NP-MRD: Showing NP-Card for 3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid (NP0330384)

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Record Information

Version

2.0

Created at

2022-09-12 15:40:30 UTC

Updated at

2022-09-12 15:40:30 UTC

NP-MRD ID

NP0330384

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid

Description

Formononetin 7-O-glucoside-6''-O-malonate belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one. Formononetin 7-O-glucoside-6''-O-malonate is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid is found in Glycyrrhiza pallidiflora, Maackia amurensis, Medicago truncatula and Pueraria montana. Based on a literature review very few articles have been published on formononetin 7-O-glucoside-6''-O-malonate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309122217402D          

 37 40  0  0  1  0            999 V2000
  -10.0026    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.1447    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  3 37  1  0  0  0  0
M  END

     RDKit          3D

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M  END

  Mrv1652309122217402D          

 37 40  0  0  1  0            999 V2000
  -10.0026    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0330384

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C1=COC2=CC(O[C@@H]3O[C@H](COC(=O)CC(O)=O)[C@@H](O)[C@H](O)[C@H]3O)=CC=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H24O12/c1-33-13-4-2-12(3-5-13)16-10-34-17-8-14(6-7-15(17)21(16)29)36-25-24(32)23(31)22(30)18(37-25)11-35-20(28)9-19(26)27/h2-8,10,18,22-25,30-32H,9,11H2,1H3,(H,26,27)/t18-,22-,23+,24-,25-/m1/s1

> <INCHI_KEY>
RDTAGQKYPGLCBK-GOZZSVHWSA-N

> <FORMULA>
C25H24O12

> <MOLECULAR_WEIGHT>
516.455

> <EXACT_MASS>
516.126776213

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
50.40303970482363

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-oxo-3-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid

> <JCHEM_LOGP>
0.9416175303333336

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.201707340594092

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3796071965269605

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649103025377329

> <JCHEM_POLAR_SURFACE_AREA>
178.28

> <JCHEM_REFRACTIVITY>
121.82430000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-oxo-3-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0     -18.672  18.480   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0     -17.338  19.250   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0     -16.004  18.480   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -14.670  19.250   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -13.337  18.480   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -13.337  16.940   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -12.003  16.170   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -10.669  16.940   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -9.336  16.170   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -9.336  14.630   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.002  13.860   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.002  12.320   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -6.668  11.550   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -6.668  10.010   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.335   9.240   0.000  0.00  0.00           O+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      -2.667   7.700   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.000   7.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.667   7.700   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.334   5.390   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -6.668   5.390   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -8.002   7.700   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -9.336   6.930   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -9.336  10.010   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -9.336  11.550   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -10.669  12.320   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -10.669  13.860   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -12.003  14.630   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0     -13.337  13.860   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0     -14.670  16.170   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -16.004  16.940   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   37                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   36                                                  
CONECT    7    6    8   34                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   33                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   31                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   29                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   16   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   14   30                                                  
CONECT   30   29                                                            
CONECT   31   12   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   10   34                                                  
CONECT   34   33    7   35                                                  
CONECT   35   34                                                            
CONECT   36    6   37                                                       
CONECT   37   36    3                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
Formononetin 7-O-glucoside-6''-O-malonic acid	Generator

Chemical Formula

C₂₅H₂₄O₁₂

Average Mass

516.4550 Da

Monoisotopic Mass

516.12678 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C1=COC2=CC(O[C@@H]3O[C@H](COC(=O)CC(O)=O)[C@@H](O)[C@H](O)[C@H]3O)=CC=C2C1=O

InChI Identifier

InChI=1S/C25H24O12/c1-33-13-4-2-12(3-5-13)16-10-34-17-8-14(6-7-15(17)21(16)29)36-25-24(32)23(31)22(30)18(37-25)11-35-20(28)9-19(26)27/h2-8,10,18,22-25,30-32H,9,11H2,1H3,(H,26,27)/t18-,22-,23+,24-,25-/m1/s1

InChI Key

RDTAGQKYPGLCBK-GOZZSVHWSA-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
Glycyrrhiza pallidiflora	LOTUS Database	35616633
Maackia amurensis	LOTUS Database	35616633
Medicago truncatula	LOTUS Database	35616633
Pueraria montana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-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 O-glycosides

Direct Parent

Isoflavonoid O-glycosides

Alternative Parents

Substituents

Isoflavonoid o-glycoside
Isoflavonoid-7-o-glycoside
4p-o-methylisoflavone
Isoflavone
Phenolic glycoside
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Pyranone
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
1,3-dicarbonyl compound
Monosaccharide
Pyran
Oxane
Heteroaromatic compound
Carboxylic acid ester
Secondary alcohol
Polyol
Organoheterocyclic compound
Ether
Acetal
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Alcohol
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monosaccharide derivative (CHEBI:80389 )
methoxyisoflavone (CHEBI:80389 )
malonate ester (CHEBI:80389 )
glycosyloxyisoflavone (CHEBI:80389 )
isoflavones (C16222 )
Isoflavonoids (C16222 )

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

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

21615451

KEGG Compound ID

C16222

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23724663

PDB ID

Not Available

ChEBI ID

80389

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid (NP0330384)

MOL for NP0330384 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid)

3D MOL for NP0330384 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid)

3D SDF for NP0330384 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid)

3D-SDF for NP0330384 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid)

PDB for NP0330384 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid)

3D PDB for NP0330384 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid)

SMILES for NP0330384 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid)

INCHI for NP0330384 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid)

Structure for NP0330384 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid)

3D Structure for NP0330384 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid)