Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 22:51:35 UTC

Update Date

2021-09-26 23:17:44 UTC

HMDB ID

HMDB0259898

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Withanolide 1

Description

15-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-10-yl acetate 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. 15-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-10-yl acetate 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 ). Withanolide 1 is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Withanolide 1 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


  Mrv1533004161515342D          

 38 43  0  0  0  0            999 V2000
    4.0880    4.8035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5562    4.1728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7441    4.3180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8365    3.3969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3047    2.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5850    1.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971    1.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0484    2.3514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7313    1.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020    1.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0083    0.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6597    0.9510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3570   -0.0617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5147   -0.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3319   -0.0939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8383   -0.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5274   -1.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0338   -2.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7102   -1.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3993   -2.3864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2038   -0.9709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6555   -0.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774    1.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0373    0.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    0.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3335    0.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0532    1.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411    1.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5214    0.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092    0.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9895    0.0982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971    1.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168    1.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1486    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8683    3.2018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608    2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6805    3.0566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926    2.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 14 21  1  0  0  0  0
 16 22  1  0  0  0  0
 10 23  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  6 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 28 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
  5 38  1  0  0  0  0
 36 38  1  0  0  0  0
M  END

HMDB0259898
     RDKit          3D
Withanolide 1
 78 83  0  0  0  0  0  0  0  0999 V2000
   -2.5752   -4.7853   -0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049   -3.4738    0.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3126   -3.4770    1.3547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7839   -2.2673   -0.4557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1129   -1.0647    0.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9452   -0.1370    0.3516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7111   -0.6823   -0.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.9484   -1.7608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5472   -0.7458   -2.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4471   -0.5022   -1.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7128    0.1616   -1.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4191   -0.7353   -2.5471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5681    1.3957   -2.0655 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7495    0.2884   -0.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1629   -1.0646    0.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3187   -0.8384    1.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5265   -1.7344    2.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1952    0.1447    0.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3426    0.3214    1.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0309    1.0545   -0.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8323    1.9955   -0.5058 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9203    0.8091   -1.0968 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4757    0.2923   -0.2717 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9295    0.5528    1.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0100    1.5521   -0.9520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0695    2.1665   -0.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2375    1.2453   -0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5017    1.7514    0.4735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6822    3.2416    0.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6072    1.5987    1.9434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6260    1.5793    2.7127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9548    1.4672    2.4876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0306    1.4268    1.7167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9304    1.5140    0.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9873    0.7910   -0.3325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6076    0.9438   -0.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3533    0.4492   -1.4233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3450   -0.4163   -0.3759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8719   -5.3720    0.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2293   -4.6745   -1.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5497   -5.3540   -0.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4445   -1.3640    1.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6803   -0.0547    1.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3883   -1.6012    0.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0994   -2.0182   -2.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6009   -0.3520   -2.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6057    0.0959   -3.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9721   -1.6558   -2.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6424   -1.4531   -0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0077   -0.4608   -3.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5033   -0.4944   -2.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2081   -1.7867   -2.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1457    2.0887   -1.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4788    0.9541    0.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5191   -1.7027   -0.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3150   -1.5570    0.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6919   -2.4233    2.3545 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4852   -2.3090    2.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6295   -1.1318    3.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0906   -0.4540    1.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8067    1.3120    1.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0022    0.3524    2.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6673   -0.1782    1.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3601    1.5741    1.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1312    0.5472    1.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5023    1.3183   -1.8889 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7243    2.3341   -1.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6864    2.3240    0.9904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3420    3.1264   -0.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4421    1.1564   -1.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7605    3.4463   -0.8512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8067    3.7433    0.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5670    3.5801    0.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1378    1.3963    3.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0322    1.3290    2.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0232    2.5488   -0.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6598    0.4451   -1.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2108   -1.1452   -0.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20 22  1  0
 10 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  1  0
 34 36  1  0
 36 37  1  0
 37 38  1  0
 38  5  1  0
 27  6  1  0
 36 28  1  0
 23  7  1  0
 38 36  1  0
 22 14  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  5 42  1  0
  6 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
 10 49  1  0
 12 50  1  0
 12 51  1  0
 12 52  1  0
 13 53  1  0
 14 54  1  0
 15 55  1  0
 15 56  1  0
 17 57  1  0
 17 58  1  0
 17 59  1  0
 19 60  1  0
 19 61  1  0
 19 62  1  0
 24 63  1  0
 24 64  1  0
 24 65  1  0
 25 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 27 70  1  0
 29 71  1  0
 29 72  1  0
 29 73  1  0
 32 74  1  0
 33 75  1  0
 34 76  1  0
 35 77  1  0
 38 78  1  0
M  END


  Mrv1533004161515342D          

 38 43  0  0  0  0            999 V2000
    4.0880    4.8035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5562    4.1728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7441    4.3180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8365    3.3969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3047    2.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5850    1.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971    1.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0484    2.3514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7313    1.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020    1.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0083    0.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6597    0.9510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3570   -0.0617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5147   -0.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3319   -0.0939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8383   -0.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5274   -1.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0338   -2.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7102   -1.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3993   -2.3864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2038   -0.9709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6555   -0.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774    1.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0373    0.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    0.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3335    0.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0532    1.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411    1.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5214    0.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092    0.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9895    0.0982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971    1.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168    1.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1486    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8683    3.2018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608    2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6805    3.0566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926    2.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 14 21  1  0  0  0  0
 16 22  1  0  0  0  0
 10 23  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  6 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 28 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
  5 38  1  0  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259898

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OC1C2OC22C(O)C=CC(=O)C2(C)C2CCC3(C)C(CCC3C(C)(O)C3CC(C)=C(C)C(=O)O3)C12

> <INCHI_IDENTIFIER>
InChI=1S/C30H40O8/c1-14-13-22(37-26(34)15(14)2)29(6,35)19-8-7-17-23-18(11-12-27(17,19)4)28(5)20(32)9-10-21(33)30(28)25(38-30)24(23)36-16(3)31/h9-10,17-19,21-25,33,35H,7-8,11-13H2,1-6H3

> <INCHI_KEY>
SHUUIGOWNXWQBK-UHFFFAOYSA-N

> <FORMULA>
C30H40O8

> <MOLECULAR_WEIGHT>
528.642

> <EXACT_MASS>
528.272318248

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
56.834629530340436

> <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]-6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-10-yl acetate

> <ALOGPS_LOGP>
2.30

> <JCHEM_LOGP>
3.2255747693333308

> <ALOGPS_LOGS>
-4.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.939587374922244

