NP-MRD: Showing NP-Card for 4',7-Dihydroxy-2',5-dimethoxyisoflavanone (NP0048888)

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Record Information

Version

2.0

Created at

2022-03-17 21:03:46 UTC

Updated at

2022-03-17 21:03:46 UTC

NP-MRD ID

NP0048888

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4',7-Dihydroxy-2',5-dimethoxyisoflavanone

Description

4',7-Dihydroxy-2',5-dimethoxyisoflavanone belongs to the class of organic compounds known as 5-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C5 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Thus, 4',7-dihydroxy-2',5-dimethoxyisoflavanone is considered to be a flavonoid lipid molecule. 4',7-Dihydroxy-2',5-dimethoxyisoflavanone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 4',7-Dihydroxy-2',5-dimethoxyisoflavanone has been detected, but not quantified in, pulses and scarlet beans. This could make 4',7-dihydroxy-2',5-dimethoxyisoflavanone a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 05061309592D          

 23 25  0  0  0  0            999 V2000
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  9  3  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  4  1  0  0  0  0
 12  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13  5  1  0  0  0  0
 13 11  2  0  0  0  0
 14  6  1  0  0  0  0
 15  7  2  0  0  0  0
 16 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  1  0  0  0  0
 18  9  1  0  0  0  0
 19 10  1  0  0  0  0
 20 17  2  0  0  0  0
 21  1  1  0  0  0  0
 21 13  1  0  0  0  0
 22  2  1  0  0  0  0
 22 14  1  0  0  0  0
 23  8  1  0  0  0  0
 23 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048888

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C=CC(O)=C1)C1COC2=CC(O)=CC(OC)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O6/c1-21-13-5-9(18)3-4-11(13)12-8-23-15-7-10(19)6-14(22-2)16(15)17(12)20/h3-7,12,18-19H,8H2,1-2H3

> <INCHI_KEY>
VXWBAOPTFLXYTN-UHFFFAOYSA-N

> <FORMULA>
C17H16O6

> <MOLECULAR_WEIGHT>
316.3053

> <EXACT_MASS>
316.094688244

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
31.405116452731693

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-3-(4-hydroxy-2-methoxyphenyl)-5-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
2.065880904333333

> <ALOGPS_LOGS>
-3.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.458669035844824

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.830760777491814

> <JCHEM_PKA_STRONGEST_BASIC>
-4.409211557235681

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
82.622

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.41e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxy-3-(4-hydroxy-2-methoxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3    4    9                                                       
CONECT    4    3   11                                                       
CONECT    5    9   13                                                       
CONECT    6   10   14                                                       
CONECT    7   10   15                                                       
CONECT    8   12   23                                                       
CONECT    9    3    5   18                                                  
CONECT   10    6    7   19                                                  
CONECT   11    4   12   13                                                  
CONECT   12    8   11   17                                                  
CONECT   13    5   11   21                                                  
CONECT   14    6   16   22                                                  
CONECT   15    7   16   23                                                  
CONECT   16   14   15   17                                                  
CONECT   17   12   16   20                                                  
CONECT   18    9                                                            
CONECT   19   10                                                            
CONECT   20   17                                                            
CONECT   21    1   13                                                       
CONECT   22    2   14                                                       
CONECT   23    8   15                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
7,4'-Dihydroxy-5,2'-dimethoxyisoflavanone	HMDB

Chemical Formula

C₁₇H₁₆O₆

Average Mass

316.3053 Da

Monoisotopic Mass

316.09469 Da

IUPAC Name

7-hydroxy-3-(4-hydroxy-2-methoxyphenyl)-5-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

7-hydroxy-3-(4-hydroxy-2-methoxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

99965-02-3

SMILES

COC1=C(C=CC(O)=C1)C1COC2=CC(O)=CC(OC)=C2C1=O

InChI Identifier

InChI=1S/C17H16O6/c1-21-13-5-9(18)3-4-11(13)12-8-23-15-7-10(19)6-14(22-2)16(15)17(12)20/h3-7,12,18-19H,8H2,1-2H3

InChI Key

VXWBAOPTFLXYTN-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Phaseolus coccineus	FooDB	KNAPSACK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C5 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

5-O-methylated isoflavonoids

Alternative Parents

Substituents

2p-methoxyisoflavonoid-skeleton
5-methoxyisoflavonoid-skeleton
Isoflavanone
Hydroxyisoflavonoid
Isoflavanol
Isoflavan
Chromone
Methoxyphenol
Chromane
1-benzopyran
Benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Aryl ketone
Aryl alkyl ketone
Phenol ether
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050505 )

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	2.78	ALOGPS
logP	2.07	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	7.83	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	82.62 m³·mol⁻¹	ChemAxon
Polarizability	31.41 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0037749

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016888

KNApSAcK ID

C00009954

Chemspider ID

24842929

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44257395

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4',7-Dihydroxy-2',5-dimethoxyisoflavanone (NP0048888)

MOL for NP0048888 (4',7-Dihydroxy-2',5-dimethoxyisoflavanone)

3D MOL for NP0048888 (4',7-Dihydroxy-2',5-dimethoxyisoflavanone)

3D SDF for NP0048888 (4',7-Dihydroxy-2',5-dimethoxyisoflavanone)

3D-SDF for NP0048888 (4',7-Dihydroxy-2',5-dimethoxyisoflavanone)

PDB for NP0048888 (4',7-Dihydroxy-2',5-dimethoxyisoflavanone)

3D PDB for NP0048888 (4',7-Dihydroxy-2',5-dimethoxyisoflavanone)

SMILES for NP0048888 (4',7-Dihydroxy-2',5-dimethoxyisoflavanone)

INCHI for NP0048888 (4',7-Dihydroxy-2',5-dimethoxyisoflavanone)

Structure for NP0048888 (4',7-Dihydroxy-2',5-dimethoxyisoflavanone)

3D Structure for NP0048888 (4',7-Dihydroxy-2',5-dimethoxyisoflavanone)