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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-04-06 16:20:32 UTC

Update Date

2022-03-07 02:51:22 UTC

HMDB ID

HMDB0012178

Secondary Accession Numbers

HMDB12178

Metabolite Identification

Common Name

5Alpha-cholesta-8-en-3-one

Description

5Alpha-cholesta-8-en-3-one is involved in the cholesterol biosynthesis II(via 24,25-dihydrolanosterol) pathway. It can be generated from the enzymatic reduction of 4a-methyl-cholesta-8-enol or enzymatic oxidation of 4a-carboxy-4b-methyl-5a-cholesta-8-en-3b-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          

 28 31  0  0  1  0            999 V2000
    9.2229  -11.7041    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2229  -12.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5084  -11.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5084  -12.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7940  -11.7041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7940  -12.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6519  -11.7041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6519  -12.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9374  -11.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9374  -12.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3665  -10.4666    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.3665  -11.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6519  -10.0541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9375  -10.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1510  -10.2116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6360  -10.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1511  -11.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4060   -9.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2130   -9.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8539   -8.8139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7650   -9.8686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5720   -9.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1240  -10.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9309  -10.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8690  -11.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2229  -10.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3831   -9.6461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0795  -12.9416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
 10  8  1  0  0  0  0
  1  9  1  0  0  0  0
  2 10  1  0  0  0  0
  2  1  1  0  0  0  0
 13 11  1  0  0  0  0
  7 12  1  0  0  0  0
 14 13  1  0  0  0  0
  9  7  2  0  0  0  0
  9 14  1  0  0  0  0
 15 11  1  0  0  0  0
 12 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  1  0  0  0  0
 18 15  1  0  0  0  0
 19 18  1  0  0  0  0
 20 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 23  1  0  0  0  0
  1 26  1  1  0  0  0
 11 27  1  1  0  0  0
 28  6  2  0  0  0  0
M  END

HMDB0012178
     RDKit          3D
5Alpha-cholesta-8-en-3-one
 72 75  0  0  0  0  0  0  0  0999 V2000
    7.6973   -0.3098   -0.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7549   -0.1202    0.7869 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0067   -1.2372    1.8052 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3212   -0.2832    0.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9872    0.7371   -0.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5949    0.5948   -1.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167    0.7661   -0.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5516    2.1134    0.4670 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2181    0.4272   -0.8303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3190   -1.0252   -1.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0808   -1.6057   -1.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9045   -0.4178   -0.8870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2024   -0.6494   -0.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8333    0.4248    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0887    1.5959    0.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6809    1.7192    0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0247    0.3991    0.0315 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1634   -0.3685    1.3014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3263    0.4235    0.2701 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7905    1.5704    1.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9372    0.5458   -1.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4194    0.7010   -0.9377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0046   -0.2108    0.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2198   -0.3166    0.0890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2320   -1.0235    1.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7544   -0.8652    0.8932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1978   -2.0814    0.2126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7607   -2.0212   -0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6630    0.6459   -0.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2557   -1.0837   -1.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7216   -0.5377   -0.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9389    0.8690    1.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8756   -0.9467    2.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2272   -2.1531    1.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0774   -1.3624    2.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6085   -0.3024    1.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2708   -1.2897   -0.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6674    0.4946   -1.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2734    1.7626   -0.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5112   -0.3991   -1.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417    1.3323   -2.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6908    0.0063    0.6073 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0498    2.9094   -0.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1644    2.0151    1.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6184    2.4171    0.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0427    1.0536   -1.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6653   -1.0855   -2.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9876   -1.5544   -0.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4051   -2.0706   -2.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1186   -2.4076   -0.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9960    0.1868   -1.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6409    2.5089    0.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1694    1.6534    1.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1591    2.3730    0.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5871    2.2590   -0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4853    0.2871    2.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8892   -1.1940    1.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7837   -0.8381    1.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6701    2.5095    0.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8495    1.5311    1.3804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1915    1.6704    2.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5474    1.4103   -1.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7665   -0.3548   -1.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8862    0.4703   -1.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6832    1.7661   -0.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6170   -0.7854    2.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5473   -2.0932    0.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3321   -0.8717    1.9419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7725   -2.2193   -0.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4456   -2.9671    0.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1819   -2.5313    0.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4972   -2.5666   -1.0657 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  1
 14 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 17  9  1  0
 26 19  1  0
 17 12  1  0
 28 13  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 18 56  1  0
 18 57  1  0
 18 58  1  0
 20 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 22 64  1  0
 22 65  1  0
 25 66  1  0
 25 67  1  0
 26 68  1  0
 27 69  1  0
 27 70  1  0
 28 71  1  0
 28 72  1  0
M  END


