NP-MRD: Showing NP-Card for withalongolide A (NP0036389)

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Record Information

Version

2.0

Created at

2021-06-20 19:34:30 UTC

Updated at

2021-06-30 00:08:01 UTC

NP-MRD ID

NP0036389

Secondary Accession Numbers

None

Natural Product Identification

Common Name

withalongolide A

Provided By

JEOL Database JEOL Logo

Description

Withalongolide A belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. withalongolide A is found in Physalis longifolia. withalongolide A was first documented in 2013 (PMID: 24273633). Based on a literature review very few articles have been published on withalongolide A (PMID: 31371177) (PMID: 29753460) (PMID: 28919755) (PMID: 25466231).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121343D          

 73 78  0  0  0  0            999 V2000
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M  END

     RDKit          3D

 73 78  0  0  0  0  0  0  0  0999 V2000
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 34 71  1  0
 11 44  1  0
 11 45  1  0
 11 46  1  0
 28 61  1  0
 28 62  1  0
 29 63  1  0
M  END


  Mrv1652306202121343D          

 73 78  0  0  0  0            999 V2000
   -1.9190   -4.9250   -4.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9881   -4.5872   -3.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
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 29 63  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036389

> <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])O[H])[C@@]3([H])C([H])([H])C([H])([H])[C@]12C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O7/c1-14-10-21(34-25(33)17(14)12-29)15(2)18-4-5-19-16-11-24-28(35-24)23(32)7-6-22(31)27(28,13-30)20(16)8-9-26(18,19)3/h6-7,15-16,18-21,23-24,29-30,32H,4-5,8-13H2,1-3H3/t15-,16-,18+,19-,20-,21+,23-,24+,26+,27-,28+/m0/s1

> <INCHI_KEY>
FJMXKFSOKLFYRC-CKNDUULBSA-N

> <FORMULA>
C28H38O7

> <MOLECULAR_WEIGHT>
486.605

> <EXACT_MASS>
486.261753564

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
53.56399619075885

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.61

> <JCHEM_LOGP>
2.3012029576666655

> <ALOGPS_LOGS>
-4.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.581735887212979

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.39168826784806

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8538493304385115

> <JCHEM_POLAR_SURFACE_AREA>
116.59000000000002

> <JCHEM_REFRACTIVITY>
128.96939999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.88e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,6S,7R,9R,11S,12S,15R,16S)-6-hydroxy-2-(hydroxymethyl)-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-16-methyl-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

