NP-MRD: Showing NP-Card for 5,7,4'-Trihydroxyisoflavone 7-O-(6''-succinylglucoside) (NP0062997)

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Record Information

Version

2.0

Created at

2022-04-28 07:31:02 UTC

Updated at

2022-04-28 07:31:02 UTC

NP-MRD ID

NP0062997

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7,4'-Trihydroxyisoflavone 7-O-(6''-succinylglucoside)

Description

6''-O-Succcinylgenistin 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. 5,7,4'-Trihydroxyisoflavone 7-O-(6''-succinylglucoside) is found in Bacillus subtilis . Based on a literature review very few articles have been published on 6''-O-Succcinylgenistin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282209312D          

 38 41  0  0  1  0            999 V2000
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   -7.8592   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304282209312D          

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M  END
> <DATABASE_ID>
NP0062997

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1[C@H](O)[C@@H](COC(=O)CCC(O)=O)O[C@@H](OC2=CC(O)=C3C(OC=C(C3=O)C3=CC=C(O)C=C3)=C2)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H24O13/c26-12-3-1-11(2-4-12)14-9-35-16-8-13(7-15(27)20(16)21(14)31)37-25-24(34)23(33)22(32)17(38-25)10-36-19(30)6-5-18(28)29/h1-4,7-9,17,22-27,32-34H,5-6,10H2,(H,28,29)/t17-,22-,23+,24-,25-/m1/s1

> <INCHI_KEY>
DWZGNQPPAXNDDD-RBZNUJCTSA-N

> <FORMULA>
C25H24O13

> <MOLECULAR_WEIGHT>
532.454

> <EXACT_MASS>
532.121690833

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
51.00247598585796

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.34

> <JCHEM_LOGP>
1.0747924536666669

> <ALOGPS_LOGS>
-3.18

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.27310043132941

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6623717384873897

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649102910432293

> <JCHEM_POLAR_SURFACE_AREA>
209.50999999999996

> <JCHEM_REFRACTIVITY>
123.87209999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.49e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-oxo-4-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-3-(4-hydroxyphenyl)-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     -12.003 -11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -13.337 -10.780   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -14.670 -11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -14.670 -13.090   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -13.337 -13.860   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -12.003 -13.090   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0     -13.337 -15.400   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0     -14.670 -16.170   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -16.004 -15.400   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -16.004 -13.860   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0     -17.338 -13.090   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0     -17.338 -16.170   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -17.338 -17.710   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -18.672 -18.480   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -20.005 -17.710   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -20.005 -16.170   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -18.672 -15.400   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0     -21.339 -18.480   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0     -16.004 -10.780   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0     -10.669 -10.780   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0     -10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -12.003  -8.470   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -10.669  -6.160   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -9.336  -8.470   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.000  -6.160   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -1.334  -8.470   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0     -10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0     -13.337  -6.160   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0     -13.337  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2    6   20                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
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    3                                                            
CONECT   20    1   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   38                                                  
CONECT   23   22   24   37                                                  
CONECT   24   23   25   36                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25   21                                                       
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   24                                                            
CONECT   37   23                                                            
CONECT   38   22                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₄O₁₃

Average Mass

532.4540 Da

Monoisotopic Mass

532.12169 Da

IUPAC Name

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

CAS Registry Number

Not Available

SMILES

O[C@H]1[C@H](O)[C@@H](COC(=O)CCC(O)=O)O[C@@H](OC2=CC(O)=C3C(OC=C(C3=O)C3=CC=C(O)C=C3)=C2)[C@@H]1O

InChI Identifier

InChI=1S/C25H24O13/c26-12-3-1-11(2-4-12)14-9-35-16-8-13(7-15(27)20(16)21(14)31)37-25-24(34)23(33)22(32)17(38-25)10-36-19(30)6-5-18(28)29/h1-4,7-9,17,22-27,32-34H,5-6,10H2,(H,28,29)/t17-,22-,23+,24-,25-/m1/s1

InChI Key

DWZGNQPPAXNDDD-RBZNUJCTSA-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

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
Hydroxyisoflavonoid
Phenolic glycoside
Glycosyl compound
Chromone
O-glycosyl compound
Benzopyran
1-benzopyran
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Sugar acid
Pyranone
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Monosaccharide
Oxane
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Acetal
Polyol
Organoheterocyclic compound
Carboxylic acid
Oxacycle
Carbonyl group
Organic oxygen compound
Organic oxide
Alcohol
Hydrocarbon derivative
Organooxygen compound
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	1.34	ALOGPS
logP	1.07	ChemAxon
logS	-3.2	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	6	ChemAxon
Polar Surface Area	209.51 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	123.87 m³·mol⁻¹	ChemAxon
Polarizability	51 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

8612495

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10437071

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5,7,4'-Trihydroxyisoflavone 7-O-(6''-succinylglucoside) (NP0062997)

MOL for NP0062997 (5,7,4'-Trihydroxyisoflavone 7-O-(6''-succinylglucoside))

3D MOL for NP0062997 (5,7,4'-Trihydroxyisoflavone 7-O-(6''-succinylglucoside))

3D SDF for NP0062997 (5,7,4'-Trihydroxyisoflavone 7-O-(6''-succinylglucoside))

3D-SDF for NP0062997 (5,7,4'-Trihydroxyisoflavone 7-O-(6''-succinylglucoside))

PDB for NP0062997 (5,7,4'-Trihydroxyisoflavone 7-O-(6''-succinylglucoside))

3D PDB for NP0062997 (5,7,4'-Trihydroxyisoflavone 7-O-(6''-succinylglucoside))

SMILES for NP0062997 (5,7,4'-Trihydroxyisoflavone 7-O-(6''-succinylglucoside))

INCHI for NP0062997 (5,7,4'-Trihydroxyisoflavone 7-O-(6''-succinylglucoside))

Structure for NP0062997 (5,7,4'-Trihydroxyisoflavone 7-O-(6''-succinylglucoside))

3D Structure for NP0062997 (5,7,4'-Trihydroxyisoflavone 7-O-(6''-succinylglucoside))