NP-MRD: Showing NP-Card for [(1r,2s,4r,6r,7r,10s,11r,14s,16s)-16-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxidanesulfonic acid (NP0177815)

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Record Information

Version

2.0

Created at

2022-09-03 15:42:32 UTC

Updated at

2022-09-03 15:42:33 UTC

NP-MRD ID

NP0177815

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1r,2s,4r,6r,7r,10s,11r,14s,16s)-16-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxidanesulfonic acid

Description

Marinobufagin 3-sulfate 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. [(1r,2s,4r,6r,7r,10s,11r,14s,16s)-16-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxidanesulfonic acid is found in Rhinella marina. [(1r,2s,4r,6r,7r,10s,11r,14s,16s)-16-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxidanesulfonic acid was first documented in 2008 (PMID: 18647476). Based on a literature review very few articles have been published on Marinobufagin 3-sulfate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032217422D          

 33 38  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
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M  END

     RDKit          3D

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M  END


  Mrv1652309032217422D          

 33 38  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0177815

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O8S/c1-21-8-5-15(32-33(27,28)29)12-23(21,26)10-7-17-16(21)6-9-22(2)18(11-19-24(17,22)31-19)14-3-4-20(25)30-13-14/h3-4,13,15-19,26H,5-12H2,1-2H3,(H,27,28,29)/t15-,16-,17+,18+,19+,21+,22+,23-,24+/m0/s1

> <INCHI_KEY>
LZHISLYKBNUAIS-OBBGIPBRSA-N

> <FORMULA>
C24H32O8S

> <MOLECULAR_WEIGHT>
480.57

> <EXACT_MASS>
480.181789164

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
49.334263586909515

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,2S,4R,6S,7R,10S,11R,14S,16S)-16-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-14-yl]oxidanesulfonic acid

> <JCHEM_LOGP>
0.7140353960058732

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.274194141487353

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.5144003475460126

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1170640350861456

> <JCHEM_POLAR_SURFACE_AREA>
122.66000000000001

> <JCHEM_REFRACTIVITY>
117.81639999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-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  S   UNK     0      11.414   2.761   0.000  0.00  0.00           S+0
HETATM    8  O   UNK     0      11.937   4.209   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       9.966   3.284   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      12.862   2.237   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.382   2.218   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.866   1.947   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.389   3.396   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.873   3.125   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.357   2.854   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.834   1.405   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.827   0.228   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.304  -1.221   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.788  -1.492   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.795  -0.314   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.123  -1.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.256  -0.264   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.689  -1.480   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.109  -2.907   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.054  -4.122   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.580  -3.912   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -3.525  -5.127   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -3.160  -2.485   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.215  -1.269   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.172   1.215   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.102   2.079   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.529   2.660   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.318   1.134   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12   17                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    5   12                                                       
CONECT   12   11    2   13   14                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   33                                                  
CONECT   17   16    2   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   33                                             
CONECT   21   20                                                            
CONECT   22   20   23   30                                                  
CONECT   23   22   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   23                                                       
CONECT   30   22   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31   33                                                       
CONECT   33   32   31   16   20                                             
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Value	Source
Marinobufagin 3-sulfuric acid	Generator
Marinobufagin 3-sulphate	Generator
Marinobufagin 3-sulphuric acid	Generator

Chemical Formula

C₂₄H₃₂O₈S

Average Mass

480.5700 Da

Monoisotopic Mass

480.18179 Da

IUPAC Name

[(1R,2S,4R,6S,7R,10S,11R,14S,16S)-16-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-14-yl]oxidanesulfonic acid

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C24H32O8S/c1-21-8-5-15(32-33(27,28)29)12-23(21,26)10-7-17-16(21)6-9-22(2)18(11-19-24(17,22)31-19)14-3-4-20(25)30-13-14/h3-4,13,15-19,26H,5-12H2,1-2H3,(H,27,28,29)/t15-,16-,17+,18+,19+,21+,22+,23-,24+/m0/s1

InChI Key

LZHISLYKBNUAIS-OBBGIPBRSA-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
Rhinella marina	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
Sulfated steroid skeleton
Naphthopyran
Naphthalene
Pyranone
Oxane
Pyran
Sulfuric acid monoester
Sulfate-ester
Alkyl sulfate
Sulfuric acid ester
Heteroaromatic compound
Organic sulfuric acid or derivatives
Cyclic alcohol
Tertiary alcohol
Lactone
Oxacycle
Ether
Dialkyl ether
Oxirane
Organoheterocyclic compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	0.71	ChemAxon
pKa (Strongest Acidic)	-1.5	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	122.66 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	117.82 m³·mol⁻¹	ChemAxon
Polarizability	49.33 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

137452

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

156064

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Miyashiro Y, Nishio T, Shimada K: Characterization of in vivo metabolites of toad venom using liquid chromatography-mass spectrometry. J Chromatogr Sci. 2008 Jul;46(6):534-8. doi: 10.1093/chromsci/46.6.534. [PubMed:18647476 ]
LOTUS database [Link]

Showing NP-Card for [(1r,2s,4r,6r,7r,10s,11r,14s,16s)-16-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxidanesulfonic acid (NP0177815)

MOL for NP0177815 ([(1r,2s,4r,6r,7r,10s,11r,14s,16s)-16-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxidanesulfonic acid)

3D MOL for NP0177815 ([(1r,2s,4r,6r,7r,10s,11r,14s,16s)-16-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxidanesulfonic acid)

3D SDF for NP0177815 ([(1r,2s,4r,6r,7r,10s,11r,14s,16s)-16-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxidanesulfonic acid)

3D-SDF for NP0177815 ([(1r,2s,4r,6r,7r,10s,11r,14s,16s)-16-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxidanesulfonic acid)

PDB for NP0177815 ([(1r,2s,4r,6r,7r,10s,11r,14s,16s)-16-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxidanesulfonic acid)

3D PDB for NP0177815 ([(1r,2s,4r,6r,7r,10s,11r,14s,16s)-16-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxidanesulfonic acid)

SMILES for NP0177815 ([(1r,2s,4r,6r,7r,10s,11r,14s,16s)-16-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxidanesulfonic acid)

INCHI for NP0177815 ([(1r,2s,4r,6r,7r,10s,11r,14s,16s)-16-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxidanesulfonic acid)

Structure for NP0177815 ([(1r,2s,4r,6r,7r,10s,11r,14s,16s)-16-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxidanesulfonic acid)

3D Structure for NP0177815 ([(1r,2s,4r,6r,7r,10s,11r,14s,16s)-16-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxidanesulfonic acid)