  Mrv0541 02241203482D          

 28 31  0  0  1  0            999 V2000
    9.2229  -11.7041    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2229  -12.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5084  -11.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5084  -12.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7940  -11.7041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7940  -12.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6519  -11.7041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6519  -12.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9374  -11.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9374  -12.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3665  -10.4666    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.3665  -11.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6519  -10.0541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9375  -10.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1510  -10.2116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6360  -10.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1511  -11.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4060   -9.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2130   -9.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8539   -8.8139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7650   -9.8686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5720   -9.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1240  -10.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9309  -10.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8690  -11.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2229  -10.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3831   -9.6461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0795  -12.9416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
 10  8  1  0  0  0  0
  1  9  1  0  0  0  0
  2 10  1  0  0  0  0
  2  1  1  0  0  0  0
 13 11  1  0  0  0  0
  7 12  1  0  0  0  0
 14 13  1  0  0  0  0
  9  7  2  0  0  0  0
  9 14  1  0  0  0  0
 15 11  1  0  0  0  0
 12 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  1  0  0  0  0
 18 15  1  0  0  0  0
 19 18  1  0  0  0  0
 20 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 23  1  0  0  0  0
  1 26  1  1  0  0  0
 11 27  1  1  0  0  0
 28  6  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012178

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)CC1CC3

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-20,23-24H,6-17H2,1-5H3/t19?,20?,23?,24?,26-,27+/m0/s1

> <INCHI_KEY>
RZSXSHNNQBIPTL-HJWVNVQISA-N

> <FORMULA>
C27H44O

> <MOLECULAR_WEIGHT>
384.6377

> <EXACT_MASS>
384.33921603

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
49.00210969441609

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
6.81

> <JCHEM_LOGP>
7.2767320076666655

> <ALOGPS_LOGS>
-6.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.962530739976856

> <JCHEM_PKA_STRONGEST_BASIC>
-7.353211484801864

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
119.32179999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.45e-04 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0012178
     RDKit          3D
5Alpha-cholesta-8-en-3-one
 72 75  0  0  0  0  0  0  0  0999 V2000
    7.6973   -0.3098   -0.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7549   -0.1202    0.7869 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0067   -1.2372    1.8052 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3212   -0.2832    0.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9872    0.7371   -0.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5949    0.5948   -1.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167    0.7661   -0.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5516    2.1134    0.4670 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2181    0.4272   -0.8303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3190   -1.0252   -1.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0808   -1.6057   -1.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9045   -0.4178   -0.8870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2024   -0.6494   -0.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8333    0.4248    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0887    1.5959    0.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6809    1.7192    0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0247    0.3991    0.0315 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1634   -0.3685    1.3014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3263    0.4235    0.2701 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7905    1.5704    1.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9372    0.5458   -1.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4194    0.7010   -0.9377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0046   -0.2108    0.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2198   -0.3166    0.0890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2320   -1.0235    1.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7544   -0.8652    0.8932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1978   -2.0814    0.2126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7607   -2.0212   -0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6630    0.6459   -0.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2557   -1.0837   -1.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7216   -0.5377   -0.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9389    0.8690    1.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8756   -0.9467    2.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2272   -2.1531    1.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0774   -1.3624    2.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6085   -0.3024    1.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2708   -1.2897   -0.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6674    0.4946   -1.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2734    1.7626   -0.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5112   -0.3991   -1.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417    1.3323   -2.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6908    0.0063    0.6073 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0498    2.9094   -0.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1644    2.0151    1.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6184    2.4171    0.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0427    1.0536   -1.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6653   -1.0855   -2.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9876   -1.5544   -0.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4051   -2.0706   -2.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1186   -2.4076   -0.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9960    0.1868   -1.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6409    2.5089    0.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1694    1.6534    1.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1591    2.3730    0.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5871    2.2590   -0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4853    0.2871    2.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8892   -1.1940    1.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7837   -0.8381    1.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6701    2.5095    0.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8495    1.5311    1.3804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1915    1.6704    2.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5474    1.4103   -1.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7665   -0.3548   -1.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8862    0.4703   -1.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6832    1.7661   -0.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6170   -0.7854    2.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5473   -2.0932    0.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3321   -0.8717    1.9419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7725   -2.2193   -0.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4456   -2.9671    0.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1819   -2.5313    0.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4972   -2.5666   -1.0657 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  1
 14 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 17  9  1  0
 26 19  1  0
 17 12  1  0
 28 13  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 18 56  1  0
 18 57  1  0
 18 58  1  0
 20 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 22 64  1  0
 22 65  1  0
 25 66  1  0
 25 67  1  0
 26 68  1  0
 27 69  1  0
 27 70  1  0
 28 71  1  0
 28 72  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      17.216 -21.848   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.216 -23.388   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.882 -21.078   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.882 -24.158   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.549 -21.848   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.549 -23.388   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.884 -21.848   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.884 -23.388   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.550 -21.078   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.550 -24.158   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.217 -19.538   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.217 -21.078   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.884 -18.768   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.550 -19.538   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.682 -19.062   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      23.587 -20.308   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.682 -21.553   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.158 -17.597   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      24.664 -17.277   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.127 -16.453   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.695 -18.421   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      27.201 -18.101   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      28.231 -19.246   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      29.738 -18.926   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      27.755 -20.710   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.216 -20.308   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      21.248 -18.006   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      13.215 -24.158   0.000  0.00  0.00           O+0
CONECT    1    3    9    2   26                                             
CONECT    2    4   10    1                                                  
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5   28                                                  
CONECT    7    8   12    9                                                  
CONECT    8    7   10                                                       
CONECT    9    1    7   14                                                  
CONECT   10    8    2                                                       
CONECT   11   13   15   12   27                                             
CONECT   12    7   11   17                                                  
CONECT   13   11   14                                                       
CONECT   14   13    9                                                       
CONECT   15   11   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   12   16                                                       
CONECT   18   15   19   20                                                  
CONECT   19   18   21                                                       
CONECT   20   18                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26    1                                                            
CONECT   27   11                                                            
CONECT   28    6                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

COMPND    HMDB0012178
HETATM    1  C1  UNL     1       7.697  -0.310  -0.378  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.755  -0.120   0.787  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.007  -1.237   1.805  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.321  -0.283   0.317  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.987   0.737  -0.748  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.595   0.595  -1.226  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.517   0.766  -0.180  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.552   2.113   0.467  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.218   0.427  -0.830  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.319  -1.025  -1.309  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.081  -1.606  -1.161  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.904  -0.418  -0.887  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.202  -0.649  -0.243  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.833   0.425   0.213  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.089   1.596   0.656  1.00  0.00           C  
HETATM   16  C16 UNL     1      -0.681   1.719   0.208  1.00  0.00           C  
HETATM   17  C17 UNL     1       0.025   0.399   0.032  1.00  0.00           C  
HETATM   18  C18 UNL     1       0.163  -0.368   1.301  1.00  0.00           C  
HETATM   19  C19 UNL     1      -4.326   0.423   0.270  1.00  0.00           C  
HETATM   20  C20 UNL     1      -4.790   1.570   1.105  1.00  0.00           C  
HETATM   21  C21 UNL     1      -4.937   0.546  -1.107  1.00  0.00           C  
HETATM   22  C22 UNL     1      -6.419   0.701  -0.938  1.00  0.00           C  
HETATM   23  C23 UNL     1      -7.005  -0.211   0.053  1.00  0.00           C  
HETATM   24  O1  UNL     1      -8.220  -0.317   0.089  1.00  0.00           O  
HETATM   25  C24 UNL     1      -6.232  -1.024   1.025  1.00  0.00           C  
HETATM   26  C25 UNL     1      -4.754  -0.865   0.893  1.00  0.00           C  
HETATM   27  C26 UNL     1      -4.198  -2.081   0.213  1.00  0.00           C  
HETATM   28  C27 UNL     1      -2.761  -2.021  -0.119  1.00  0.00           C  
HETATM   29  H1  UNL     1       7.663   0.646  -0.979  1.00  0.00           H  
HETATM   30  H2  UNL     1       7.256  -1.084  -1.037  1.00  0.00           H  
HETATM   31  H3  UNL     1       8.722  -0.538  -0.045  1.00  0.00           H  
HETATM   32  H4  UNL     1       6.939   0.869   1.213  1.00  0.00           H  
HETATM   33  H5  UNL     1       7.876  -0.947   2.458  1.00  0.00           H  
HETATM   34  H6  UNL     1       7.227  -2.153   1.229  1.00  0.00           H  
HETATM   35  H7  UNL     1       6.077  -1.362   2.370  1.00  0.00           H  
HETATM   36  H8  UNL     1       4.609  -0.302   1.141  1.00  0.00           H  
HETATM   37  H9  UNL     1       5.271  -1.290  -0.192  1.00  0.00           H  
HETATM   38  H10 UNL     1       5.667   0.495  -1.613  1.00  0.00           H  
HETATM   39  H11 UNL     1       5.273   1.763  -0.446  1.00  0.00           H  
HETATM   40  H12 UNL     1       3.511  -0.399  -1.737  1.00  0.00           H  
HETATM   41  H13 UNL     1       3.442   1.332  -2.070  1.00  0.00           H  
HETATM   42  H14 UNL     1       2.691   0.006   0.607  1.00  0.00           H  
HETATM   43  H15 UNL     1       2.050   2.909  -0.114  1.00  0.00           H  
HETATM   44  H16 UNL     1       2.164   2.015   1.493  1.00  0.00           H  
HETATM   45  H17 UNL     1       3.618   2.417   0.558  1.00  0.00           H  
HETATM   46  H18 UNL     1       1.043   1.054  -1.703  1.00  0.00           H  
HETATM   47  H19 UNL     1       1.665  -1.085  -2.348  1.00  0.00           H  
HETATM   48  H20 UNL     1       1.988  -1.554  -0.620  1.00  0.00           H  
HETATM   49  H21 UNL     1      -0.405  -2.071  -2.135  1.00  0.00           H  
HETATM   50  H22 UNL     1      -0.119  -2.408  -0.416  1.00  0.00           H  
HETATM   51  H23 UNL     1      -0.996   0.187  -1.814  1.00  0.00           H  
HETATM   52  H24 UNL     1      -2.641   2.509   0.286  1.00  0.00           H  
HETATM   53  H25 UNL     1      -2.169   1.653   1.772  1.00  0.00           H  
HETATM   54  H26 UNL     1      -0.159   2.373   0.944  1.00  0.00           H  
HETATM   55  H27 UNL     1      -0.587   2.259  -0.772  1.00  0.00           H  
HETATM   56  H28 UNL     1       0.485   0.287   2.163  1.00  0.00           H  
HETATM   57  H29 UNL     1       0.889  -1.194   1.147  1.00  0.00           H  
HETATM   58  H30 UNL     1      -0.784  -0.838   1.650  1.00  0.00           H  
HETATM   59  H31 UNL     1      -4.670   2.509   0.491  1.00  0.00           H  
HETATM   60  H32 UNL     1      -5.849   1.531   1.380  1.00  0.00           H  
HETATM   61  H33 UNL     1      -4.191   1.670   2.037  1.00  0.00           H  
HETATM   62  H34 UNL     1      -4.547   1.410  -1.671  1.00  0.00           H  
HETATM   63  H35 UNL     1      -4.766  -0.355  -1.730  1.00  0.00           H  
HETATM   64  H36 UNL     1      -6.886   0.470  -1.938  1.00  0.00           H  
HETATM   65  H37 UNL     1      -6.683   1.766  -0.743  1.00  0.00           H  
HETATM   66  H38 UNL     1      -6.617  -0.785   2.046  1.00  0.00           H  
HETATM   67  H39 UNL     1      -6.547  -2.093   0.847  1.00  0.00           H  
HETATM   68  H40 UNL     1      -4.332  -0.872   1.942  1.00  0.00           H  
HETATM   69  H41 UNL     1      -4.773  -2.219  -0.742  1.00  0.00           H  
HETATM   70  H42 UNL     1      -4.446  -2.967   0.833  1.00  0.00           H  
HETATM   71  H43 UNL     1      -2.182  -2.531   0.681  1.00  0.00           H  
HETATM   72  H44 UNL     1      -2.497  -2.567  -1.066  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    4   32
CONECT    3   33   34   35
CONECT    4    5   36   37
CONECT    5    6   38   39
CONECT    6    7   40   41
CONECT    7    8    9   42
CONECT    8   43   44   45
CONECT    9   10   17   46
CONECT   10   11   47   48
CONECT   11   12   49   50
CONECT   12   13   17   51
CONECT   13   14   14   28
CONECT   14   15   19
CONECT   15   16   52   53
CONECT   16   17   54   55
CONECT   17   18
CONECT   18   56   57   58
CONECT   19   20   21   26
CONECT   20   59   60   61
CONECT   21   22   62   63
CONECT   22   23   64   65
CONECT   23   24   24   25
CONECT   25   26   66   67
CONECT   26   27   68
CONECT   27   28   69   70
CONECT   28   71   72
END

HMDB0012178
     RDKit          3D
5Alpha-cholesta-8-en-3-one
 72 75  0  0  0  0  0  0  0  0999 V2000
    7.6973   -0.3098   -0.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7549   -0.1202    0.7869 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0067   -1.2372    1.8052 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3212   -0.2832    0.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9872    0.7371   -0.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5949    0.5948   -1.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167    0.7661   -0.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5516    2.1134    0.4670 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2181    0.4272   -0.8303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3190   -1.0252   -1.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0808   -1.6057   -1.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9045   -0.4178   -0.8870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2024   -0.6494   -0.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8333    0.4248    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0887    1.5959    0.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6809    1.7192    0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0247    0.3991    0.0315 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1634   -0.3685    1.3014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3263    0.4235    0.2701 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7905    1.5704    1.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9372    0.5458   -1.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4194    0.7010   -0.9377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0046   -0.2108    0.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2198   -0.3166    0.0890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2320   -1.0235    1.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7544   -0.8652    0.8932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1978   -2.0814    0.2126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7607   -2.0212   -0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6630    0.6459   -0.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2557   -1.0837   -1.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7216   -0.5377   -0.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9389    0.8690    1.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8756   -0.9467    2.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2272   -2.1531    1.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0774   -1.3624    2.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6085   -0.3024    1.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2708   -1.2897   -0.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6674    0.4946   -1.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2734    1.7626   -0.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5112   -0.3991   -1.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417    1.3323   -2.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6908    0.0063    0.6073 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0498    2.9094   -0.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1644    2.0151    1.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6184    2.4171    0.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0427    1.0536   -1.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6653   -1.0855   -2.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9876   -1.5544   -0.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4051   -2.0706   -2.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1186   -2.4076   -0.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9960    0.1868   -1.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6409    2.5089    0.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1694    1.6534    1.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1591    2.3730    0.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5871    2.2590   -0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4853    0.2871    2.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8892   -1.1940    1.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7837   -0.8381    1.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6701    2.5095    0.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8495    1.5311    1.3804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1915    1.6704    2.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5474    1.4103   -1.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7665   -0.3548   -1.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8862    0.4703   -1.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6832    1.7661   -0.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6170   -0.7854    2.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5473   -2.0932    0.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3321   -0.8717    1.9419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7725   -2.2193   -0.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4456   -2.9671    0.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1819   -2.5313    0.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4972   -2.5666   -1.0657 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  1
 14 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 17  9  1  0
 26 19  1  0
 17 12  1  0
 28 13  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 18 56  1  0
 18 57  1  0
 18 58  1  0
 20 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 22 64  1  0
 22 65  1  0
 25 66  1  0
 25 67  1  0
 26 68  1  0
 27 69  1  0
 27 70  1  0
 28 71  1  0
 28 72  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5a-Cholesta-8-en-3-one	Generator
5Α-cholesta-8-en-3-one	Generator

Chemical Formula

C₂₇H₄₄O

Average Molecular Weight

384.6377

Monoisotopic Molecular Weight

384.33921603

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)CC1CC3

InChI Identifier

InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-20,23-24H,6-17H2,1-5H3/t19?,20?,23?,24?,26-,27+/m0/s1

InChI Key

RZSXSHNNQBIPTL-HJWVNVQISA-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
Oxosteroid
3-oxosteroid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Metabolic syndrome (HMDB: HMDB0012178)

Disposition

Biological location

Cytoplasm (HMDB: HMDB0012178)
Cell membrane (HMDB: HMDB0012178)

Biofluid or Excreta

Urine (HMDB: HMDB0012178)

Tissue substructure

Cellular substructure

Extracellular (HMDB: HMDB0012178)
Membrane (HMDB: HMDB0012178)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012178)

Source

Endogenous

Endogenous (HMDB: HMDB0012178)

Animal

Animal (HMDB: HMDB0012178)

Exogenous

Food

Food (HMDB: HMDB0012178)

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: HMDB0012178)

Molecular messenger

Signaling molecule (HMDB: HMDB0012178)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012178)

Emulsifier (HMDB: HMDB0012178)

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	0.00024 g/L	ALOGPS
logP	6.81	ALOGPS
logP	7.28	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	19.96	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	119.32 m³·mol⁻¹	ChemAxon
Polarizability	49 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	193.031	31661259
DarkChem	[M-H]-	190.6	31661259
DeepCCS	[M-2H]-	234.79	30932474
DeepCCS	[M+Na]+	210.115	30932474
AllCCS	[M+H]+	203.0	32859911
AllCCS	[M+H-H2O]+	200.8	32859911
AllCCS	[M+NH4]+	205.0	32859911
AllCCS	[M+Na]+	205.6	32859911
AllCCS	[M-H]-	203.2	32859911
AllCCS	[M+Na-2H]-	204.9	32859911
AllCCS	[M+HCOO]-	206.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5Alpha-cholesta-8-en-3-one	CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)CC1CC3	3037.1	Standard polar	33892256
5Alpha-cholesta-8-en-3-one	CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)CC1CC3	3135.0	Standard non polar	33892256
5Alpha-cholesta-8-en-3-one	CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)CC1CC3	3157.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5Alpha-cholesta-8-en-3-one,1TMS,isomer #1	CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C)=CC1CC3	3214.6	Semi standard non polar	33892256
5Alpha-cholesta-8-en-3-one,1TMS,isomer #1	CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C)=CC1CC3	3078.1	Standard non polar	33892256
5Alpha-cholesta-8-en-3-one,1TMS,isomer #1	CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C)=CC1CC3	3353.9	Standard polar	33892256
5Alpha-cholesta-8-en-3-one,1TMS,isomer #2	CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)CC1CC3	3214.0	Semi standard non polar	33892256
5Alpha-cholesta-8-en-3-one,1TMS,isomer #2	CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)CC1CC3	3039.4	Standard non polar	33892256
5Alpha-cholesta-8-en-3-one,1TMS,isomer #2	CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)CC1CC3	3355.6	Standard polar	33892256
5Alpha-cholesta-8-en-3-one,1TBDMS,isomer #1	CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=CC1CC3	3453.9	Semi standard non polar	33892256
5Alpha-cholesta-8-en-3-one,1TBDMS,isomer #1	CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=CC1CC3	3284.3	Standard non polar	33892256
5Alpha-cholesta-8-en-3-one,1TBDMS,isomer #1	CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=CC1CC3	3479.9	Standard polar	33892256
5Alpha-cholesta-8-en-3-one,1TBDMS,isomer #2	CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)CC1CC3	3449.0	Semi standard non polar	33892256
5Alpha-cholesta-8-en-3-one,1TBDMS,isomer #2	CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)CC1CC3	3231.2	Standard non polar	33892256
5Alpha-cholesta-8-en-3-one,1TBDMS,isomer #2	CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)CC1CC3	3481.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5Alpha-cholesta-8-en-3-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ar3-2029000000-0b0d2a81fb90511def27	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5Alpha-cholesta-8-en-3-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5Alpha-cholesta-8-en-3-one 10V, Positive-QTOF	splash10-000i-0019000000-18f96b5e9c50f8c53f53	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5Alpha-cholesta-8-en-3-one 20V, Positive-QTOF	splash10-0ap0-3119000000-b62cf9c7a5e44b68f233	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5Alpha-cholesta-8-en-3-one 40V, Positive-QTOF	splash10-0a4i-4139000000-3500c98ca0ba8e0a2679	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5Alpha-cholesta-8-en-3-one 10V, Negative-QTOF	splash10-001i-0009000000-713e469cefa5ad7160d1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5Alpha-cholesta-8-en-3-one 20V, Negative-QTOF	splash10-001i-0009000000-5d059b2d1fa5085dd8b7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5Alpha-cholesta-8-en-3-one 40V, Negative-QTOF	splash10-0gb9-3019000000-959e3591f88af78165ac	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5Alpha-cholesta-8-en-3-one 10V, Positive-QTOF	splash10-000i-0009000000-4745a68682bde38fa4df	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5Alpha-cholesta-8-en-3-one 20V, Positive-QTOF	splash10-05g0-6469000000-24b202fc67e5feac6e17	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5Alpha-cholesta-8-en-3-one 40V, Positive-QTOF	splash10-0a4l-8940000000-b40b678f31dd694374ae	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5Alpha-cholesta-8-en-3-one 10V, Negative-QTOF	splash10-001i-0009000000-4d7a5f3b63c0fb62f1d7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5Alpha-cholesta-8-en-3-one 20V, Negative-QTOF	splash10-001i-0009000000-4d7a5f3b63c0fb62f1d7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5Alpha-cholesta-8-en-3-one 40V, Negative-QTOF	splash10-001i-0019000000-16743e49fdb5efac3a3e	2021-09-24	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

FDB028832

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

25203379

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 5Alpha-cholesta-8-en-3-one (HMDB0012178)

MOL for HMDB0012178 (5Alpha-cholesta-8-en-3-one)

3D MOL for HMDB0012178 (5Alpha-cholesta-8-en-3-one)

3D SDF for HMDB0012178 (5Alpha-cholesta-8-en-3-one)

3D-SDF for HMDB0012178 (5Alpha-cholesta-8-en-3-one)

PDB for HMDB0012178 (5Alpha-cholesta-8-en-3-one)

3D PDB for HMDB0012178 (5Alpha-cholesta-8-en-3-one)

SMILES for HMDB0012178 (5Alpha-cholesta-8-en-3-one)

INCHI for HMDB0012178 (5Alpha-cholesta-8-en-3-one)

Structure for HMDB0012178 (5Alpha-cholesta-8-en-3-one)

3D Structure for HMDB0012178 (5Alpha-cholesta-8-en-3-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra