NP-MRD: Showing NP-Card for withanolide D (NP0035451)

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Record Information

Version

2.0

Created at

2021-06-20 18:53:36 UTC

Updated at

2021-06-30 00:06:26 UTC

NP-MRD ID

NP0035451

Secondary Accession Numbers

None

Natural Product Identification

Common Name

withanolide D

Provided By

JEOL Database JEOL Logo

Description

Withanolide d belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. Thus, withanolide D is considered to be a sterol. withanolide D is found in Acnistus arborescens, Apis cerana, Iochroma fuchsioides and Physalis viscosa. withanolide D was first documented in 1975 (PMID: 1125091). Based on a literature review a small amount of articles have been published on Withanolide d (PMID: 17103214) (PMID: 17417907) (PMID: 20836852) (PMID: 22479585).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120533D          

 72 77  0  0  0  0            999 V2000
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M  END

     RDKit          3D

 72 77  0  0  0  0  0  0  0  0999 V2000
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 31 66  1  0
 31 67  1  0
 30 64  1  0
 30 65  1  0
 14 49  1  0
 14 50  1  0
 13 47  1  0
 13 48  1  0
 34 71  1  0
 34 72  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  4 38  1  0
  4 39  1  0
  4 40  1  0
 28 60  1  0
 28 61  1  0
 28 62  1  0
 22 57  1  0
 33 68  1  0
 33 69  1  0
 33 70  1  0
 11 45  1  0
 10 42  1  0
 10 43  1  0
 10 44  1  0
M  END


  Mrv1652306202120533D          

 72 77  0  0  0  0            999 V2000
   -4.9144   -4.3668    2.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2266   -2.9150    1.9425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4647   -2.3928    1.8085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7526   -3.1658    1.8057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6506   -0.9139    1.7063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7532   -0.3948    1.8284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5407   -0.1616    1.5084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3309   -0.7937    1.0228 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2050    0.2963    0.9892 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9766    0.8973    2.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7059    1.3617    0.1623 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0852   -0.8021   -1.0790 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7410   -0.6646   -1.8067 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2319   -0.2585   -0.7090 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5859    0.3436   -1.1191 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3280   -0.6226   -2.0493 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.7902    1.2502   -2.6366 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7824    0.7385   -0.3842 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2562    0.7236    0.8427 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7942    0.8391    1.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3864    0.6450    2.2001 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8724    1.2469   -0.1287 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8400    2.7916   -0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4355    0.6223    0.1584 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6043    1.4342    1.1969 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2159    0.8446    1.4966 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6148    0.6505    0.2162 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9501    2.0219   -0.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0165   -2.0174    1.8778 C   0  0  2  0  0  0  0  0  0  0  0  0
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    5.6221    2.2379   -2.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8611    0.6795   -0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8681    0.6376    1.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6107    3.2082    0.8404 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8092    3.2143   -0.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0998    3.1655   -0.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4683    2.4635    0.8500 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2915    1.5106    2.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
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 12  9  1  0  0  0  0
 17 16  1  0  0  0  0
  9  8  1  0  0  0  0
  8  7  1  0  0  0  0
 29 16  1  0  0  0  0
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 27 25  1  0  0  0  0
 27 20  1  0  0  0  0
  8 34  1  0  0  0  0
  7  5  1  0  0  0  0
  5  3  1  0  0  0  0
  3  2  2  0  0  0  0
  2 34  1  0  0  0  0
 29 30  1  0  0  0  0
 25 26  2  0  0  0  0
 16 15  1  0  0  0  0
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 32 31  1  0  0  0  0
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 10 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0035451

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C([H])=C([H])C(=O)[C@]2(C([H])([H])[H])[C@@]3([H])C([H])([H])C([H])([H])[C@@]4(C([H])([H])[H])[C@@]([H])(C([H])([H])C([H])([H])[C@]4([H])[C@](O[H])(C([H])([H])[H])[C@]4([H])OC(=O)C(=C(C([H])([H])[H])C4([H])[H])C([H])([H])[H])[C@]3([H])C([H])([H])[C@@]3([H])O[C@@]123

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O6/c1-14-12-22(33-24(31)15(14)2)27(5,32)19-7-6-17-16-13-23-28(34-23)21(30)9-8-20(29)26(28,4)18(16)10-11-25(17,19)3/h8-9,16-19,21-23,30,32H,6-7,10-13H2,1-5H3/t16-,17-,18-,19-,21-,22+,23+,25-,26-,27+,28+/m0/s1

> <INCHI_KEY>
SASUFNRGCZMRFD-JCUIILOWSA-N

> <FORMULA>
C28H38O6

> <MOLECULAR_WEIGHT>
470.606

> <EXACT_MASS>
470.266838944

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
52.576231200421205

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,6S,7R,9R,11S,12S,15S,16S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadec-4-en-3-one

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
3.7813992359999977

> <ALOGPS_LOGS>
-4.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.946276780691107

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.279908259252313

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3314299384025157

> <JCHEM_POLAR_SURFACE_AREA>
96.36000000000001

> <JCHEM_REFRACTIVITY>
126.87109999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.77e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,6S,7R,9R,11S,12S,15S,16S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadec-4-en-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 72 77  0  0  0  0  0  0  0  0999 V2000
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    4.2129   -0.8221   -3.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3118    0.0222   -2.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6221    2.2379   -2.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8611    0.6795   -0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8681    0.6376    1.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6107    3.2082    0.8404 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8092    3.2143   -0.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0998    3.1655   -0.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6095   -0.3645    0.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4683    2.4635    0.8500 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    1.5069    2.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2915    1.5106    2.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3448   -0.1141    2.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0604    2.5741   -0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4737    2.6635    0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5843    1.9302   -1.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1756   -2.5662    1.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7465   -1.7394    2.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
 12  9  1  0
 17 16  1  0
  9  8  1  0
  8  7  1  0
 29 16  1  0
 21 20  1  0
 27 25  1  0
 27 20  1  0
  8 34  1  0
  7  5  1  0
  5  3  1  0
  3  2  2  0
  2 34  1  0
 29 30  1  0
 25 26  2  0
 16 15  1  0
  5  6  2  0
 32 31  1  0
  2  1  1  0
 31 30  1  0
  3  4  1  0
 32 15  1  0
 27 28  1  6
 24 23  2  0
 20 19  1  6
 18 19  1  0
 24 25  1  0
 21 22  1  0
 23 21  1  0
 16 52  1  6
 27 29  1  0
 32 33  1  6
 20 18  1  0
  9 11  1  6
 14 13  1  0
  8 41  1  6
 13 12  1  0
  9 10  1  0
 12 32  1  0
 12 46  1  1
 15 14  1  0
 15 51  1  1
 18 17  1  0
 29 63  1  1
 24 59  1  0
 23 58  1  0
 21 56  1  6
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 17 54  1  0
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 34 71  1  0
 34 72  1  0
  1 35  1  0
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  1 37  1  0
  4 38  1  0
  4 39  1  0
  4 40  1  0
 28 60  1  0
 28 61  1  0
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 22 57  1  0
 33 68  1  0
 33 69  1  0
 33 70  1  0
 11 45  1  0
 10 42  1  0
 10 43  1  0
 10 44  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.914  -4.367   2.179  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.227  -2.915   1.942  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.465  -2.393   1.809  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.753  -3.166   1.806  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.651  -0.914   1.706  0.00  0.00           C+0
HETATM    6  O   UNK     0      -7.753  -0.395   1.828  0.00  0.00           O+0
HETATM    7  O   UNK     0      -5.541  -0.162   1.508  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.331  -0.794   1.023  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.205   0.296   0.989  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.977   0.897   2.384  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.706   1.362   0.162  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.884  -0.255   0.366  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.085  -0.802  -1.079  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.741  -0.665  -1.807  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.232  -0.259  -0.709  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.586   0.344  -1.119  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.328  -0.623  -2.049  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.692  -0.148  -2.390  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.790   1.250  -2.637  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.478   0.747  -1.456  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.981   0.825  -1.632  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.331   2.057  -2.253  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.782   0.739  -0.384  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.256   0.724   0.843  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.794   0.839   1.055  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.386   0.645   2.200  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.872   1.247  -0.129  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.840   2.792  -0.147  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.436   0.622   0.158  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.604   1.434   1.197  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.216   0.845   1.497  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.615   0.651   0.216  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.950   2.022  -0.415  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.016  -2.017   1.878  0.00  0.00           C+0
HETATM   35  H   UNK     0      -4.223  -4.468   3.022  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.441  -4.799   1.291  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.793  -4.968   2.422  0.00  0.00           H+0
HETATM   38  H   UNK     0      -8.281  -3.030   2.755  0.00  0.00           H+0
HETATM   39  H   UNK     0      -7.609  -4.237   1.645  0.00  0.00           H+0
HETATM   40  H   UNK     0      -8.405  -2.822   0.995  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.554  -1.096  -0.009  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.436   1.846   2.323  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.924   1.146   2.875  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.426   0.215   3.037  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.593   1.589   0.505  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.574  -1.107   0.989  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.854  -0.253  -1.632  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.397  -1.852  -1.044  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.805   0.099  -2.590  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.454  -1.607  -2.285  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.463  -1.185  -0.156  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.424   1.286  -1.655  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.765  -0.755  -2.980  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.410  -1.612  -1.583  0.00  0.00           H+0
HETATM   55  H   UNK     0       4.213  -0.822  -3.058  0.00  0.00           H+0
HETATM   56  H   UNK     0       6.312   0.022  -2.302  0.00  0.00           H+0
HETATM   57  H   UNK     0       5.622   2.238  -2.899  0.00  0.00           H+0
HETATM   58  H   UNK     0       7.861   0.680  -0.501  0.00  0.00           H+0
HETATM   59  H   UNK     0       6.868   0.638   1.733  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.611   3.208   0.840  0.00  0.00           H+0
HETATM   61  H   UNK     0       4.809   3.214  -0.433  0.00  0.00           H+0
HETATM   62  H   UNK     0       3.100   3.166  -0.862  0.00  0.00           H+0
HETATM   63  H   UNK     0       2.610  -0.365   0.617  0.00  0.00           H+0
HETATM   64  H   UNK     0       1.468   2.463   0.850  0.00  0.00           H+0
HETATM   65  H   UNK     0       2.144   1.507   2.146  0.00  0.00           H+0
HETATM   66  H   UNK     0      -0.292   1.511   2.200  0.00  0.00           H+0
HETATM   67  H   UNK     0       0.345  -0.114   2.015  0.00  0.00           H+0
HETATM   68  H   UNK     0      -0.060   2.574  -0.728  0.00  0.00           H+0
HETATM   69  H   UNK     0      -1.474   2.664   0.302  0.00  0.00           H+0
HETATM   70  H   UNK     0      -1.584   1.930  -1.302  0.00  0.00           H+0
HETATM   71  H   UNK     0      -3.176  -2.566   1.441  0.00  0.00           H+0
HETATM   72  H   UNK     0      -3.747  -1.739   2.902  0.00  0.00           H+0
CONECT    1    2   35   36   37                                             
CONECT    2    3   34    1                                                  
CONECT    3    5    2    4                                                  
CONECT    4    3   38   39   40                                             
CONECT    5    7    3    6                                                  
CONECT    6    5                                                            
CONECT    7    8    5                                                       
CONECT    8    9    7   34   41                                             
CONECT    9   12    8   11   10                                             
CONECT   10    9   42   43   44                                             
CONECT   11    9   45                                                       
CONECT   12    9   13   32   46                                             
CONECT   13   14   12   47   48                                             
CONECT   14   13   15   49   50                                             
CONECT   15   16   32   14   51                                             
CONECT   16   17   29   15   52                                             
CONECT   17   16   18   53   54                                             
CONECT   18   19   20   17   55                                             
CONECT   19   20   18                                                       
CONECT   20   21   27   19   18                                             
CONECT   21   20   22   23   56                                             
CONECT   22   21   57                                                       
CONECT   23   24   21   58                                                  
CONECT   24   23   25   59                                                  
CONECT   25   27   26   24                                                  
CONECT   26   25                                                            
CONECT   27   25   20   28   29                                             
CONECT   28   27   60   61   62                                             
CONECT   29   16   30   27   63                                             
CONECT   30   29   31   64   65                                             
CONECT   31   32   30   66   67                                             
CONECT   32   31   15   33   12                                             
CONECT   33   32   68   69   70                                             
CONECT   34    8    2   71   72                                             
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    4                                                            
CONECT   39    4                                                            
CONECT   40    4                                                            
CONECT   41    8                                                            
CONECT   42   10                                                            
CONECT   43   10                                                            
CONECT   44   10                                                            
CONECT   45   11                                                            
CONECT   46   12                                                            
CONECT   47   13                                                            
CONECT   48   13                                                            
CONECT   49   14                                                            
CONECT   50   14                                                            
CONECT   51   15                                                            
CONECT   52   16                                                            
CONECT   53   17                                                            
CONECT   54   17                                                            
CONECT   55   18                                                            
CONECT   56   21                                                            
CONECT   57   22                                                            
CONECT   58   23                                                            
CONECT   59   24                                                            
CONECT   60   28                                                            
CONECT   61   28                                                            
CONECT   62   28                                                            
CONECT   63   29                                                            
CONECT   64   30                                                            
CONECT   65   30                                                            
CONECT   66   31                                                            
CONECT   67   31                                                            
CONECT   68   33                                                            
CONECT   69   33                                                            
CONECT   70   33                                                            
CONECT   71   34                                                            
CONECT   72   34                                                            
MASTER        0    0    0    0    0    0    0    0   72    0  154    0
END

RDKit          3D

72 77  0  0  0  0  0  0  0  0999 V2000
   -4.9144   -4.3668    2.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2266   -2.9150    1.9425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4647   -2.3928    1.8085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7526   -3.1658    1.8057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6506   -0.9139    1.7063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7532   -0.3948    1.8284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5407   -0.1616    1.5084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3309   -0.7937    1.0228 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2050    0.2963    0.9892 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9766    0.8973    2.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7059    1.3617    0.1623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8840   -0.2551    0.3664 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0852   -0.8021   -1.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7410   -0.6646   -1.8067 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2319   -0.2585   -0.7090 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5859    0.3436   -1.1191 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3280   -0.6226   -2.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6915   -0.1483   -2.3905 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7902    1.2502   -2.6366 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4781    0.7468   -1.4558 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9814    0.8249   -1.6320 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3309    2.0570   -2.2529 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7824    0.7385   -0.3842 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2562    0.7236    0.8427 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7942    0.8391    1.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3864    0.6450    2.2001 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8724    1.2469   -0.1287 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8400    2.7916   -0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4355    0.6223    0.1584 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6043    1.4342    1.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2159    0.8446    1.4966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6148    0.6505    0.2162 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9501    2.0219   -0.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0165   -2.0174    1.8778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2225   -4.4679    3.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4405   -4.7990    1.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7929   -4.9679    2.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2805   -3.0297    2.7552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6094   -4.2369    1.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4046   -2.8222    0.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5536   -1.0964   -0.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4358    1.8461    2.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9236    1.1462    2.8750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4258    0.2145    3.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5925    1.5892    0.5055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5742   -1.1067    0.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8545   -0.2526   -1.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3970   -1.8522   -1.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8047    0.0986   -2.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4541   -1.6067   -2.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4632   -1.1852   -0.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4238    1.2858   -1.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7650   -0.7549   -2.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4096   -1.6120   -1.5829 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2129   -0.8221   -3.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3118    0.0222   -2.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6221    2.2379   -2.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8611    0.6795   -0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8681    0.6376    1.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6107    3.2082    0.8404 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8092    3.2143   -0.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0998    3.1655   -0.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6095   -0.3645    0.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4683    2.4635    0.8500 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    1.5069    2.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2915    1.5106    2.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3448   -0.1141    2.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0604    2.5741   -0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4737    2.6635    0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5843    1.9302   -1.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1756   -2.5662    1.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7465   -1.7394    2.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
 12  9  1  0
 17 16  1  0
  9  8  1  0
  8  7  1  0
 29 16  1  0
 21 20  1  0
 27 25  1  0
 27 20  1  0
  8 34  1  0
  7  5  1  0
  5  3  1  0
  3  2  2  0
  2 34  1  0
 29 30  1  0
 25 26  2  0
 16 15  1  0
  5  6  2  0
 32 31  1  0
  2  1  1  0
 31 30  1  0
  3  4  1  0
 32 15  1  0
 27 28  1  6
 24 23  2  0
 20 19  1  6
 18 19  1  0
 24 25  1  0
 21 22  1  0
 23 21  1  0
 16 52  1  6
 27 29  1  0
 32 33  1  6
 20 18  1  0
  9 11  1  6
 14 13  1  0
  8 41  1  6
 13 12  1  0
  9 10  1  0
 12 32  1  0
 12 46  1  1
 15 14  1  0
 15 51  1  1
 18 17  1  0
 29 63  1  1
 24 59  1  0
 23 58  1  0
 21 56  1  6
 18 55  1  6
 17 53  1  0
 17 54  1  0
 31 66  1  0
 31 67  1  0
 30 64  1  0
 30 65  1  0
 14 49  1  0
 14 50  1  0
 13 47  1  0
 13 48  1  0
 34 71  1  0
 34 72  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  4 38  1  0
  4 39  1  0
  4 40  1  0
 28 60  1  0
 28 61  1  0
 28 62  1  0
 22 57  1  0
 33 68  1  0
 33 69  1  0
 33 70  1  0
 11 45  1  0
 10 42  1  0
 10 43  1  0
 10 44  1  0
M  END

View in JSmol

Synonyms

Value	Source
4beta,20alpha-Dihydroxy-1-oxo-5beta,6beta-epoxy-20S,22R-witha-2,24-dienolide	ChEBI
4b,20a-Dihydroxy-1-oxo-5b,6b-epoxy-20S,22R-witha-2,24-dienolide	Generator
4Β,20α-dihydroxy-1-oxo-5β,6β-epoxy-20S,22R-witha-2,24-dienolide	Generator
5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-Oic acid delta-lactone	MeSH
Dihydrowithanolide D	MeSH

Chemical Formula

C₂₈H₃₈O₆

Average Mass

470.6060 Da

Monoisotopic Mass

470.26684 Da

IUPAC Name

(1S,2R,6S,7R,9R,11S,12S,15S,16S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadec-4-en-3-one

Traditional Name

(1S,2R,6S,7R,9R,11S,12S,15S,16S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadec-4-en-3-one

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C([H])=C([H])C(=O)[C@]2(C([H])([H])[H])[C@@]3([H])C([H])([H])C([H])([H])[C@@]4(C([H])([H])[H])[C@@]([H])(C([H])([H])C([H])([H])[C@]4([H])[C@](O[H])(C([H])([H])[H])[C@]4([H])OC(=O)C(=C(C([H])([H])[H])C4([H])[H])C([H])([H])[H])[C@]3([H])C([H])([H])[C@@]3([H])O[C@@]123

InChI Identifier

InChI=1S/C28H38O6/c1-14-12-22(33-24(31)15(14)2)27(5,32)19-7-6-17-16-13-23-28(34-23)21(30)9-8-20(29)26(28,4)18(16)10-11-25(17,19)3/h8-9,16-19,21-23,30,32H,6-7,10-13H2,1-5H3/t16-,17-,18-,19-,21-,22+,23+,25-,26-,27+,28+/m0/s1

InChI Key

SASUFNRGCZMRFD-JCUIILOWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acnistus arborescens	JEOL database	Roumy, V., et al, J. Nat. Prod. 73, 1313 (2010)
Apis cerana	LOTUS Database	35616633
Iochroma fuchsioides	LOTUS Database	35616633
Physalis viscosa	LOTUS Database	35616633
Solanum torvum	KNApSAcK Database	22123792
Tubocapsicum anomalum	KNApSAcK Database	22123792
Withania somnifera	KNApSAcK Database	22123792

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
Tertiary alcohol
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
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

tertiary alcohol (CHEBI:10041 )
secondary alcohol (CHEBI:10041 )
epoxide (CHEBI:10041 )
enone (CHEBI:10041 )
delta-lactone (CHEBI:10041 )
4-hydroxy steroid (CHEBI:10041 )
ergostanoid (CHEBI:10041 )
withanolide (CHEBI:10041 )
20-hydroxy steroid (CHEBI:10041 )
Steroids (C08842 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	2.7	ALOGPS
logP	3.78	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	13.28	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.36 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	126.87 m³·mol⁻¹	ChemAxon
Polarizability	52.58 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003677

Chemspider ID

141995

KEGG Compound ID

C08842

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

10041

Good Scents ID

Not Available

References

General References

Chowdhury K, Neogy RK: Mode of action of Withaferin A and Withanolide D. Biochem Pharmacol. 1975 Apr 15;24(8):919-20. doi: 10.1016/0006-2952(75)90165-3. [PubMed:1125091 ]
Bandyopadhyay M, Jha S, Tepfer D: Changes in morphological phenotypes and withanolide composition of Ri-transformed roots of Withania somnifera. Plant Cell Rep. 2007 May;26(5):599-609. doi: 10.1007/s00299-006-0260-0. Epub 2006 Nov 15. [PubMed:17103214 ]
Hsieh PW, Huang ZY, Chen JH, Chang FR, Wu CC, Yang YL, Chiang MY, Yen MH, Chen SL, Yen HF, Lubken T, Hung WC, Wu YC: Cytotoxic withanolides from Tubocapsicum anomalum. J Nat Prod. 2007 May;70(5):747-53. doi: 10.1021/np0605541. Epub 2007 Apr 7. [PubMed:17417907 ]
Mondal S, Mandal C, Sangwan R, Chandra S, Mandal C: Withanolide D induces apoptosis in leukemia by targeting the activation of neutral sphingomyelinase-ceramide cascade mediated by synergistic activation of c-Jun N-terminal kinase and p38 mitogen-activated protein kinase. Mol Cancer. 2010 Sep 13;9:239. doi: 10.1186/1476-4598-9-239. [PubMed:20836852 ]
Mondal S, Bhattacharya K, Mallick A, Sangwan R, Mandal C: Bak compensated for Bax in p53-null cells to release cytochrome c for the initiation of mitochondrial signaling during Withanolide D-induced apoptosis. PLoS One. 2012;7(3):e34277. doi: 10.1371/journal.pone.0034277. Epub 2012 Mar 29. [PubMed:22479585 ]
Roumy, V., et al. (2010). Roumy, V., et al, J. Nat. Prod. 73, 1313 (2010). J. Nat. Prod..

Showing NP-Card for withanolide D (NP0035451)

MOL for NP0035451 (withanolide D)

3D MOL for NP0035451 (withanolide D)

3D SDF for NP0035451 (withanolide D)

3D-SDF for NP0035451 (withanolide D)

PDB for NP0035451 (withanolide D)

3D PDB for NP0035451 (withanolide D)

SMILES for NP0035451 (withanolide D)

INCHI for NP0035451 (withanolide D)

Structure for NP0035451 (withanolide D)

3D Structure for NP0035451 (withanolide D)