NP-MRD: Showing NP-Card for withaferin A (NP0036396)

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Record Information

Version

2.0

Created at

2021-06-20 19:34:48 UTC

Updated at

2023-02-13 19:34:20 UTC

NP-MRD ID

NP0036396

Secondary Accession Numbers

None

Natural Product Identification

Common Name

withaferin A

Provided By

JEOL Database JEOL Logo

Description

withaferin A is found in Physalis longifolia, Vassobia breviflora and Withania aristata. withaferin A was first documented in 2013 (PMID: 22935676). Based on a literature review a small amount of articles have been published on withaferin A (PMID: 22989414) (PMID: 23107437) (PMID: 23129310).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121343D          

 72 77  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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 13 48  1  0
 10 42  1  6
 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
  5 40  1  0
 22 57  1  0
 33 68  1  0
 33 69  1  0
 33 70  1  0
 11 43  1  0
 11 44  1  0
 11 45  1  0
 28 60  1  0
 28 61  1  0
 28 62  1  0
M  END


  Mrv1652306202121343D          

 72 77  0  0  0  0            999 V2000
   -5.2468    0.8853    2.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1441    1.7673    1.7893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2613    3.0854    1.5194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5160    3.9068    1.5988 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4959    4.7182    2.7654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0602    3.8783    1.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0833    5.1046    1.1612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9396    3.1969    0.7976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0245    1.7853    0.5075 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5766    1.2462    0.3039 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2606    1.4337    1.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5536   -0.2216   -0.2086 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3845   -0.3999   -1.5122 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7379   -1.5402   -2.3094 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2955   -2.1182   -1.3532 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4077   -3.0069   -1.9338 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7915   -4.1831   -2.6996 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8141   -5.1384   -3.1916 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9963   -4.5324   -3.7027 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1409   -5.3160   -2.4835 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9306   -6.5828   -2.7455 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0300   -6.2969   -3.6030 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4939   -7.2514   -1.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4475   -6.7391   -0.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8519   -5.4071   -0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7032   -5.0891    1.1254 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5072   -4.4709   -1.2467 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7893   -3.6656   -1.5554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3102   -3.5312   -0.7754 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7707   -2.3499    0.1305 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6294   -1.4344    0.6040 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8119   -0.8839   -0.5759 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6771    0.0721   -1.4321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8164    1.0779    1.6063 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9018    0.3299    3.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5415    0.1639    1.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.4190    3.2927    1.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6236    4.5522    0.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7662    5.3564    2.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3291    1.3935    1.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4835   -2.2834   -2.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2697   -2.7516   -0.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0864   -4.7264   -2.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2209   -3.8143   -3.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3831   -5.9633   -3.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2949   -7.3070   -3.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7032   -5.6334   -4.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9634   -8.2188   -1.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8494   -7.2632    0.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5964   -2.8778   -2.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2105   -3.2045   -0.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5805   -4.3036   -1.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6521   -4.1538   -0.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2828   -2.7276    1.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5037   -1.7323   -0.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807   -2.0010    1.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0665   -0.6259    1.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5326   -0.4279   -1.8932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1083    0.5340   -2.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0819    0.8852   -0.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9757    0.0307    1.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2902    1.0981    2.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 10  1  0  0  0  0
 17 16  1  0  0  0  0
 10  9  1  0  0  0  0
  9  8  1  0  0  0  0
 29 16  1  0  0  0  0
 21 20  1  0  0  0  0
 27 25  1  0  0  0  0
 27 20  1  0  0  0  0
  9 34  1  0  0  0  0
  8  6  1  0  0  0  0
  6  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
  6  7  2  0  0  0  0
 16 15  1  0  0  0  0
  2  1  1  0  0  0  0
 32 31  1  0  0  0  0
  3  4  1  0  0  0  0
 31 30  1  0  0  0  0
  4  5  1  0  0  0  0
 32 15  1  0  0  0  0
 25 26  2  0  0  0  0
 24 23  2  0  0  0  0
 21 22  1  0  0  0  0
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 20 19  1  6  0  0  0
 18 19  1  0  0  0  0
 23 21  1  0  0  0  0
 16 52  1  6  0  0  0
 27 29  1  0  0  0  0
 32 33  1  6  0  0  0
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  9 41  1  6  0  0  0
 15 14  1  0  0  0  0
 10 11  1  0  0  0  0
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 29 63  1  1  0  0  0
 18 17  1  0  0  0  0
 27 28  1  6  0  0  0
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 28 60  1  0  0  0  0
 28 61  1  0  0  0  0
 28 62  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036396

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C1=C(C([H])([H])[H])C([H])([H])[C@@]([H])(OC1=O)[C@@]([H])(C([H])([H])[H])[C@@]1([H])C([H])([H])C([H])([H])[C@@]2([H])[C@]3([H])C([H])([H])[C@@]4([H])O[C@]44[C@@]([H])(O[H])C([H])=C([H])C(=O)[C@]4(C([H])([H])[H])[C@@]3([H])C([H])([H])C([H])([H])[C@]12C([H])([H])[H]

> <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/t15-,16-,18+,19-,20-,21+,23-,24+,26+,27-,28+/m0/s1

> <INCHI_KEY>
DBRXOUCRJQVYJQ-CKNDUULBSA-N

> <FORMULA>
C28H38O6

> <MOLECULAR_WEIGHT>
470.606

> <EXACT_MASS>
470.266838944

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
52.64526411066189

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.64

> <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>
(1S,2R,6S,7R,9R,11S,12S,15R,16S)-6-hydroxy-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-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
   -5.2468    0.8853    2.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1441    1.7673    1.7893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2613    3.0854    1.5194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5160    3.9068    1.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4959    4.7182    2.7654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0602    3.8783    1.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0833    5.1046    1.1612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9396    3.1969    0.7976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0245    1.7853    0.5075 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5766    1.2462    0.3039 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2606    1.4337    1.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3831   -5.9633   -3.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2949   -7.3070   -3.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7032   -5.6334   -4.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9634   -8.2188   -1.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8494   -7.2632    0.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5964   -2.8778   -2.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2105   -3.2045   -0.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5805   -4.3036   -1.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6521   -4.1538   -0.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2828   -2.7276    1.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5037   -1.7323   -0.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807   -2.0010    1.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0665   -0.6259    1.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5326   -0.4279   -1.8932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1083    0.5340   -2.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0819    0.8852   -0.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9757    0.0307    1.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2902    1.0981    2.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 10  1  0
 17 16  1  0
 10  9  1  0
  9  8  1  0
 29 16  1  0
 21 20  1  0
 27 25  1  0
 27 20  1  0
  9 34  1  0
  8  6  1  0
  6  3  1  0
  3  2  2  0
  2 34  1  0
 29 30  1  0
  6  7  2  0
 16 15  1  0
  2  1  1  0
 32 31  1  0
  3  4  1  0
 31 30  1  0
  4  5  1  0
 32 15  1  0
 25 26  2  0
 24 23  2  0
 21 22  1  0
 24 25  1  0
 20 19  1  6
 18 19  1  0
 23 21  1  0
 16 52  1  6
 27 29  1  0
 32 33  1  6
 20 18  1  0
  9 41  1  6
 15 14  1  0
 10 11  1  0
 14 13  1  0
 12 46  1  1
 13 12  1  0
 15 51  1  1
 12 32  1  0
 29 63  1  1
 18 17  1  0
 27 28  1  6
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 10 42  1  6
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 34 72  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
 22 57  1  0
 33 68  1  0
 33 69  1  0
 33 70  1  0
 11 43  1  0
 11 44  1  0
 11 45  1  0
 28 60  1  0
 28 61  1  0
 28 62  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      -5.247   0.885   2.304  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.144   1.767   1.789  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.261   3.085   1.519  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.516   3.907   1.599  0.00  0.00           C+0
HETATM    5  O   UNK     0      -5.496   4.718   2.765  0.00  0.00           O+0
HETATM    6  C   UNK     0      -3.060   3.878   1.137  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.083   5.105   1.161  0.00  0.00           O+0
HETATM    8  O   UNK     0      -1.940   3.197   0.798  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.025   1.785   0.507  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.577   1.246   0.304  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.261   1.434   1.577  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.554  -0.222  -0.209  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.385  -0.400  -1.512  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.738  -1.540  -2.309  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.296  -2.118  -1.353  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.408  -3.007  -1.934  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.792  -4.183  -2.700  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.814  -5.138  -3.192  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.996  -4.532  -3.703  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.141  -5.316  -2.483  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.931  -6.583  -2.745  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.030  -6.297  -3.603  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.494  -7.251  -1.545  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.447  -6.739  -0.313  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.852  -5.407  -0.055  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.703  -5.089   1.125  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.507  -4.471  -1.247  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.789  -3.666  -1.555  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.310  -3.531  -0.775  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.771  -2.350   0.131  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.629  -1.434   0.604  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.812  -0.884  -0.576  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.677   0.072  -1.432  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.816   1.078   1.606  0.00  0.00           C+0
HETATM   35  H   UNK     0      -4.902   0.330   3.183  0.00  0.00           H+0
HETATM   36  H   UNK     0      -5.542   0.164   1.535  0.00  0.00           H+0
HETATM   37  H   UNK     0      -6.138   1.437   2.612  0.00  0.00           H+0
HETATM   38  H   UNK     0      -6.419   3.293   1.633  0.00  0.00           H+0
HETATM   39  H   UNK     0      -5.624   4.552   0.719  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.766   5.356   2.635  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.563   1.708  -0.445  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.120   1.892  -0.459  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.085   2.410   2.039  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.038   0.664   2.322  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.329   1.393   1.352  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.021  -0.850   0.564  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.390   0.510  -2.123  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.426  -0.640  -1.270  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.270  -1.153  -3.222  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.484  -2.283  -2.610  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.270  -2.752  -0.648  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.021  -2.422  -2.629  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.086  -4.726  -2.059  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.221  -3.814  -3.559  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.383  -5.963  -3.744  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.295  -7.307  -3.268  0.00  0.00           H+0
HETATM   57  H   UNK     0       4.703  -5.633  -4.240  0.00  0.00           H+0
HETATM   58  H   UNK     0       4.963  -8.219  -1.701  0.00  0.00           H+0
HETATM   59  H   UNK     0       4.849  -7.263   0.547  0.00  0.00           H+0
HETATM   60  H   UNK     0       4.596  -2.878  -2.292  0.00  0.00           H+0
HETATM   61  H   UNK     0       5.210  -3.204  -0.655  0.00  0.00           H+0
HETATM   62  H   UNK     0       5.580  -4.304  -1.964  0.00  0.00           H+0
HETATM   63  H   UNK     0       1.652  -4.154  -0.148  0.00  0.00           H+0
HETATM   64  H   UNK     0       3.283  -2.728   1.021  0.00  0.00           H+0
HETATM   65  H   UNK     0       3.504  -1.732  -0.398  0.00  0.00           H+0
HETATM   66  H   UNK     0       0.981  -2.001   1.284  0.00  0.00           H+0
HETATM   67  H   UNK     0       2.067  -0.626   1.196  0.00  0.00           H+0
HETATM   68  H   UNK     0       2.533  -0.428  -1.893  0.00  0.00           H+0
HETATM   69  H   UNK     0       1.108   0.534  -2.245  0.00  0.00           H+0
HETATM   70  H   UNK     0       2.082   0.885  -0.821  0.00  0.00           H+0
HETATM   71  H   UNK     0      -2.976   0.031   1.328  0.00  0.00           H+0
HETATM   72  H   UNK     0      -2.290   1.098   2.567  0.00  0.00           H+0
CONECT    1    2   35   36   37                                             
CONECT    2    3   34    1                                                  
CONECT    3    6    2    4                                                  
CONECT    4    3    5   38   39                                             
CONECT    5    4   40                                                       
CONECT    6    8    3    7                                                  
CONECT    7    6                                                            
CONECT    8    9    6                                                       
CONECT    9   10    8   34   41                                             
CONECT   10   12    9   11   42                                             
CONECT   11   10   43   44   45                                             
CONECT   12   10   46   13   32                                             
CONECT   13   14   12   47   48                                             
CONECT   14   15   13   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   29   28                                             
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    9    2   71   72                                             
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    4                                                            
CONECT   39    4                                                            
CONECT   40    5                                                            
CONECT   41    9                                                            
CONECT   42   10                                                            
CONECT   43   11                                                            
CONECT   44   11                                                            
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
   -5.2468    0.8853    2.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1441    1.7673    1.7893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2613    3.0854    1.5194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5160    3.9068    1.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4959    4.7182    2.7654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0602    3.8783    1.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0833    5.1046    1.1612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9396    3.1969    0.7976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0245    1.7853    0.5075 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5766    1.2462    0.3039 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2606    1.4337    1.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5536   -0.2216   -0.2086 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3845   -0.3999   -1.5122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7379   -1.5402   -2.3094 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2955   -2.1182   -1.3532 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4077   -3.0069   -1.9338 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7915   -4.1831   -2.6996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8141   -5.1384   -3.1916 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9963   -4.5324   -3.7027 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1409   -5.3160   -2.4835 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9306   -6.5828   -2.7455 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0300   -6.2969   -3.6030 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4939   -7.2514   -1.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4475   -6.7391   -0.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8519   -5.4071   -0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7032   -5.0891    1.1254 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5072   -4.4709   -1.2467 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7893   -3.6656   -1.5554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3102   -3.5312   -0.7754 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7707   -2.3499    0.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6294   -1.4344    0.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8119   -0.8839   -0.5759 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6771    0.0721   -1.4321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8164    1.0779    1.6063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9018    0.3299    3.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5415    0.1639    1.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1376    1.4369    2.6121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4190    3.2927    1.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6236    4.5522    0.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7662    5.3564    2.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5635    1.7076   -0.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1203    1.8923   -0.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0853    2.4104    2.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0378    0.6635    2.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3291    1.3935    1.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0208   -0.8496    0.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3897    0.5101   -2.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4258   -0.6398   -1.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2697   -1.1534   -3.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4835   -2.2834   -2.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2697   -2.7516   -0.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0208   -2.4217   -2.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0864   -4.7264   -2.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2209   -3.8143   -3.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3831   -5.9633   -3.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2949   -7.3070   -3.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7032   -5.6334   -4.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9634   -8.2188   -1.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8494   -7.2632    0.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5964   -2.8778   -2.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2105   -3.2045   -0.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5805   -4.3036   -1.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6521   -4.1538   -0.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2828   -2.7276    1.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5037   -1.7323   -0.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807   -2.0010    1.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0665   -0.6259    1.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5326   -0.4279   -1.8932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1083    0.5340   -2.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0819    0.8852   -0.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9757    0.0307    1.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2902    1.0981    2.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 10  1  0
 17 16  1  0
 10  9  1  0
  9  8  1  0
 29 16  1  0
 21 20  1  0
 27 25  1  0
 27 20  1  0
  9 34  1  0
  8  6  1  0
  6  3  1  0
  3  2  2  0
  2 34  1  0
 29 30  1  0
  6  7  2  0
 16 15  1  0
  2  1  1  0
 32 31  1  0
  3  4  1  0
 31 30  1  0
  4  5  1  0
 32 15  1  0
 25 26  2  0
 24 23  2  0
 21 22  1  0
 24 25  1  0
 20 19  1  6
 18 19  1  0
 23 21  1  0
 16 52  1  6
 27 29  1  0
 32 33  1  6
 20 18  1  0
  9 41  1  6
 15 14  1  0
 10 11  1  0
 14 13  1  0
 12 46  1  1
 13 12  1  0
 15 51  1  1
 12 32  1  0
 29 63  1  1
 18 17  1  0
 27 28  1  6
 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
 10 42  1  6
 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
  5 40  1  0
 22 57  1  0
 33 68  1  0
 33 69  1  0
 33 70  1  0
 11 43  1  0
 11 44  1  0
 11 45  1  0
 28 60  1  0
 28 61  1  0
 28 62  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
4beta,27-Dihydroxy-1-oxo-5beta,6beta-epoxywitha-2,24-dienolide	ChEBI
4b,27-Dihydroxy-1-oxo-5b,6b-epoxywitha-2,24-dienolide	Generator
4Β,27-dihydroxy-1-oxo-5β,6β-epoxywitha-2,24-dienolide	Generator
5,6-Epoxy-4,22,27-trihydroxy-1-oxoergosta-2,24-dienoic acid delta-lactone	MeSH

Chemical Formula

C₂₈H₃₈O₆

Average Mass

470.6060 Da

Monoisotopic Mass

470.26684 Da

IUPAC Name

(1S,2R,6S,7R,9R,11S,12S,15R,16S)-6-hydroxy-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl]-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,15R,16S)-6-hydroxy-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-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]OC([H])([H])C1=C(C([H])([H])[H])C([H])([H])[C@@]([H])(OC1=O)[C@@]([H])(C([H])([H])[H])[C@@]1([H])C([H])([H])C([H])([H])[C@@]2([H])[C@]3([H])C([H])([H])[C@@]4([H])O[C@]44[C@@]([H])(O[H])C([H])=C([H])C(=O)[C@]4(C([H])([H])[H])[C@@]3([H])C([H])([H])C([H])([H])[C@]12C([H])([H])[H]

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/t15-,16-,18+,19-,20-,21+,23-,24+,26+,27-,28+/m0/s1

InChI Key

DBRXOUCRJQVYJQ-CKNDUULBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Methanol, simulated)	Jaewoo.choi	Oregon State University	BENFRA	2023-04-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acnistus arborescens	KNApSAcK Database	22123792
Physalis longifolia	JEOL database	Zhang, H., et al, J. Nat. Prod. 74, 2532 (2011)
Solanum torvum	KNApSAcK Database	22123792
Vassobia breviflora	LOTUS Database	35616633
Withania aristata	LOTUS Database	35616633
Withania ashwagandha	KNApSAcK Database	22123792
Withania coagulans	KNApSAcK Database	22123792
Withania somnifera	KNApSAcK Database	22123792

Chemical Taxonomy

Classification

Not classified

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	2.64	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	52.65 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

C00003676

Chemspider ID

233064

KEGG Compound ID

C08841

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Withaferin_A

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

69120

Good Scents ID

Not Available

References

General References

Hahm ER, Singh SV: Withaferin A-induced apoptosis in human breast cancer cells is associated with suppression of inhibitor of apoptosis family protein expression. Cancer Lett. 2013 Jun 28;334(1):101-8. doi: 10.1016/j.canlet.2012.08.026. Epub 2012 Aug 27. [PubMed:22935676 ]
Jilani K, Lupescu A, Zbidah M, Shaik N, Lang F: Withaferin A-stimulated Ca2+ entry, ceramide formation and suicidal death of erythrocytes. Toxicol In Vitro. 2013 Feb;27(1):52-8. doi: 10.1016/j.tiv.2012.09.004. Epub 2012 Sep 16. [PubMed:22989414 ]
Li W, Zhao Y: Withaferin A suppresses tumor promoter 12-O-tetradecanoylphorbol 13-acetate-induced decreases in isocitrate dehydrogenase 1 activity and mitochondrial function in skin epidermal JB6 cells. Cancer Sci. 2013 Feb;104(2):143-8. doi: 10.1111/cas.12051. Epub 2012 Dec 7. [PubMed:23107437 ]
Grogan PT, Sleder KD, Samadi AK, Zhang H, Timmermann BN, Cohen MS: Cytotoxicity of withaferin A in glioblastomas involves induction of an oxidative stress-mediated heat shock response while altering Akt/mTOR and MAPK signaling pathways. Invest New Drugs. 2013 Jun;31(3):545-57. doi: 10.1007/s10637-012-9888-5. Epub 2012 Nov 6. [PubMed:23129310 ]
Zhang, H., et al. (2011). Zhang, H., et al, J. Nat. Prod. 74, 2532 (2011). J. Nat. Prod..

Showing NP-Card for withaferin A (NP0036396)

MOL for NP0036396 (withaferin A)

3D MOL for NP0036396 (withaferin A)

3D SDF for NP0036396 (withaferin A)

3D-SDF for NP0036396 (withaferin A)

PDB for NP0036396 (withaferin A)

3D PDB for NP0036396 (withaferin A)

SMILES for NP0036396 (withaferin A)

INCHI for NP0036396 (withaferin A)

Structure for NP0036396 (withaferin A)

3D Structure for NP0036396 (withaferin A)