NP-MRD: Showing NP-Card for (2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)-3-methoxyphenoxy]oxane-2-carboxylic acid (NP0235317)

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Record Information

Version

2.0

Created at

2022-09-06 17:52:21 UTC

Updated at

2022-09-06 17:52:21 UTC

NP-MRD ID

NP0235317

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)-3-methoxyphenoxy]oxane-2-carboxylic acid

Description

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-(5-hydroxy-7,8-dimethoxy-4-oxo-4H-chromen-2-yl)-3-methoxyphenoxy]oxane-2-carboxylic acid belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. (2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)-3-methoxyphenoxy]oxane-2-carboxylic acid is found in Scutellaria baicalensis. Based on a literature review very few articles have been published on (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-(5-hydroxy-7,8-dimethoxy-4-oxo-4H-chromen-2-yl)-3-methoxyphenoxy]oxane-2-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062219522D          

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M  END

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M  END


  Mrv1652309062219522D          

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M  END
> <DATABASE_ID>
NP0235317

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)C=C(OC2=C1OC)C1=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=CC=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C24H24O13/c1-32-11-5-4-6-12(36-24-19(29)17(27)18(28)22(37-24)23(30)31)16(11)13-7-9(25)15-10(26)8-14(33-2)20(34-3)21(15)35-13/h4-8,17-19,22,24,26-29H,1-3H3,(H,30,31)/t17-,18-,19+,22-,24+/m0/s1

> <INCHI_KEY>
PQLPFYVPSLASRG-YPQORGHUSA-N

> <FORMULA>
C24H24O13

> <MOLECULAR_WEIGHT>
520.443

> <EXACT_MASS>
520.121690833

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
48.84650619564625

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-(5-hydroxy-7,8-dimethoxy-4-oxo-4H-chromen-2-yl)-3-methoxyphenoxy]oxane-2-carboxylic acid

> <JCHEM_LOGP>
0.5894471029999993

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.878872566868478

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.887630589694448

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6868270495675235

> <JCHEM_POLAR_SURFACE_AREA>
190.67

> <JCHEM_REFRACTIVITY>
122.33439999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)-3-methoxyphenoxy]oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.668   2.310   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  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.002  -3.080   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  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   21                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    9   20                                                  
CONECT   20   19                                                            
CONECT   21    7    3   22                                                  
CONECT   22   21   23   37                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   36                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33   26   37                                                  
CONECT   37   36   22                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-[2-(5-hydroxy-7,8-dimethoxy-4-oxo-4H-chromen-2-yl)-3-methoxyphenoxy]oxane-2-carboxylate	Generator

Chemical Formula

C₂₄H₂₄O₁₃

Average Mass

520.4430 Da

Monoisotopic Mass

520.12169 Da

IUPAC Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-(5-hydroxy-7,8-dimethoxy-4-oxo-4H-chromen-2-yl)-3-methoxyphenoxy]oxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)-3-methoxyphenoxy]oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)C=C(OC2=C1OC)C1=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=CC=C1OC

InChI Identifier

InChI=1S/C24H24O13/c1-32-11-5-4-6-12(36-24-19(29)17(27)18(28)22(37-24)23(30)31)16(11)13-7-9(25)15-10(26)8-14(33-2)20(34-3)21(15)35-13/h4-8,17-19,22,24,26-29H,1-3H3,(H,30,31)/t17-,18-,19+,22-,24+/m0/s1

InChI Key

PQLPFYVPSLASRG-YPQORGHUSA-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
Scutellaria baicalensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

8-O-methylated flavonoids

Alternative Parents

Substituents

8-methoxyflavonoid-skeleton
2p-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
5-hydroxyflavonoid
Phenolic glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Anisole
Methoxybenzene
Phenol ether
Phenoxy compound
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Beta-hydroxy acid
Pyranone
Monosaccharide
Pyran
Hydroxy acid
Benzenoid
Monocyclic benzene moiety
Oxane
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Polyol
Oxacycle
Ether
Acetal
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
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	0.59	ChemAxon
pKa (Strongest Acidic)	2.89	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	190.67 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	122.33 m³·mol⁻¹	ChemAxon
Polarizability	48.85 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

14825641

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)-3-methoxyphenoxy]oxane-2-carboxylic acid (NP0235317)

MOL for NP0235317 ((2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)-3-methoxyphenoxy]oxane-2-carboxylic acid)

3D MOL for NP0235317 ((2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)-3-methoxyphenoxy]oxane-2-carboxylic acid)

3D SDF for NP0235317 ((2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)-3-methoxyphenoxy]oxane-2-carboxylic acid)

3D-SDF for NP0235317 ((2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)-3-methoxyphenoxy]oxane-2-carboxylic acid)

PDB for NP0235317 ((2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)-3-methoxyphenoxy]oxane-2-carboxylic acid)

3D PDB for NP0235317 ((2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)-3-methoxyphenoxy]oxane-2-carboxylic acid)

SMILES for NP0235317 ((2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)-3-methoxyphenoxy]oxane-2-carboxylic acid)

INCHI for NP0235317 ((2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)-3-methoxyphenoxy]oxane-2-carboxylic acid)

Structure for NP0235317 ((2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)-3-methoxyphenoxy]oxane-2-carboxylic acid)

3D Structure for NP0235317 ((2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)-3-methoxyphenoxy]oxane-2-carboxylic acid)