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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:42:28 UTC

Update Date

2022-03-07 02:53:54 UTC

HMDB ID

HMDB0033934

Secondary Accession Numbers

HMDB33934

Metabolite Identification

Common Name

beta-Sitostenone

Description

beta-Sitostenone, also known as β-sitostenone, belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. Thus, beta-sitostenone is considered to be a sterol. Based on a literature review a significant number of articles have been published on beta-Sitostenone.

Structure

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


  Mrv0541 02241221522D          

 30 33  0  0  0  0            999 V2000
   -3.3995   -0.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1140   -1.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1140   -1.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3995   -2.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6851   -1.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6851   -1.0096    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9706   -0.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9706   -2.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2561   -1.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2561   -1.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2561    0.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9706    0.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1728    0.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5417    0.2279    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5417   -0.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8872   -0.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8872    0.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8285   -2.2471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6851   -0.1846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5417    1.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8873    1.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1728    1.4654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6017    1.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3162    1.8779    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0307    1.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7451    1.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0307    0.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5417    1.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3162    2.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0307    3.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 18  2  0  0  0  0
  4  5  2  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  7  6  1  0  0  0  0
  6 19  1  1  0  0  0
 12  7  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 13 14  1  0  0  0  0
 22 13  1  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 14 20  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 28  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 24 29  1  1  0  0  0
 29 30  1  0  0  0  0
M  END

HMDB0033934
     RDKit          3D
beta-Sitostenone
 78 81  0  0  0  0  0  0  0  0999 V2000
    6.4121    2.4826    0.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5869    0.9873    0.9426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5797    0.2648   -0.0084 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2406    0.7468    0.5088 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1484    0.1480   -0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7566    0.6219    0.1233 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7043    2.1489   -0.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149   -0.0076   -0.7678 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7463   -1.5089   -0.7299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2843   -1.8033    0.3788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3761   -1.0062   -0.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6639   -0.8868    0.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.3865   -1.0509    0.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6625   -1.1281    1.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.6100    0.1699    1.4405 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2248    0.8358   -0.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8546    0.5810   -0.8809 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7845    1.2313    1.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5571   -0.0496   -0.4882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9218    1.1684   -1.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4998    0.9858   -1.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7031    0.3452   -0.3876 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8445    1.2229    0.8032 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8661   -1.1829    0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3646   -1.3392   -0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1555   -2.1122   -0.7879 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.3988    3.0078    0.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9492    2.7137   -0.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7080    0.6560   -1.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2217    1.8399    0.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1929    0.3506    1.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4202    2.6723    0.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9053    0.3590   -1.7957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6629   -2.0238   -0.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2386   -1.8931   -1.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0514   -1.4249    1.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4486   -2.8980    0.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5664   -2.5070   -0.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5495   -2.9689    0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0654   -3.1590    1.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1820   -2.0097    2.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.3991    1.8847   -0.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0969    0.9263    2.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5663    2.2273    0.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7849    1.3203    1.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7841   -0.7185   -1.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6778   -1.6415   -1.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
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 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
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  3 28  1  0
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 26  8  1  0
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  1 31  1  0
  1 32  1  0
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  2 34  1  0
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 28 72  1  0
 29 73  1  0
 29 74  1  0
 29 75  1  0
 30 76  1  0
 30 77  1  0
 30 78  1  0
M  END


  Mrv0541 02241221522D          

 30 33  0  0  0  0            999 V2000
   -3.3995   -0.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1140   -1.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1140   -1.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3995   -2.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6851   -1.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1728    1.4654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.7451    1.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  6  1  0  0  0  0
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  3 18  2  0  0  0  0
  4  5  2  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  7  6  1  0  0  0  0
  6 19  1  1  0  0  0
 12  7  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
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 22 13  1  0  0  0  0
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 15 16  1  0  0  0  0
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 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 28  1  6  0  0  0
 23 24  1  0  0  0  0
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 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 24 29  1  1  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033934

