NP-MRD: Showing NP-Card for 6-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4-oxochromen-8-yl]oxy}-3,5-dihydroxy-4-(sulfooxy)oxane-2-carboxylic acid (NP0320856)

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Record Information

Version

2.0

Created at

2022-09-11 22:44:41 UTC

Updated at

2022-09-11 22:44:41 UTC

NP-MRD ID

NP0320856

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4-oxochromen-8-yl]oxy}-3,5-dihydroxy-4-(sulfooxy)oxane-2-carboxylic acid

Description

6-{[2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4-oxo-4H-chromen-8-yl]oxy}-3,5-dihydroxy-4-(sulfooxy)oxane-2-carboxylic acid belongs to the class of organic compounds known as flavonoid-8-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C8-position. 6-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4-oxochromen-8-yl]oxy}-3,5-dihydroxy-4-(sulfooxy)oxane-2-carboxylic acid is found in Malva sylvestris. 6-{[2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4-oxo-4H-chromen-8-yl]oxy}-3,5-dihydroxy-4-(sulfooxy)oxane-2-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 04121513232D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 04121513232D          

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M  END
> <DATABASE_ID>
NP0320856

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1C(OC2=C(O)C=C(O)C3=C2OC(=C(O)C3=O)C2=CC=C(O)C(O)=C2)OC(C(O)C1OS(O)(=O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H18O17S/c22-6-2-1-5(3-7(6)23)15-12(27)11(26)10-8(24)4-9(25)16(17(10)35-15)36-21-14(29)18(38-39(32,33)34)13(28)19(37-21)20(30)31/h1-4,13-14,18-19,21-25,27-29H,(H,30,31)(H,32,33,34)

> <INCHI_KEY>
PINIBBFPUYDUQL-UHFFFAOYSA-N

> <FORMULA>
C21H18O17S

> <MOLECULAR_WEIGHT>
574.42

> <EXACT_MASS>
574.026470294

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
49.78203116096049

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4-oxo-4H-chromen-8-yl]oxy}-3,5-dihydroxy-4-(sulfooxy)oxane-2-carboxylic acid

> <ALOGPS_LOGP>
0.55

> <JCHEM_LOGP>
-2.132146973632639

> <ALOGPS_LOGS>
-1.98

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.4197654889083404

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.4035165929228155

> <JCHEM_PKA_STRONGEST_BASIC>
-4.008070664845989

> <JCHEM_POLAR_SURFACE_AREA>
287.27

> <JCHEM_REFRACTIVITY>
120.8467

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.96e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4-oxochromen-8-yl]oxy}-3,5-dihydroxy-4-(sulfooxy)oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   33  S   UNK     0       1.334 -10.010   0.000  0.00  0.00           S+0
HETATM   34  O   UNK     0       2.667 -10.780   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       2.104  -8.676   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       0.564 -11.344   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4   27                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   26                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16    5   11                                                  
CONECT   18   15   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   18                                                       
CONECT   26   14                                                            
CONECT   27    3   28                                                       
CONECT   28   27   29   37                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    2   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33                                                            
CONECT   37   28   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
6-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4-oxo-4H-chromen-8-yl]oxy}-3,5-dihydroxy-4-(sulfooxy)oxane-2-carboxylate	Generator
6-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4-oxo-4H-chromen-8-yl]oxy}-3,5-dihydroxy-4-(sulphooxy)oxane-2-carboxylate	Generator
6-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4-oxo-4H-chromen-8-yl]oxy}-3,5-dihydroxy-4-(sulphooxy)oxane-2-carboxylic acid	Generator

Chemical Formula

C₂₁H₁₈O₁₇S

Average Mass

574.4200 Da

Monoisotopic Mass

574.02647 Da

IUPAC Name

6-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4-oxo-4H-chromen-8-yl]oxy}-3,5-dihydroxy-4-(sulfooxy)oxane-2-carboxylic acid

Traditional Name

6-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4-oxochromen-8-yl]oxy}-3,5-dihydroxy-4-(sulfooxy)oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC1C(OC2=C(O)C=C(O)C3=C2OC(=C(O)C3=O)C2=CC=C(O)C(O)=C2)OC(C(O)C1OS(O)(=O)=O)C(O)=O

InChI Identifier

InChI=1S/C21H18O17S/c22-6-2-1-5(3-7(6)23)15-12(27)11(26)10-8(24)4-9(25)16(17(10)35-15)36-21-14(29)18(38-39(32,33)34)13(28)19(37-21)20(30)31/h1-4,13-14,18-19,21-25,27-29H,(H,30,31)(H,32,33,34)

InChI Key

PINIBBFPUYDUQL-UHFFFAOYSA-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
Malva sylvestris	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-8-O-glucuronides

Alternative Parents

Substituents

Flavonoid-8-o-glucuronide
Flavonoid-8-o-glycoside
3-hydroxyflavone
Hydroxyflavonoid
Flavone
3'-hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3-hydroxyflavonoid
Phenolic glycoside
O-glucuronide
1-o-glucuronide
Glucuronic acid or derivatives
Chromone
O-glycosyl compound
Glycosyl compound
1-benzopyran
Benzopyran
Catechol
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Beta-hydroxy acid
Pyranone
Monocyclic benzene moiety
Benzenoid
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Hydroxy acid
Pyran
Monosaccharide
Oxane
Organic sulfuric acid or derivatives
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Carboxylic acid
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
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	0.55	ALOGPS
logP	-2.1	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	-2.4	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	287.27 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	120.85 m³·mol⁻¹	ChemAxon
Polarizability	49.78 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

Not Available

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

85097767

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4-oxochromen-8-yl]oxy}-3,5-dihydroxy-4-(sulfooxy)oxane-2-carboxylic acid (NP0320856)

MOL for NP0320856 (6-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4-oxochromen-8-yl]oxy}-3,5-dihydroxy-4-(sulfooxy)oxane-2-carboxylic acid)

3D MOL for NP0320856 (6-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4-oxochromen-8-yl]oxy}-3,5-dihydroxy-4-(sulfooxy)oxane-2-carboxylic acid)

3D SDF for NP0320856 (6-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4-oxochromen-8-yl]oxy}-3,5-dihydroxy-4-(sulfooxy)oxane-2-carboxylic acid)

3D-SDF for NP0320856 (6-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4-oxochromen-8-yl]oxy}-3,5-dihydroxy-4-(sulfooxy)oxane-2-carboxylic acid)

PDB for NP0320856 (6-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4-oxochromen-8-yl]oxy}-3,5-dihydroxy-4-(sulfooxy)oxane-2-carboxylic acid)

3D PDB for NP0320856 (6-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4-oxochromen-8-yl]oxy}-3,5-dihydroxy-4-(sulfooxy)oxane-2-carboxylic acid)

SMILES for NP0320856 (6-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4-oxochromen-8-yl]oxy}-3,5-dihydroxy-4-(sulfooxy)oxane-2-carboxylic acid)

INCHI for NP0320856 (6-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4-oxochromen-8-yl]oxy}-3,5-dihydroxy-4-(sulfooxy)oxane-2-carboxylic acid)

Structure for NP0320856 (6-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4-oxochromen-8-yl]oxy}-3,5-dihydroxy-4-(sulfooxy)oxane-2-carboxylic acid)

3D Structure for NP0320856 (6-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4-oxochromen-8-yl]oxy}-3,5-dihydroxy-4-(sulfooxy)oxane-2-carboxylic acid)