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.26496392618262

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3314307776848544

> <JCHEM_POLAR_SURFACE_AREA>
122.66000000000001

> <JCHEM_REFRACTIVITY>
137.30709999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.05e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-10-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259898
     RDKit          3D
Withanolide 1
 78 83  0  0  0  0  0  0  0  0999 V2000
   -2.5752   -4.7853   -0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049   -3.4738    0.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3126   -3.4770    1.3547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7839   -2.2673   -0.4557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1129   -1.0647    0.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9452   -0.1370    0.3516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7111   -0.6823   -0.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.9484   -1.7608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5472   -0.7458   -2.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4471   -0.5022   -1.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7128    0.1616   -1.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4191   -0.7353   -2.5471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5681    1.3957   -2.0655 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7495    0.2884   -0.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1629   -1.0646    0.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3187   -0.8384    1.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5265   -1.7344    2.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1952    0.1447    0.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3426    0.3214    1.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0309    1.0545   -0.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8323    1.9955   -0.5058 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9203    0.8091   -1.0968 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4757    0.2923   -0.2717 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9295    0.5528    1.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0100    1.5521   -0.9520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0695    2.1665   -0.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2375    1.2453   -0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5017    1.7514    0.4735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6822    3.2416    0.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6072    1.5987    1.9434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6260    1.5793    2.7127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9548    1.4672    2.4876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0306    1.4268    1.7167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9304    1.5140    0.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9873    0.7910   -0.3325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6076    0.9438   -0.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3533    0.4492   -1.4233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3450   -0.4163   -0.3759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8719   -5.3720    0.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2293   -4.6745   -1.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5497   -5.3540   -0.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4445   -1.3640    1.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6803   -0.0547    1.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3883   -1.6012    0.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0994   -2.0182   -2.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6009   -0.3520   -2.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6057    0.0959   -3.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9721   -1.6558   -2.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6424   -1.4531   -0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0077   -0.4608   -3.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5033   -0.4944   -2.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2081   -1.7867   -2.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1457    2.0887   -1.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4788    0.9541    0.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5191   -1.7027   -0.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3150   -1.5570    0.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6919   -2.4233    2.3545 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4852   -2.3090    2.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6295   -1.1318    3.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0906   -0.4540    1.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8067    1.3120    1.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0022    0.3524    2.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6673   -0.1782    1.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3601    1.5741    1.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1312    0.5472    1.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5023    1.3183   -1.8889 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7243    2.3341   -1.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6864    2.3240    0.9904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3420    3.1264   -0.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4421    1.1564   -1.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7605    3.4463   -0.8512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8067    3.7433    0.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5670    3.5801    0.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1378    1.3963    3.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0322    1.3290    2.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0232    2.5488   -0.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6598    0.4451   -1.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2108   -1.1452   -0.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20 22  1  0
 10 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  1  0
 34 36  1  0
 36 37  1  0
 37 38  1  0
 38  5  1  0
 27  6  1  0
 36 28  1  0
 23  7  1  0
 38 36  1  0
 22 14  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  5 42  1  0
  6 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
 10 49  1  0
 12 50  1  0
 12 51  1  0
 12 52  1  0
 13 53  1  0
 14 54  1  0
 15 55  1  0
 15 56  1  0
 17 57  1  0
 17 58  1  0
 17 59  1  0
 19 60  1  0
 19 61  1  0
 19 62  1  0
 24 63  1  0
 24 64  1  0
 24 65  1  0
 25 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 27 70  1  0
 29 71  1  0
 29 72  1  0
 29 73  1  0
 32 74  1  0
 33 75  1  0
 34 76  1  0
 35 77  1  0
 38 78  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       7.631   8.967   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.638   7.789   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.122   8.060   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.162   6.341   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.169   5.164   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.692   3.715   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.208   3.444   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.424   4.389   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.698   3.525   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.270   2.046   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.216   0.830   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.431   1.775   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.000  -0.115   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.161  -0.386   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.686  -0.175   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.631  -1.391   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.051  -2.817   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.996  -4.033   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.526  -3.028   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.945  -4.455   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      11.580  -1.812   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      16.157  -1.180   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.731   1.996   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.403   0.610   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.738   0.818   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.222   1.089   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.699   2.538   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.183   2.809   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.707   1.361   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.191   1.632   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.714   0.183   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.675   1.903   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.151   3.351   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.144   4.528   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.621   5.977   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       3.660   4.257   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.137   5.706   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       4.653   5.435   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   38                                                  
CONECT    6    5    7   27                                                  
CONECT    7    6    8   23                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   23                                                  
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   14                                                       
CONECT   22   16                                                            
CONECT   23   10    7   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    6   28                                                  
CONECT   28   27   29   30   36                                             
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   28   37   38                                             
CONECT   37   36   38                                                       
CONECT   38   37    5   36                                                  
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

COMPND    HMDB0259898
HETATM    1  C1  UNL     1      -2.575  -4.785  -0.435  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.905  -3.474   0.187  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.313  -3.477   1.355  1.00  0.00           O  
HETATM    4  O2  UNL     1      -2.784  -2.267  -0.456  1.00  0.00           O  
HETATM    5  C3  UNL     1      -3.113  -1.065   0.192  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.945  -0.137   0.352  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.711  -0.682  -0.305  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.841  -0.948  -1.761  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.547  -0.746  -2.325  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.447  -0.502  -1.084  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.713   0.162  -1.504  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.419  -0.735  -2.547  1.00  0.00           C  
HETATM   13  O3  UNL     1       2.568   1.396  -2.066  1.00  0.00           O  
HETATM   14  C11 UNL     1       3.749   0.288  -0.406  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.163  -1.065   0.132  1.00  0.00           C  
HETATM   16  C13 UNL     1       5.319  -0.838   1.037  1.00  0.00           C  
HETATM   17  C14 UNL     1       5.526  -1.734   2.215  1.00  0.00           C  
HETATM   18  C15 UNL     1       6.195   0.145   0.845  1.00  0.00           C  
HETATM   19  C16 UNL     1       7.343   0.321   1.793  1.00  0.00           C  
HETATM   20  C17 UNL     1       6.031   1.055  -0.282  1.00  0.00           C  
HETATM   21  O4  UNL     1       6.832   1.995  -0.506  1.00  0.00           O  
HETATM   22  O5  UNL     1       4.920   0.809  -1.097  1.00  0.00           O  
HETATM   23  C18 UNL     1       0.476   0.292  -0.272  1.00  0.00           C  
HETATM   24  C19 UNL     1       0.929   0.553   1.117  1.00  0.00           C  
HETATM   25  C20 UNL     1      -0.010   1.552  -0.952  1.00  0.00           C  
HETATM   26  C21 UNL     1      -1.069   2.167  -0.013  1.00  0.00           C  
HETATM   27  C22 UNL     1      -2.238   1.245  -0.130  1.00  0.00           C  
HETATM   28  C23 UNL     1      -3.502   1.751   0.474  1.00  0.00           C  
HETATM   29  C24 UNL     1      -3.682   3.242   0.212  1.00  0.00           C  
HETATM   30  C25 UNL     1      -3.607   1.599   1.943  1.00  0.00           C  
HETATM   31  O6  UNL     1      -2.626   1.579   2.713  1.00  0.00           O  
HETATM   32  C26 UNL     1      -4.955   1.467   2.488  1.00  0.00           C  
HETATM   33  C27 UNL     1      -6.031   1.427   1.717  1.00  0.00           C  
HETATM   34  C28 UNL     1      -5.930   1.514   0.225  1.00  0.00           C  
HETATM   35  O7  UNL     1      -6.987   0.791  -0.332  1.00  0.00           O  
HETATM   36  C29 UNL     1      -4.608   0.944  -0.150  1.00  0.00           C  
HETATM   37  O8  UNL     1      -4.353   0.449  -1.423  1.00  0.00           O  
HETATM   38  C30 UNL     1      -4.345  -0.416  -0.376  1.00  0.00           C  
HETATM   39  H1  UNL     1      -1.872  -5.372   0.163  1.00  0.00           H  
HETATM   40  H2  UNL     1      -2.229  -4.675  -1.470  1.00  0.00           H  
HETATM   41  H3  UNL     1      -3.550  -5.354  -0.494  1.00  0.00           H  
HETATM   42  H4  UNL     1      -3.444  -1.364   1.219  1.00  0.00           H  
HETATM   43  H5  UNL     1      -1.680  -0.055   1.428  1.00  0.00           H  
HETATM   44  H6  UNL     1      -0.388  -1.601   0.243  1.00  0.00           H  
HETATM   45  H7  UNL     1      -1.099  -2.018  -2.014  1.00  0.00           H  
HETATM   46  H8  UNL     1      -1.601  -0.352  -2.294  1.00  0.00           H  
HETATM   47  H9  UNL     1       0.606   0.096  -3.034  1.00  0.00           H  
HETATM   48  H10 UNL     1       0.972  -1.656  -2.794  1.00  0.00           H  
HETATM   49  H11 UNL     1       1.642  -1.453  -0.609  1.00  0.00           H  
HETATM   50  H12 UNL     1       3.008  -0.461  -3.547  1.00  0.00           H  
HETATM   51  H13 UNL     1       4.503  -0.494  -2.564  1.00  0.00           H  
HETATM   52  H14 UNL     1       3.208  -1.787  -2.315  1.00  0.00           H  
HETATM   53  H15 UNL     1       3.146   2.089  -1.709  1.00  0.00           H  
HETATM   54  H16 UNL     1       3.479   0.954   0.409  1.00  0.00           H  
HETATM   55  H17 UNL     1       4.519  -1.703  -0.715  1.00  0.00           H  
HETATM   56  H18 UNL     1       3.315  -1.557   0.580  1.00  0.00           H  
HETATM   57  H19 UNL     1       4.692  -2.423   2.355  1.00  0.00           H  
HETATM   58  H20 UNL     1       6.485  -2.309   2.072  1.00  0.00           H  
HETATM   59  H21 UNL     1       5.630  -1.132   3.132  1.00  0.00           H  
HETATM   60  H22 UNL     1       8.091  -0.454   1.592  1.00  0.00           H  
HETATM   61  H23 UNL     1       7.807   1.312   1.593  1.00  0.00           H  
HETATM   62  H24 UNL     1       7.002   0.352   2.848  1.00  0.00           H  
HETATM   63  H25 UNL     1       1.667  -0.178   1.451  1.00  0.00           H  
HETATM   64  H26 UNL     1       1.360   1.574   1.190  1.00  0.00           H  
HETATM   65  H27 UNL     1       0.131   0.547   1.894  1.00  0.00           H  
HETATM   66  H28 UNL     1      -0.502   1.318  -1.889  1.00  0.00           H  
HETATM   67  H29 UNL     1       0.724   2.334  -1.086  1.00  0.00           H  
HETATM   68  H30 UNL     1      -0.686   2.324   0.990  1.00  0.00           H  
HETATM   69  H31 UNL     1      -1.342   3.126  -0.535  1.00  0.00           H  
HETATM   70  H32 UNL     1      -2.442   1.156  -1.237  1.00  0.00           H  
HETATM   71  H33 UNL     1      -3.760   3.446  -0.851  1.00  0.00           H  
HETATM   72  H34 UNL     1      -2.807   3.743   0.698  1.00  0.00           H  
HETATM   73  H35 UNL     1      -4.567   3.580   0.785  1.00  0.00           H  
HETATM   74  H36 UNL     1      -5.138   1.396   3.556  1.00  0.00           H  
HETATM   75  H37 UNL     1      -7.032   1.329   2.122  1.00  0.00           H  
HETATM   76  H38 UNL     1      -6.023   2.549  -0.143  1.00  0.00           H  
HETATM   77  H39 UNL     1      -6.660   0.445  -1.206  1.00  0.00           H  
HETATM   78  H40 UNL     1      -5.211  -1.145  -0.391  1.00  0.00           H  
CONECT    1    2   39   40   41
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   38   42
CONECT    6    7   27   43
CONECT    7    8   23   44
CONECT    8    9   45   46
CONECT    9   10   47   48
CONECT   10   11   23   49
CONECT   11   12   13   14
CONECT   12   50   51   52
CONECT   13   53
CONECT   14   15   22   54
CONECT   15   16   55   56
CONECT   16   17   18   18
CONECT   17   57   58   59
CONECT   18   19   20
CONECT   19   60   61   62
CONECT   20   21   21   22
CONECT   23   24   25
CONECT   24   63   64   65
CONECT   25   26   66   67
CONECT   26   27   68   69
CONECT   27   28   70
CONECT   28   29   30   36
CONECT   29   71   72   73
CONECT   30   31   31   32
CONECT   32   33   33   74
CONECT   33   34   75
CONECT   34   35   36   76
CONECT   35   77
CONECT   36   37   38
CONECT   37   38
CONECT   38   78
END

HMDB0259898
     RDKit          3D
Withanolide 1
 78 83  0  0  0  0  0  0  0  0999 V2000
   -2.5752   -4.7853   -0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049   -3.4738    0.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3126   -3.4770    1.3547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7839   -2.2673   -0.4557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1129   -1.0647    0.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9452   -0.1370    0.3516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7111   -0.6823   -0.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.9484   -1.7608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5472   -0.7458   -2.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4471   -0.5022   -1.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7128    0.1616   -1.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4191   -0.7353   -2.5471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5681    1.3957   -2.0655 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7495    0.2884   -0.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1629   -1.0646    0.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3187   -0.8384    1.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5265   -1.7344    2.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1952    0.1447    0.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3426    0.3214    1.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0309    1.0545   -0.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8323    1.9955   -0.5058 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9203    0.8091   -1.0968 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4757    0.2923   -0.2717 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9295    0.5528    1.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0100    1.5521   -0.9520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0695    2.1665   -0.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2375    1.2453   -0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5017    1.7514    0.4735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6822    3.2416    0.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6072    1.5987    1.9434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6260    1.5793    2.7127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9548    1.4672    2.4876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0306    1.4268    1.7167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9304    1.5140    0.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9873    0.7910   -0.3325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6076    0.9438   -0.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3533    0.4492   -1.4233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3450   -0.4163   -0.3759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8719   -5.3720    0.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2293   -4.6745   -1.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5497   -5.3540   -0.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4445   -1.3640    1.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6803   -0.0547    1.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3883   -1.6012    0.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0994   -2.0182   -2.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6009   -0.3520   -2.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6057    0.0959   -3.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9721   -1.6558   -2.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6424   -1.4531   -0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0077   -0.4608   -3.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5033   -0.4944   -2.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2081   -1.7867   -2.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1457    2.0887   -1.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4788    0.9541    0.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5191   -1.7027   -0.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3150   -1.5570    0.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6919   -2.4233    2.3545 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4852   -2.3090    2.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6295   -1.1318    3.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0906   -0.4540    1.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8067    1.3120    1.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0022    0.3524    2.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6673   -0.1782    1.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3601    1.5741    1.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1312    0.5472    1.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5023    1.3183   -1.8889 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7243    2.3341   -1.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6864    2.3240    0.9904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3420    3.1264   -0.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4421    1.1564   -1.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7605    3.4463   -0.8512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8067    3.7433    0.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5670    3.5801    0.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1378    1.3963    3.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0322    1.3290    2.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0232    2.5488   -0.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6598    0.4451   -1.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2108   -1.1452   -0.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20 22  1  0
 10 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  1  0
 34 36  1  0
 36 37  1  0
 37 38  1  0
 38  5  1  0
 27  6  1  0
 36 28  1  0
 23  7  1  0
 38 36  1  0
 22 14  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  5 42  1  0
  6 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
 10 49  1  0
 12 50  1  0
 12 51  1  0
 12 52  1  0
 13 53  1  0
 14 54  1  0
 15 55  1  0
 15 56  1  0
 17 57  1  0
 17 58  1  0
 17 59  1  0
 19 60  1  0
 19 61  1  0
 19 62  1  0
 24 63  1  0
 24 64  1  0
 24 65  1  0
 25 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 27 70  1  0
 29 71  1  0
 29 72  1  0
 29 73  1  0
 32 74  1  0
 33 75  1  0
 34 76  1  0
 35 77  1  0
 38 78  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
15-[1-(4,5-Dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0,.0,.0,]octadec-4-en-10-yl acetic acid	Generator
15-[1-(4,5-Dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-10-yl acetic acid	Generator