> <DATABASE_NAME>
hmdb

> <SMILES>
CC[C@H](CC[C@@H](C)C1CCC2C3CCC4=CC(=O)CC[C@]4(C)C3CC[C@]12C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h18-21,24-27H,7-17H2,1-6H3/t20-,21-,24?,25?,26?,27?,28+,29-/m1/s1

> <INCHI_KEY>
RUVUHIUYGJBLGI-AXAJWWPKSA-N

> <FORMULA>
C29H48O

> <MOLECULAR_WEIGHT>
412.6908

> <EXACT_MASS>
412.370516158

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
52.86690421608813

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

> <ALOGPS_LOGP>
6.95

> <JCHEM_LOGP>
8.411722740000002

> <ALOGPS_LOGS>
-7.40

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.087826253912493

> <JCHEM_PKA_STRONGEST_BASIC>
-4.817440235063846

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
128.71469999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.63e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0033934
     RDKit          3D
beta-Sitostenone
 78 81  0  0  0  0  0  0  0  0999 V2000
    6.4121    2.4826    0.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5869    0.9873    0.9426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5797    0.2648   -0.0084 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2406    0.7468    0.5088 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1484    0.1480   -0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7566    0.6219    0.1233 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7043    2.1489   -0.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149   -0.0076   -0.7678 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7463   -1.5089   -0.7299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2843   -1.8033    0.3788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3761   -1.0062   -0.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6639   -0.8868    0.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3097   -2.3042    0.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5316   -2.2084    1.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3865   -1.0509    0.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6625   -1.1281    1.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5720   -0.0376    0.7978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6100    0.1699    1.4405 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2248    0.8358   -0.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8546    0.5810   -0.8809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8647    0.1653    0.1866 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7845    1.2313    1.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5571   -0.0496   -0.4882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9218    1.1684   -1.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4998    0.9858   -1.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7031    0.3452   -0.3876 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8445    1.2229    0.8032 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8661   -1.1829    0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3646   -1.3392   -0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1555   -2.1122   -0.7879 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8400    2.8502    1.6739 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3988    3.0078    0.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9492    2.7137   -0.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6129    0.7363    0.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3970    0.6468    1.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7080    0.6560   -1.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2217    1.8399    0.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1929    0.3506    1.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1431   -0.9307   -0.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2688    0.3969   -1.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6774    0.3851    1.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7161    2.5268   -0.4126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0336    2.4381   -0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4202    2.6723    0.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9053    0.3590   -1.7957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6629   -2.0238   -0.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2386   -1.8931   -1.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0514   -1.4249    1.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4486   -2.8980    0.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5289   -1.4481   -1.2799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6973   -0.6397    1.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5664   -2.5070   -0.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5495   -2.9689    0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0654   -3.1590    1.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1820   -2.0097    2.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0774   -2.0252    1.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9955    0.6398   -1.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3991    1.8847   -0.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5264    1.4828   -1.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8947   -0.2487   -1.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0969    0.9263    2.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5663    2.2273    0.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7849    1.3203    1.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7841   -0.7185   -1.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9406    2.0121   -0.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5058    1.5101   -1.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1076    1.9915   -1.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3930    0.3783   -2.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1570    1.0538    1.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8760    2.2905    0.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8913    1.1021    1.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7296   -1.4860    1.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9998   -1.2645    0.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6088   -0.6006   -1.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5535   -2.3425   -0.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8942   -2.8398   -1.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5083   -2.8087   -0.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6778   -1.6415   -1.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  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  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  1
  3 28  1  0
 28 29  1  0
 28 30  1  0
 26  8  1  0
 26 11  1  0
 23 12  1  0
 21 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  6
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  1
  7 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
 12 51  1  0
 13 52  1  0
 13 53  1  0
 14 54  1  0
 14 55  1  0
 16 56  1  0
 19 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 22 61  1  0
 22 62  1  0
 22 63  1  0
 23 64  1  0
 24 65  1  0
 24 66  1  0
 25 67  1  0
 25 68  1  0
 27 69  1  0
 27 70  1  0
 27 71  1  0
 28 72  1  0
 29 73  1  0
 29 74  1  0
 29 75  1  0
 30 76  1  0
 30 77  1  0
 30 78  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      -6.346  -1.115   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.679  -1.885   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.679  -3.425   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.346  -4.195   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.012  -3.425   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.012  -1.885   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.678  -1.115   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.678  -4.195   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.345  -3.425   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.345  -1.885   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.345   1.195   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.678   0.425   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.323   1.195   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.011   0.425   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.011  -1.115   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.656  -1.115   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.656   0.425   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -9.013  -4.195   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -5.012  -0.345   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.011   1.965   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.656   3.505   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.323   2.735   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.990   2.735   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.324   3.505   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.657   2.735   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.991   3.505   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.657   1.195   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.011   3.505   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.324   5.045   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.657   5.815   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    1    5    7   19                                             
CONECT    7    6   12   10                                                  
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    7    9   15                                                  
CONECT   11   12   14                                                       
CONECT   12    7   11                                                       
CONECT   13   14   22   17                                                  
CONECT   14   11   13   15   20                                             
CONECT   15   10   14   16                                                  
CONECT   16   15   17                                                       
CONECT   17   13   16                                                       
CONECT   18    3                                                            
CONECT   19    6                                                            
CONECT   20   14                                                            
CONECT   21   22   23                                                       
CONECT   22   13   21   28                                                  
CONECT   23   21   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   22                                                            
CONECT   29   24   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

COMPND    HMDB0033934
HETATM    1  C1  UNL     1       6.412   2.483   0.817  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.587   0.987   0.943  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.580   0.265  -0.008  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.241   0.747   0.509  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.148   0.148  -0.300  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.757   0.622   0.123  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.704   2.149  -0.058  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.715  -0.008  -0.768  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.746  -1.509  -0.730  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.284  -1.803   0.379  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.376  -1.006  -0.264  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.664  -0.887   0.392  1.00  0.00           C  
HETATM   13  C13 UNL     1      -3.310  -2.304   0.351  1.00  0.00           C  
HETATM   14  C14 UNL     1      -4.532  -2.208   1.213  1.00  0.00           C  
HETATM   15  C15 UNL     1      -5.387  -1.051   0.845  1.00  0.00           C  
HETATM   16  C16 UNL     1      -6.663  -1.128   1.125  1.00  0.00           C  
HETATM   17  C17 UNL     1      -7.572  -0.038   0.798  1.00  0.00           C  
HETATM   18  O1  UNL     1      -8.610   0.170   1.441  1.00  0.00           O  
HETATM   19  C18 UNL     1      -7.225   0.836  -0.341  1.00  0.00           C  
HETATM   20  C19 UNL     1      -5.855   0.581  -0.881  1.00  0.00           C  
HETATM   21  C20 UNL     1      -4.865   0.165   0.187  1.00  0.00           C  
HETATM   22  C21 UNL     1      -4.785   1.231   1.261  1.00  0.00           C  
HETATM   23  C22 UNL     1      -3.557  -0.050  -0.488  1.00  0.00           C  
HETATM   24  C23 UNL     1      -2.922   1.168  -1.042  1.00  0.00           C  
HETATM   25  C24 UNL     1      -1.500   0.986  -1.505  1.00  0.00           C  
HETATM   26  C25 UNL     1      -0.703   0.345  -0.388  1.00  0.00           C  
HETATM   27  C26 UNL     1      -0.844   1.223   0.803  1.00  0.00           C  
HETATM   28  C27 UNL     1       5.866  -1.183   0.161  1.00  0.00           C  
HETATM   29  C28 UNL     1       7.365  -1.339  -0.223  1.00  0.00           C  
HETATM   30  C29 UNL     1       5.155  -2.112  -0.788  1.00  0.00           C  
HETATM   31  H1  UNL     1       5.840   2.850   1.674  1.00  0.00           H  
HETATM   32  H2  UNL     1       7.399   3.008   0.817  1.00  0.00           H  
HETATM   33  H3  UNL     1       5.949   2.714  -0.162  1.00  0.00           H  
HETATM   34  H4  UNL     1       7.613   0.736   0.681  1.00  0.00           H  
HETATM   35  H5  UNL     1       6.397   0.647   1.980  1.00  0.00           H  
HETATM   36  H6  UNL     1       5.708   0.656  -1.023  1.00  0.00           H  
HETATM   37  H7  UNL     1       4.222   1.840   0.635  1.00  0.00           H  
HETATM   38  H8  UNL     1       4.193   0.351   1.579  1.00  0.00           H  
HETATM   39  H9  UNL     1       3.143  -0.931  -0.032  1.00  0.00           H  
HETATM   40  H10 UNL     1       3.269   0.397  -1.342  1.00  0.00           H  
HETATM   41  H11 UNL     1       1.677   0.385   1.181  1.00  0.00           H  
HETATM   42  H12 UNL     1       2.716   2.527  -0.413  1.00  0.00           H  
HETATM   43  H13 UNL     1       1.034   2.438  -0.889  1.00  0.00           H  
HETATM   44  H14 UNL     1       1.420   2.672   0.864  1.00  0.00           H  
HETATM   45  H15 UNL     1       0.905   0.359  -1.796  1.00  0.00           H  
HETATM   46  H16 UNL     1       1.663  -2.024  -0.643  1.00  0.00           H  
HETATM   47  H17 UNL     1       0.239  -1.893  -1.668  1.00  0.00           H  
HETATM   48  H18 UNL     1       0.051  -1.425   1.344  1.00  0.00           H  
HETATM   49  H19 UNL     1      -0.449  -2.898   0.342  1.00  0.00           H  
HETATM   50  H20 UNL     1      -1.529  -1.448  -1.280  1.00  0.00           H  
HETATM   51  H21 UNL     1      -2.697  -0.640   1.460  1.00  0.00           H  
HETATM   52  H22 UNL     1      -3.566  -2.507  -0.711  1.00  0.00           H  
HETATM   53  H23 UNL     1      -2.550  -2.969   0.766  1.00  0.00           H  
HETATM   54  H24 UNL     1      -5.065  -3.159   1.183  1.00  0.00           H  
HETATM   55  H25 UNL     1      -4.182  -2.010   2.260  1.00  0.00           H  
HETATM   56  H26 UNL     1      -7.077  -2.025   1.617  1.00  0.00           H  
HETATM   57  H27 UNL     1      -7.995   0.640  -1.140  1.00  0.00           H  
HETATM   58  H28 UNL     1      -7.399   1.885  -0.025  1.00  0.00           H  
HETATM   59  H29 UNL     1      -5.526   1.483  -1.437  1.00  0.00           H  
HETATM   60  H30 UNL     1      -5.895  -0.249  -1.621  1.00  0.00           H  
HETATM   61  H31 UNL     1      -4.097   0.926   2.084  1.00  0.00           H  
HETATM   62  H32 UNL     1      -4.566   2.227   0.846  1.00  0.00           H  
HETATM   63  H33 UNL     1      -5.785   1.320   1.787  1.00  0.00           H  
HETATM   64  H34 UNL     1      -3.784  -0.718  -1.381  1.00  0.00           H  
HETATM   65  H35 UNL     1      -2.941   2.012  -0.323  1.00  0.00           H  
HETATM   66  H36 UNL     1      -3.506   1.510  -1.924  1.00  0.00           H  
HETATM   67  H37 UNL     1      -1.108   1.992  -1.721  1.00  0.00           H  
HETATM   68  H38 UNL     1      -1.393   0.378  -2.422  1.00  0.00           H  
HETATM   69  H39 UNL     1      -0.157   1.054   1.629  1.00  0.00           H  
HETATM   70  H40 UNL     1      -0.876   2.290   0.435  1.00  0.00           H  
HETATM   71  H41 UNL     1      -1.891   1.102   1.214  1.00  0.00           H  
HETATM   72  H42 UNL     1       5.730  -1.486   1.196  1.00  0.00           H  
HETATM   73  H43 UNL     1       8.000  -1.264   0.673  1.00  0.00           H  
HETATM   74  H44 UNL     1       7.609  -0.601  -1.013  1.00  0.00           H  
HETATM   75  H45 UNL     1       7.553  -2.343  -0.658  1.00  0.00           H  
HETATM   76  H46 UNL     1       5.894  -2.840  -1.261  1.00  0.00           H  
HETATM   77  H47 UNL     1       4.508  -2.809  -0.196  1.00  0.00           H  
HETATM   78  H48 UNL     1       4.678  -1.642  -1.643  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3   34   35
CONECT    3    4   28   36
CONECT    4    5   37   38
CONECT    5    6   39   40
CONECT    6    7    8   41
CONECT    7   42   43   44
CONECT    8    9   26   45
CONECT    9   10   46   47
CONECT   10   11   48   49
CONECT   11   12   26   50
CONECT   12   13   23   51
CONECT   13   14   52   53
CONECT   14   15   54   55
CONECT   15   16   16   21
CONECT   16   17   56
CONECT   17   18   18   19
CONECT   19   20   57   58
CONECT   20   21   59   60
CONECT   21   22   23
CONECT   22   61   62   63
CONECT   23   24   64
CONECT   24   25   65   66
CONECT   25   26   67   68
CONECT   26   27
CONECT   27   69   70   71
CONECT   28   29   30   72
CONECT   29   73   74   75
CONECT   30   76   77   78
END

