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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:15:25 UTC

Update Date

2022-03-07 02:54:05 UTC

HMDB ID

HMDB0034415

Secondary Accession Numbers

HMDB34415

Metabolite Identification

Common Name

Withanolide A

Description

Withanolide A belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. Thus, withanolide a is considered to be a sterol lipid molecule. Withanolide A is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

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


  Mrv0541 02241210092D          

 34 39  0  0  0  0            999 V2000
    2.0505    0.5657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4991    1.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7535    1.9624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5604    2.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8147    2.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1078    1.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6922    1.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4364    0.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9217   -0.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4364   -1.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3471   -0.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4903   -0.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4903   -1.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2052   -0.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2052   -0.0323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9188   -1.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9188   -2.0944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2052   -2.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4903   -2.0944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7769   -2.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0620   -2.9192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0620   -2.0944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0620   -1.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7769   -0.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7769   -0.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0620    0.3801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3471   -0.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2618    0.7883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4903   -2.9192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9188    1.6929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1117    1.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8573    0.7362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4087    0.1244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9052    1.8043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 32  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 31  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 34  1  0  0  0  0
  8  9  1  0  0  0  0
  8 27  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 23  1  0  0  0  0
 11 27  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 19  1  0  0  0  0
 13 24  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 29  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END

HMDB0034415
     RDKit          3D
Withanolide A
 72 77  0  0  0  0  0  0  0  0999 V2000
    7.2003   -0.2465    0.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7395   -0.1358    0.5167 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3367    0.8015    1.3572 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3358    1.7026    2.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9046    0.9398    1.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4924    1.8219    2.4254 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0763    0.0449    0.9542 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4707   -0.3260   -0.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4378   -1.1727   -1.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3967   -2.4605   -0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1357   -1.4975   -2.2840 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2259   -0.5660   -1.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4358   -1.7248   -2.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6521   -2.0823   -1.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6281   -1.0566   -0.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0315   -0.7493    0.2828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0924   -1.5620   -0.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6898   -1.1681   -1.5786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4299   -1.1250   -0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8065    0.2701   -0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1691    0.9261   -1.2303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0800    0.3147    0.8228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3858    1.7341    1.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4878    2.7062    1.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7516    0.9587    0.7263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8165    0.4525    2.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9758    1.3463   -1.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8695    0.6345   -1.7795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1523    0.0383   -0.7692 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5665    1.2082    0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7761   -1.0789   -0.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4036   -0.9781   -0.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6944   -0.6733    1.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6695    0.7398    0.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6419    2.5318    1.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9177    2.1861    2.9086 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2507    1.1550    2.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7713    0.5538   -0.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4158   -2.3395    0.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3927   -2.9720   -0.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6757   -3.2133   -0.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6775   -2.2917   -2.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5087    0.1745   -2.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1030   -1.3531   -3.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0641   -2.5954   -2.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9305   -2.6693   -0.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2755   -1.8515   -0.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.9364   -0.1363    0.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8848    1.2048   -1.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0710    2.1451   -0.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5100    1.6035   -0.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6573   -1.9029    0.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1877   -1.4941   -1.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  9 12  1  0
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 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
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 23 24  2  0
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 34  2  1  0
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 29 16  1  0
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 27 20  1  0
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  4 40  1  0
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 17 53  1  0
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 29 63  1  0
 30 64  1  0
 30 65  1  0
 31 66  1  0
 31 67  1  0
 33 68  1  0
 33 69  1  0
 33 70  1  0
 34 71  1  0
 34 72  1  0
M  END


  Mrv0541 02241210092D          

 34 39  0  0  0  0            999 V2000
    2.0505    0.5657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4991    1.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7535    1.9624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5604    2.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8147    2.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1078    1.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6922    1.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4364    0.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9217   -0.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4364   -1.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3471   -0.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4903   -0.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4903   -1.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2052   -0.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8573    0.7362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4087    0.1244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  1 32  1  0  0  0  0
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  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 31  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 34  1  0  0  0  0
  8  9  1  0  0  0  0
  8 27  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 23  1  0  0  0  0
 11 27  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 19  1  0  0  0  0
 13 24  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 29  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
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 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034415

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(C)C(=O)OC(C1)C(C)(O)C1CCC2C3C4OC4C4(O)CC=CC(=O)C4(C)C3CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O6/c1-14-13-20(33-24(30)15(14)2)27(5,31)18-9-8-16-21-17(10-12-25(16,18)3)26(4)19(29)7-6-11-28(26,32)23-22(21)34-23/h6-7,16-18,20-23,31-32H,8-13H2,1-5H3

> <INCHI_KEY>
DXWHOKCXBGLTMQ-UHFFFAOYSA-N

> <FORMULA>
C28H38O6

> <MOLECULAR_WEIGHT>
470.5977

> <EXACT_MASS>
470.266838948

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
51.85321071853424

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
15-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.0²,⁴.0⁵,¹⁰.0¹⁴,¹⁸]octadec-7-en-9-one

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
3.703445505999998

> <ALOGPS_LOGS>
-4.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.85865391456004

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.016008923436715

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3314307765309374

> <JCHEM_POLAR_SURFACE_AREA>
96.36

> <JCHEM_REFRACTIVITY>
126.94809999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.53e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.0²,⁴.0⁵,¹⁰.0¹⁴,¹⁸]octadec-7-en-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034415
     RDKit          3D
Withanolide A
 72 77  0  0  0  0  0  0  0  0999 V2000
    7.2003   -0.2465    0.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7395   -0.1358    0.5167 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3367    0.8015    1.3572 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3358    1.7026    2.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9046    0.9398    1.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4924    1.8219    2.4254 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0763    0.0449    0.9542 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4707   -0.3260   -0.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4378   -1.1727   -1.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3967   -2.4605   -0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1357   -1.4975   -2.2840 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2259   -0.5660   -1.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4358   -1.7248   -2.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6521   -2.0823   -1.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6281   -1.0566   -0.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0315   -0.7493    0.2828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0924   -1.5620   -0.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6898   -1.1681   -1.5786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4299   -1.1250   -0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8065    0.2701   -0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1691    0.9261   -1.2303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0800    0.3147    0.8228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3858    1.7341    1.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4878    2.7062    1.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0973    2.3996    0.8114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2644    3.3108    0.6275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7516    0.9587    0.7263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8165    0.4525    2.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3355    0.7320    0.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9758    1.3463   -1.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8695    0.6345   -1.7795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1523    0.0383   -0.7692 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5665    1.2082    0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7761   -1.0789   -0.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4036   -0.9781   -0.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6944   -0.6733    1.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6695    0.7398    0.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6419    2.5318    1.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9177    2.1861    2.9086 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2507    1.1550    2.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7713    0.5538   -0.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4158   -2.3395    0.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3927   -2.9720   -0.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6757   -3.2133   -0.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6775   -2.2917   -2.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5087    0.1745   -2.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1030   -1.3531   -3.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0641   -2.5954   -2.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5870   -2.0042   -1.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6557   -3.1064   -0.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0267   -1.4519    0.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1439   -1.0534    1.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9305   -2.6693   -0.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2755   -1.8515   -0.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1214    1.8912   -1.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8976   -0.2628    1.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9364   -0.1363    0.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4236    1.9677    1.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8262    3.6896    1.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9439   -0.6269    2.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8497    0.7314    2.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5981    1.0284    2.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7453    1.1462    1.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8848    1.2048   -1.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8486    2.4463   -1.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2985    1.3992   -2.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2357   -0.1076   -2.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6391    1.0985    1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0710    2.1451   -0.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5100    1.6035   -0.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6573   -1.9029    0.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1877   -1.4941   -1.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  9 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  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
  8 34  1  0
 34  2  1  0
 32 12  1  0
 32 15  1  0
 29 16  1  0
 19 17  1  0
 27 20  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  4 38  1  0
  4 39  1  0
  4 40  1  0
  8 41  1  0
 10 42  1  0
 10 43  1  0
 10 44  1  0
 11 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 16 52  1  0
 17 53  1  0
 19 54  1  0
 21 55  1  0
 22 56  1  0
 22 57  1  0
 23 58  1  0
 24 59  1  0
 28 60  1  0
 28 61  1  0
 28 62  1  0
 29 63  1  0
 30 64  1  0
 30 65  1  0
 31 66  1  0
 31 67  1  0
 33 68  1  0
 33 69  1  0
 33 70  1  0
 34 71  1  0
 34 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  O   UNK     0       3.828   1.056   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.798   2.200   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.273   3.663   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.779   3.984   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.254   5.449   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.201   2.968   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.292   1.880   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.815   0.414   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.721  -0.830   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.815  -2.077   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.648  -1.600   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.649  -0.830   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.649  -2.370   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.983  -1.600   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.983  -0.060   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -7.315  -2.370   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -7.315  -3.909   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.983  -4.679   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.649  -3.909   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.317  -4.679   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.982  -5.449   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.982  -3.909   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.982  -2.370   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.317  -1.600   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.317  -0.060   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.982   0.709   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.648  -0.060   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.489   1.472   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.649  -5.449   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.315   3.160   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.809   2.839   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.334   1.374   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.363   0.232   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       1.690   3.368   0.000  0.00  0.00           O+0
CONECT    1    2   32                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   31                                                  
CONECT    5    4                                                            
CONECT    6    7                                                            
CONECT    7    2    6    8   34                                             
CONECT    8    7    9   27                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   23   27                                                  
CONECT   12   13                                                            
CONECT   13   12   14   19   24                                             
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   13   18   20   29                                             
CONECT   20   19   21   22                                                  
CONECT   21   20   22                                                       
CONECT   22   20   21   23                                                  
CONECT   23   11   22   24                                                  
CONECT   24   13   23   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27    8   11   26   28                                             
CONECT   28   27                                                            
CONECT   29   19                                                            
CONECT   30   31                                                            
CONECT   31    4   30   32                                                  
CONECT   32    1   31   33                                                  
CONECT   33   32                                                            
CONECT   34    7                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

COMPND    HMDB0034415
HETATM    1  C1  UNL     1       7.200  -0.247   0.250  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.740  -0.136   0.517  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.337   0.802   1.357  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.336   1.703   2.003  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.905   0.940   1.628  1.00  0.00           C  
HETATM    6  O1  UNL     1       3.492   1.822   2.425  1.00  0.00           O  
HETATM    7  O2  UNL     1       3.076   0.045   0.954  1.00  0.00           O  
HETATM    8  C6  UNL     1       3.471  -0.326  -0.349  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.438  -1.173  -1.055  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.397  -2.460  -0.318  1.00  0.00           C  
HETATM   11  O3  UNL     1       3.136  -1.497  -2.284  1.00  0.00           O  
HETATM   12  C9  UNL     1       1.226  -0.566  -1.555  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.436  -1.725  -2.216  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.652  -2.082  -1.268  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.628  -1.057  -0.118  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.031  -0.749   0.283  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.092  -1.562  -0.413  1.00  0.00           C  
HETATM   18  O4  UNL     1      -3.690  -1.168  -1.579  1.00  0.00           O  
HETATM   19  C15 UNL     1      -4.430  -1.125  -0.397  1.00  0.00           C  
HETATM   20  C16 UNL     1      -4.806   0.270  -0.031  1.00  0.00           C  
HETATM   21  O5  UNL     1      -5.169   0.926  -1.230  1.00  0.00           O  
HETATM   22  C17 UNL     1      -6.080   0.315   0.823  1.00  0.00           C  
HETATM   23  C18 UNL     1      -6.386   1.734   1.128  1.00  0.00           C  
HETATM   24  C19 UNL     1      -5.488   2.706   1.128  1.00  0.00           C  
HETATM   25  C20 UNL     1      -4.097   2.400   0.811  1.00  0.00           C  
HETATM   26  O6  UNL     1      -3.264   3.311   0.627  1.00  0.00           O  
HETATM   27  C21 UNL     1      -3.752   0.959   0.726  1.00  0.00           C  
HETATM   28  C22 UNL     1      -3.817   0.452   2.179  1.00  0.00           C  
HETATM   29  C23 UNL     1      -2.335   0.732   0.280  1.00  0.00           C  
HETATM   30  C24 UNL     1      -1.976   1.346  -1.030  1.00  0.00           C  
HETATM   31  C25 UNL     1      -0.869   0.635  -1.779  1.00  0.00           C  
HETATM   32  C26 UNL     1       0.152   0.038  -0.769  1.00  0.00           C  
HETATM   33  C27 UNL     1       0.566   1.208   0.028  1.00  0.00           C  
HETATM   34  C28 UNL     1       4.776  -1.079  -0.153  1.00  0.00           C  
HETATM   35  H1  UNL     1       7.404  -0.978  -0.559  1.00  0.00           H  
HETATM   36  H2  UNL     1       7.694  -0.673   1.170  1.00  0.00           H  
HETATM   37  H3  UNL     1       7.669   0.740   0.078  1.00  0.00           H  
HETATM   38  H4  UNL     1       6.642   2.532   1.319  1.00  0.00           H  
HETATM   39  H5  UNL     1       5.918   2.186   2.909  1.00  0.00           H  
HETATM   40  H6  UNL     1       7.251   1.155   2.310  1.00  0.00           H  
HETATM   41  H7  UNL     1       3.771   0.554  -0.964  1.00  0.00           H  
HETATM   42  H8  UNL     1       2.416  -2.339   0.791  1.00  0.00           H  
HETATM   43  H9  UNL     1       3.393  -2.972  -0.516  1.00  0.00           H  
HETATM   44  H10 UNL     1       1.676  -3.213  -0.651  1.00  0.00           H  
HETATM   45  H11 UNL     1       3.678  -2.292  -2.174  1.00  0.00           H  
HETATM   46  H12 UNL     1       1.509   0.174  -2.364  1.00  0.00           H  
HETATM   47  H13 UNL     1       0.103  -1.353  -3.212  1.00  0.00           H  
HETATM   48  H14 UNL     1       1.064  -2.595  -2.415  1.00  0.00           H  
HETATM   49  H15 UNL     1      -1.587  -2.004  -1.870  1.00  0.00           H  
HETATM   50  H16 UNL     1      -0.656  -3.106  -0.879  1.00  0.00           H  
HETATM   51  H17 UNL     1      -0.027  -1.452   0.723  1.00  0.00           H  
HETATM   52  H18 UNL     1      -2.144  -1.053   1.371  1.00  0.00           H  
HETATM   53  H19 UNL     1      -2.930  -2.669  -0.224  1.00  0.00           H  
HETATM   54  H20 UNL     1      -5.276  -1.851  -0.345  1.00  0.00           H  
HETATM   55  H21 UNL     1      -5.121   1.891  -1.167  1.00  0.00           H  
HETATM   56  H22 UNL     1      -5.898  -0.263   1.763  1.00  0.00           H  
HETATM   57  H23 UNL     1      -6.936  -0.136   0.302  1.00  0.00           H  
HETATM   58  H24 UNL     1      -7.424   1.968   1.365  1.00  0.00           H  
HETATM   59  H25 UNL     1      -5.826   3.690   1.363  1.00  0.00           H  
HETATM   60  H26 UNL     1      -3.944  -0.627   2.231  1.00  0.00           H  
HETATM   61  H27 UNL     1      -2.850   0.731   2.645  1.00  0.00           H  
HETATM   62  H28 UNL     1      -4.598   1.028   2.740  1.00  0.00           H  
HETATM   63  H29 UNL     1      -1.745   1.146   1.155  1.00  0.00           H  
HETATM   64  H30 UNL     1      -2.885   1.205  -1.696  1.00  0.00           H  
HETATM   65  H31 UNL     1      -1.849   2.446  -1.016  1.00  0.00           H  
HETATM   66  H32 UNL     1      -0.298   1.399  -2.342  1.00  0.00           H  
HETATM   67  H33 UNL     1      -1.236  -0.108  -2.478  1.00  0.00           H  
HETATM   68  H34 UNL     1       0.639   1.098   1.104  1.00  0.00           H  
HETATM   69  H35 UNL     1      -0.071   2.145  -0.140  1.00  0.00           H  
HETATM   70  H36 UNL     1       1.510   1.603  -0.471  1.00  0.00           H  
HETATM   71  H37 UNL     1       4.657  -1.903   0.611  1.00  0.00           H  
HETATM   72  H38 UNL     1       5.188  -1.494  -1.069  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3    3   34
CONECT    3    4    5
CONECT    4   38   39   40
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   34   41
CONECT    9   10   11   12
CONECT   10   42   43   44
CONECT   11   45
CONECT   12   13   32   46
CONECT   13   14   47   48
CONECT   14   15   49   50
CONECT   15   16   32   51
CONECT   16   17   29   52
CONECT   17   18   19   53
CONECT   18   19
CONECT   19   20   54
CONECT   20   21   22   27
CONECT   21   55
CONECT   22   23   56   57
CONECT   23   24   24   58
CONECT   24   25   59
CONECT   25   26   26   27
CONECT   27   28   29
CONECT   28   60   61   62
CONECT   29   30   63
CONECT   30   31   64   65
CONECT   31   32   66   67
CONECT   32   33
CONECT   33   68   69   70
CONECT   34   71   72
END

HMDB0034415
     RDKit          3D
Withanolide A
 72 77  0  0  0  0  0  0  0  0999 V2000
    7.2003   -0.2465    0.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7395   -0.1358    0.5167 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3367    0.8015    1.3572 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3358    1.7026    2.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9046    0.9398    1.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4924    1.8219    2.4254 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0763    0.0449    0.9542 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4707   -0.3260   -0.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4378   -1.1727   -1.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3967   -2.4605   -0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1357   -1.4975   -2.2840 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2259   -0.5660   -1.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4358   -1.7248   -2.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6521   -2.0823   -1.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6281   -1.0566   -0.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0315   -0.7493    0.2828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0924   -1.5620   -0.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6898   -1.1681   -1.5786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4299   -1.1250   -0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8065    0.2701   -0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1691    0.9261   -1.2303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0800    0.3147    0.8228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3858    1.7341    1.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4878    2.7062    1.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0973    2.3996    0.8114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2644    3.3108    0.6275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7516    0.9587    0.7263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8165    0.4525    2.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3355    0.7320    0.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9758    1.3463   -1.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8695    0.6345   -1.7795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1523    0.0383   -0.7692 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5665    1.2082    0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7761   -1.0789   -0.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4036   -0.9781   -0.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6944   -0.6733    1.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6695    0.7398    0.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6419    2.5318    1.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9177    2.1861    2.9086 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2507    1.1550    2.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7713    0.5538   -0.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4158   -2.3395    0.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3927   -2.9720   -0.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6757   -3.2133   -0.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6775   -2.2917   -2.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5087    0.1745   -2.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1030   -1.3531   -3.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0641   -2.5954   -2.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5870   -2.0042   -1.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6557   -3.1064   -0.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0267   -1.4519    0.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1439   -1.0534    1.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9305   -2.6693   -0.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2755   -1.8515   -0.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1214    1.8912   -1.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8976   -0.2628    1.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9364   -0.1363    0.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4236    1.9677    1.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8262    3.6896    1.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9439   -0.6269    2.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8497    0.7314    2.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5981    1.0284    2.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7453    1.1462    1.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8848    1.2048   -1.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8486    2.4463   -1.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2985    1.3992   -2.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2357   -0.1076   -2.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6391    1.0985    1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0710    2.1451   -0.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5100    1.6035   -0.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6573   -1.9029    0.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1877   -1.4941   -1.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  9 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  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
  8 34  1  0
 34  2  1  0
 32 12  1  0
 32 15  1  0
 29 16  1  0
 19 17  1  0
 27 20  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  4 38  1  0
  4 39  1  0
  4 40  1  0
  8 41  1  0
 10 42  1  0
 10 43  1  0
 10 44  1  0
 11 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 16 52  1  0
 17 53  1  0
 19 54  1  0
 21 55  1  0
 22 56  1  0
 22 57  1  0
 23 58  1  0
 24 59  1  0
 28 60  1  0
 28 61  1  0
 28 62  1  0
 29 63  1  0
 30 64  1  0
 30 65  1  0
 31 66  1  0
 31 67  1  0
 33 68  1  0
 33 69  1  0
 33 70  1  0
 34 71  1  0
 34 72  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Withanolide a	HMDB
6,7-Epoxy-5,20-dihydroxy-1-oxowitha-2,24-dienolide	HMDB

Chemical Formula

C₂₈H₃₈O₆

Average Molecular Weight

470.5977

Monoisotopic Molecular Weight

470.266838948

IUPAC Name

15-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.0²,⁴.0⁵,¹⁰.0¹⁴,¹⁸]octadec-7-en-9-one

Traditional Name

15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.0²,⁴.0⁵,¹⁰.0¹⁴,¹⁸]octadec-7-en-9-one

CAS Registry Number

32911-62-9

SMILES

CC1=C(C)C(=O)OC(C1)C(C)(O)C1CCC2C3C4OC4C4(O)CC=CC(=O)C4(C)C3CCC12C

InChI Identifier

InChI=1S/C28H38O6/c1-14-13-20(33-24(30)15(14)2)27(5,31)18-9-8-16-21-17(10-12-25(16,18)3)26(4)19(29)7-6-11-28(26,32)23-22(21)34-23/h6-7,16-18,20-23,31-32H,8-13H2,1-5H3

InChI Key

DXWHOKCXBGLTMQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Withanolides and derivatives

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0034415)
Cell membrane (HMDB: HMDB0034415)

Biofluid or Excreta

Urine (HMDB: HMDB0034415)

Tissue substructure

Hepatic tissue (HMDB: HMDB0034415)

Cellular substructure

Extracellular (HMDB: HMDB0034415)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034415)

Source

Endogenous

Endogenous (HMDB: HMDB0034415)

Plant

Plant (HMDB: HMDB0034415)

Animal

Animal (HMDB: HMDB0034415)

Exogenous

Food

Food (HMDB: HMDB0034415)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0034415)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0034415)

Cellular process

Cell signaling (HMDB: HMDB0034415)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0034415)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0034415)

Nutrient

Nutrient (HMDB: HMDB0034415)

Molecular messenger

Signaling molecule (HMDB: HMDB0034415)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0034415)

Emulsifier (HMDB: HMDB0034415)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	282 - 284 °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	0.0055 g/L	ALOGPS
logP	2.62	ALOGPS
logP	3.7	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	13.02	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.36 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	126.95 m³·mol⁻¹	ChemAxon
Polarizability	51.85 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	208.644	31661259
DarkChem	[M-H]-	202.746	31661259
DeepCCS	[M-2H]-	240.287	30932474
DeepCCS	[M+Na]+	215.563	30932474
AllCCS	[M+H]+	214.2	32859911
AllCCS	[M+H-H2O]+	212.3	32859911
AllCCS	[M+NH4]+	216.0	32859911
AllCCS	[M+Na]+	216.5	32859911
AllCCS	[M-H]-	216.7	32859911
AllCCS	[M+Na-2H]-	218.4	32859911
AllCCS	[M+HCOO]-	220.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Withanolide A	CC1=C(C)C(=O)OC(C1)C(C)(O)C1CCC2C3C4OC4C4(O)CC=CC(=O)C4(C)C3CCC12C	4424.3	Standard polar	33892256
Withanolide A	CC1=C(C)C(=O)OC(C1)C(C)(O)C1CCC2C3C4OC4C4(O)CC=CC(=O)C4(C)C3CCC12C	3309.1	Standard non polar	33892256
Withanolide A	CC1=C(C)C(=O)OC(C1)C(C)(O)C1CCC2C3C4OC4C4(O)CC=CC(=O)C4(C)C3CCC12C	4003.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Withanolide A,1TMS,isomer #1	CC1=C(C)C(=O)OC(C(C)(O[Si](C)(C)C)C2CCC3C4C5OC5C5(O)CC=CC(=O)C5(C)C4CCC32C)C1	3999.3	Semi standard non polar	33892256
Withanolide A,1TMS,isomer #2	CC1=C(C)C(=O)OC(C(C)(O)C2CCC3C4C5OC5C5(O[Si](C)(C)C)CC=CC(=O)C5(C)C4CCC32C)C1	3964.5	Semi standard non polar	33892256
Withanolide A,2TMS,isomer #1	CC1=C(C)C(=O)OC(C(C)(O[Si](C)(C)C)C2CCC3C4C5OC5C5(O[Si](C)(C)C)CC=CC(=O)C5(C)C4CCC32C)C1	3928.1	Semi standard non polar	33892256
Withanolide A,1TBDMS,isomer #1	CC1=C(C)C(=O)OC(C(C)(O[Si](C)(C)C(C)(C)C)C2CCC3C4C5OC5C5(O)CC=CC(=O)C5(C)C4CCC32C)C1	4214.7	Semi standard non polar	33892256
Withanolide A,1TBDMS,isomer #2	CC1=C(C)C(=O)OC(C(C)(O)C2CCC3C4C5OC5C5(O[Si](C)(C)C(C)(C)C)CC=CC(=O)C5(C)C4CCC32C)C1	4167.7	Semi standard non polar	33892256
Withanolide A,2TBDMS,isomer #1	CC1=C(C)C(=O)OC(C(C)(O[Si](C)(C)C(C)(C)C)C2CCC3C4C5OC5C5(O[Si](C)(C)C(C)(C)C)CC=CC(=O)C5(C)C4CCC32C)C1	4370.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Withanolide A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fb9-3459800000-128836e394d82c665d09	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withanolide A GC-MS (2 TMS) - 70eV, Positive	splash10-006t-6119272000-3c7ea27335b4c5216450	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withanolide A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withanolide A 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 - Withanolide A 10V, Positive-QTOF	splash10-00di-0003900000-c53f7d24b369f1317e27	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide A 20V, Positive-QTOF	splash10-0udi-9047500000-dadb4690c6be0d0dc033	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide A 40V, Positive-QTOF	splash10-0fbc-9363100000-ee564454ab333122972e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide A 10V, Negative-QTOF	splash10-014i-0002900000-4cdae16ec27d6f79bf4f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide A 20V, Negative-QTOF	splash10-0uxr-1829700000-efa5a97f2fd7a2c792d2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide A 40V, Negative-QTOF	splash10-014i-9202000000-b789b60a8bbf844a0487	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide A 10V, Positive-QTOF	splash10-00di-0002900000-5303548550f1cbb4cf23	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide A 20V, Positive-QTOF	splash10-002b-2109200000-159c88a2cdea516a2417	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide A 40V, Positive-QTOF	splash10-0udj-2498000000-514dba599686c57d956d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide A 10V, Negative-QTOF	splash10-014i-0000900000-58ba31b1929152abcb3d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide A 20V, Negative-QTOF	splash10-014i-0002900000-032082183a3018297bcd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide A 40V, Negative-QTOF	splash10-016r-9106800000-b17fc59f9348c3350718	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

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

FDB012812

KNApSAcK ID

C00032513

Chemspider ID

26504521

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14236710

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 Withanolide A (HMDB0034415)

MOL for HMDB0034415 (Withanolide A)

3D MOL for HMDB0034415 (Withanolide A)

3D SDF for HMDB0034415 (Withanolide A)

3D-SDF for HMDB0034415 (Withanolide A)

PDB for HMDB0034415 (Withanolide A)

3D PDB for HMDB0034415 (Withanolide A)

SMILES for HMDB0034415 (Withanolide A)

INCHI for HMDB0034415 (Withanolide A)

Structure for HMDB0034415 (Withanolide A)

3D Structure for HMDB0034415 (Withanolide A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra