NP-MRD: Showing NP-Card for 20S,21-epoxyresibufogenin (NP0024600)

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Record Information

Version

2.0

Created at

2021-06-19 16:56:17 UTC

Updated at

2021-06-29 23:49:02 UTC

NP-MRD ID

NP0024600

Secondary Accession Numbers

None

Natural Product Identification

Common Name

20S,21-epoxyresibufogenin

Provided By

JEOL Database JEOL Logo

Description

20R,21-Epoxyresibufogenin belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. 20S,21-epoxyresibufogenin is found in Ch'an Su. 20S,21-epoxyresibufogenin was first documented in 2002 (PMID: 12141860). Based on a literature review a small amount of articles have been published on 20R,21-Epoxyresibufogenin (PMID: 20599324) (PMID: 17451794).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192118563D          

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     RDKit          3D

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M  END


  Mrv1652306192118563D          

 61 67  0  0  0  0            999 V2000
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    2.9863    0.7683    1.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3420   -0.8624    2.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
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  4  5  1  0  0  0  0
 11 29  1  0  0  0  0
  2  1  1  6  0  0  0
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 15 17  1  0  0  0  0
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  2  8  1  0  0  0  0
 26 17  1  0  0  0  0
 15 16  1  1  0  0  0
 12 11  1  0  0  0  0
  8 41  1  1  0  0  0
 15 29  1  0  0  0  0
 11 46  1  1  0  0  0
  2 12  1  0  0  0  0
 29 28  1  1  0  0  0
 27 28  1  0  0  0  0
 18 24  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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  5  7  1  0  0  0  0
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 23 21  1  0  0  0  0
 21 20  1  0  0  0  0
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  7  8  1  0  0  0  0
 21 22  2  0  0  0  0
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  2  3  1  0  0  0  0
 24 25  1  0  0  0  0
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  3  4  1  0  0  0  0
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 19 56  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0024600

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])[C@]([H])(C([H])([H])C([H])([H])[C@]3([H])[C@]2([H])C([H])([H])C([H])([H])[C@]2(C([H])([H])[H])[C@]([H])(C([H])([H])[C@@]4([H])O[C@@]324)[C@@]23O[C@]2([H])OC(=O)C([H])=C3[H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O5/c1-21-8-5-14(25)11-13(21)3-4-16-15(21)6-9-22(2)17(12-18-24(16,22)28-18)23-10-7-19(26)27-20(23)29-23/h7,10,13-18,20,25H,3-6,8-9,11-12H2,1-2H3/t13-,14+,15+,16-,17+,18-,20+,21+,22-,23-,24-/m1/s1

> <INCHI_KEY>
JZDMFDWKCWMAMI-LXXIVLROSA-N

> <FORMULA>
C24H32O5

> <MOLECULAR_WEIGHT>
400.515

> <EXACT_MASS>
400.22497413

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
43.61154968695422

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,6R)-6-[(1R,2S,4R,6S,7R,10S,11S,14S,16R)-14-hydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0^{2,4}.0^{2,7}.0^{11,16}]octadecan-6-yl]-2,7-dioxabicyclo[4.1.0]hept-4-en-3-one

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
3.5144220976666674

> <ALOGPS_LOGS>
-5.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.29639631665519

