NP-MRD: Showing NP-Card for cinobufagin (NP0033965)

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Record Information

Version

2.0

Created at

2021-06-20 17:50:01 UTC

Updated at

2021-06-30 00:04:03 UTC

NP-MRD ID

NP0033965

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cinobufagin

Provided By

JEOL Database JEOL Logo

Description

cinobufagin is found in Bufo bufo, Phrynoidis asper and Syncephalastrum racemosum. cinobufagin was first documented in 2021 (PMID: 34425836). Based on a literature review a small amount of articles have been published on Cinobufagin (PMID: 34309954) (PMID: 34299492) (PMID: 34087213) (PMID: 33908580).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202119503D          

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M  END


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    0.5325   -1.1736    1.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
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 32  5  1  0  0  0  0
  5  6  1  0  0  0  0
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  6  7  1  0  0  0  0
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 18 17  1  0  0  0  0
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 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
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  8  9  2  0  0  0  0
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 24 23  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0033965

> <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])(C4=C([H])OC(=O)C([H])=C4[H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@@]4([H])O[C@@]324)C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O6/c1-14(27)31-22-21(15-4-7-20(29)30-13-15)25(3)11-9-18-19(26(25)23(22)32-26)6-5-16-12-17(28)8-10-24(16,18)2/h4,7,13,16-19,21-23,28H,5-6,8-12H2,1-3H3/t16-,17+,18+,19-,21+,22-,23-,24+,25-,26-/m1/s1

> <INCHI_KEY>
SCULJPGYOQQXTK-OLRINKBESA-N

> <FORMULA>
C26H34O6

> <MOLECULAR_WEIGHT>
442.552

> <EXACT_MASS>
442.235538815

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
47.79726944389705

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,4R,5R,6S,7R,10S,11S,14S,16R)-14-hydroxy-7,11-dimethyl-6-(2-oxo-2H-pyran-5-yl)-3-oxapentacyclo[8.8.0.0^{2,4}.0^{2,7}.0^{11,16}]octadecan-5-yl acetate

> <ALOGPS_LOGP>
3.21

> <JCHEM_LOGP>
2.807737002333333

> <ALOGPS_LOGS>
-4.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.296396316655187

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3564014885275215

> <JCHEM_POLAR_SURFACE_AREA>
85.36000000000001

> <JCHEM_REFRACTIVITY>
116.77609999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4R,5R,6S,7R,10S,11S,14S,16R)-14-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0^{2,4}.0^{2,7}.0^{11,16}]octadecan-5-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 66 71  0  0  0  0  0  0  0  0999 V2000
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  1 35  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      -1.647  -5.468   3.289  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.693  -4.497   2.150  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.644  -4.356   1.395  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.524  -3.803   2.081  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.445  -2.885   0.989  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.187  -3.542  -0.412  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.295  -4.993  -0.420  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.438  -5.439   0.342  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.825  -6.719   0.319  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.099  -7.721  -0.479  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.467  -8.891  -0.492  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.012  -7.282  -1.182  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.357  -5.929  -1.127  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.683  -2.463  -1.192  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.710  -3.078  -2.155  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.275  -1.518  -1.964  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.385  -0.212  -2.420  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.999   0.573  -1.235  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.013  -0.331  -0.475  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.644   0.401   0.719  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.242   1.748   0.331  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.240   2.659  -0.396  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.169   3.178   0.594  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.138   4.086  -0.071  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.761   5.297  -0.492  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.497   3.412  -1.282  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.560   2.922  -2.270  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.618   1.962  -1.650  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.716   1.781  -2.730  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.356  -1.642  -0.104  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.014  -2.393   0.925  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.690  -1.926   1.206  0.00  0.00           C+0
HETATM   33  H   UNK     0      -1.497  -4.931   4.229  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.844  -6.192   3.126  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.597  -6.007   3.344  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.361  -2.280   0.949  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.173  -3.573  -0.901  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.992  -4.735   0.950  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.678  -7.076   0.882  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.237  -5.766  -1.735  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.222  -3.719  -2.896  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.268  -2.312  -2.703  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.462  -3.670  -1.624  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.130  -1.248  -1.329  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.692  -2.038  -2.836  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.145  -0.433  -3.176  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.386   0.387  -2.915  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.171   0.765  -0.540  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.833  -0.585  -1.158  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.436  -0.219   1.159  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.905   0.552   1.513  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.616   2.249   1.232  0.00  0.00           H+0
HETATM   53  H   UNK     0       4.120   1.582  -0.304  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.804   3.540  -0.737  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.641   2.344   1.069  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.674   3.732   1.395  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.643   4.355   0.648  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.137   5.725   0.296  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.149   4.126  -1.800  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.128   2.577  -0.959  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.062   2.459  -3.129  0.00  0.00           H+0
HETATM   62  H   UNK     0       1.074   3.802  -2.680  0.00  0.00           H+0
HETATM   63  H   UNK     0       3.224   2.732  -2.934  0.00  0.00           H+0
HETATM   64  H   UNK     0       2.292   1.440  -3.681  0.00  0.00           H+0
HETATM   65  H   UNK     0       3.487   1.063  -2.438  0.00  0.00           H+0
HETATM   66  H   UNK     0       0.533  -1.174   1.959  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5   32    6    4   36                                             
CONECT    6   14    5    7   37                                             
CONECT    7    6    8   13                                                  
CONECT    8    7    9   38                                                  
CONECT    9    8   10   39                                                  
CONECT   10    9   12   11                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13    7   12   40                                                  
CONECT   14    6   15   16   30                                             
CONECT   15   14   41   42   43                                             
CONECT   16   14   17   44   45                                             
CONECT   17   18   16   46   47                                             
CONECT   18   19   17   28   48                                             
CONECT   19   20   18   30   49                                             
CONECT   20   21   19   50   51                                             
CONECT   21   22   20   52   53                                             
CONECT   22   21   54   23   28                                             
CONECT   23   22   24   55   56                                             
CONECT   24   25   26   23   57                                             
CONECT   25   24   58                                                       
CONECT   26   24   27   59   60                                             
CONECT   27   28   26   61   62                                             
CONECT   28   29   27   22   18                                             
CONECT   29   28   63   64   65                                             
CONECT   30   32   31   19   14                                             
CONECT   31   30   32                                                       
CONECT   32    5   30   31   66                                             
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    5                                                            
CONECT   37    6                                                            
CONECT   38    8                                                            
CONECT   39    9                                                            
CONECT   40   13                                                            
CONECT   41   15                                                            
CONECT   42   15                                                            
CONECT   43   15                                                            
CONECT   44   16                                                            
CONECT   45   16                                                            
CONECT   46   17                                                            
CONECT   47   17                                                            
CONECT   48   18                                                            
CONECT   49   19                                                            
CONECT   50   20                                                            
CONECT   51   20                                                            
CONECT   52   21                                                            
CONECT   53   21                                                            
CONECT   54   22                                                            
CONECT   55   23                                                            
CONECT   56   23                                                            
CONECT   57   24                                                            
CONECT   58   25                                                            
CONECT   59   26                                                            
CONECT   60   26                                                            
CONECT   61   27                                                            
CONECT   62   27                                                            
CONECT   63   29                                                            
CONECT   64   29                                                            
CONECT   65   29                                                            
CONECT   66   32                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  142    0
END

RDKit          3D

66 71  0  0  0  0  0  0  0  0999 V2000
   -1.6468   -5.4682    3.2888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6927   -4.4967    2.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2953   -4.9929   -0.4199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4377   -5.4392    0.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8250   -6.7192    0.3191 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6827   -2.4635   -1.1917 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7096   -3.0776   -2.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2753   -1.5178   -1.9644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3852   -0.2121   -2.4204 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0132   -0.3309   -0.4754 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6442    0.4007    0.7190 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2416    1.7483    0.3313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2403    2.6594   -0.3957 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1689    3.1776    0.5936 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1380    4.0863   -0.0714 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7611    5.2972   -0.4924 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4970    3.4119   -1.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6178    1.9624   -1.6495 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7164    1.7808   -2.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3559   -1.6424   -0.1036 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.6895   -1.9255    1.2056 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4967   -4.9313    4.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8441   -6.1916    3.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5970   -6.0071    3.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3609   -2.2796    0.9494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1729   -3.5733   -0.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9915   -4.7350    0.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6776   -7.0764    0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2370   -5.7660   -1.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2220   -3.7192   -2.8964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2675   -2.3119   -2.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4616   -3.6699   -1.6237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1301   -1.2485   -1.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8333   -0.5849   -1.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4355   -0.2190    1.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6163    2.2493    1.2324 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1197    1.5822   -0.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8038    3.5397   -0.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6410    2.3441    1.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6739    3.7316    1.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6432    4.3551    0.6482 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1366    5.7252    0.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1486    4.1260   -1.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0618    2.4591   -3.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0742    3.8024   -2.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2235    2.7315   -2.9344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2918    1.4400   -3.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4872    1.0635   -2.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5325   -1.1736    1.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 14  6  1  0
 32  5  1  0
  5  6  1  0
 21 20  1  0
 24 25  1  0
 20 19  1  0
 28 29  1  6
 18 19  1  0
 22 54  1  6
 23 22  1  0
 14 15  1  6
 30 32  1  0
 28 27  1  0
 30 31  1  1
 32 31  1  0
 28 22  1  0
  6  7  1  0
  7  8  1  0
 18 17  1  0
 19 30  1  0
 14 16  1  0
 16 17  1  0
  7 13  2  0
  8  9  2  0
  9 10  1  0
 10 12  1  0
 12 13  1  0
 14 30  1  0
 10 11  2  0
 26 24  1  0
  5  4  1  0
 26 27  1  0
  4  2  1  0
 24 23  1  0
  2  1  1  0
 28 18  1  0
  2  3  2  0
 26 59  1  0
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 24 57  1  1
 23 55  1  0
 23 56  1  0
 27 61  1  0
 27 62  1  0
 21 52  1  0
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 20 50  1  0
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 18 48  1  1
 19 49  1  6
 16 44  1  0
 16 45  1  0
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 17 47  1  0
 32 66  1  1
  5 36  1  6
  6 37  1  6
 25 58  1  0
 29 63  1  0
 29 64  1  0
 29 65  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
  8 38  1  0
  9 39  1  0
 13 40  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₄O₆

Average Mass

442.5520 Da

Monoisotopic Mass

442.23554 Da

IUPAC Name

(1R,2S,4R,5R,6S,7R,10S,11S,14S,16R)-14-hydroxy-7,11-dimethyl-6-(2-oxo-2H-pyran-5-yl)-3-oxapentacyclo[8.8.0.0^{2,4}.0^{2,7}.0^{11,16}]octadecan-5-yl acetate

Traditional Name

(1R,2S,4R,5R,6S,7R,10S,11S,14S,16R)-14-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0^{2,4}.0^{2,7}.0^{11,16}]octadecan-5-yl acetate

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])(C4=C([H])OC(=O)C([H])=C4[H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@@]4([H])O[C@@]324)C1([H])[H]

InChI Identifier

InChI=1S/C26H34O6/c1-14(27)31-22-21(15-4-7-20(29)30-13-15)25(3)11-9-18-19(26(25)23(22)32-26)6-5-16-12-17(28)8-10-24(16,18)2/h4,7,13,16-19,21-23,28H,5-6,8-12H2,1-3H3/t16-,17+,18+,19-,21+,22-,23-,24+,25-,26-/m1/s1

InChI Key

SCULJPGYOQQXTK-OLRINKBESA-N

Experimental Spectra

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

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Bufo bufo	LOTUS Database	35616633
Phrynoidis asper	LOTUS Database	35616633
Syncephalastrum racemosum	JEOL database	Ma, X. -C., et al, J. Nat. Prod. 71, 1268 (2008)

Species Where Detected

Species Name	Source	Reference
Bufo bufo gargarizans	KNApSAcK Database	22123792
Bufo gargarizans	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	3.21	ALOGPS
logP	2.81	ChemAxon
logS	-4.9	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	85.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	116.78 m³·mol⁻¹	ChemAxon
Polarizability	47.8 Å³	ChemAxon
Number of Rings	6	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

C00045524

Chemspider ID

10142947

KEGG Compound ID

C16931

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cinobufagin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Niu J, Wang J, Zhang Q, Zou Z, Ding Y: Cinobufagin-induced DNA damage response activates G2/M checkpoint and apoptosis to cause selective cytotoxicity in cancer cells. Cancer Cell Int. 2021 Aug 23;21(1):446. doi: 10.1186/s12935-021-02150-0. [PubMed:34425836 ]
Hsu SS, Lin YS, Liang WZ: Investigation of cytotoxic effect of the bufanolide steroid compound cinobufagin and its related underlying mechanism in brain cell models. J Biochem Mol Toxicol. 2021 Oct;35(10):e22862. doi: 10.1002/jbt.22862. Epub 2021 Jul 26. [PubMed:34309954 ]
Rodriguez C, Ibanez R, Mojica L, Ng M, Spadafora C, Durant-Archibold AA, Gutierrez M: Bufadienolides from the Skin Secretions of the Neotropical Toad Rhinella alata (Anura: Bufonidae): Antiprotozoal Activity against Trypanosoma cruzi. Molecules. 2021 Jul 12;26(14). pii: molecules26144217. doi: 10.3390/molecules26144217. [PubMed:34299492 ]
Aloi E, Guo JH, Guzzi R, Jiang RW, Ladefoged LK, Marsh D, Esmann M, Bartucci R, Fedosova NU: Geometry and water accessibility of the inhibitor binding site of Na(+)-pump: Pulse- and CW-EPR study. Biophys J. 2021 Jul 6;120(13):2679-2690. doi: 10.1016/j.bpj.2021.05.018. Epub 2021 Jun 2. [PubMed:34087213 ]
Long Y, Wang Z, Fan J, Yuan L, Tong C, Zhao Y, Liu B: A hybrid membrane coating nanodrug system against gastric cancer via the VEGFR2/STAT3 signaling pathway. J Mater Chem B. 2021 May 12;9(18):3838-3855. doi: 10.1039/d1tb00029b. [PubMed:33908580 ]
Ma, X. -C., et al. (2008). Ma, X. -C., et al, J. Nat. Prod. 71, 1268 (2008). J. Nat. Prod..

Showing NP-Card for cinobufagin (NP0033965)

MOL for NP0033965 (cinobufagin)

3D MOL for NP0033965 (cinobufagin)

3D SDF for NP0033965 (cinobufagin)

3D-SDF for NP0033965 (cinobufagin)

PDB for NP0033965 (cinobufagin)

3D PDB for NP0033965 (cinobufagin)

SMILES for NP0033965 (cinobufagin)

INCHI for NP0033965 (cinobufagin)

Structure for NP0033965 (cinobufagin)

3D Structure for NP0033965 (cinobufagin)