 73 78  0  0  0  0  0  0  0  0999 V2000
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    0.2095   -0.2287    0.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9043    1.8355    2.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1950    2.9086    0.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5620    1.8030    0.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0875    3.9782    1.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4433    4.2366    3.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8263    3.9360    5.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8983    3.2554    4.8975 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6443    0.8499    5.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2454    0.7361    5.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5394    2.0712    4.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2816    2.6131    6.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5823    0.0674    2.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5091   -1.2713    3.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9087   -0.2516    3.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3220   -2.3209    2.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0696   -2.0929    1.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4175   -0.9573    2.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5025    0.3418    1.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5702    0.5524    2.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2118   -4.8128   -1.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5814   -3.3979   -2.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 10  9  1  0
  9  8  1  0
 30 16  1  0
 21 20  1  0
 27 25  1  0
 27 20  1  0
  9 35  1  0
  8  6  1  0
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  3  2  2  0
  2 35  1  0
 30 31  1  0
  6  7  2  0
 16 15  1  0
  2  1  1  0
 33 32  1  0
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 32 31  1  0
  4  5  1  0
 33 15  1  0
 25 26  2  0
 24 23  2  0
 21 22  1  0
 24 25  1  0
 20 19  1  1
 18 19  1  0
 23 21  1  0
 16 53  1  1
 27 30  1  0
 33 34  1  1
 20 18  1  0
  9 42  1  6
 15 14  1  0
 10 11  1  0
 14 13  1  0
 12 47  1  6
 13 12  1  0
 15 52  1  6
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 12 10  1  0
 28 29  1  0
 24 60  1  0
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 14 50  1  0
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  4 39  1  0
  4 40  1  0
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 11 44  1  0
 11 45  1  0
 11 46  1  0
 28 61  1  0
 28 62  1  0
 29 63  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      -1.919  -4.925  -4.294  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.988  -4.587  -3.293  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.311  -4.802  -3.462  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.979  -5.338  -4.696  0.00  0.00           C+0
HETATM    5  O   UNK     0      -5.353  -6.695  -4.498  0.00  0.00           O+0
HETATM    6  C   UNK     0      -5.258  -4.543  -2.343  0.00  0.00           C+0
HETATM    7  O   UNK     0      -6.401  -4.986  -2.372  0.00  0.00           O+0
HETATM    8  O   UNK     0      -4.800  -3.832  -1.285  0.00  0.00           O+0
HETATM    9  C   UNK     0      -3.564  -3.095  -1.402  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.215  -2.513   0.001  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.018  -3.638   1.026  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.006  -1.536  -0.043  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.220  -0.385  -1.069  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.454   0.837  -0.545  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.657   0.295   0.634  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.084   1.298   1.649  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.799   2.318   0.924  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.478   3.247   1.855  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.683   3.698   2.945  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.813   2.848   3.278  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.943   3.603   3.953  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.451   4.475   4.961  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.988   2.754   4.582  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.860   1.440   4.777  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.621   0.714   4.412  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.621  -0.501   4.616  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.393   1.478   3.852  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.423   1.677   5.048  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.934   2.593   6.021  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.742   0.535   2.732  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.103  -0.641   3.313  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.732  -1.559   2.252  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.592  -0.770   1.253  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.832  -0.172   1.961  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.482  -3.990  -2.006  0.00  0.00           C+0
HETATM   36  H   UNK     0      -1.123  -5.503  -3.811  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.480  -4.008  -4.700  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.280  -5.528  -5.130  0.00  0.00           H+0
HETATM   39  H   UNK     0      -5.875  -4.757  -4.946  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.336  -5.292  -5.577  0.00  0.00           H+0
HETATM   41  H   UNK     0      -6.043  -6.685  -3.805  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.777  -2.261  -2.083  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.105  -1.957   0.325  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.031  -4.102   0.931  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.772  -4.425   0.917  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.122  -3.260   2.046  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.128  -2.108  -0.376  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.848  -0.681  -2.056  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.279  -0.126  -1.180  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.807   1.258  -1.321  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.151   1.622  -0.232  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.210  -0.229   0.195  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.904   1.835   2.139  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.195   2.909   0.226  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.562   1.803   0.328  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.087   3.978   1.340  0.00  0.00           H+0
HETATM   57  H   UNK     0       3.443   4.237   3.212  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.826   3.936   5.492  0.00  0.00           H+0
HETATM   59  H   UNK     0       4.898   3.255   4.898  0.00  0.00           H+0
HETATM   60  H   UNK     0       4.644   0.850   5.237  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.245   0.736   5.579  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.539   2.071   4.704  0.00  0.00           H+0
HETATM   63  H   UNK     0       0.282   2.613   6.748  0.00  0.00           H+0
HETATM   64  H   UNK     0       1.582   0.067   2.194  0.00  0.00           H+0
HETATM   65  H   UNK     0       0.509  -1.271   3.965  0.00  0.00           H+0
HETATM   66  H   UNK     0      -0.909  -0.252   3.943  0.00  0.00           H+0
HETATM   67  H   UNK     0      -1.322  -2.321   2.769  0.00  0.00           H+0
HETATM   68  H   UNK     0       0.070  -2.093   1.726  0.00  0.00           H+0
HETATM   69  H   UNK     0      -3.418  -0.957   2.451  0.00  0.00           H+0
HETATM   70  H   UNK     0      -3.502   0.342   1.266  0.00  0.00           H+0
HETATM   71  H   UNK     0      -2.570   0.552   2.736  0.00  0.00           H+0
HETATM   72  H   UNK     0      -2.212  -4.813  -1.335  0.00  0.00           H+0
HETATM   73  H   UNK     0      -1.581  -3.398  -2.198  0.00  0.00           H+0
CONECT    1    2   36   37   38                                             
CONECT    2    3   35    1                                                  
CONECT    3    6    2    4                                                  
CONECT    4    3    5   39   40                                             
CONECT    5    4   41                                                       
CONECT    6    8    3    7                                                  
CONECT    7    6                                                            
CONECT    8    9    6                                                       
CONECT    9   10    8   35   42                                             
CONECT   10    9   11   12   43                                             
CONECT   11   10   44   45   46                                             
CONECT   12   47   13   33   10                                             
CONECT   13   14   12   48   49                                             
CONECT   14   15   13   50   51                                             
CONECT   15   16   33   14   52                                             
CONECT   16   17   30   15   53                                             
CONECT   17   16   18   54   55                                             
CONECT   18   19   20   17   56                                             
CONECT   19   20   18                                                       
CONECT   20   21   27   19   18                                             
CONECT   21   20   22   23   57                                             
CONECT   22   21   58                                                       
CONECT   23   24   21   59                                                  
CONECT   24   23   25   60                                                  
CONECT   25   27   26   24                                                  
CONECT   26   25                                                            
CONECT   27   25   20   30   28                                             
CONECT   28   27   29   61   62                                             
CONECT   29   28   63                                                       
CONECT   30   16   31   27   64                                             
CONECT   31   30   32   65   66                                             
CONECT   32   33   31   67   68                                             
CONECT   33   32   15   34   12                                             
CONECT   34   33   69   70   71                                             
CONECT   35    9    2   72   73                                             
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    4                                                            
CONECT   40    4                                                            
CONECT   41    5                                                            
CONECT   42    9                                                            
CONECT   43   10                                                            
CONECT   44   11                                                            
CONECT   45   11                                                            
CONECT   46   11                                                            
CONECT   47   12                                                            
CONECT   48   13                                                            
CONECT   49   13                                                            
CONECT   50   14                                                            
CONECT   51   14                                                            
CONECT   52   15                                                            
CONECT   53   16                                                            
CONECT   54   17                                                            
CONECT   55   17                                                            
CONECT   56   18                                                            
CONECT   57   21                                                            
CONECT   58   22                                                            
CONECT   59   23                                                            
CONECT   60   24                                                            
CONECT   61   28                                                            
CONECT   62   28                                                            
CONECT   63   29                                                            
CONECT   64   30                                                            
CONECT   65   31                                                            
CONECT   66   31                                                            
CONECT   67   32                                                            
CONECT   68   32                                                            
CONECT   69   34                                                            
CONECT   70   34                                                            
CONECT   71   34                                                            
CONECT   72   35                                                            
CONECT   73   35                                                            
MASTER        0    0    0    0    0    0    0    0   73    0  156    0
END

RDKit          3D

73 78  0  0  0  0  0  0  0  0999 V2000
   -1.9190   -4.9250   -4.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9881   -4.5872   -3.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3107   -4.8024   -3.4625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9795   -5.3383   -4.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3525   -6.6954   -4.4983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2579   -4.5426   -2.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4012   -4.9863   -2.3718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7995   -3.8324   -1.2845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5641   -3.0949   -1.4021 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2145   -2.5129    0.0006 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0180   -3.6384    1.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0060   -1.5355   -0.0434 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2201   -0.3848   -1.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4536    0.8367   -0.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6571    0.2947    0.6341 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0838    1.2981    1.6491 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7987    2.3177    0.9239 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6828    3.6982    2.9448 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8133    2.8479    3.2782 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9426    3.6026    3.9529 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4513    4.4751    4.9613 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9877    2.7537    4.5818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8601    1.4398    4.7765 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6211   -0.5014    4.6157 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4229    1.6772    5.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9335    2.5930    6.0208 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7419    0.5349    2.7319 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1028   -0.6414    3.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7321   -1.5593    2.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5923   -0.7700    1.2532 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8321   -0.1724    1.9614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4825   -3.9897   -2.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1234   -5.5025   -3.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3356   -5.2920   -5.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0425   -6.6849   -3.8051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7770   -2.2611   -2.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1216   -3.2601    2.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1283   -2.1085   -0.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8478   -0.6807   -2.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2793   -0.1261   -1.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1509    1.6219   -0.2316 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2095   -0.2287    0.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1950    2.9086    0.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5620    1.8030    0.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0875    3.9782    1.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4433    4.2366    3.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8263    3.9360    5.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8983    3.2554    4.8975 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6443    0.8499    5.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2454    0.7361    5.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5394    2.0712    4.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2816    2.6131    6.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5823    0.0674    2.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5091   -1.2713    3.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9087   -0.2516    3.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3220   -2.3209    2.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0696   -2.0929    1.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4175   -0.9573    2.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5025    0.3418    1.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5702    0.5524    2.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2118   -4.8128   -1.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5814   -3.3979   -2.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 10  9  1  0
  9  8  1  0
 30 16  1  0
 21 20  1  0
 27 25  1  0
 27 20  1  0
  9 35  1  0
  8  6  1  0
  6  3  1  0
  3  2  2  0
  2 35  1  0
 30 31  1  0
  6  7  2  0
 16 15  1  0
  2  1  1  0
 33 32  1  0
  3  4  1  0
 32 31  1  0
  4  5  1  0
 33 15  1  0
 25 26  2  0
 24 23  2  0
 21 22  1  0
 24 25  1  0
 20 19  1  1
 18 19  1  0
 23 21  1  0
 16 53  1  1
 27 30  1  0
 33 34  1  1
 20 18  1  0
  9 42  1  6
 15 14  1  0
 10 11  1  0
 14 13  1  0
 12 47  1  6
 13 12  1  0
 15 52  1  6
 12 33  1  0
 30 64  1  6
 18 17  1  0
 27 28  1  1
 12 10  1  0
 28 29  1  0
 24 60  1  0
 23 59  1  0
 21 57  1  6
 18 56  1  6
 17 54  1  0
 17 55  1  0
 32 67  1  0
 32 68  1  0
 31 65  1  0
 31 66  1  0
 14 50  1  0
 14 51  1  0
 13 48  1  0
 13 49  1  0
 10 43  1  1
 35 72  1  0
 35 73  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
 22 58  1  0
 34 69  1  0
 34 70  1  0
 34 71  1  0
 11 44  1  0
 11 45  1  0
 11 46  1  0
 28 61  1  0
 28 62  1  0
 29 63  1  0
M  END

View in JSmol

Synonyms

Value	Source
19-Hydroxywithaferin a	ChEBI

Chemical Formula

C₂₈H₃₈O₇

Average Mass

486.6050 Da

Monoisotopic Mass

486.26175 Da

IUPAC Name

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

Traditional Name

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

InChI Identifier

InChI=1S/C28H38O7/c1-14-10-21(34-25(33)17(14)12-29)15(2)18-4-5-19-16-11-24-28(35-24)23(32)7-6-22(31)27(28,13-30)20(16)8-9-26(18,19)3/h6-7,15-16,18-21,23-24,29-30,32H,4-5,8-13H2,1-3H3/t15-,16-,18+,19-,20-,21+,23-,24+,26+,27-,28+/m0/s1

InChI Key

FJMXKFSOKLFYRC-CKNDUULBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, 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
Physalis longifolia	JEOL database	Zhang, H., et al, J. Nat. Prod. 74, 2532 (2011)

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Withanolides and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

secondary alcohol (CHEBI:69106 )
epoxide (CHEBI:69106 )
enone (CHEBI:69106 )
primary alcohol (CHEBI:69106 )
delta-lactone (CHEBI:69106 )
27-hydroxy steroid (CHEBI:69106 )
4-hydroxy steroid (CHEBI:69106 )
19-hydroxy steroid (CHEBI:69106 )
ergostanoid (CHEBI:69106 )
withanolide (CHEBI:69106 )

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	1.61	ALOGPS
logP	2.3	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	13.39	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	116.59 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	128.97 m³·mol⁻¹	ChemAxon
Polarizability	53.56 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

Not Available

Chemspider ID

28490134

KEGG Compound ID

Not Available

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

69106

Good Scents ID

Not Available

References

General References

Wang T, Subramanian C, Yu M, White PT, Kuai R, Sanchez J, Moon JJ, Timmermann BN, Schwendeman A, Cohen MS: Mimetic sHDL nanoparticles: A novel drug-delivery strategy to target triple-negative breast cancer. Surgery. 2019 Dec;166(6):1168-1175. doi: 10.1016/j.surg.2019.06.010. Epub 2019 Jul 29. [PubMed:31371177 ]
Subramanian C, White PT, Kuai R, Kalidindi A, Castle VP, Moon JJ, Timmermann BN, Schwendeman A, Cohen MS: Synthetic high-density lipoprotein nanoconjugate targets neuroblastoma stem cells, blocking migration and self-renewal. Surgery. 2018 May 9. pii: S0039-6060(18)30080-1. doi: 10.1016/j.surg.2018.01.023. [PubMed:29753460 ]
Kuai R, Subramanian C, White PT, Timmermann BN, Moon JJ, Cohen MS, Schwendeman A: Synthetic high-density lipoprotein nanodisks for targeted withalongolide delivery to adrenocortical carcinoma. Int J Nanomedicine. 2017 Sep 6;12:6581-6594. doi: 10.2147/IJN.S140591. eCollection 2017. [PubMed:28919755 ]
Cao CM, Kindscher K, Gallagher RJ, Zhang H, Timmermann BN: Analysis of Major Withanolides in Physalis longifolia Nutt. by HPLC-PDA. J Chromatogr Sci. 2015 Aug;53(7):1044-7. doi: 10.1093/chromsci/bmu162. Epub 2014 Dec 2. [PubMed:25466231 ]
Motiwala HF, Bazzill J, Samadi A, Zhang H, Timmermann BN, Cohen MS, Aube J: Synthesis and Cytotoxicity of Semisynthetic Withalongolide A Analogues. ACS Med Chem Lett. 2013 Nov 14;4(11). doi: 10.1021/ml400267q. [PubMed:24273633 ]
Zhang, H., et al. (2011). Zhang, H., et al, J. Nat. Prod. 74, 2532 (2011). J. Nat. Prod..

Showing NP-Card for withalongolide A (NP0036389)

MOL for NP0036389 (withalongolide A)

3D MOL for NP0036389 (withalongolide A)

3D SDF for NP0036389 (withalongolide A)

3D-SDF for NP0036389 (withalongolide A)

PDB for NP0036389 (withalongolide A)

3D PDB for NP0036389 (withalongolide A)

SMILES for NP0036389 (withalongolide A)

INCHI for NP0036389 (withalongolide A)

Structure for NP0036389 (withalongolide A)

3D Structure for NP0036389 (withalongolide A)