NP-MRD: Showing NP-Card for 5-[(1r,2s,4r,5r,6r,7r,10s,11s,14s,16r)-5,14-dihydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl]pyran-2-one (NP0280024)

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Record Information

Version

2.0

Created at

2022-09-09 05:37:04 UTC

Updated at

2022-09-09 05:37:04 UTC

NP-MRD ID

NP0280024

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[(1r,2s,4r,5r,6r,7r,10s,11s,14s,16r)-5,14-dihydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl]pyran-2-one

Description

Desacetylcinobufagin 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. Thus, desacetylcinobufagin is considered to be a sterol. 5-[(1r,2s,4r,5r,6r,7r,10s,11s,14s,16r)-5,14-dihydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl]pyran-2-one is found in Bufo bufo and Bufo gargarizans. 5-[(1r,2s,4r,5r,6r,7r,10s,11s,14s,16r)-5,14-dihydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl]pyran-2-one was first documented in 2005 (PMID: 15862355). Based on a literature review a significant number of articles have been published on Desacetylcinobufagin (PMID: 25204176) (PMID: 35928275) (PMID: 31214612) (PMID: 25884245) (PMID: 23421737) (PMID: 21711170).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092207372D          

 29 34  0  0  1  0            999 V2000
    3.1176   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3979    0.2673    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9298   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7419   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0222    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8343    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4904    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6782    1.0432    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1464    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0540    0.7528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5858    0.1221    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3055   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4934   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9616   -0.1684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6017   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1370   -0.1416    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3693   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0584   -1.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5648   -2.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3820   -2.0955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8884   -2.7469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6929   -1.3314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1866   -0.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0923    0.6509    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8682    0.9312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5906    1.1139    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3547    1.4248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2419    0.6076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
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M  END

     RDKit          3D

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    4.1812   -0.3938    2.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1110   -1.7395    1.7540 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2200    1.4583   -0.9131 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0043    1.0641   -1.9807 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8499    1.7734   -1.4795 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3817    0.9577   -2.5307 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9855    0.6323   -1.1868 C   0  0  2  0  0  0  0  0  0  0  0  0
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 17 55  1  1
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 19 56  1  0
M  END


  Mrv1652309092207372D          

 29 34  0  0  1  0            999 V2000
    3.1176   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3979    0.2673    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9298   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7419   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0222    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8343    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4904    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6782    1.0432    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1464    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0280024

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@@H](O)CC[C@]34C)[C@]11O[C@@H]1[C@H](O)[C@@H]2C1=COC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O5/c1-22-9-7-15(25)11-14(22)4-5-17-16(22)8-10-23(2)19(13-3-6-18(26)28-12-13)20(27)21-24(17,23)29-21/h3,6,12,14-17,19-21,25,27H,4-5,7-11H2,1-2H3/t14-,15+,16+,17-,19+,20-,21-,22+,23-,24-/m1/s1

> <INCHI_KEY>
IXZHDDUFQVXHIL-UOAIQHMYSA-N

> <FORMULA>
C24H32O5

> <MOLECULAR_WEIGHT>
400.515

> <EXACT_MASS>
400.22497413

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
43.72760767778667

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
2.366611592000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.296396316655187

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.755583150652406

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3564021673643665

> <JCHEM_POLAR_SURFACE_AREA>
79.29

> <JCHEM_REFRACTIVITY>
107.62459999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       5.820  -0.949   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.343   0.499   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.336  -0.678   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.852  -0.407   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.375   1.041   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.891   1.312   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.382   2.218   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.866   1.947   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.873   3.125   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.357   2.854   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.834   1.405   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.827   0.228   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.304  -1.221   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.788  -1.492   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.795  -0.314   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.123  -1.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.256  -0.264   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.689  -1.480   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.109  -2.907   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.054  -4.122   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.580  -3.912   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.525  -5.127   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -3.160  -2.485   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.215  -1.269   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.172   1.215   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.621   1.738   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.102   2.079   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.529   2.660   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.318   1.134   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8   12                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   29                                                  
CONECT   12   11    2   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   29                                             
CONECT   16   15                                                            
CONECT   17   15   18   25                                                  
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   18                                                       
CONECT   25   17   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27   29                                                       
CONECT   29   28   11   27   15                                             
MASTER        0    0    0    0    0    0    0    0   29    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₂O₅

Average Mass

400.5150 Da

Monoisotopic Mass

400.22497 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@@H](O)CC[C@]34C)[C@]11O[C@@H]1[C@H](O)[C@@H]2C1=COC(=O)C=C1

InChI Identifier

InChI=1S/C24H32O5/c1-22-9-7-15(25)11-14(22)4-5-17-16(22)8-10-23(2)19(13-3-6-18(26)28-12-13)20(27)21-24(17,23)29-21/h3,6,12,14-17,19-21,25,27H,4-5,7-11H2,1-2H3/t14-,15+,16+,17-,19+,20-,21-,22+,23-,24-/m1/s1

InChI Key

IXZHDDUFQVXHIL-UOAIQHMYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Bufo bufo	LOTUS Database	35616633
Bufo gargarizans	LOTUS Database	35616633

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
Pyranone
Pyran
Oxane
Cyclic alcohol
Heteroaromatic compound
Lactone
Secondary alcohol
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.37	ChemAxon
pKa (Strongest Acidic)	13.76	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.29 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	107.62 m³·mol⁻¹	ChemAxon
Polarizability	43.73 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

10051823

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11877495

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang PW, Jiang RW, Ye WC, Tian HY: [Bufadienolides from venom of Bufo bufo gargarizans]. Zhongguo Zhong Yao Za Zhi. 2014 Mar;39(5):841-5. [PubMed:25204176 ]
Li M, Qin Y, Li Z, Lan J, Zhang T, Ding Y: Comparative Pharmacokinetics of Cinobufacini Capsule and Injection by UPLC-MS/MS. Front Pharmacol. 2022 Jul 18;13:944041. doi: 10.3389/fphar.2022.944041. eCollection 2022. [PubMed:35928275 ]
de Medeiros DSS, Rego TB, Dos Santos APA, Pontes AS, Moreira-Dill LS, Matos NB, Zuliani JP, Stabeli RG, Teles CBG, Soares AM, Sperotto ARM, Moura DJ, Saffi J, Caldeira CADS, Pimenta DC, Calderon LA: Biochemical and Biological Profile of Parotoid Secretion of the Amazonian Rhinella marina (Anura: Bufonidae). Biomed Res Int. 2019 Feb 21;2019:2492315. doi: 10.1155/2019/2492315. eCollection 2019. [PubMed:31214612 ]
Jiang L, Liang SC, Wang C, Ge GB, Huo XK, Qi XY, Deng S, Liu KX, Ma XC: Identifying and applying a highly selective probe to simultaneously determine the O-glucuronidation activity of human UGT1A3 and UGT1A4. Sci Rep. 2015 Apr 17;5:9627. doi: 10.1038/srep09627. [PubMed:25884245 ]
Zhu ZT, Den S, Wang Y, Zhao YY, Wang L, Chen HR, Liu D: Novel microbial transformation of desacetylcinobufagin by Fusarium avenaceum AS 3.4594. J Asian Nat Prod Res. 2013;15(3):294-9. doi: 10.1080/10286020.2013.763227. Epub 2013 Feb 19. [PubMed:23421737 ]
He X, Hu H, Wu Y, Zeng X: Urinary metabolites of cinobufagin in rats and their antiproliferative activities. Nat Prod Res. 2012;26(6):489-99. doi: 10.1080/14786419.2010.510798. Epub 2011 Jun 28. [PubMed:21711170 ]
Ning J, Wu TH, Tian Y, Wang CY, Tian G, Zhang BJ, Liu KX, Ma XC: Identification of cinobufagin metabolites in the bile of rats. Xenobiotica. 2010 Jan;40(1):48-54. doi: 10.3109/00498250903331049. [PubMed:19895259 ]
Ye M, Guo D: A new bufadienolide obtained from the biotransformation of cinobufagin by Alternaria alternata. Nat Prod Res. 2008 Jan 10;22(1):26-30. doi: 10.1080/14786410601130141. [PubMed:17999335 ]
Qiao L, Zhou YZ, Qi XL, Lin LH, Chen H, Pang LY, Pei YH: Biotransformation of cinobufagin by Cunninghamella elegans. J Antibiot (Tokyo). 2007 Apr;60(4):261-4. doi: 10.1038/ja.2007.32. [PubMed:17456977 ]
Ye M, Guo D: Substrate specificity for the 12beta-hydroxylation of bufadienolides by Alternaria alternata. J Biotechnol. 2005 May 25;117(3):253-62. doi: 10.1016/j.jbiotec.2005.02.002. Epub 2005 Apr 9. [PubMed:15862355 ]
LOTUS database [Link]

Showing NP-Card for 5-[(1r,2s,4r,5r,6r,7r,10s,11s,14s,16r)-5,14-dihydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl]pyran-2-one (NP0280024)

MOL for NP0280024 (5-[(1r,2s,4r,5r,6r,7r,10s,11s,14s,16r)-5,14-dihydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl]pyran-2-one)

3D MOL for NP0280024 (5-[(1r,2s,4r,5r,6r,7r,10s,11s,14s,16r)-5,14-dihydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl]pyran-2-one)

3D SDF for NP0280024 (5-[(1r,2s,4r,5r,6r,7r,10s,11s,14s,16r)-5,14-dihydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl]pyran-2-one)

3D-SDF for NP0280024 (5-[(1r,2s,4r,5r,6r,7r,10s,11s,14s,16r)-5,14-dihydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl]pyran-2-one)

PDB for NP0280024 (5-[(1r,2s,4r,5r,6r,7r,10s,11s,14s,16r)-5,14-dihydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl]pyran-2-one)

3D PDB for NP0280024 (5-[(1r,2s,4r,5r,6r,7r,10s,11s,14s,16r)-5,14-dihydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl]pyran-2-one)

SMILES for NP0280024 (5-[(1r,2s,4r,5r,6r,7r,10s,11s,14s,16r)-5,14-dihydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl]pyran-2-one)

INCHI for NP0280024 (5-[(1r,2s,4r,5r,6r,7r,10s,11s,14s,16r)-5,14-dihydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl]pyran-2-one)

Structure for NP0280024 (5-[(1r,2s,4r,5r,6r,7r,10s,11s,14s,16r)-5,14-dihydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl]pyran-2-one)

3D Structure for NP0280024 (5-[(1r,2s,4r,5r,6r,7r,10s,11s,14s,16r)-5,14-dihydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl]pyran-2-one)