Chemical Formula

C₃₀H₄₀O₈

Average Molecular Weight

528.642

Monoisotopic Molecular Weight

528.272318248

IUPAC Name

15-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-10-yl acetate

Traditional Name

15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-10-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1C2OC22C(O)C=CC(=O)C2(C)C2CCC3(C)C(CCC3C(C)(O)C3CC(C)=C(C)C(=O)O3)C12

InChI Identifier

InChI=1S/C30H40O8/c1-14-13-22(37-26(34)15(14)2)29(6,35)19-8-7-17-23-18(11-12-27(17,19)4)28(5)20(32)9-10-21(33)30(28)25(38-30)24(23)36-16(3)31/h9-10,17-19,21-25,33,35H,7-8,11-13H2,1-6H3

InChI Key

SHUUIGOWNXWQBK-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
Steroid ester
5,6-epoxysteroid
Dihydropyranone
Oxepane
Cyclohexenone
Dicarboxylic acid or derivatives
Pyran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Oxacycle
Ether
Oxirane
Dialkyl ether
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Organic oxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
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	2.3	ALOGPS
logP	3.23	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	13.26	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	122.66 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	137.31 m³·mol⁻¹	ChemAxon
Polarizability	56.83 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]+	222.977	32859911
AllCCS	[M+H-H2O]+	221.422	32859911
AllCCS	[M+Na]+	224.793	32859911
AllCCS	[M+NH4]+	224.392	32859911
AllCCS	[M-H]-	225.242	32859911
AllCCS	[M+Na-2H]-	227.555	32859911
AllCCS	[M+HCOO]-	230.244	32859911
DeepCCS	[M-2H]-	244.782	30932474
DeepCCS	[M+Na]+	220.206	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Withanolide 1	CC(=O)OC1C2OC22C(O)C=CC(=O)C2(C)C2CCC3(C)C(CCC3C(C)(O)C3CC(C)=C(C)C(=O)O3)C12	4698.3	Standard polar	33892256
Withanolide 1	CC(=O)OC1C2OC22C(O)C=CC(=O)C2(C)C2CCC3(C)C(CCC3C(C)(O)C3CC(C)=C(C)C(=O)O3)C12	3516.0	Standard non polar	33892256
Withanolide 1	CC(=O)OC1C2OC22C(O)C=CC(=O)C2(C)C2CCC3(C)C(CCC3C(C)(O)C3CC(C)=C(C)C(=O)O3)C12	4014.4	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 1 GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withanolide 1 GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withanolide 1 GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withanolide 1 GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withanolide 1 GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withanolide 1 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

73981783

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 Withanolide 1 (HMDB0259898)

MOL for HMDB0259898 (Withanolide 1)

3D MOL for HMDB0259898 (Withanolide 1)

3D SDF for HMDB0259898 (Withanolide 1)

3D-SDF for HMDB0259898 (Withanolide 1)

PDB for HMDB0259898 (Withanolide 1)

3D PDB for HMDB0259898 (Withanolide 1)

SMILES for HMDB0259898 (Withanolide 1)

INCHI for HMDB0259898 (Withanolide 1)

Structure for HMDB0259898 (Withanolide 1)

3D Structure for HMDB0259898 (Withanolide 1)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra