NP-MRD: Showing NP-Card for 5alpha-Cholestanone (NP0000331)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-06-29 00:46:31 UTC

NP-MRD ID

NP0000331

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5alpha-Cholestanone

Description

5Alpha-Cholestanone, also known as 5α-cholestanone, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 5alpha-cholestanone is considered to be a sterol lipid molecule. 5Alpha-Cholestanone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.

Structure

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


  Mrv1652305271900002D          

 33 36  0  0  1  0            999 V2000
   19.3690  -10.2106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3690  -11.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0835  -11.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7979  -11.0356    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.7979  -10.2106    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.0835   -9.7981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5124  -11.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2269  -11.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2269  -10.2106    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.5124   -9.7981    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.9414   -9.7981    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.9414   -8.9731    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.2269   -8.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5124   -8.9731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7261  -10.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2110   -9.3856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7261   -8.7181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.6545  -11.4481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0277   -8.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9810   -7.9335    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.4290   -7.3204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7880   -7.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0429   -6.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8499   -6.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5124  -10.6231    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.7979   -9.3856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2269   -9.3856    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.0277  -10.6186    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.4478   -8.5664    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.8038  -11.7288    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.1049   -6.0212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9118   -5.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5528   -5.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
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 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
  2 18  2  0  0  0  0
 12 19  1  1  0  0  0
 17 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 10 25  1  6  0  0  0
  5 26  1  1  0  0  0
  9 27  1  1  0  0  0
 11 28  1  6  0  0  0
 17 29  1  6  0  0  0
  4 30  1  6  0  0  0
 31 24  1  0  0  0  0
 32 31  1  0  0  0  0
 33 31  1  0  0  0  0
M  END

HMDB0000871
     RDKit          3D
5alpha-Cholestanone
 74 77  0  0  0  0  0  0  0  0999 V2000
    8.0024    1.1863   -0.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7049    0.3598   -0.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0976   -1.5791   -2.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652305271900002D          

 33 36  0  0  1  0            999 V2000
   19.3690  -10.2106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3690  -11.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   20.7979  -10.2106    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.0835   -9.7981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0000331

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O/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/h18-20,22-25H,6-17H2,1-5H3/t19-,20+,22+,23-,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
PESKGJQREUXSRR-UXIWKSIVSA-N

> <FORMULA>
C27H46O

> <MOLECULAR_WEIGHT>
386.6535

> <EXACT_MASS>
386.354866094

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
50.38612374506893

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
6.65

> <JCHEM_LOGP>
7.725969313666669

> <ALOGPS_LOGS>
-7.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.352808751885236

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
118.73839999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.45e-05 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0000871
     RDKit          3D
5alpha-Cholestanone
 74 77  0  0  0  0  0  0  0  0999 V2000
    8.0024    1.1863   -0.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7049    0.3598   -0.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9328   -0.9521   -0.8349 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6958    1.2162   -0.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3536    0.4729   -0.9396 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8642    0.1286    0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5738   -0.5882    0.5735 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4030   -0.7934    2.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.0340   -0.1347 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4955   -0.0018   -1.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1001   -0.5084   -2.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6999    0.0003   -0.9624 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1344   -0.3006   -0.9618 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7630    0.3115   -2.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2475    0.3665   -2.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7897    0.8957   -0.8247 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2856    0.7445   -0.8665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9014    0.5193    0.4474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0271    0.0740    0.5017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2017    0.8149    1.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7082    0.8489    1.6058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1660    0.2012    0.3733 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5713   -1.2556    0.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6890    0.4008    0.2889 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0139   -0.0894    1.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5129   -0.0888    1.4817 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0834   -0.5783    0.1954 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0073   -2.0758    0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1051    1.6802   -1.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8691    1.9602    0.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8103    0.4651    0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4509    0.1859    0.9391 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9975   -1.2359   -0.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7538   -0.8895   -1.9231 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3138   -1.7432   -0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4588    2.0647   -0.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0142    1.6386   -1.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7026    1.1503   -1.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5260   -0.4323   -1.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8427    1.1034    1.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6473   -0.4762    0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7548   -1.6396    0.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4508   -0.8847    2.4778 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9952    0.1087    2.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9359   -1.7451    2.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3422    1.0779    0.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2677   -0.6309   -2.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5079    1.0509   -2.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0976   -1.5791   -2.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2103    0.0067   -3.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5578    1.1013   -0.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4325   -1.3423   -0.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4795   -0.3488   -3.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2903    1.2969   -2.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5833    1.1075   -2.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7197   -0.5885   -2.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5527    1.9912   -0.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5528   -0.1468   -1.5065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7664    1.6602   -1.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5861    1.7797    2.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5426    0.0352    2.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3906    1.9290    1.5879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3131    0.3586    2.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7528   -1.9473    0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3732   -1.4634    1.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0058   -1.5508   -0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4987    1.4789    0.1232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3951   -1.0872    1.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3008    0.5986    2.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2123   -0.7824    2.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0938    0.9060    1.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3877   -2.5001    1.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7353   -2.4416   -0.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626   -2.5549   -0.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 27  9  1  0
 27 12  1  0
 24 13  1  0
 22 16  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  6
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  1
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  1
 13 52  1  1
 14 53  1  0
 14 54  1  0
 15 55  1  0
 15 56  1  0
 16 57  1  1
 17 58  1  0
 17 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 23 64  1  0
 23 65  1  0
 23 66  1  0
 24 67  1  6
 25 68  1  0
 25 69  1  0
 26 70  1  0
 26 71  1  0
 28 72  1  0
 28 73  1  0
 28 74  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      36.155 -19.060   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      36.155 -20.600   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      37.489 -21.370   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      38.823 -20.600   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      38.823 -19.060   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      37.489 -18.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      40.156 -21.370   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      41.490 -20.600   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      41.490 -19.060   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      40.156 -18.290   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      42.824 -18.290   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      42.824 -16.750   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      41.490 -15.980   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      40.156 -16.750   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      44.289 -18.766   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      45.194 -17.520   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      44.289 -16.274   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      34.822 -21.370   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      42.985 -15.218   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      44.765 -14.809   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      43.734 -13.665   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      46.271 -14.489   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      46.747 -13.024   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      48.253 -12.704   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0      40.156 -19.830   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0      38.823 -17.520   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0      41.490 -17.520   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      42.985 -19.821   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0      45.636 -15.991   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      38.834 -21.894   0.000  0.00  0.00           H+0
HETATM   31  C   UNK     0      48.729 -11.240   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      50.235 -10.919   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      47.699 -10.095   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   30                                             
CONECT    5    4    6   10   26                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   27                                             
CONECT   10    9    5   14   25                                             
CONECT   11    9   12   15   28                                             
CONECT   12   11   13   17   19                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   20   29                                             
CONECT   18    2                                                            
CONECT   19   12                                                            
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   31                                                       
CONECT   25   10                                                            
CONECT   26    5                                                            
CONECT   27    9                                                            
CONECT   28   11                                                            
CONECT   29   17                                                            
CONECT   30    4                                                            
CONECT   31   24   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0000871
HETATM    1  C1  UNL     1       8.002   1.186  -0.061  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.705   0.360  -0.131  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.933  -0.952  -0.835  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.696   1.216  -0.797  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.354   0.473  -0.940  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.864   0.129   0.399  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.574  -0.588   0.573  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.403  -0.793   2.057  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.436  -0.034  -0.135  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.496  -0.002  -1.631  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.100  -0.508  -2.114  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.700   0.000  -0.962  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.134  -0.301  -0.962  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.763   0.312  -2.193  1.00  0.00           C  
HETATM   15  C15 UNL     1      -4.247   0.367  -2.134  1.00  0.00           C  
HETATM   16  C16 UNL     1      -4.790   0.896  -0.825  1.00  0.00           C  
HETATM   17  C17 UNL     1      -6.286   0.744  -0.867  1.00  0.00           C  
HETATM   18  C18 UNL     1      -6.901   0.519   0.447  1.00  0.00           C  
HETATM   19  O1  UNL     1      -8.027   0.074   0.502  1.00  0.00           O  
HETATM   20  C19 UNL     1      -6.202   0.815   1.721  1.00  0.00           C  
HETATM   21  C20 UNL     1      -4.708   0.849   1.606  1.00  0.00           C  
HETATM   22  C21 UNL     1      -4.166   0.201   0.373  1.00  0.00           C  
HETATM   23  C22 UNL     1      -4.571  -1.256   0.315  1.00  0.00           C  
HETATM   24  C23 UNL     1      -2.689   0.401   0.289  1.00  0.00           C  
HETATM   25  C24 UNL     1      -2.014  -0.089   1.505  1.00  0.00           C  
HETATM   26  C25 UNL     1      -0.513  -0.089   1.482  1.00  0.00           C  
HETATM   27  C26 UNL     1       0.083  -0.578   0.195  1.00  0.00           C  
HETATM   28  C27 UNL     1      -0.007  -2.076   0.127  1.00  0.00           C  
HETATM   29  H1  UNL     1       8.105   1.680  -1.041  1.00  0.00           H  
HETATM   30  H2  UNL     1       7.869   1.960   0.705  1.00  0.00           H  
HETATM   31  H3  UNL     1       8.810   0.465   0.160  1.00  0.00           H  
HETATM   32  H4  UNL     1       6.451   0.186   0.939  1.00  0.00           H  
HETATM   33  H5  UNL     1       7.997  -1.236  -0.663  1.00  0.00           H  
HETATM   34  H6  UNL     1       6.754  -0.890  -1.923  1.00  0.00           H  
HETATM   35  H7  UNL     1       6.314  -1.743  -0.345  1.00  0.00           H  
HETATM   36  H8  UNL     1       5.459   2.065  -0.091  1.00  0.00           H  
HETATM   37  H9  UNL     1       6.014   1.639  -1.750  1.00  0.00           H  
HETATM   38  H10 UNL     1       3.703   1.150  -1.524  1.00  0.00           H  
HETATM   39  H11 UNL     1       4.526  -0.432  -1.590  1.00  0.00           H  
HETATM   40  H12 UNL     1       3.843   1.103   1.004  1.00  0.00           H  
HETATM   41  H13 UNL     1       4.647  -0.476   0.978  1.00  0.00           H  
HETATM   42  H14 UNL     1       2.755  -1.640   0.168  1.00  0.00           H  
HETATM   43  H15 UNL     1       3.451  -0.885   2.478  1.00  0.00           H  
HETATM   44  H16 UNL     1       1.995   0.109   2.542  1.00  0.00           H  
HETATM   45  H17 UNL     1       1.936  -1.745   2.329  1.00  0.00           H  
HETATM   46  H18 UNL     1       1.342   1.078   0.154  1.00  0.00           H  
HETATM   47  H19 UNL     1       2.268  -0.631  -2.068  1.00  0.00           H  
HETATM   48  H20 UNL     1       1.508   1.051  -2.049  1.00  0.00           H  
HETATM   49  H21 UNL     1       0.098  -1.579  -2.282  1.00  0.00           H  
HETATM   50  H22 UNL     1      -0.210   0.007  -3.033  1.00  0.00           H  
HETATM   51  H23 UNL     1      -0.558   1.101  -0.916  1.00  0.00           H  
HETATM   52  H24 UNL     1      -2.433  -1.342  -0.879  1.00  0.00           H  
HETATM   53  H25 UNL     1      -2.479  -0.349  -3.048  1.00  0.00           H  
HETATM   54  H26 UNL     1      -2.290   1.297  -2.417  1.00  0.00           H  
HETATM   55  H27 UNL     1      -4.583   1.108  -2.918  1.00  0.00           H  
HETATM   56  H28 UNL     1      -4.720  -0.588  -2.424  1.00  0.00           H  
HETATM   57  H29 UNL     1      -4.553   1.991  -0.765  1.00  0.00           H  
HETATM   58  H30 UNL     1      -6.553  -0.147  -1.507  1.00  0.00           H  
HETATM   59  H31 UNL     1      -6.766   1.660  -1.310  1.00  0.00           H  
HETATM   60  H32 UNL     1      -6.586   1.780   2.165  1.00  0.00           H  
HETATM   61  H33 UNL     1      -6.543   0.035   2.464  1.00  0.00           H  
HETATM   62  H34 UNL     1      -4.391   1.929   1.588  1.00  0.00           H  
HETATM   63  H35 UNL     1      -4.313   0.359   2.539  1.00  0.00           H  
HETATM   64  H36 UNL     1      -3.753  -1.947   0.553  1.00  0.00           H  
HETATM   65  H37 UNL     1      -5.373  -1.463   1.082  1.00  0.00           H  
HETATM   66  H38 UNL     1      -5.006  -1.551  -0.649  1.00  0.00           H  
HETATM   67  H39 UNL     1      -2.499   1.479   0.123  1.00  0.00           H  
HETATM   68  H40 UNL     1      -2.395  -1.087   1.810  1.00  0.00           H  
HETATM   69  H41 UNL     1      -2.301   0.599   2.356  1.00  0.00           H  
HETATM   70  H42 UNL     1      -0.212  -0.782   2.289  1.00  0.00           H  
HETATM   71  H43 UNL     1      -0.094   0.906   1.726  1.00  0.00           H  
HETATM   72  H44 UNL     1      -0.388  -2.500   1.104  1.00  0.00           H  
HETATM   73  H45 UNL     1      -0.735  -2.442  -0.632  1.00  0.00           H  
HETATM   74  H46 UNL     1       0.963  -2.555  -0.148  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   27   46
CONECT   10   11   47   48
CONECT   11   12   49   50
CONECT   12   13   27   51
CONECT   13   14   24   52
CONECT   14   15   53   54
CONECT   15   16   55   56
CONECT   16   17   22   57
CONECT   17   18   58   59
CONECT   18   19   19   20
CONECT   20   21   60   61
CONECT   21   22   62   63
CONECT   22   23   24
CONECT   23   64   65   66
CONECT   24   25   67
CONECT   25   26   68   69
CONECT   26   27   70   71
CONECT   27   28
CONECT   28   72   73   74
END

HMDB0000871
     RDKit          3D
5alpha-Cholestanone
 74 77  0  0  0  0  0  0  0  0999 V2000
    8.0024    1.1863   -0.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7049    0.3598   -0.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9328   -0.9521   -0.8349 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6958    1.2162   -0.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3536    0.4729   -0.9396 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8642    0.1286    0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5738   -0.5882    0.5735 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4030   -0.7934    2.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.0340   -0.1347 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4955   -0.0018   -1.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1001   -0.5084   -2.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6999    0.0003   -0.9624 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1344   -0.3006   -0.9618 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7630    0.3115   -2.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2475    0.3665   -2.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7897    0.8957   -0.8247 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2856    0.7445   -0.8665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9014    0.5193    0.4474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0271    0.0740    0.5017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2017    0.8149    1.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7082    0.8489    1.6058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1660    0.2012    0.3733 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5713   -1.2556    0.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6890    0.4008    0.2889 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0139   -0.0894    1.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5129   -0.0888    1.4817 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0834   -0.5783    0.1954 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0073   -2.0758    0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1051    1.6802   -1.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8691    1.9602    0.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8103    0.4651    0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4509    0.1859    0.9391 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9975   -1.2359   -0.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7538   -0.8895   -1.9231 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3138   -1.7432   -0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4588    2.0647   -0.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0142    1.6386   -1.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7026    1.1503   -1.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5260   -0.4323   -1.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8427    1.1034    1.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6473   -0.4762    0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7548   -1.6396    0.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4508   -0.8847    2.4778 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9952    0.1087    2.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9359   -1.7451    2.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3422    1.0779    0.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2677   -0.6309   -2.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5079    1.0509   -2.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0976   -1.5791   -2.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2103    0.0067   -3.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5578    1.1013   -0.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4325   -1.3423   -0.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4795   -0.3488   -3.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2903    1.2969   -2.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5833    1.1075   -2.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7197   -0.5885   -2.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5527    1.9912   -0.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5528   -0.1468   -1.5065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7664    1.6602   -1.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5861    1.7797    2.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5426    0.0352    2.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3906    1.9290    1.5879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3131    0.3586    2.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7528   -1.9473    0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3732   -1.4634    1.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0058   -1.5508   -0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4987    1.4789    0.1232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3951   -1.0872    1.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3008    0.5986    2.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2123   -0.7824    2.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0938    0.9060    1.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3877   -2.5001    1.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7353   -2.4416   -0.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626   -2.5549   -0.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 27  9  1  0
 27 12  1  0
 24 13  1  0
 22 16  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  6
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  1
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  1
 13 52  1  1
 14 53  1  0
 14 54  1  0
 15 55  1  0
 15 56  1  0
 16 57  1  1
 17 58  1  0
 17 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 23 64  1  0
 23 65  1  0
 23 66  1  0
 24 67  1  6
 25 68  1  0
 25 69  1  0
 26 70  1  0
 26 71  1  0
 28 72  1  0
 28 73  1  0
 28 74  1  0
M  END

View in JSmol

Synonyms

Value	Source
5a-Cholestanone	Generator
5Α-cholestanone	Generator
(5a,17b)-17-Octylandrostan-3-one	HMDB
(5alpha)-Cholestan-3-one	HMDB
(5alpha)-Cholestanone	HMDB
5a(H)-Cholestan-3-one	HMDB
5a-Cholestan-3-one	HMDB
5alpha-Cholestane-3-one	HMDB
5alpha-Coprostanone	HMDB
Coprostanone, (5alpha)-isomer	HMDB
Coprostanone, (5beta)-isomer	HMDB
Coprostanone	HMDB
5-alpha-Cholestan-3-one	HMDB

Chemical Formula

C₂₇H₄₆O

Average Mass

386.6535 Da

Monoisotopic Mass

386.35487 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

566-88-1

SMILES

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

InChI Identifier

InChI=1S/C27H46O/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/h18-20,22-25H,6-17H2,1-5H3/t19-,20+,22+,23-,24+,25+,26+,27-/m1/s1

InChI Key

PESKGJQREUXSRR-UXIWKSIVSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol-skeleton
3-oxo-5-alpha-steroid
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

3-oxo steroid (CHEBI:17762 )
Cholesterol and derivatives (LMST01010174 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	128 - 130 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.4e-05 g/L	ALOGPS
logP	6.65	ALOGPS
logP	7.73	ChemAxon
logS	-7.4	ALOGPS
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	118.74 m³·mol⁻¹	ChemAxon
Polarizability	50.39 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

External Links

HMDB ID

HMDB0000871

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022292

KNApSAcK ID

Not Available

Chemspider ID

83174

KEGG Compound ID

C03238

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5832

PubChem Compound

92128

PDB ID

Not Available

ChEBI ID

17762

Good Scents ID

Not Available

References

General References

McNamara DJ, Proia A, Miettinen TA: Thin-layer and gas--liquid chromatographic identification of neutral steroids in human and rat feces. J Lipid Res. 1981 Mar;22(3):474-84. [PubMed:7240972 ]
Strandberg TE, Tilvis RS, Miettinen TA: Metabolic variables of cholesterol during squalene feeding in humans: comparison with cholestyramine treatment. J Lipid Res. 1990 Sep;31(9):1637-43. [PubMed:2246614 ]
Reddy BS, Wynder EL: Metabolic epidemiology of colon cancer. Fecal bile acids and neutral sterols in colon cancer patients and patients with adenomatous polyps. Cancer. 1977 Jun;39(6):2533-9. [PubMed:872053 ]
Shefer S, Hauser S, Mosbach EH: Biosynthesis of cholestanol: 5-alpha-cholestan-3-one reductase of rat liver. J Lipid Res. 1966 Nov;7(6):763-71. [PubMed:4381999 ]

Showing NP-Card for 5alpha-Cholestanone (NP0000331)

MOL for NP0000331 (5alpha-Cholestanone)

3D MOL for NP0000331 (5alpha-Cholestanone)

3D SDF for NP0000331 (5alpha-Cholestanone)

3D-SDF for NP0000331 (5alpha-Cholestanone)

PDB for NP0000331 (5alpha-Cholestanone)

3D PDB for NP0000331 (5alpha-Cholestanone)

SMILES for NP0000331 (5alpha-Cholestanone)

INCHI for NP0000331 (5alpha-Cholestanone)

Structure for NP0000331 (5alpha-Cholestanone)

3D Structure for NP0000331 (5alpha-Cholestanone)