NP-MRD: Showing NP-Card for 5,6,7,3',4'-Pentahydroxyisoflavone (NP0339452)

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Record Information

Version

2.0

Created at

2024-09-11 21:55:46 UTC

Updated at

2024-09-11 21:55:46 UTC

NP-MRD ID

NP0339452

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,6,7,3',4'-Pentahydroxyisoflavone

Description

5,6,7,3',4'-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. 5,6,7,3',4'-Pentahydroxyisoflavone is a polyphenol metabolite detected in biological fluids (PMID: 20428313 ). 5,6,7,3',4'-Pentahydroxyisoflavone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02271201322D          

 22 24  0  0  0  0            999 V2000
   -2.1747   -1.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1747   -0.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8891    0.1839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4602    0.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7457   -0.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7457   -1.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4602   -1.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0313   -2.2911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0313   -1.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6832   -1.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6832   -0.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0313    0.1839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1122   -2.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8266   -2.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8266   -1.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1122   -1.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3977   -1.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3977   -2.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5411   -1.0536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5411   -2.7036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8891   -1.4661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4602   -2.2911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5 12  1  0  0  0  0
  6  7  2  0  0  0  0
  6  9  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 17  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  2  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 15 19  1  0  0  0  0
 14 20  1  0  0  0  0
  1 21  1  0  0  0  0
  7 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339452

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1O)C1=COC2=CC(O)=C(O)C(O)=C2C1=O

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

> <INCHI_KEY>
BIDDAFIPYBBDES-UHFFFAOYSA-N

> <FORMULA>
C15H10O7

> <MOLECULAR_WEIGHT>
302.2357

> <EXACT_MASS>
302.042652674

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
28.41358732768821

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(3,4-dihydroxyphenyl)-5,6,7-trihydroxy-4H-chromen-4-one

> <ALOGPS_LOGP>
2.34

> <JCHEM_LOGP>
2.469741746333333

> <ALOGPS_LOGS>
-3.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.606209648879927

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.774259718733982

> <JCHEM_PKA_STRONGEST_BASIC>
-5.331025311123871

> <JCHEM_POLAR_SURFACE_AREA>
127.45000000000002

> <JCHEM_REFRACTIVITY>
75.64470000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(3,4-dihydroxyphenyl)-5,6,7-trihydroxychromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.059  -1.967   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.059  -0.427   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -5.393   0.343   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.726   0.343   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.392  -0.427   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.392  -1.967   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.726  -2.737   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.058  -4.277   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.058  -2.737   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.275  -1.967   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.275  -0.427   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.058   0.343   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.943  -5.047   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.276  -4.277   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.276  -2.737   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.943  -1.967   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.609  -2.737   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.609  -4.277   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.610  -1.967   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.610  -5.047   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -5.393  -2.737   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.726  -4.277   0.000  0.00  0.00           O+0
CONECT    1    2    7   21                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    9                                                  
CONECT    7    1    6   22                                                  
CONECT    8    9                                                            
CONECT    9    6    8   10                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12    5   11                                                       
CONECT   13   14   18                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   10   16   18                                                  
CONECT   18   13   17                                                       
CONECT   19   15                                                            
CONECT   20   14                                                            
CONECT   21    1                                                            
CONECT   22    7                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₀O₇

Average Mass

302.2357 Da

Monoisotopic Mass

302.04265 Da

IUPAC Name

3-(3,4-dihydroxyphenyl)-5,6,7-trihydroxy-4H-chromen-4-one

Traditional Name

3-(3,4-dihydroxyphenyl)-5,6,7-trihydroxychromen-4-one

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1O)C1=COC2=CC(O)=C(O)C(O)=C2C1=O

InChI Identifier

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

InChI Key

BIDDAFIPYBBDES-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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

Isoflavone
Hydroxyisoflavonoid
Chromone
Benzopyran
1-benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Benzenoid
Monocyclic benzene moiety
Pyran
Vinylogous acid
Heteroaromatic compound
Polyol
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
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	2.34	ALOGPS
logP	2.47	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	6.77	ChemAxon
pKa (Strongest Basic)	-5.3	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	28.41 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

HMDB0041687

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029848

KNApSAcK ID

Not Available

Chemspider ID

8908436

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10733103

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 5,6,7,3',4'-Pentahydroxyisoflavone (NP0339452)

MOL for NP0339452 (5,6,7,3',4'-Pentahydroxyisoflavone)

3D MOL for NP0339452 (5,6,7,3',4'-Pentahydroxyisoflavone)

3D SDF for NP0339452 (5,6,7,3',4'-Pentahydroxyisoflavone)

3D-SDF for NP0339452 (5,6,7,3',4'-Pentahydroxyisoflavone)

PDB for NP0339452 (5,6,7,3',4'-Pentahydroxyisoflavone)

3D PDB for NP0339452 (5,6,7,3',4'-Pentahydroxyisoflavone)

SMILES for NP0339452 (5,6,7,3',4'-Pentahydroxyisoflavone)

INCHI for NP0339452 (5,6,7,3',4'-Pentahydroxyisoflavone)

Structure for NP0339452 (5,6,7,3',4'-Pentahydroxyisoflavone)

3D Structure for NP0339452 (5,6,7,3',4'-Pentahydroxyisoflavone)