1.8589    1.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5570    2.9635    0.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1755    2.8184   -0.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9750    2.0317   -1.5585 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  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  1
 27 28  2  0
 27 29  1  0
 25 30  1  0
 30 31  1  0
 31 32  1  0
 17  9  1  0
 30 19  1  0
 17 12  1  0
 32 13  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  5 42  1  0
  5 43  1  0
  6 44  1  0
  6 45  1  0
  7 46  1  0
  8 47  1  0
  8 48  1  0
  8 49  1  0
  9 50  1  0
 10 51  1  0
 10 52  1  0
 11 53  1  0
 11 54  1  0
 12 55  1  0
 15 56  1  0
 15 57  1  0
 16 58  1  0
 16 59  1  0
 18 60  1  0
 18 61  1  0
 18 62  1  0
 20 63  1  0
 20 64  1  0
 20 65  1  0
 21 66  1  0
 21 67  1  0
 22 68  1  0
 22 69  1  0
 23 70  1  1
 24 71  1  0
 26 72  1  0
 26 73  1  0
 26 74  1  0
 29 75  1  0
 30 76  1  0
 31 77  1  0
 31 78  1  0
 32 79  1  0
 32 80  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      33.230 -13.828   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      30.805 -12.742   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      33.786 -19.114   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.445 -19.641   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.175 -21.927   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.611 -27.111   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.989 -16.641   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      31.084 -15.395   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.361 -18.028   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      28.842 -25.007   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      32.546 -21.927   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.640 -23.173   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.508 -25.777   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      27.508 -21.157   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      23.507 -23.467   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.842 -20.387   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      24.841 -22.697   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      31.710 -13.988   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      32.266 -19.274   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.842 -23.467   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      31.640 -20.681   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      30.176 -22.697   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      27.508 -22.697   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      26.175 -25.007   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      23.507 -25.007   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      24.071 -27.111   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      30.176 -21.157   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      26.175 -23.467   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      24.841 -25.777   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      22.174 -25.777   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      24.841 -28.444   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      22.531 -27.111   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4   27                                                            
CONECT    5   28                                                            
CONECT    6   29                                                            
CONECT    7    8    9                                                       
CONECT    8    7   18                                                       
CONECT    9    7   19                                                       
CONECT   10   20   13                                                       
CONECT   11   21   12                                                       
CONECT   12   11   22                                                       
CONECT   13   10   24                                                       
CONECT   14   23   16                                                       
CONECT   15   17   25                                                       
CONECT   16   14   27                                                       
CONECT   17   15   28                                                       
CONECT   18    1    2    8                                                  
CONECT   19    3    9   21                                                  
CONECT   20   10   22   23                                                  
CONECT   21   11   19   27                                                  
CONECT   22   12   20   27                                                  
CONECT   23   14   20   28                                                  
CONECT   24   13   28   29                                                  
CONECT   25   15   30   29                                                  
CONECT   26   29   31   32                                                  
CONECT   27    4   16   21   22                                             
CONECT   28    5   17   23   24                                             
CONECT   29    6   24   25   26                                             
CONECT   30   25                                                            
CONECT   31   26                                                            
CONECT   32   26                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

COMPND    HMDB0012165
HETATM    1  C1  UNL     1       6.117   2.350   0.856  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.908   1.103   1.166  1.00  0.00           C  
HETATM    3  C3  UNL     1       8.366   1.391   0.895  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.428  -0.055   0.289  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.948  -0.326   0.555  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.559  -1.469  -0.339  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.104  -1.867  -0.196  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.874  -3.009  -1.141  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.188  -0.743  -0.271  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.217   0.059  -1.565  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.850   0.768  -1.632  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.284   0.491  -0.293  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.155   0.648  -0.106  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.873  -0.319   0.388  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.263  -1.446   1.193  1.00  0.00           C  
HETATM   16  C16 UNL     1       0.245  -1.343   1.247  1.00  0.00           C  
HETATM   17  C17 UNL     1       0.737  -0.975  -0.098  1.00  0.00           C  
HETATM   18  C18 UNL     1       0.088  -1.747  -1.213  1.00  0.00           C  
HETATM   19  C19 UNL     1      -3.347  -0.395   0.195  1.00  0.00           C  
HETATM   20  C20 UNL     1      -3.575  -1.488  -0.867  1.00  0.00           C  
HETATM   21  C21 UNL     1      -3.915  -0.904   1.475  1.00  0.00           C  
HETATM   22  C22 UNL     1      -5.409  -0.952   1.396  1.00  0.00           C  
HETATM   23  C23 UNL     1      -5.875   0.473   1.205  1.00  0.00           C  
HETATM   24  O1  UNL     1      -7.266   0.467   1.246  1.00  0.00           O  
HETATM   25  C24 UNL     1      -5.388   1.064  -0.085  1.00  0.00           C  
HETATM   26  C25 UNL     1      -6.245   0.487  -1.195  1.00  0.00           C  
HETATM   27  C26 UNL     1      -5.684   2.518  -0.059  1.00  0.00           C  
HETATM   28  O2  UNL     1      -6.133   3.053   0.987  1.00  0.00           O  
HETATM   29  O3  UNL     1      -5.475   3.326  -1.176  1.00  0.00           O  
HETATM   30  C27 UNL     1      -3.931   0.875  -0.327  1.00  0.00           C  
HETATM   31  C28 UNL     1      -3.117   2.007   0.271  1.00  0.00           C  
HETATM   32  C29 UNL     1      -1.774   1.936  -0.475  1.00  0.00           C  
HETATM   33  H1  UNL     1       5.355   2.514   1.648  1.00  0.00           H  
HETATM   34  H2  UNL     1       6.776   3.267   0.856  1.00  0.00           H  
HETATM   35  H3  UNL     1       5.653   2.303  -0.151  1.00  0.00           H  
HETATM   36  H4  UNL     1       6.723   0.796   2.215  1.00  0.00           H  
HETATM   37  H5  UNL     1       8.539   2.476   1.081  1.00  0.00           H  
HETATM   38  H6  UNL     1       8.620   1.091  -0.143  1.00  0.00           H  
HETATM   39  H7  UNL     1       9.001   0.771   1.571  1.00  0.00           H  
HETATM   40  H8  UNL     1       7.051  -0.954   0.449  1.00  0.00           H  
HETATM   41  H9  UNL     1       6.588   0.273  -0.757  1.00  0.00           H  
HETATM   42  H10 UNL     1       4.428   0.615   0.347  1.00  0.00           H  
HETATM   43  H11 UNL     1       4.779  -0.578   1.603  1.00  0.00           H  
HETATM   44  H12 UNL     1       4.837  -1.275  -1.392  1.00  0.00           H  
HETATM   45  H13 UNL     1       5.172  -2.348  -0.019  1.00  0.00           H  
HETATM   46  H14 UNL     1       3.028  -2.313   0.841  1.00  0.00           H  
HETATM   47  H15 UNL     1       2.994  -2.752  -2.203  1.00  0.00           H  
HETATM   48  H16 UNL     1       1.954  -3.596  -0.916  1.00  0.00           H  
HETATM   49  H17 UNL     1       3.712  -3.745  -0.935  1.00  0.00           H  
HETATM   50  H18 UNL     1       2.492   0.005   0.523  1.00  0.00           H  
HETATM   51  H19 UNL     1       2.982   0.860  -1.547  1.00  0.00           H  
HETATM   52  H20 UNL     1       2.290  -0.564  -2.459  1.00  0.00           H  
HETATM   53  H21 UNL     1       0.982   1.870  -1.754  1.00  0.00           H  
HETATM   54  H22 UNL     1       0.213   0.365  -2.420  1.00  0.00           H  
HETATM   55  H23 UNL     1       0.874   1.042   0.496  1.00  0.00           H  
HETATM   56  H24 UNL     1      -1.586  -2.427   0.801  1.00  0.00           H  
HETATM   57  H25 UNL     1      -1.701  -1.356   2.225  1.00  0.00           H  
HETATM   58  H26 UNL     1       0.632  -2.271   1.665  1.00  0.00           H  
HETATM   59  H27 UNL     1       0.463  -0.483   1.946  1.00  0.00           H  
HETATM   60  H28 UNL     1      -0.293  -2.708  -0.817  1.00  0.00           H  
HETATM   61  H29 UNL     1       0.773  -1.868  -2.077  1.00  0.00           H  
HETATM   62  H30 UNL     1      -0.791  -1.213  -1.629  1.00  0.00           H  
HETATM   63  H31 UNL     1      -4.657  -1.590  -1.050  1.00  0.00           H  
HETATM   64  H32 UNL     1      -3.156  -1.137  -1.847  1.00  0.00           H  
HETATM   65  H33 UNL     1      -3.185  -2.454  -0.548  1.00  0.00           H  
HETATM   66  H34 UNL     1      -3.559  -0.279   2.323  1.00  0.00           H  
HETATM   67  H35 UNL     1      -3.535  -1.964   1.585  1.00  0.00           H  
HETATM   68  H36 UNL     1      -5.842  -1.277   2.379  1.00  0.00           H  
HETATM   69  H37 UNL     1      -5.775  -1.560   0.571  1.00  0.00           H  
HETATM   70  H38 UNL     1      -5.522   1.055   2.079  1.00  0.00           H  
HETATM   71  H39 UNL     1      -7.643  -0.455   1.113  1.00  0.00           H  
HETATM   72  H40 UNL     1      -7.089   1.164  -1.455  1.00  0.00           H  
HETATM   73  H41 UNL     1      -6.749  -0.468  -0.889  1.00  0.00           H  
HETATM   74  H42 UNL     1      -5.656   0.297  -2.102  1.00  0.00           H  
HETATM   75  H43 UNL     1      -5.258   4.299  -1.024  1.00  0.00           H  
HETATM   76  H44 UNL     1      -3.749   0.920  -1.419  1.00  0.00           H  
HETATM   77  H45 UNL     1      -2.944   1.859   1.355  1.00  0.00           H  
HETATM   78  H46 UNL     1      -3.557   2.964   0.011  1.00  0.00           H  
HETATM   79  H47 UNL     1      -1.176   2.818  -0.174  1.00  0.00           H  
HETATM   80  H48 UNL     1      -1.975   2.032  -1.558  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3    4   36
CONECT    3   37   38   39
CONECT    4    5   40   41
CONECT    5    6   42   43
CONECT    6    7   44   45
CONECT    7    8    9   46
CONECT    8   47   48   49
CONECT    9   10   17   50
CONECT   10   11   51   52
CONECT   11   12   53   54
CONECT   12   13   17   55
CONECT   13   14   14   32
CONECT   14   15   19
CONECT   15   16   56   57
CONECT   16   17   58   59
CONECT   17   18
CONECT   18   60   61   62
CONECT   19   20   21   30
CONECT   20   63   64   65
CONECT   21   22   66   67
CONECT   22   23   68   69
CONECT   23   24   25   70
CONECT   24   71
CONECT   25   26   27   30
CONECT   26   72   73   74
CONECT   27   28   28   29
CONECT   29   75
CONECT   30   31   76
CONECT   31   32   77   78
CONECT   32   79   80
END

HMDB0012165
     RDKit          3D
4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol
 80 83  0  0  0  0  0  0  0  0999 V2000
    6.1175    2.3504    0.8555 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9076    1.1032    1.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3664    1.3913    0.8949 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4277   -0.0554    0.2893 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9476   -0.3257    0.5548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5586   -1.4688   -0.3390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1037   -1.8675   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8745   -3.0089   -1.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1885   -0.7429   -0.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2170    0.0594   -1.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8498    0.7676   -1.6322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2841    0.4906   -0.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1545    0.6481   -0.1060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8734   -0.3193    0.3877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2632   -1.4456    1.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2453   -1.3427    1.2466 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7371   -0.9753   -0.0975 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0883   -1.7465   -1.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3466   -0.3954    0.1951 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -3.9145   -0.9040    1.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4093   -0.9519    1.3959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8747    0.4726    1.2049 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2665    0.4668    1.2465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3882    1.0640   -0.0850 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2448    0.4870   -1.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6835    2.5176   -0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1330    3.0527    0.9866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4753    3.3260   -1.1765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9308    0.8750   -0.3273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1167    2.0071    0.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7741    1.9361   -0.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3552    2.5145    1.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7762    3.2667    0.8564 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6528    2.3031   -0.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7228    0.7958    2.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5390    2.4764    1.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6203    1.0907   -0.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0009    0.7712    1.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0509   -0.9535    0.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5875    0.2731   -0.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4279    0.6155    0.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792   -0.5781    1.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8369   -1.2747   -1.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1715   -2.3479   -0.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0281   -2.3128    0.8407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9935   -2.7525   -2.2035 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542   -3.5963   -0.9158 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7120   -3.7455   -0.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4918    0.0046    0.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9821    0.8602   -1.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2896   -0.5641   -2.4589 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9821    1.8701   -1.7536 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2134    0.3647   -2.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8735    1.0425    0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5864   -2.4267    0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7013   -1.3558    2.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6320   -2.2714    1.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4626   -0.4831    1.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2929   -2.7076   -0.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7734   -1.8681   -2.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7914   -1.2134   -1.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6565   -1.5897   -1.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1564   -1.1366   -1.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1850   -2.4542   -0.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5587   -0.2788    2.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5352   -1.9637    1.5847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8425   -1.2774    2.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7751   -1.5597    0.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5223    1.0553    2.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6428   -0.4549    1.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0890    1.1639   -1.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7487   -0.4680   -0.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6562    0.2974   -2.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2577    4.2988   -1.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7493    0.9198   -1.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9438    1.8589    1.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5570    2.9635    0.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1755    2.8184   -0.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9750    2.0317   -1.5585 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  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  1
 27 28  2  0
 27 29  1  0
 25 30  1  0
 30 31  1  0
 31 32  1  0
 17  9  1  0
 30 19  1  0
 17 12  1  0
 32 13  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  5 42  1  0
  5 43  1  0
  6 44  1  0
  6 45  1  0
  7 46  1  0
  8 47  1  0
  8 48  1  0
  8 49  1  0
  9 50  1  0
 10 51  1  0
 10 52  1  0
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 15 56  1  0
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 16 59  1  0
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 20 64  1  0
 20 65  1  0
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 21 67  1  0
 22 68  1  0
 22 69  1  0
 23 70  1  1
 24 71  1  0
 26 72  1  0
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 26 74  1  0
 29 75  1  0
 30 76  1  0
 31 77  1  0
 31 78  1  0
 32 79  1  0
 32 80  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

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

Chemical Formula

C₂₉H₄₈O₃

Average Molecular Weight

444.6896

Monoisotopic Molecular Weight

444.360345402

IUPAC Name

(2S,5S,6S,15R)-5-hydroxy-2,6,15-trimethyl-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-2,6,15-trimethyl-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@](C)(C1CC3)C(O)=O

InChI Identifier

InChI=1S/C29H48O3/c1-18(2)8-7-9-19(3)21-11-12-22-20-10-13-24-28(5,23(20)14-16-27(21,22)4)17-15-25(30)29(24,6)26(31)32/h18-19,21-22,24-25,30H,7-17H2,1-6H3,(H,31,32)/t19?,21?,22?,24?,25-,27+,28+,29-/m0/s1

InChI Key

GLCDBDRQLZKKOJ-XQTRBMGCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0012165)
Cell membrane (HMDB: HMDB0012165)

Cellular substructure

Extracellular (HMDB: HMDB0012165)
Membrane (HMDB: HMDB0012165)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012165)

Source

Endogenous

Endogenous (HMDB: HMDB0012165)

Animal

Animal (HMDB: HMDB0012165)

Exogenous

Food

Food (HMDB: HMDB0012165)

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

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0012165)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0012165)

Cellular process

Cell signaling (HMDB: HMDB0012165)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0012165)

Metabolic pathway

Kandutsch-Russell Pathway (Cholesterol Biosynthesis) (PathBank: SMP0121060)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0012165)

Nutrient

Nutrient (HMDB: HMDB0012165)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012165)

Emulsifier (HMDB: HMDB0012165)

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	0.0013 g/L	ALOGPS
logP	6.82	ALOGPS
logP	7	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	4.59	ChemAxon
pKa (Strongest Basic)	-3	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	130.94 m³·mol⁻¹	ChemAxon
Polarizability	55.14 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]+	206.26	31661259
DarkChem	[M-H]-	203.421	31661259
DeepCCS	[M-2H]-	244.624	30932474
DeepCCS	[M+Na]+	220.282	30932474
AllCCS	[M+H]+	212.8	32859911
AllCCS	[M+H-H2O]+	211.0	32859911
AllCCS	[M+NH4]+	214.4	32859911
AllCCS	[M+Na]+	214.9	32859911
AllCCS	[M-H]-	210.2	32859911
AllCCS	[M+Na-2H]-	212.5	32859911
AllCCS	[M+HCOO]-	215.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol	CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@](C)(C1CC3)C(O)=O	3336.6	Standard polar	33892256
4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol	CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@](C)(C1CC3)C(O)=O	3293.7	Standard non polar	33892256
4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol	CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@](C)(C1CC3)C(O)=O	3521.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4alpha-Carboxy-4beta-methyl-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@@](C)(C(=O)O)C1CC3	3569.0	Semi standard non polar	33892256
4alpha-Carboxy-4beta-methyl-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@@](C)(C(=O)O[Si](C)(C)C)C1CC3	3492.1	Semi standard non polar	33892256
4alpha-Carboxy-4beta-methyl-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@@](C)(C(=O)O[Si](C)(C)C)C1CC3	3502.9	Semi standard non polar	33892256
4alpha-Carboxy-4beta-methyl-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@@](C)(C(=O)O)C1CC3	3796.9	Semi standard non polar	33892256
4alpha-Carboxy-4beta-methyl-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@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)C1CC3	3748.6	Semi standard non polar	33892256
4alpha-Carboxy-4beta-methyl-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@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)C1CC3	3983.3	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-4beta-methyl-5alpha-cholesta-8-en-3beta-ol GC-MS (Non-derivatized) - 70eV, Positive	splash10-03xr-1009600000-218f2e8215c950df3ac7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol GC-MS (2 TMS) - 70eV, Positive	splash10-00di-3001290000-b4abb9bc6f63998dba1f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4alpha-Carboxy-4beta-methyl-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-4beta-methyl-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-4beta-methyl-5alpha-cholesta-8-en-3beta-ol 10V, Positive-QTOF	splash10-004j-0002900000-cecfa0f4033bf3bdf954	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol 20V, Positive-QTOF	splash10-0a7j-4009800000-a4c68b0092c77b998c0a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol 40V, Positive-QTOF	splash10-0a4l-6239200000-ddf379dda298914e4227	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol 10V, Negative-QTOF	splash10-0006-0003900000-f421950834a235d62ebe	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol 20V, Negative-QTOF	splash10-000w-0009500000-aaf74005758f1f8e1526	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol 40V, Negative-QTOF	splash10-001i-1009200000-3569c0a5ed13ef7146c4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol 10V, Positive-QTOF	splash10-0002-0003900000-b25c29c14d35d5ad44f9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol 20V, Positive-QTOF	splash10-000x-6549500000-a3078c32c9df4bcd0f6d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol 40V, Positive-QTOF	splash10-0a4r-9325000000-d47ea2df9f60bd5e7270	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol 10V, Negative-QTOF	splash10-0006-0000900000-bd91a2756ebb8372ba0c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol 20V, Negative-QTOF	splash10-0006-0005900000-2b2a94bde2a836d1f636	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol 40V, Negative-QTOF	splash10-0006-5005900000-ab5cd89938370df58100	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

FDB028819

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

25202944

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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol (HMDB0012165)

MOL for HMDB0012165 (4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol)

3D MOL for HMDB0012165 (4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol)

3D SDF for HMDB0012165 (4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol)

3D-SDF for HMDB0012165 (4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol)

PDB for HMDB0012165 (4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol)

3D PDB for HMDB0012165 (4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol)

SMILES for HMDB0012165 (4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol)

INCHI for HMDB0012165 (4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol)

Structure for HMDB0012165 (4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol)

3D Structure for HMDB0012165 (4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra