NP-MRD: Showing NP-Card for Gossypetin 8-glucoside-3-sulfate (NP0054025)

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Record Information

Version

2.0

Created at

2022-04-28 00:30:36 UTC

Updated at

2022-04-28 00:30:36 UTC

NP-MRD ID

NP0054025

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gossypetin 8-glucoside-3-sulfate

Description

Gossypetin 8-glucoside-3-sulfate belongs to the class of organic compounds known as flavonoid-8-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C8-position. Gossypetin 8-glucoside-3-sulfate is found in Malva sylvestris . Based on a literature review very few articles have been published on Gossypetin 8-glucoside-3-sulfate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282202302D          

 38 41  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4289    0.8250    0.0000 O   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


  Mrv1652304282202302D          

 38 41  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0054025

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=C3OC(C4=CC=C(O)C(O)=C4)=C(OS(O)(=O)=O)C(=O)C3=C(O)C=C2O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O16S/c22-5-11-13(27)15(29)16(30)21(34-11)36-18-10(26)4-9(25)12-14(28)20(37-38(31,32)33)17(35-19(12)18)6-1-2-7(23)8(24)3-6/h1-4,11,13,15-16,21-27,29-30H,5H2,(H,31,32,33)/t11-,13-,15+,16-,21+/m1/s1

> <INCHI_KEY>
DMAOYRIREVHKFQ-OFEDHLHNSA-N

> <FORMULA>
C21H20O16S

> <MOLECULAR_WEIGHT>
560.44

> <EXACT_MASS>
560.047205738

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
49.48078715038458

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-3-yl]oxidanesulfonic acid

> <ALOGPS_LOGP>
-0.01

> <JCHEM_LOGP>
-3.048297575081253

> <ALOGPS_LOGS>
-1.93

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.7436550625283616

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.5572508971304595

> <JCHEM_PKA_STRONGEST_BASIC>
-3.648395386296187

> <JCHEM_POLAR_SURFACE_AREA>
270.19999999999993

> <JCHEM_REFRACTIVITY>
120.97929999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.52e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-3-yl]oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   25  S   UNK     0       5.335  -4.620   0.000  0.00  0.00           S+0
HETATM   26  O   UNK     0       3.795  -4.620   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       6.875  -4.620   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.335  -6.160   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   38                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   37                                                  
CONECT    4    3    5   22                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   18                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    8                                                       
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16   11                                                            
CONECT   17   10                                                            
CONECT   18    9                                                            
CONECT   19    5   20                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   22   24                                                  
CONECT   22   21    4   23                                                  
CONECT   23   22                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25                                                            
CONECT   29   20   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   36                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33   29                                                       
CONECT   35   33                                                            
CONECT   36   32                                                            
CONECT   37    3                                                            
CONECT   38    1                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
Gossypetin 8-glucoside-3-sulfuric acid	Generator
Gossypetin 8-glucoside-3-sulphate	Generator
Gossypetin 8-glucoside-3-sulphuric acid	Generator

Chemical Formula

C₂₁H₂₀O₁₆S

Average Mass

560.4400 Da

Monoisotopic Mass

560.04721 Da

IUPAC Name

[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-3-yl]oxidanesulfonic acid

Traditional Name

[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-3-yl]oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=C3OC(C4=CC=C(O)C(O)=C4)=C(OS(O)(=O)=O)C(=O)C3=C(O)C=C2O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C21H20O16S/c22-5-11-13(27)15(29)16(30)21(34-11)36-18-10(26)4-9(25)12-14(28)20(37-38(31,32)33)17(35-19(12)18)6-1-2-7(23)8(24)3-6/h1-4,11,13,15-16,21-27,29-30H,5H2,(H,31,32,33)/t11-,13-,15+,16-,21+/m1/s1

InChI Key

DMAOYRIREVHKFQ-OFEDHLHNSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Malva sylvestris	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-8-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C8-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-8-O-glycosides

Alternative Parents

Substituents

Flavonoid-8-o-glycoside
3-sulfated flavonoid
Hydroxyflavonoid
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
7-hydroxyflavonoid
Phenolic glycoside
Hexose monosaccharide
Chromone
O-glycosyl compound
Glycosyl compound
Benzopyran
1-benzopyran
Arylsulfate
Catechol
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Sulfuric acid ester
Pyran
Sulfuric acid monoester
Oxane
Sulfate-ester
Heteroaromatic compound
Organic sulfuric acid or derivatives
Vinylogous acid
Secondary alcohol
Oxacycle
Acetal
Organoheterocyclic compound
Polyol
Alcohol
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organic oxygen compound
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	-0.01	ALOGPS
logP	-3	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	-2.6	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	270.2 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	120.98 m³·mol⁻¹	ChemAxon
Polarizability	49.48 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00006075

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101421038

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Gossypetin 8-glucoside-3-sulfate (NP0054025)

MOL for NP0054025 (Gossypetin 8-glucoside-3-sulfate)

3D MOL for NP0054025 (Gossypetin 8-glucoside-3-sulfate)

3D SDF for NP0054025 (Gossypetin 8-glucoside-3-sulfate)

3D-SDF for NP0054025 (Gossypetin 8-glucoside-3-sulfate)

PDB for NP0054025 (Gossypetin 8-glucoside-3-sulfate)

3D PDB for NP0054025 (Gossypetin 8-glucoside-3-sulfate)

SMILES for NP0054025 (Gossypetin 8-glucoside-3-sulfate)

INCHI for NP0054025 (Gossypetin 8-glucoside-3-sulfate)

Structure for NP0054025 (Gossypetin 8-glucoside-3-sulfate)

3D Structure for NP0054025 (Gossypetin 8-glucoside-3-sulfate)