HMDB0033934
     RDKit          3D
beta-Sitostenone
 78 81  0  0  0  0  0  0  0  0999 V2000
    6.4121    2.4826    0.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5869    0.9873    0.9426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5797    0.2648   -0.0084 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2406    0.7468    0.5088 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1484    0.1480   -0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7566    0.6219    0.1233 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7043    2.1489   -0.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149   -0.0076   -0.7678 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7463   -1.5089   -0.7299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2843   -1.8033    0.3788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3761   -1.0062   -0.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6639   -0.8868    0.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3097   -2.3042    0.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5316   -2.2084    1.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3865   -1.0509    0.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6625   -1.1281    1.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5720   -0.0376    0.7978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6100    0.1699    1.4405 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2248    0.8358   -0.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8546    0.5810   -0.8809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8647    0.1653    0.1866 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7845    1.2313    1.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5571   -0.0496   -0.4882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9218    1.1684   -1.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4998    0.9858   -1.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7031    0.3452   -0.3876 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8445    1.2229    0.8032 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8661   -1.1829    0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3646   -1.3392   -0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1555   -2.1122   -0.7879 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8400    2.8502    1.6739 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3988    3.0078    0.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9492    2.7137   -0.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6129    0.7363    0.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3970    0.6468    1.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7080    0.6560   -1.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2217    1.8399    0.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1929    0.3506    1.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1431   -0.9307   -0.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2688    0.3969   -1.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6774    0.3851    1.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7161    2.5268   -0.4126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0336    2.4381   -0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4202    2.6723    0.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9053    0.3590   -1.7957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6629   -2.0238   -0.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2386   -1.8931   -1.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0514   -1.4249    1.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4486   -2.8980    0.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5289   -1.4481   -1.2799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6973   -0.6397    1.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5664   -2.5070   -0.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5495   -2.9689    0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0654   -3.1590    1.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1820   -2.0097    2.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0774   -2.0252    1.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9955    0.6398   -1.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3991    1.8847   -0.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5264    1.4828   -1.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8947   -0.2487   -1.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0969    0.9263    2.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5663    2.2273    0.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7849    1.3203    1.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7841   -0.7185   -1.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9406    2.0121   -0.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5058    1.5101   -1.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1076    1.9915   -1.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3930    0.3783   -2.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1570    1.0538    1.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8760    2.2905    0.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8913    1.1021    1.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7296   -1.4860    1.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9998   -1.2645    0.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6088   -0.6006   -1.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5535   -2.3425   -0.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8942   -2.8398   -1.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5083   -2.8087   -0.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6778   -1.6415   -1.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  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  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  1
  3 28  1  0
 28 29  1  0
 28 30  1  0
 26  8  1  0
 26 11  1  0
 23 12  1  0
 21 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  6
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  1
  7 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
 12 51  1  0
 13 52  1  0
 13 53  1  0
 14 54  1  0
 14 55  1  0
 16 56  1  0
 19 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 22 61  1  0
 22 62  1  0
 22 63  1  0
 23 64  1  0
 24 65  1  0
 24 66  1  0
 25 67  1  0
 25 68  1  0
 27 69  1  0
 27 70  1  0
 27 71  1  0
 28 72  1  0
 29 73  1  0
 29 74  1  0
 29 75  1  0
 30 76  1  0
 30 77  1  0
 30 78  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
b-Sitostenone	Generator
Β-sitostenone	Generator
4-Stigmasten-3-one	HMDB
laquo deltaraquo 4-Sitosterol-3-one	HMDB
Sitost-4-en-3-one	HMDB
Sitostenone	HMDB

Chemical Formula

C₂₉H₄₈O

Average Molecular Weight

412.6908

Monoisotopic Molecular Weight

412.370516158

IUPAC Name

(2R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

Traditional Name

(2R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

CAS Registry Number

1058-61-3

SMILES

CC[C@H](CC[C@@H](C)C1CCC2C3CCC4=CC(=O)CC[C@]4(C)C3CC[C@]12C)C(C)C

InChI Identifier

InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h18-21,24-27H,7-17H2,1-6H3/t20-,21-,24?,25?,26?,27?,28+,29-/m1/s1

InChI Key

RUVUHIUYGJBLGI-AXAJWWPKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

Triterpenoid
Stigmastane-skeleton
Oxosteroid
3-oxosteroid
3-oxo-delta-4-steroid
Delta-4-steroid
Cyclohexenone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

steroid (CHEBI:68105 )

Ontology

Not Available

Urine (HMDB: HMDB0033934)

Cytoplasm (HMDB: HMDB0033934)
Cell membrane (HMDB: HMDB0033934)

Tissue substructure

Hepatic tissue (HMDB: HMDB0033934)

Cellular substructure

Extracellular (HMDB: HMDB0033934)
Membrane (HMDB: HMDB0033934)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033934)

Source

Endogenous

Endogenous (HMDB: HMDB0033934)

Plant

Animal

Animal (HMDB: HMDB0033934)

Exogenous

Food

Food (HMDB: HMDB0033934)

Soy

Soy bean (FooDB: FOOD00085)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Fruit

Other fruit

Date (FooDB: FOOD00135)

Herb and spice

Spice

Cardamom (FooDB: FOOD00074)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0033934)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0033934)

Cellular process

Cell signaling (HMDB: HMDB0033934)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0033934)

