NP-MRD: Showing NP-Card for 3-({6-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)-3-oxopropanoic acid (NP0311782)

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Record Information

Version

2.0

Created at

2022-09-11 08:01:17 UTC

Updated at

2022-09-11 08:01:17 UTC

NP-MRD ID

NP0311782

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-({6-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)-3-oxopropanoic acid

Description

3-({6-[5,7-Dihydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)-3-oxopropanoic acid belongs to the class of organic compounds known as isoflavonoid c-glycosides. These are c-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one. 3-({6-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)-3-oxopropanoic acid is found in Pueraria montana. Based on a literature review very few articles have been published on 3-({6-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)-3-oxopropanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112210012D          

 37 40  0  0  0  0            999 V2000
    7.1447   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   15.7184   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.5749   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.7171   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
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  9 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END

     RDKit          3D

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    3.6128    3.0990    0.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309112210012D          

 37 40  0  0  0  0            999 V2000
    7.1447   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2881   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.2894   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.8605   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0311782

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1C(O)C(COC(=O)CC(O)=O)OC(C1O)C1=C2OC=C(C(=O)C2=C(O)C=C1O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H22O13/c25-10-3-1-9(2-4-10)11-7-36-23-17(19(11)31)12(26)5-13(27)18(23)24-22(34)21(33)20(32)14(37-24)8-35-16(30)6-15(28)29/h1-5,7,14,20-22,24-27,32-34H,6,8H2,(H,28,29)

> <INCHI_KEY>
ONAKFDCVYIMHKF-UHFFFAOYSA-N

> <FORMULA>
C24H22O13

> <MOLECULAR_WEIGHT>
518.427

> <EXACT_MASS>
518.106040768

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
48.617211559344284

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-({6-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)-3-oxopropanoic acid

> <JCHEM_LOGP>
0.6529053409999995

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.144850699546011

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2385697512907896

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6454384174713406

> <JCHEM_POLAR_SURFACE_AREA>
220.50999999999996

> <JCHEM_REFRACTIVITY>
120.2968

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-({6-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)-3-oxopropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  O   UNK     0      13.337  -1.540   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      14.670   0.770   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      16.004  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.338  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      17.338   0.770   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      18.672  -1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      20.005  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.339  -1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      22.673  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      24.006  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.340  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.340   0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      24.006   1.540   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      26.674   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.007   0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      29.341   1.540   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      28.007  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.341  -1.540   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      30.675  -0.770   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      29.341  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      30.675  -3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      32.008  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      33.342  -3.850   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      33.342  -5.390   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      34.676  -6.160   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      32.008  -6.160   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      30.675  -5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      28.007  -3.850   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      26.674  -3.080   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      26.674  -1.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      24.006  -3.080   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      25.340  -3.850   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      22.673  -3.850   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      22.673  -5.390   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      21.339  -3.080   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      20.005  -3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   36                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   32                                                  
CONECT   12   11   13   31                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   31                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   29                                                  
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   22                                                       
CONECT   29   21   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   12   18                                                  
CONECT   32   11   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34    9   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
3-({6-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)-3-oxopropanoate	Generator

Chemical Formula

C₂₄H₂₂O₁₃

Average Mass

518.4270 Da

Monoisotopic Mass

518.10604 Da

IUPAC Name

3-({6-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)-3-oxopropanoic acid

Traditional Name

3-({6-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)-3-oxopropanoic acid

CAS Registry Number

Not Available

SMILES

OC1C(O)C(COC(=O)CC(O)=O)OC(C1O)C1=C2OC=C(C(=O)C2=C(O)C=C1O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C24H22O13/c25-10-3-1-9(2-4-10)11-7-36-23-17(19(11)31)12(26)5-13(27)18(23)24-22(34)21(33)20(32)14(37-24)8-35-16(30)6-15(28)29/h1-5,7,14,20-22,24-27,32-34H,6,8H2,(H,28,29)

InChI Key

ONAKFDCVYIMHKF-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
Pueraria montana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavonoid c-glycosides. These are c-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavonoid C-glycosides

Direct Parent

Isoflavonoid C-glycosides

Alternative Parents

Substituents

Isoflavonoid c-glycoside
Isoflavonoid-8-c-glycoside
Hydroxyisoflavonoid
Isoflavone
Phenolic glycoside
C-glycosyl compound
Chromone
Glycosyl compound
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Benzenoid
1,3-dicarbonyl compound
Pyran
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Ether
Carboxylic acid derivative
Dialkyl ether
Polyol
Carboxylic acid
Alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	0.65	ChemAxon
pKa (Strongest Acidic)	3.24	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	220.51 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	120.3 m³·mol⁻¹	ChemAxon
Polarizability	48.62 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

162945683

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-({6-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)-3-oxopropanoic acid (NP0311782)

MOL for NP0311782 (3-({6-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)-3-oxopropanoic acid)

3D MOL for NP0311782 (3-({6-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)-3-oxopropanoic acid)

3D SDF for NP0311782 (3-({6-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)-3-oxopropanoic acid)

3D-SDF for NP0311782 (3-({6-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)-3-oxopropanoic acid)

PDB for NP0311782 (3-({6-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)-3-oxopropanoic acid)

3D PDB for NP0311782 (3-({6-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)-3-oxopropanoic acid)

SMILES for NP0311782 (3-({6-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)-3-oxopropanoic acid)

INCHI for NP0311782 (3-({6-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)-3-oxopropanoic acid)

Structure for NP0311782 (3-({6-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)-3-oxopropanoic acid)

3D Structure for NP0311782 (3-({6-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)-3-oxopropanoic acid)