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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 22:51:30 UTC

Update Date

2021-09-26 23:17:44 UTC

HMDB ID

HMDB0259897

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Withaferin A

Description

NSC-101088 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. NSC-101088 is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Withaferin a is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Withaferin A is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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


  Mrv1533004161523342D          

 34 39  0  0  0  0            999 V2000
    5.6974    3.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0083    2.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8256    2.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3319    3.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1492    3.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4601    2.5168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2773    2.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5882    1.6398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9537    1.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2646    1.1013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1365    1.9784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6555    3.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020    2.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7313    1.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0484    0.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971    1.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5850    1.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3047    0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926    0.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6805    0.2434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608    1.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1486    0.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8683    0.0982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168    1.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971    2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9895    3.2018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411    1.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5214    2.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0532    1.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3335    2.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774    2.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0373    2.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  3 11  1  0  0  0  0
  5 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  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
 20 21  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 17 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 13 33  1  0  0  0  0
 16 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END

HMDB0259897
     RDKit          3D
Withaferin A
 72 77  0  0  0  0  0  0  0  0999 V2000
    6.5585    0.0218   -2.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6826   -0.3769   -1.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0823   -0.0686    0.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3184    0.6371    0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1118    0.9950   -0.5949 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2039   -0.4657    1.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5249   -0.2019    2.4255 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0474   -1.1164    0.9579 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4711   -1.2737   -0.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3329   -0.2868   -0.5170 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9575    1.0736   -0.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2712   -0.6050    0.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7766   -2.0088    0.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4286   -2.0604    1.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9915   -0.6889    1.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3080   -0.7683    0.3109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2986   -1.3404    1.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6005   -1.4983    0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6877   -1.6780   -0.7180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0521   -0.4512   -0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5278   -0.0965   -0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2936   -1.2569   -0.0226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7144    0.7782    1.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8493    1.7889    1.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8288    1.9156    0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4890    3.0925   -0.2025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1891    0.7250   -0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2776    0.9671   -1.9786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7743    0.6083   -0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7681    1.2174   -0.9688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4706    0.4313   -1.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0206    0.1985    0.3818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1857    1.4347    1.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4474   -1.0840   -1.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6320    1.1248   -2.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0736   -0.3013   -3.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5237   -0.5064   -2.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9101    0.0634    1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0134    1.5895    0.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5359    1.8906   -0.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1353   -2.3377   -0.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9286   -0.3582   -1.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4832    1.1762    0.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2613    1.9054   -0.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7476    1.1423   -1.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6582   -0.5472    1.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5308   -2.2176   -0.8212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4543   -2.8039    0.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1221   -2.8434    0.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0846   -2.3502    2.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2313   -0.3367    2.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2871   -1.4706   -0.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3311   -0.5961    2.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8840   -2.2753    1.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3514   -2.1027    1.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8846    0.4581   -0.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2160   -1.0123   -0.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4898    0.6330    1.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9016    2.4907    2.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0045    2.0001   -2.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7663    0.1843   -2.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3658    0.8757   -2.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6704    1.2083    0.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5659    2.2963   -0.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1232    1.2590   -2.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6793   -0.5419   -1.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2234    0.9789   -1.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0305    2.3704    0.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2056    1.5636    1.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4983    1.4403    2.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7598   -2.0714   -1.8816 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9680   -0.5358   -2.2849 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
  4  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
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 18 19  1  0
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 21 22  1  0
 21 23  1  0
 23 24  2  0
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 25 26  2  0
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 29 30  1  0
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 31 32  1  0
 32 33  1  0
  9 34  1  0
 34  2  1  0
 32 12  1  0
 32 15  1  0
 29 16  1  0
 20 18  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
  5 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
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 14 50  1  0
 15 51  1  0
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 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


  Mrv1533004161523342D          

 34 39  0  0  0  0            999 V2000
    5.6974    3.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0083    2.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8256    2.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3319    3.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1492    3.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4601    2.5168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2773    2.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5882    1.6398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9537    1.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2646    1.1013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1365    1.9784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6555    3.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020    2.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7313    1.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0484    0.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971    1.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5850    1.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3047    0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926    0.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6805    0.2434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1486    0.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8683    0.0982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8971    2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9895    3.2018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0532    1.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3335    2.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774    2.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0373    2.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
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  5  6  2  0  0  0  0
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  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
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  3 11  1  0  0  0  0
  5 12  1  0  0  0  0
  2 13  1  0  0  0  0
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 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
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 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
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 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 17 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 13 33  1  0  0  0  0
 16 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259897

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C1CCC2C3CC4OC44C(O)C=CC(=O)C4(C)C3CCC12C)C1CC(C)=C(CO)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O6/c1-14-11-21(33-25(32)17(14)13-29)15(2)18-5-6-19-16-12-24-28(34-24)23(31)8-7-22(30)27(28,4)20(16)9-10-26(18,19)3/h7-8,15-16,18-21,23-24,29,31H,5-6,9-13H2,1-4H3

> <INCHI_KEY>
DBRXOUCRJQVYJQ-UHFFFAOYSA-N

> <FORMULA>
C28H38O6

> <MOLECULAR_WEIGHT>
470.606

> <EXACT_MASS>
470.266838944

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
52.66016876086695

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-hydroxy-15-{1-[5-(hydroxymethyl)-4-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl}-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
3.581974114333331

> <ALOGPS_LOGS>
-4.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.889975795355074

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.428069037500109

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8538493304385115

> <JCHEM_POLAR_SURFACE_AREA>
96.36000000000001

> <JCHEM_REFRACTIVITY>
127.19469999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.30e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-15-{1-[5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl}-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259897
     RDKit          3D
Withaferin A
 72 77  0  0  0  0  0  0  0  0999 V2000
    6.5585    0.0218   -2.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6826   -0.3769   -1.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0823   -0.0686    0.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3184    0.6371    0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1118    0.9950   -0.5949 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2039   -0.4657    1.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5249   -0.2019    2.4255 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0474   -1.1164    0.9579 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4711   -1.2737   -0.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3329   -0.2868   -0.5170 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9575    1.0736   -0.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2712   -0.6050    0.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7766   -2.0088    0.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4286   -2.0604    1.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9915   -0.6889    1.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3080   -0.7683    0.3109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2986   -1.3404    1.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6005   -1.4983    0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6877   -1.6780   -0.7180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0521   -0.4512   -0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5278   -0.0965   -0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2936   -1.2569   -0.0226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7144    0.7782    1.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8493    1.7889    1.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8288    1.9156    0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4890    3.0925   -0.2025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1891    0.7250   -0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2776    0.9671   -1.9786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7743    0.6083   -0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7681    1.2174   -0.9688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4706    0.4313   -1.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0206    0.1985    0.3818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1857    1.4347    1.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4474   -1.0840   -1.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6320    1.1248   -2.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0736   -0.3013   -3.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5237   -0.5064   -2.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9101    0.0634    1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0134    1.5895    0.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5359    1.8906   -0.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1353   -2.3377   -0.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9286   -0.3582   -1.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4832    1.1762    0.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2613    1.9054   -0.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7476    1.1423   -1.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6582   -0.5472    1.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5308   -2.2176   -0.8212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4543   -2.8039    0.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1221   -2.8434    0.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0846   -2.3502    2.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2313   -0.3367    2.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2871   -1.4706   -0.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3311   -0.5961    2.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8840   -2.2753    1.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3514   -2.1027    1.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8846    0.4581   -0.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2160   -1.0123   -0.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4898    0.6330    1.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9016    2.4907    2.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0045    2.0001   -2.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7663    0.1843   -2.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3658    0.8757   -2.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6704    1.2083    0.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5659    2.2963   -0.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1232    1.2590   -2.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6793   -0.5419   -1.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2234    0.9789   -1.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0305    2.3704    0.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2056    1.5636    1.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4983    1.4403    2.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7598   -2.0714   -1.8816 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9680   -0.5358   -2.2849 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
  4  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 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
 21 22  1  0
 21 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
  9 34  1  0
 34  2  1  0
 32 12  1  0
 32 15  1  0
 29 16  1  0
 20 18  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
  5 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 11 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
 17 54  1  0
 18 55  1  0
 21 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                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      10.635   6.757   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.216   5.330   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.741   5.119   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.686   6.335   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.212   6.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.792   4.698   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.318   4.487   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      17.898   3.061   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      14.847   3.482   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      15.427   2.056   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      13.321   3.693   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      16.157   7.340   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.270   4.114   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.698   2.635   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.424   1.771   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.208   2.716   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.692   2.445   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.169   0.996   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.653   0.725   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.137   0.454   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.660   1.903   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.144   1.632   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.621   0.183   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.151   2.809   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.675   4.257   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.191   4.528   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.714   5.977   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.183   3.351   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.707   4.799   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.699   3.622   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.222   5.071   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.738   5.342   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.731   4.164   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.403   5.550   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    3                                                       
CONECT   12    5                                                            
CONECT   13    2   14   33                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   33                                                  
CONECT   17   16   18   30                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19   21                                                       
CONECT   21   20   19   22   28                                             
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   21   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   17   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   13   16   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

