NP-MRD: Showing NP-Card for 3,4',7-Trihydroxyflavone (NP0047814)

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Record Information

Version

2.0

Created at

2022-03-17 20:46:25 UTC

Updated at

2022-03-17 20:46:25 UTC

NP-MRD ID

NP0047814

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4',7-Trihydroxyflavone

Description

3,4',7-Trihydroxyflavone, also known as 5-deoxykaempferol, belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, 3,4',7-trihydroxyflavone is considered to be a flavonoid lipid molecule. 3,4',7-Trihydroxyflavone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3,4',7-Trihydroxyflavone is a bitter tasting compound. Outside of the human body, 3,4',7-Trihydroxyflavone has been detected, but not quantified in, a few different foods, such as chickpea, lentils, and pulses. 3,4',7-Trihydroxyflavone is found in Acacia spp. , Anthyllis vulneraria , Baptisia calycosa, Baptisia lecontei, Baptisia simplicifolia, Brucea javanica, Butea spp., Clematis hexapetala, Dermatophyllum secundiflorum, Dorycnium pentaphyllum, Erythrina fusca, Lathyrus pratensis, Leontopodium nanum, Lotus corniculatus , Lotus maritimus, Millettia spp., Platymiscium praecox, Pterocarpus marsupium , Rhus spp., Robinia pseudoacacia , Rohdea chinensis, Schinopsis lorentzii , Scutellaria baicalensis, Sophora secundiflora , Trifolium subterraneum , Ulex spp. and Umtiza listerana. This could make 3,4',7-trihydroxyflavone a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307292D          

 20 22  0  0  0  0            999 V2000
    2.8579   -2.4750    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
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  6  5  2  0  0  0  0
  8  1  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 10  7  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12 11  2  0  0  0  0
 13 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15  8  1  0  0  0  0
 15 14  2  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 13  2  0  0  0  0
 19 14  1  0  0  0  0
 20 12  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047814

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)C1=C(O)C(=O)C2=C(O1)C=C(O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)15-14(19)13(18)11-6-5-10(17)7-12(11)20-15/h1-7,16-17,19H

> <INCHI_KEY>
OBWHQJYOOCRPST-UHFFFAOYSA-N

> <FORMULA>
C15H10O5

> <MOLECULAR_WEIGHT>
270.2369

> <EXACT_MASS>
270.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
26.695937843253994

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
2.29

> <JCHEM_LOGP>
2.1134301073333335

> <ALOGPS_LOGS>
-3.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.496724516241246

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.318397621402287

> <JCHEM_PKA_STRONGEST_BASIC>
-3.781296104684704

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
72.9004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,7,4'-trihydroxyflavone

> <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       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002  -4.620   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   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       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    3    8                                                       
CONECT    2    4    8                                                       
CONECT    3    1    9                                                       
CONECT    4    2    9                                                       
CONECT    5    6   10                                                       
CONECT    6    5   11                                                       
CONECT    7   10   12                                                       
CONECT    8    1    2   15                                                  
CONECT    9    3    4   16                                                  
CONECT   10    5    7   17                                                  
CONECT   11    6   12   13                                                  
CONECT   12    7   11   20                                                  
CONECT   13   11   14   18                                                  
CONECT   14   13   15   19                                                  
CONECT   15    8   14   20                                                  
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   13                                                            
CONECT   19   14                                                            
CONECT   20   12   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
5-Deoxykaempferol	Kegg
3,7,4'-Trihydroxyflavone	Kegg
3,7,4-Trihydroxyflavone	HMDB
3,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	HMDB
4',7-Dihydroxyflavonol	HMDB
Resokaempferol	HMDB

Chemical Formula

C₁₅H₁₀O₅

Average Mass

270.2369 Da

Monoisotopic Mass

270.05282 Da

IUPAC Name

3,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Traditional Name

3,7,4'-trihydroxyflavone

CAS Registry Number

2034-65-3

SMILES

OC1=CC=C(C=C1)C1=C(O)C(=O)C2=C(O1)C=C(O)C=C2

InChI Identifier

InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)15-14(19)13(18)11-6-5-10(17)7-12(11)20-15/h1-7,16-17,19H

InChI Key

OBWHQJYOOCRPST-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acacia spp.	Plant	KNApSAcK
Anthyllis vulneraria	Plant	KNApSAcK
Baptisia calycosa	Plant	KNApSAcK
Baptisia lecontei	Plant	KNApSAcK
Baptisia simplicifolia	Plant	KNApSAcK
Brucea javanica	LOTUS Database	35616633
Butea spp.	Plant	KNApSAcK
Cicer arietinum	FooDB	KNAPSACK
Clematis hexapetala	LOTUS Database	35616633
Dermatophyllum secundiflorum	LOTUS Database	35616633
Dorycnium pentaphyllum	Plant	KNApSAcK
Erythrina fusca	LOTUS Database	35616633
Lathyrus pratensis	Plant	KNApSAcK
Lens culinaris	FooDB	KNAPSACK
Leontopodium nanum	LOTUS Database	35616633
Lotus corniculatus	Plant	KNApSAcK
Lotus maritimus	Plant	KNApSAcK
Millettia spp.	Plant	KNApSAcK
Platymiscium praecox	Plant	KNApSAcK
Pterocarpus marsupium	Plant	KNApSAcK
Rhus spp.	Plant	KNApSAcK
Robinia pseudoacacia	Plant	KNApSAcK
Rohdea chinensis	LOTUS Database	35616633
Schinopsis lorentzii	Plant	KNApSAcK
Scutellaria baicalensis	LOTUS Database	35616633
Sophora secundiflora	Plant	KNApSAcK
Trifolium subterraneum	Plant	KNApSAcK
Ulex spp.	Plant	KNApSAcK
Umtiza listerana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavonols

Alternative Parents

Substituents

3-hydroxyflavone
3-hydroxyflavonoid
4'-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

trihydroxyflavone (CHEBI:27431 )
flavonols (C10037 )
Flavones and Flavonols (LMPK12111552 )

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	2.29	ALOGPS
logP	2.11	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	6.32	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.9 m³·mol⁻¹	ChemAxon
Polarizability	26.7 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

HMDB0034004

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281611

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3,4',7-Trihydroxyflavone (NP0047814)

MOL for NP0047814 (3,4',7-Trihydroxyflavone)

3D MOL for NP0047814 (3,4',7-Trihydroxyflavone)

3D SDF for NP0047814 (3,4',7-Trihydroxyflavone)

3D-SDF for NP0047814 (3,4',7-Trihydroxyflavone)

PDB for NP0047814 (3,4',7-Trihydroxyflavone)

3D PDB for NP0047814 (3,4',7-Trihydroxyflavone)

SMILES for NP0047814 (3,4',7-Trihydroxyflavone)

INCHI for NP0047814 (3,4',7-Trihydroxyflavone)

Structure for NP0047814 (3,4',7-Trihydroxyflavone)

3D Structure for NP0047814 (3,4',7-Trihydroxyflavone)