NP-MRD: Showing NP-Card for 2',4',5,7,8-Pentahydroxyisoflavone (NP0047589)

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Record Information

Version

2.0

Created at

2022-03-17 20:42:40 UTC

Updated at

2022-03-17 20:42:40 UTC

NP-MRD ID

NP0047589

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2',4',5,7,8-Pentahydroxyisoflavone

Description

2',4',5,7,8-Pentahydroxyisoflavone belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. Thus, 2',4',5,7,8-pentahydroxyisoflavone is considered to be a flavonoid lipid molecule. 2',4',5,7,8-Pentahydroxyisoflavone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 2',4',5,7,8-Pentahydroxyisoflavone has been detected, but not quantified in, lima beans and pulses. This could make 2',4',5,7,8-pentahydroxyisoflavone a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307012D          

 22 24  0  0  0  0            999 V2000
    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
    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
    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
    0.7145    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
    1.4289    0.8250    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
    6.4302    3.7125    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
    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
    1.4289    0.0000    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
  2  1  2  0  0  0  0
  6  1  1  0  0  0  0
  6  3  2  0  0  0  0
  7  2  1  0  0  0  0
  8  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  3  1  0  0  0  0
  9  7  2  0  0  0  0
 10  4  2  0  0  0  0
 11  4  1  0  0  0  0
 12 10  1  0  0  0  0
 13  8  1  0  0  0  0
 13 12  1  0  0  0  0
 14 11  2  0  0  0  0
 15 12  2  0  0  0  0
 15 14  1  0  0  0  0
 16  6  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 20 13  2  0  0  0  0
 21 14  1  0  0  0  0
 22  5  1  0  0  0  0
 22 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047589

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(O)=C(C=C1)C1=COC2=C(C(O)=CC(O)=C2O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O7/c16-6-1-2-7(9(17)3-6)8-5-22-15-12(13(8)20)10(18)4-11(19)14(15)21/h1-5,16-19,21H

> <INCHI_KEY>
LOLNVJIGYUJCIY-UHFFFAOYSA-N

> <FORMULA>
C15H10O7

> <MOLECULAR_WEIGHT>
302.2357

> <EXACT_MASS>
302.042652674

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
28.309111948601586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2,4-dihydroxyphenyl)-5,7,8-trihydroxy-4H-chromen-4-one

> <ALOGPS_LOGP>
2.26

> <JCHEM_LOGP>
2.469741746333333

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.501874392083723

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.777544811000452

> <JCHEM_PKA_STRONGEST_BASIC>
-5.101025511698901

> <JCHEM_POLAR_SURFACE_AREA>
127.45000000000002

> <JCHEM_REFRACTIVITY>
75.64470000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(2,4-dihydroxyphenyl)-5,7,8-trihydroxychromen-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       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   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  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667   6.160   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       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    7                                                       
CONECT    3    6    9                                                       
CONECT    4   10   11                                                       
CONECT    5    8   22                                                       
CONECT    6    1    3   16                                                  
CONECT    7    2    8    9                                                  
CONECT    8    5    7   13                                                  
CONECT    9    3    7   17                                                  
CONECT   10    4   12   18                                                  
CONECT   11    4   14   19                                                  
CONECT   12   10   13   15                                                  
CONECT   13    8   12   20                                                  
CONECT   14   11   15   21                                                  
CONECT   15   12   14   22                                                  
CONECT   16    6                                                            
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19   11                                                            
CONECT   20   13                                                            
CONECT   21   14                                                            
CONECT   22    5   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
3-(2,4-Dihydroxyphenyl)-5,7,8-trihydroxy-4H-1-benzopyran-4-one, 9ci	HMDB
5,7,8,2',4'-Pentahydroxyisoflavone	HMDB

Chemical Formula

C₁₅H₁₀O₇

Average Mass

302.2357 Da

Monoisotopic Mass

302.04265 Da

IUPAC Name

3-(2,4-dihydroxyphenyl)-5,7,8-trihydroxy-4H-chromen-4-one

Traditional Name

3-(2,4-dihydroxyphenyl)-5,7,8-trihydroxychromen-4-one

CAS Registry Number

104363-16-8

SMILES

OC1=CC(O)=C(C=C1)C1=COC2=C(C(O)=CC(O)=C2O)C1=O

InChI Identifier

InChI=1S/C15H10O7/c16-6-1-2-7(9(17)3-6)8-5-22-15-12(13(8)20)10(18)4-11(19)14(15)21/h1-5,16-19,21H

InChI Key

LOLNVJIGYUJCIY-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Phaseolus lunatus	FooDB	KNAPSACK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflav-2-enes

Direct Parent

Isoflavones

Alternative Parents

Substituents

Hydroxyisoflavonoid
Isoflavone
Chromone
Benzopyran
1-benzopyran
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Polyol
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050441 )

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	2.26	ALOGPS
logP	2.47	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	6.78	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.45 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	75.64 m³·mol⁻¹	ChemAxon
Polarizability	28.31 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

HMDB0033264

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011287

KNApSAcK ID

C00009867

Chemspider ID

24842899

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44257373

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2',4',5,7,8-Pentahydroxyisoflavone (NP0047589)

MOL for NP0047589 (2',4',5,7,8-Pentahydroxyisoflavone)

3D MOL for NP0047589 (2',4',5,7,8-Pentahydroxyisoflavone)

3D SDF for NP0047589 (2',4',5,7,8-Pentahydroxyisoflavone)

3D-SDF for NP0047589 (2',4',5,7,8-Pentahydroxyisoflavone)

PDB for NP0047589 (2',4',5,7,8-Pentahydroxyisoflavone)

3D PDB for NP0047589 (2',4',5,7,8-Pentahydroxyisoflavone)

SMILES for NP0047589 (2',4',5,7,8-Pentahydroxyisoflavone)

INCHI for NP0047589 (2',4',5,7,8-Pentahydroxyisoflavone)

Structure for NP0047589 (2',4',5,7,8-Pentahydroxyisoflavone)

3D Structure for NP0047589 (2',4',5,7,8-Pentahydroxyisoflavone)