COMPND    HMDB0259897
HETATM    1  C1  UNL     1       6.558   0.022  -2.241  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.683  -0.377  -1.101  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.082  -0.069   0.115  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.318   0.637   0.477  1.00  0.00           C  
HETATM    5  O1  UNL     1       8.112   0.995  -0.595  1.00  0.00           O  
HETATM    6  C5  UNL     1       5.204  -0.466   1.226  1.00  0.00           C  
HETATM    7  O2  UNL     1       5.525  -0.202   2.425  1.00  0.00           O  
HETATM    8  O3  UNL     1       4.047  -1.116   0.958  1.00  0.00           O  
HETATM    9  C6  UNL     1       3.471  -1.274  -0.325  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.333  -0.287  -0.517  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.957   1.074  -0.372  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.271  -0.605   0.459  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.777  -2.009   0.226  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.429  -2.060   1.140  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.992  -0.689   1.069  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.308  -0.768   0.311  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.299  -1.340   1.336  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.600  -1.498   0.646  1.00  0.00           C  
HETATM   19  O4  UNL     1      -4.688  -1.678  -0.718  1.00  0.00           O  
HETATM   20  C16 UNL     1      -5.052  -0.451  -0.171  1.00  0.00           C  
HETATM   21  C17 UNL     1      -6.528  -0.096  -0.112  1.00  0.00           C  
HETATM   22  O5  UNL     1      -7.294  -1.257  -0.023  1.00  0.00           O  
HETATM   23  C18 UNL     1      -6.714   0.778   1.074  1.00  0.00           C  
HETATM   24  C19 UNL     1      -5.849   1.789   1.198  1.00  0.00           C  
HETATM   25  C20 UNL     1      -4.829   1.916   0.163  1.00  0.00           C  
HETATM   26  O6  UNL     1      -4.489   3.093  -0.203  1.00  0.00           O  
HETATM   27  C21 UNL     1      -4.189   0.725  -0.464  1.00  0.00           C  
HETATM   28  C22 UNL     1      -4.278   0.967  -1.979  1.00  0.00           C  
HETATM   29  C23 UNL     1      -2.774   0.608  -0.018  1.00  0.00           C  
HETATM   30  C24 UNL     1      -1.768   1.217  -0.969  1.00  0.00           C  
HETATM   31  C25 UNL     1      -0.471   0.431  -1.010  1.00  0.00           C  
HETATM   32  C26 UNL     1       0.021   0.198   0.382  1.00  0.00           C  
HETATM   33  C27 UNL     1       0.186   1.435   1.196  1.00  0.00           C  
HETATM   34  C28 UNL     1       4.447  -1.084  -1.430  1.00  0.00           C  
HETATM   35  H1  UNL     1       6.632   1.125  -2.343  1.00  0.00           H  
HETATM   36  H2  UNL     1       6.074  -0.301  -3.209  1.00  0.00           H  
HETATM   37  H3  UNL     1       7.524  -0.506  -2.226  1.00  0.00           H  
HETATM   38  H4  UNL     1       7.910   0.063   1.232  1.00  0.00           H  
HETATM   39  H5  UNL     1       7.013   1.590   0.975  1.00  0.00           H  
HETATM   40  H6  UNL     1       8.536   1.891  -0.438  1.00  0.00           H  
HETATM   41  H7  UNL     1       3.135  -2.338  -0.372  1.00  0.00           H  
HETATM   42  H8  UNL     1       1.929  -0.358  -1.547  1.00  0.00           H  
HETATM   43  H9  UNL     1       3.483   1.176   0.600  1.00  0.00           H  
HETATM   44  H10 UNL     1       2.261   1.905  -0.571  1.00  0.00           H  
HETATM   45  H11 UNL     1       3.748   1.142  -1.150  1.00  0.00           H  
HETATM   46  H12 UNL     1       1.658  -0.547   1.493  1.00  0.00           H  
HETATM   47  H13 UNL     1       0.531  -2.218  -0.821  1.00  0.00           H  
HETATM   48  H14 UNL     1       1.454  -2.804   0.592  1.00  0.00           H  
HETATM   49  H15 UNL     1      -1.122  -2.843   0.771  1.00  0.00           H  
HETATM   50  H16 UNL     1      -0.085  -2.350   2.164  1.00  0.00           H  
HETATM   51  H17 UNL     1      -1.231  -0.337   2.093  1.00  0.00           H  
HETATM   52  H18 UNL     1      -2.287  -1.471  -0.522  1.00  0.00           H  
HETATM   53  H19 UNL     1      -3.331  -0.596   2.160  1.00  0.00           H  
HETATM   54  H20 UNL     1      -2.884  -2.275   1.775  1.00  0.00           H  
HETATM   55  H21 UNL     1      -5.351  -2.103   1.233  1.00  0.00           H  
HETATM   56  H22 UNL     1      -6.885   0.458  -0.981  1.00  0.00           H  
HETATM   57  H23 UNL     1      -8.216  -1.012  -0.297  1.00  0.00           H  
HETATM   58  H24 UNL     1      -7.490   0.633   1.807  1.00  0.00           H  
HETATM   59  H25 UNL     1      -5.902   2.491   2.035  1.00  0.00           H  
HETATM   60  H26 UNL     1      -4.004   2.000  -2.242  1.00  0.00           H  
HETATM   61  H27 UNL     1      -3.766   0.184  -2.549  1.00  0.00           H  
HETATM   62  H28 UNL     1      -5.366   0.876  -2.269  1.00  0.00           H  
HETATM   63  H29 UNL     1      -2.670   1.208   0.936  1.00  0.00           H  
HETATM   64  H30 UNL     1      -1.566   2.296  -0.699  1.00  0.00           H  
HETATM   65  H31 UNL     1      -2.123   1.259  -2.019  1.00  0.00           H  
HETATM   66  H32 UNL     1      -0.679  -0.542  -1.475  1.00  0.00           H  
HETATM   67  H33 UNL     1       0.223   0.979  -1.657  1.00  0.00           H  
HETATM   68  H34 UNL     1      -0.031   2.370   0.641  1.00  0.00           H  
HETATM   69  H35 UNL     1       1.206   1.564   1.613  1.00  0.00           H  
HETATM   70  H36 UNL     1      -0.498   1.440   2.071  1.00  0.00           H  
HETATM   71  H37 UNL     1       4.760  -2.071  -1.882  1.00  0.00           H  
HETATM   72  H38 UNL     1       3.968  -0.536  -2.285  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3    3   34
CONECT    3    4    6
CONECT    4    5   38   39
CONECT    5   40
CONECT    6    7    7    8
CONECT    8    9
CONECT    9   10   34   41
CONECT   10   11   12   42
CONECT   11   43   44   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   53   54
CONECT   18   19   20   55
CONECT   19   20
CONECT   20   21   27
CONECT   21   22   23   56
CONECT   22   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