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3560296438097792

> <JCHEM_POLAR_SURFACE_AREA>
71.59

> <JCHEM_REFRACTIVITY>
105.17649999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.74e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,6R)-6-[(1R,2S,4R,6S,7R,10S,11S,14S,16R)-14-hydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0^{2,4}.0^{2,7}.0^{11,16}]octadecan-6-yl]-2,7-dioxabicyclo[4.1.0]hept-4-en-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 61 67  0  0  0  0  0  0  0  0999 V2000
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 19 56  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       3.490  -2.204  -1.341  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.468  -1.052  -1.525  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.564  -0.630  -3.022  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.792   0.643  -3.364  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.231   1.813  -2.492  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.579   2.168  -2.794  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.137   1.467  -1.009  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.894   0.167  -0.643  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.742  -0.128   0.857  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.343  -0.604   1.232  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.884  -1.810   0.396  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.017  -1.517  -1.120  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.515  -2.745  -1.900  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.972  -2.962  -1.639  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.323  -3.200  -0.153  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.052  -4.672   0.210  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.824  -2.740   0.123  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.920  -3.757  -0.195  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.267  -3.968  -1.609  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.470  -4.369  -2.036  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.574  -4.656  -1.110  0.00  0.00           C+0
HETATM   22  O   UNK     0      -7.651  -5.043  -1.549  0.00  0.00           O+0
HETATM   23  O   UNK     0      -6.353  -4.473   0.214  0.00  0.00           O+0
HETATM   24  C   UNK     0      -5.131  -3.912   0.728  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.022  -4.815   0.770  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.830  -2.186   1.569  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.447  -1.666   1.773  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.535  -2.679   2.164  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.513  -2.276   0.768  0.00  0.00           C+0
HETATM   30  H   UNK     0       3.292  -3.029  -2.034  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.510  -1.856  -1.543  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.490  -2.618  -0.330  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.236  -1.437  -3.684  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.620  -0.464  -3.278  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.971   0.881  -4.420  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.716   0.474  -3.253  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.609   2.691  -2.703  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.617   2.406  -3.736  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.559   2.292  -0.421  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.079   1.391  -0.737  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.961   0.363  -0.821  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.472  -0.888   1.159  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.986   0.768   1.441  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.631   0.222   1.121  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.342  -0.862   2.298  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.548  -2.649   0.641  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.326  -0.694  -1.349  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.641  -2.605  -2.977  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.078  -3.644  -1.626  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.503  -2.080  -2.020  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.309  -3.807  -2.250  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.573  -5.356  -0.467  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.018  -4.900   0.153  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.372  -4.906   1.231  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.023  -1.859  -0.507  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.505  -3.793  -2.361  0.00  0.00           H+0
HETATM   57  H   UNK     0      -5.685  -4.520  -3.087  0.00  0.00           H+0
HETATM   58  H   UNK     0      -5.247  -3.239   1.568  0.00  0.00           H+0
HETATM   59  H   UNK     0      -3.046  -2.958   2.315  0.00  0.00           H+0
HETATM   60  H   UNK     0      -3.575  -1.391   1.678  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.344  -0.662   2.146  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    1    8   12    3                                             
CONECT    3    2    4   33   34                                             
CONECT    4    5    3   35   36                                             
CONECT    5    4    6    7   37                                             
CONECT    6    5   38                                                       
CONECT    7    5    8   39   40                                             
CONECT    8    2   41    9    7                                             
CONECT    9    8   10   42   43                                             
CONECT   10    9   11   44   45                                             
CONECT   11   29   12   46   10                                             
CONECT   12   13   11    2   47                                             
CONECT   13   12   14   48   49                                             
CONECT   14   15   13   50   51                                             
CONECT   15   14   17   16   29                                             
CONECT   16   15   52   53   54                                             
CONECT   17   15   26   18   55                                             
CONECT   18   24   19   17   25                                             
CONECT   19   18   20   56                                                  
CONECT   20   21   19   57                                                  
CONECT   21   23   20   22                                                  
CONECT   22   21                                                            
CONECT   23   24   21                                                       
CONECT   24   18   23   25   58                                             
CONECT   25   18   24                                                       
CONECT   26   17   27   59   60                                             
CONECT   27   28   29   26   61                                             
CONECT   28   29   27                                                       
CONECT   29   11   15   28   27                                             
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    3                                                            
CONECT   34    3                                                            
CONECT   35    4                                                            
CONECT   36    4                                                            
CONECT   37    5                                                            
CONECT   38    6                                                            
CONECT   39    7                                                            
CONECT   40    7                                                            
CONECT   41    8                                                            
CONECT   42    9                                                            
CONECT   43    9                                                            
CONECT   44   10                                                            
CONECT   45   10                                                            
CONECT   46   11                                                            
CONECT   47   12                                                            
CONECT   48   13                                                            
CONECT   49   13                                                            
CONECT   50   14                                                            
CONECT   51   14                                                            
CONECT   52   16                                                            
CONECT   53   16                                                            
CONECT   54   16                                                            
CONECT   55   17                                                            
CONECT   56   19                                                            
CONECT   57   20                                                            
CONECT   58   24                                                            
CONECT   59   26                                                            
CONECT   60   26                                                            
CONECT   61   27                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  134    0
END

RDKit          3D

61 67  0  0  0  0  0  0  0  0999 V2000
    3.4902   -2.2043   -1.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4678   -1.0520   -1.5249 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5640   -0.6298   -3.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7923    0.6428   -3.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2314    1.8135   -2.4920 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5787    2.1680   -2.7938 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1367    1.4667   -1.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8937    0.1669   -0.6427 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7418   -0.1276    0.8572 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3430   -0.6039    1.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8835   -1.8095    0.3961 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0167   -1.5167   -1.1204 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5154   -2.7453   -1.9002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9721   -2.9621   -1.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232   -3.1996   -0.1525 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0520   -4.6715    0.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8236   -2.7397    0.1232 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9200   -3.7570   -0.1953 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2669   -3.9676   -1.6095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4695   -4.3690   -2.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5738   -4.6563   -1.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6511   -5.0431   -1.5487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3533   -4.4734    0.2138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1306   -3.9118    0.7277 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0225   -4.8151    0.7702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8303   -2.1864    1.5689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4468   -1.6656    1.7730 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5353   -2.6786    2.1644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5133   -2.2764    0.7676 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2921   -3.0285   -2.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5103   -1.8564   -1.5431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4901   -2.6181   -0.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2363   -1.4374   -3.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6200   -0.4636   -3.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714    0.8814   -4.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7158    0.4736   -3.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6093    2.6905   -2.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6170    2.4062   -3.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5585    2.2920   -0.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0786    1.3915   -0.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9607    0.3634   -0.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4716   -0.8881    1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9863    0.7683    1.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6308    0.2221    1.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3420   -0.8624    2.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5476   -2.6489    0.6413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3257   -0.6942   -1.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6406   -2.6052   -2.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0784   -3.6443   -1.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5027   -2.0800   -2.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3086   -3.8071   -2.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5725   -5.3563   -0.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0181   -4.9000    0.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3723   -4.9062    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0226   -1.8588   -0.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5053   -3.7929   -2.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6847   -4.5201   -3.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2475   -3.2392    1.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0458   -2.9585    2.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5753   -1.3912    1.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3441   -0.6618    2.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
  4  5  1  0
 11 29  1  0
  2  1  1  6
 14 15  1  0
  5  6  1  0
 15 17  1  0
 14 13  1  0
  2  8  1  0
 26 17  1  0
 15 16  1  1
 12 11  1  0
  8 41  1  1
 15 29  1  0
 11 46  1  1
  2 12  1  0
 29 28  1  1
 27 28  1  0
 18 24  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 29 27  1  0
  5  7  1  0
 18 19  1  0
 24 23  1  0
 23 21  1  0
 21 20  1  0
 20 19  2  0
 17 18  1  0
  7  8  1  0
 21 22  2  0
 18 25  1  1
  2  3  1  0
 24 25  1  0
 27 26  1  0
 12 47  1  6
  3  4  1  0
 17 55  1  6
  6 38  1  0
 27 61  1  1
 26 59  1  0
 26 60  1  0
 14 50  1  0
 14 51  1  0
 13 48  1  0
 13 49  1  0
  9 42  1  0
  9 43  1  0
  7 39  1  0
  7 40  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  1
  1 30  1  0
  1 31  1  0
  1 32  1  0
 10 44  1  0
 10 45  1  0
 16 52  1  0
 16 53  1  0
 16 54  1  0
 24 58  1  1
 20 57  1  0
 19 56  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₂O₅

Average Mass

400.5150 Da

Monoisotopic Mass

400.22497 Da

IUPAC Name

(1R,6R)-6-[(1R,2S,4R,6S,7R,10S,11S,14S,16R)-14-hydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0^{2,4}.0^{2,7}.0^{11,16}]octadecan-6-yl]-2,7-dioxabicyclo[4.1.0]hept-4-en-3-one

Traditional Name

(1R,6R)-6-[(1R,2S,4R,6S,7R,10S,11S,14S,16R)-14-hydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0^{2,4}.0^{2,7}.0^{11,16}]octadecan-6-yl]-2,7-dioxabicyclo[4.1.0]hept-4-en-3-one

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])[C@]([H])(C([H])([H])C([H])([H])[C@]3([H])[C@]2([H])C([H])([H])C([H])([H])[C@]2(C([H])([H])[H])[C@]([H])(C([H])([H])[C@@]4([H])O[C@@]324)[C@@]23O[C@]2([H])OC(=O)C([H])=C3[H])C1([H])[H]

InChI Identifier

InChI=1S/C24H32O5/c1-21-8-5-14(25)11-13(21)3-4-16-15(21)6-9-22(2)17(12-18-24(16,22)28-18)23-10-7-19(26)27-20(23)29-23/h7,10,13-18,20,25H,3-6,8-9,11-12H2,1-2H3/t13-,14+,15+,16-,17+,18-,20+,21+,22-,23-,24-/m1/s1

InChI Key

JZDMFDWKCWMAMI-LXXIVLROSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, NULL, 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
Ch'an Su	JEOL database	Kamano, Y., et al, J. Nat. Prod. 65, 1001 (2002)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Bufanolides and derivatives

Alternative Parents

Substituents

Bufanolide-skeleton
Naphthopyran
Naphthalene
Enol ester epoxide
Dihydropyranone
Oxane
Pyran
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

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	3.05	ALOGPS
logP	3.51	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.59 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	105.18 m³·mol⁻¹	ChemAxon
Polarizability	43.61 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

8267934

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10092398

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Vardanyan M, Melemedjian OK, Price TJ, Ossipov MH, Lai J, Roberts E, Boos TL, Deschamps JR, Jacobson AE, Rice KC, Porreca F: Reversal of pancreatitis-induced pain by an orally available, small molecule interleukin-6 receptor antagonist. Pain. 2010 Nov;151(2):257-265. doi: 10.1016/j.pain.2010.05.022. Epub 2010 Jul 4. [PubMed:20599324 ]
Kino T, Boos TL, Sulima A, Siegel EM, Gold PW, Rice KC, Chrousos GP: 3-O-Formyl-20R,21-epoxyresibufogenin suppresses IL-6-type cytokine actions by targeting the glycoprotein 130 subunit: potential clinical implications. J Allergy Clin Immunol. 2007 Aug;120(2):437-44. doi: 10.1016/j.jaci.2007.03.018. Epub 2007 Apr 23. [PubMed:17451794 ]
Kamano Y, Nogawa T, Yamashita A, Hayashi M, Inoue M, Drasar P, Pettit GR: Isolation and structure of a 20,21-epoxybufenolide series from "Ch'an Su". J Nat Prod. 2002 Jul;65(7):1001-5. doi: 10.1021/np0200360. [PubMed:12141860 ]
Kamano, Y., et al. (2002). Kamano, Y., et al, J. Nat. Prod. 65, 1001 (2002). J. Nat. Prod..

Showing NP-Card for 20S,21-epoxyresibufogenin (NP0024600)

MOL for NP0024600 (20S,21-epoxyresibufogenin)

3D MOL for NP0024600 (20S,21-epoxyresibufogenin)

3D SDF for NP0024600 (20S,21-epoxyresibufogenin)

3D-SDF for NP0024600 (20S,21-epoxyresibufogenin)

PDB for NP0024600 (20S,21-epoxyresibufogenin)

3D PDB for NP0024600 (20S,21-epoxyresibufogenin)

SMILES for NP0024600 (20S,21-epoxyresibufogenin)

INCHI for NP0024600 (20S,21-epoxyresibufogenin)

Structure for NP0024600 (20S,21-epoxyresibufogenin)

3D Structure for NP0024600 (20S,21-epoxyresibufogenin)