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	95 - 96.5 °C	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	1.6e-05 g/L	ALOGPS
logP	6.95	ALOGPS
logP	8.41	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	19.09	ChemAxon
pKa (Strongest Basic)	-4.8	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	6	ChemAxon
Refractivity	128.71 m³·mol⁻¹	ChemAxon
Polarizability	52.87 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	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	197.127	31661259
DarkChem	[M-H]-	196.142	31661259
DeepCCS	[M-2H]-	237.81	30932474
DeepCCS	[M+Na]+	213.288	30932474
AllCCS	[M+H]+	208.4	32859911
AllCCS	[M+H-H2O]+	206.5	32859911
AllCCS	[M+NH4]+	210.3	32859911
AllCCS	[M+Na]+	210.8	32859911
AllCCS	[M-H]-	206.4	32859911
AllCCS	[M+Na-2H]-	208.5	32859911
AllCCS	[M+HCOO]-	210.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
beta-Sitostenone	CC[C@H](CC[C@@H](C)C1CCC2C3CCC4=CC(=O)CC[C@]4(C)C3CC[C@]12C)C(C)C	3966.6	Standard polar	33892256
beta-Sitostenone	CC[C@H](CC[C@@H](C)C1CCC2C3CCC4=CC(=O)CC[C@]4(C)C3CC[C@]12C)C(C)C	3485.0	Standard non polar	33892256
beta-Sitostenone	CC[C@H](CC[C@@H](C)C1CCC2C3CCC4=CC(=O)CC[C@]4(C)C3CC[C@]12C)C(C)C	3440.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
beta-Sitostenone,1TMS,isomer #1	CC[C@H](CC[C@@H](C)C1CCC2C3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)C3CC[C@@]21C)C(C)C	3345.0	Semi standard non polar	33892256
beta-Sitostenone,1TMS,isomer #1	CC[C@H](CC[C@@H](C)C1CCC2C3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)C3CC[C@@]21C)C(C)C	3399.9	Standard non polar	33892256
beta-Sitostenone,1TBDMS,isomer #1	CC[C@H](CC[C@@H](C)C1CCC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)C3CC[C@@]21C)C(C)C	3573.6	Semi standard non polar	33892256
beta-Sitostenone,1TBDMS,isomer #1	CC[C@H](CC[C@@H](C)C1CCC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)C3CC[C@@]21C)C(C)C	3614.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Sitostenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-000t-3129000000-15ebf2ee5480bfd577c7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Sitostenone 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 - beta-Sitostenone 10V, Positive-QTOF	splash10-03di-1115900000-b4d381028de9800d2e43	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sitostenone 20V, Positive-QTOF	splash10-03dj-7229200000-28c62fdbbd0322f6f3b5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sitostenone 40V, Positive-QTOF	splash10-0005-9045000000-88ed42bed31da02b16cc	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sitostenone 10V, Negative-QTOF	splash10-03di-0000900000-a3b18c4a22bf0e167d5f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sitostenone 20V, Negative-QTOF	splash10-03di-0001900000-7c7eb5ad66f7a269c890	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sitostenone 40V, Negative-QTOF	splash10-0002-2019000000-9799ee0044320c2ac354	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sitostenone 10V, Positive-QTOF	splash10-03di-0013900000-dd3f19a6784ecef0a3a8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sitostenone 20V, Positive-QTOF	splash10-0203-9236200000-f893636a370cd6916e85	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sitostenone 40V, Positive-QTOF	splash10-0a4l-9620000000-d480b6411e0b1ddc74b5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sitostenone 10V, Negative-QTOF	splash10-03di-0000900000-363450e12a0ea926276e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sitostenone 20V, Negative-QTOF	splash10-03di-0000900000-04f321f2b318172184db	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sitostenone 40V, Negative-QTOF	splash10-0btd-0029800000-808df1c4b5b606832bba	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

Not Available

KNApSAcK ID

C00029821

Chemspider ID

4588409

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5484202

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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for beta-Sitostenone (HMDB0033934)

MOL for HMDB0033934 (beta-Sitostenone)

3D MOL for HMDB0033934 (beta-Sitostenone)

3D SDF for HMDB0033934 (beta-Sitostenone)

3D-SDF for HMDB0033934 (beta-Sitostenone)

PDB for HMDB0033934 (beta-Sitostenone)

3D PDB for HMDB0033934 (beta-Sitostenone)

SMILES for HMDB0033934 (beta-Sitostenone)

INCHI for HMDB0033934 (beta-Sitostenone)

Structure for HMDB0033934 (beta-Sitostenone)

3D Structure for HMDB0033934 (beta-Sitostenone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra