NP-MRD: Showing NP-Card for Isorhamnetin 3-glucuronide-7-sulfate (NP0054022)

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Record Information

Version

2.0

Created at

2022-04-28 00:30:29 UTC

Updated at

2022-04-28 00:30:29 UTC

NP-MRD ID

NP0054022

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isorhamnetin 3-glucuronide-7-sulfate

Description

(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-7-(sulfooxy)-4H-chromen-3-yl]oxy}oxane-2-carboxylic acid belongs to the class of organic compounds known as flavonoid-3-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C3-position. Isorhamnetin 3-glucuronide-7-sulfate is found in Frankenia pulverulenta. Based on a literature review very few articles have been published on (2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-7-(sulfooxy)-4H-chromen-3-yl]oxy}oxane-2-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282202302D          

 39 42  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282202302D          

 39 42  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0054022

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C1=C(O[C@@H]2O[C@@H]([C@@H](O)[C@@H](O)[C@@H]2O)C(O)=O)C(=O)C2=C(O)C=C(OS(O)(=O)=O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C22H20O16S/c1-34-11-4-7(2-3-9(11)23)18-19(36-22-17(28)15(26)16(27)20(37-22)21(29)30)14(25)13-10(24)5-8(6-12(13)35-18)38-39(31,32)33/h2-6,15-17,20,22-24,26-28H,1H3,(H,29,30)(H,31,32,33)/t15-,16+,17+,20+,22-/m1/s1

> <INCHI_KEY>
WZDPRCUVWISQMO-ITIJKJFXSA-N

> <FORMULA>
C22H20O16S

> <MOLECULAR_WEIGHT>
572.45

> <EXACT_MASS>
572.047205738

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
50.99105136953166

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-7-(sulfooxy)-4H-chromen-3-yl]oxy}oxane-2-carboxylic acid

> <ALOGPS_LOGP>
0.34

> <JCHEM_LOGP>
-2.339204451194961

> <ALOGPS_LOGS>
-2.29

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.612621458277306

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.627851525926582

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6868297480420704

> <JCHEM_POLAR_SURFACE_AREA>
256.03999999999996

> <JCHEM_REFRACTIVITY>
123.61699999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.95e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-7-(sulfooxy)chromen-3-yl]oxy}oxane-2-carboxylic 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       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   36  S   UNK     0      -4.001  -0.770   0.000  0.00  0.00           S+0
HETATM   37  O   UNK     0      -5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -4.771   0.564   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -3.231  -2.104   0.000  0.00  0.00           O+0
CONECT    1    2    6   35                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   25                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   24                                                  
CONECT   15   14   16   23                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   13                                                       
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   16                                                            
CONECT   23   15                                                            
CONECT   24   14                                                            
CONECT   25    8   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29   25                                                       
CONECT   31   29   32                                                       
CONECT   32   31                                                            
CONECT   33   28                                                            
CONECT   34    3                                                            
CONECT   35    1   36                                                       
CONECT   36   35   37   38   39                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   36                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
(2S,3S,4R,5S,6S)-3,4,5-Trihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-7-(sulfooxy)-4H-chromen-3-yl]oxy}oxane-2-carboxylate	Generator
(2S,3S,4R,5S,6S)-3,4,5-Trihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-7-(sulphooxy)-4H-chromen-3-yl]oxy}oxane-2-carboxylate	Generator
(2S,3S,4R,5S,6S)-3,4,5-Trihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-7-(sulphooxy)-4H-chromen-3-yl]oxy}oxane-2-carboxylic acid	Generator

Chemical Formula

C₂₂H₂₀O₁₆S

Average Mass

572.4500 Da

Monoisotopic Mass

572.04721 Da

IUPAC Name

(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-7-(sulfooxy)-4H-chromen-3-yl]oxy}oxane-2-carboxylic acid

Traditional Name

(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-7-(sulfooxy)chromen-3-yl]oxy}oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C1=C(O[C@@H]2O[C@@H]([C@@H](O)[C@@H](O)[C@@H]2O)C(O)=O)C(=O)C2=C(O)C=C(OS(O)(=O)=O)C=C2O1

InChI Identifier

InChI=1S/C22H20O16S/c1-34-11-4-7(2-3-9(11)23)18-19(36-22-17(28)15(26)16(27)20(37-22)21(29)30)14(25)13-10(24)5-8(6-12(13)35-18)38-39(31,32)33/h2-6,15-17,20,22-24,26-28H,1H3,(H,29,30)(H,31,32,33)/t15-,16+,17+,20+,22-/m1/s1

InChI Key

WZDPRCUVWISQMO-ITIJKJFXSA-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
Frankenia pulverulenta	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glucuronides

Alternative Parents

Substituents

Flavonoid-3-o-glucuronide
Flavonoid-3-o-glycoside
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
5-hydroxyflavonoid
4'-hydroxyflavonoid
O-glucuronide
1-o-glucuronide
Glucuronic acid or derivatives
O-glycosyl compound
Glycosyl compound
Chromone
Arylsulfate
1-benzopyran
Methoxyphenol
Benzopyran
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Beta-hydroxy acid
Alkyl aryl ether
Benzenoid
Sulfuric acid ester
Sulfate-ester
Sulfuric acid monoester
Pyran
Oxane
Monosaccharide
Hydroxy acid
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Organic sulfuric acid or derivatives
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	0.34	ALOGPS
logP	-2.3	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	-2.6	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	256.04 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	123.62 m³·mol⁻¹	ChemAxon
Polarizability	50.99 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

162929763

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Isorhamnetin 3-glucuronide-7-sulfate (NP0054022)

MOL for NP0054022 (Isorhamnetin 3-glucuronide-7-sulfate)

3D MOL for NP0054022 (Isorhamnetin 3-glucuronide-7-sulfate)

3D SDF for NP0054022 (Isorhamnetin 3-glucuronide-7-sulfate)

3D-SDF for NP0054022 (Isorhamnetin 3-glucuronide-7-sulfate)

PDB for NP0054022 (Isorhamnetin 3-glucuronide-7-sulfate)

3D PDB for NP0054022 (Isorhamnetin 3-glucuronide-7-sulfate)

SMILES for NP0054022 (Isorhamnetin 3-glucuronide-7-sulfate)

INCHI for NP0054022 (Isorhamnetin 3-glucuronide-7-sulfate)

Structure for NP0054022 (Isorhamnetin 3-glucuronide-7-sulfate)

3D Structure for NP0054022 (Isorhamnetin 3-glucuronide-7-sulfate)