NP-MRD: Showing NP-Card for 7,4'-Dihydroxy-6-methoxyisoflavone 7-O-(6''-succinylglucoside) (NP0062998)

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Record Information

Version

2.0

Created at

2022-04-28 07:31:05 UTC

Updated at

2022-04-28 07:31:05 UTC

NP-MRD ID

NP0062998

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7,4'-Dihydroxy-6-methoxyisoflavone 7-O-(6''-succinylglucoside)

Description

Glycitein 7-O-beta-(6''-O-succinyl)-D-glucoside 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. 7,4'-Dihydroxy-6-methoxyisoflavone 7-O-(6''-succinylglucoside) is found in Bacillus subtilis and Medicago sativa . 7,4'-Dihydroxy-6-methoxyisoflavone 7-O-(6''-succinylglucoside) was first documented in 1999 (PMID: 10598027). Based on a literature review very few articles have been published on Glycitein 7-O-beta-(6''-O-succinyl)-D-glucoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282209312D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282209312D          

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 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 25 37  1  1  0  0  0
 24 38  1  6  0  0  0
 23 39  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0062998

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O[C@@H]2O[C@H](COC(=O)CCC(O)=O)[C@@H](O)[C@H](O)[C@H]2O)C=C2OC=C(C(=O)C2=C1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H26O13/c1-35-17-8-14-16(36-10-15(22(14)31)12-2-4-13(27)5-3-12)9-18(17)38-26-25(34)24(33)23(32)19(39-26)11-37-21(30)7-6-20(28)29/h2-5,8-10,19,23-27,32-34H,6-7,11H2,1H3,(H,28,29)/t19-,23-,24+,25-,26-/m1/s1

> <INCHI_KEY>
GVXJPLOLMFXZFW-OMJUENHASA-N

> <FORMULA>
C26H26O13

> <MOLECULAR_WEIGHT>
546.481

> <EXACT_MASS>
546.137340897

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
53.203115704137396

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.00

> <JCHEM_LOGP>
0.5706865096666676

> <ALOGPS_LOGS>
-3.35

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.962559794796093

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6624760300235777

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649102930618218

> <JCHEM_POLAR_SURFACE_AREA>
198.50999999999996

> <JCHEM_REFRACTIVITY>
128.35439999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.44e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-oxo-4-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[3-(4-hydroxyphenyl)-6-methoxy-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}butanoic 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  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2    6   21                                                  
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   15                                                            
CONECT   19    2   20                                                       
CONECT   20   19                                                            
CONECT   21    1   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24   39                                                  
CONECT   24   23   25   38                                                  
CONECT   25   24   26   37                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   22                                                       
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   25                                                            
CONECT   38   24                                                            
CONECT   39   23                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
Glycitein 7-O-b-(6''-O-succinyl)-D-glucoside	Generator
Glycitein 7-O-β-(6''-O-succinyl)-D-glucoside	Generator

Chemical Formula

C₂₆H₂₆O₁₃

Average Mass

546.4810 Da

Monoisotopic Mass

546.13734 Da

IUPAC Name

4-oxo-4-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[3-(4-hydroxyphenyl)-6-methoxy-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methoxy}butanoic acid

Traditional Name

4-oxo-4-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[3-(4-hydroxyphenyl)-6-methoxy-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}butanoic acid

CAS Registry Number

Not Available

SMILES

COC1=C(O[C@@H]2O[C@H](COC(=O)CCC(O)=O)[C@@H](O)[C@H](O)[C@H]2O)C=C2OC=C(C(=O)C2=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C26H26O13/c1-35-17-8-14-16(36-10-15(22(14)31)12-2-4-13(27)5-3-12)9-18(17)38-26-25(34)24(33)23(32)19(39-26)11-37-21(30)7-6-20(28)29/h2-5,8-10,19,23-27,32-34H,6-7,11H2,1H3,(H,28,29)/t19-,23-,24+,25-,26-/m1/s1

InChI Key

GVXJPLOLMFXZFW-OMJUENHASA-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
Bacillus subtilis	Bacteria	KNApSAcK
Medicago sativa	Plant	KNApSAcK

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-7-o-glycoside
Isoflavonoid o-glycoside
Saccharolipid
Isoflavone
Phenolic glycoside
O-glycosyl compound
Glycosyl compound
Chromone
1-benzopyran
Benzopyran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Sugar acid
Pyranone
Phenol
Fatty acid ester
Alkyl aryl ether
Fatty acyl
Benzenoid
Pyran
Oxane
Monosaccharide
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
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	1	ALOGPS
logP	0.57	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	3.66	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	198.51 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	128.35 m³·mol⁻¹	ChemAxon
Polarizability	53.2 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

103885000

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100992110

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Toda T, Uesugi T, Hirai K, Nukaya H, Tsuji K, Ishida H: New 6-O-acyl isoflavone glycosides from soybeans fermented with Bacillus subtilis (natto). I. 6-O-succinylated isoflavone glycosides and their preventive effects on bone loss in ovariectomized rats fed a calcium-deficient diet. Biol Pharm Bull. 1999 Nov;22(11):1193-201. doi: 10.1248/bpb.22.1193. [PubMed:10598027 ]

Showing NP-Card for 7,4'-Dihydroxy-6-methoxyisoflavone 7-O-(6''-succinylglucoside) (NP0062998)

MOL for NP0062998 (7,4'-Dihydroxy-6-methoxyisoflavone 7-O-(6''-succinylglucoside))

3D MOL for NP0062998 (7,4'-Dihydroxy-6-methoxyisoflavone 7-O-(6''-succinylglucoside))

3D SDF for NP0062998 (7,4'-Dihydroxy-6-methoxyisoflavone 7-O-(6''-succinylglucoside))

3D-SDF for NP0062998 (7,4'-Dihydroxy-6-methoxyisoflavone 7-O-(6''-succinylglucoside))

PDB for NP0062998 (7,4'-Dihydroxy-6-methoxyisoflavone 7-O-(6''-succinylglucoside))

3D PDB for NP0062998 (7,4'-Dihydroxy-6-methoxyisoflavone 7-O-(6''-succinylglucoside))

SMILES for NP0062998 (7,4'-Dihydroxy-6-methoxyisoflavone 7-O-(6''-succinylglucoside))

INCHI for NP0062998 (7,4'-Dihydroxy-6-methoxyisoflavone 7-O-(6''-succinylglucoside))

Structure for NP0062998 (7,4'-Dihydroxy-6-methoxyisoflavone 7-O-(6''-succinylglucoside))

3D Structure for NP0062998 (7,4'-Dihydroxy-6-methoxyisoflavone 7-O-(6''-succinylglucoside))