HMDB0259897
     RDKit          3D
Withaferin A
 72 77  0  0  0  0  0  0  0  0999 V2000
    6.5585    0.0218   -2.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6826   -0.3769   -1.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0823   -0.0686    0.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3184    0.6371    0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1118    0.9950   -0.5949 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2039   -0.4657    1.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5249   -0.2019    2.4255 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0474   -1.1164    0.9579 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4711   -1.2737   -0.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3329   -0.2868   -0.5170 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9575    1.0736   -0.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2712   -0.6050    0.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7766   -2.0088    0.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4286   -2.0604    1.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9915   -0.6889    1.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3080   -0.7683    0.3109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2986   -1.3404    1.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6005   -1.4983    0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6877   -1.6780   -0.7180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0521   -0.4512   -0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5278   -0.0965   -0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2936   -1.2569   -0.0226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7144    0.7782    1.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8493    1.7889    1.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8288    1.9156    0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4890    3.0925   -0.2025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1891    0.7250   -0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2776    0.9671   -1.9786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7743    0.6083   -0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7681    1.2174   -0.9688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4706    0.4313   -1.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0206    0.1985    0.3818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1857    1.4347    1.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4474   -1.0840   -1.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6320    1.1248   -2.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0736   -0.3013   -3.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5237   -0.5064   -2.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9101    0.0634    1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0134    1.5895    0.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5359    1.8906   -0.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1353   -2.3377   -0.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9286   -0.3582   -1.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4832    1.1762    0.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2613    1.9054   -0.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7476    1.1423   -1.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6582   -0.5472    1.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5308   -2.2176   -0.8212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4543   -2.8039    0.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1221   -2.8434    0.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0846   -2.3502    2.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2313   -0.3367    2.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2871   -1.4706   -0.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3311   -0.5961    2.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8840   -2.2753    1.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3514   -2.1027    1.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8846    0.4581   -0.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2160   -1.0123   -0.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4898    0.6330    1.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9016    2.4907    2.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0045    2.0001   -2.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7663    0.1843   -2.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3658    0.8757   -2.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6704    1.2083    0.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5659    2.2963   -0.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1232    1.2590   -2.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6793   -0.5419   -1.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2234    0.9789   -1.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0305    2.3704    0.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2056    1.5636    1.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4983    1.4403    2.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7598   -2.0714   -1.8816 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9680   -0.5358   -2.2849 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
  4  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 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
 21 22  1  0
 21 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
  9 34  1  0
 34  2  1  0
 32 12  1  0
 32 15  1  0
 29 16  1  0
 20 18  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
  5 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 11 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
 17 54  1  0
 18 55  1  0
 21 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

Not Available

Chemical Formula

C₂₈H₃₈O₆

Average Molecular Weight

470.606

Monoisotopic Molecular Weight

470.266838944

IUPAC Name

6-hydroxy-15-{1-[5-(hydroxymethyl)-4-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl}-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one

Traditional Name

6-hydroxy-15-{1-[5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl}-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one

CAS Registry Number

Not Available

SMILES

CC(C1CCC2C3CC4OC44C(O)C=CC(=O)C4(C)C3CCC12C)C1CC(C)=C(CO)C(=O)O1

InChI Identifier

InChI=1S/C28H38O6/c1-14-11-21(33-25(32)17(14)13-29)15(2)18-5-6-19-16-12-24-28(34-24)23(31)8-7-22(30)27(28,4)20(16)9-10-26(18,19)3/h7-8,15-16,18-21,23-24,29,31H,5-6,9-13H2,1-4H3

InChI Key

DBRXOUCRJQVYJQ-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

Substituents

Withanolide-skeleton
5,6-epoxysteroid
Dihydropyranone
Oxepane
Cyclohexenone
Pyran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Primary alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.64	ALOGPS
logP	3.58	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	13.43	ChemAxon
pKa (Strongest Basic)	-2.9	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	3	ChemAxon
Refractivity	127.19 m³·mol⁻¹	ChemAxon
Polarizability	52.66 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
AllCCS	[M+H]+	214.88	32859911
AllCCS	[M+H-H2O]+	212.978	32859911
AllCCS	[M+Na]+	217.118	32859911
AllCCS	[M+NH4]+	216.622	32859911
AllCCS	[M-H]-	214.822	32859911
AllCCS	[M+Na-2H]-	216.554	32859911
AllCCS	[M+HCOO]-	218.614	32859911
DeepCCS	[M-2H]-	238.55	30932474
DeepCCS	[M+Na]+	213.778	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Withaferin A	CC(C1CCC2C3CC4OC44C(O)C=CC(=O)C4(C)C3CCC12C)C1CC(C)=C(CO)C(=O)O1	3701.0	Standard polar	33892256
Withaferin A	CC(C1CCC2C3CC4OC44C(O)C=CC(=O)C4(C)C3CCC12C)C1CC(C)=C(CO)C(=O)O1	3482.9	Standard non polar	33892256
Withaferin A	CC(C1CCC2C3CC4OC44C(O)C=CC(=O)C4(C)C3CCC12C)C1CC(C)=C(CO)C(=O)O1	4081.9	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 - Withaferin A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zfr-6139800000-0b47079167c2a76bc5fc	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withaferin A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withaferin A GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withaferin A GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withaferin A GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withaferin A GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withaferin A GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withaferin A GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

580064

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Withaferin A (HMDB0259897)

MOL for HMDB0259897 (Withaferin A)

3D MOL for HMDB0259897 (Withaferin A)

3D SDF for HMDB0259897 (Withaferin A)

3D-SDF for HMDB0259897 (Withaferin A)

PDB for HMDB0259897 (Withaferin A)

3D PDB for HMDB0259897 (Withaferin A)

SMILES for HMDB0259897 (Withaferin A)

INCHI for HMDB0259897 (Withaferin A)

Structure for HMDB0259897 (Withaferin A)

3D Structure for HMDB0259897 (Withaferin A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra