NP-MRD: Showing NP-Card for 3,6-Dihydroxyflavone (NP0138402)

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Record Information

Version

1.0

Created at

2022-05-31 17:57:53 UTC

Updated at

2022-05-31 17:57:53 UTC

NP-MRD ID

NP0138402

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,6-Dihydroxyflavone

Description

3,6-Dihydroxy-2-phenyl-4H-chromen-4-one, also known as 36-dihydroxy-flavone, 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. 3,6-Dihydroxy-2-phenyl-4H-chromen-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa). 3,6-Dihydroxy-2-phenyl-4h-chromen-4-one is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 3-hydroxy-2-phenyl-4h-chromen-4-one. This aromatic-hydroxylation-of-fused-benzene-ring-pattern1 occurs in humans. It is generated by cyp1a2, cyp2a6, cyp2c8, cyp2c9, cyp2c19, and cyp2e1 enzymes via an aromatic-hydroxylation-of-fused-benzene-ring-pattern1 reaction.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 31  0  0  0  0  0  0  0  0999 V2000
    2.0729   -2.6543    0.0325 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4562   -1.5533   -0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0740   -1.4933    0.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5690   -2.6773    0.3682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6341   -0.3344    0.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0706   -0.1726    0.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9261   -1.2109    0.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2967   -0.9342    0.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7916    0.3423    0.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9219    1.3875    0.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5903    1.1445    0.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0956    0.7650   -0.0968 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3876    0.7688   -0.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0703    1.9480   -0.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4451    1.9690   -0.6524 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1641    0.7986   -0.6135 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5340    0.8482   -0.7917 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000   -0.3817   -0.3991 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1288   -0.3900   -0.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2100   -3.5938    0.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5768   -2.2186    0.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9306   -1.8057    0.8217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8495    0.5249    0.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2610    2.4161    0.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9119    1.9801    0.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5504    2.9043   -0.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9461    2.9267   -0.8216 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0767    0.0023   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0384   -1.3059   -0.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 18  2  0
 18 19  1  0
 19 13  2  0
 13 12  1  0
 12  5  1  0
  5  3  2  0
  3  4  1  0
  3  2  1  0
  2  1  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
  2 19  1  0
 11  6  1  0
 17 28  1  0
 18 29  1  0
  4 20  1  0
  7 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
 14 26  1  0
 15 27  1  0
M  END


  Mrv1652308231901422D          

 19 21  0  0  0  0            999 V2000
    4.2868   -2.4750    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
    3.5724   -2.8875    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
    2.8579   -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
    0.0000   -1.6500    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
    2.8579   -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
    0.7145   -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
   -1.4289    0.0000    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
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  6  2  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 10  8  2  0  0  0  0
 11  8  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  9  1  0  0  0  0
 15 14  2  0  0  0  0
 16 10  1  0  0  0  0
 17 13  2  0  0  0  0
 18 14  1  0  0  0  0
 19 12  1  0  0  0  0
 19 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138402

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(OC(=C(O)C2=O)C2=CC=CC=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O4/c16-10-6-7-12-11(8-10)13(17)14(18)15(19-12)9-4-2-1-3-5-9/h1-8,16,18H

> <INCHI_KEY>
XHLOLFKZCUCROE-UHFFFAOYSA-N

> <FORMULA>
C15H10O4

> <MOLECULAR_WEIGHT>
254.241

> <EXACT_MASS>
254.057908802

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
25.664807371536284

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,6-dihydroxy-2-phenyl-4H-chromen-4-one

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
2.416995429

> <ALOGPS_LOGS>
-3.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.636084154919475

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.742155185768631

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7681997195824595

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
70.91950000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.10e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,6-dihydroxy-2-phenylchromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-AUG-19         0                                  
HETATM    1  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -3.080   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       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -0.770   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      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    9                                                       
CONECT    5    3    9                                                       
CONECT    6    7   10                                                       
CONECT    7    6   12                                                       
CONECT    8   10   11                                                       
CONECT    9    4    5   15                                                  
CONECT   10    6    8   16                                                  
CONECT   11    8   12   13                                                  
CONECT   12    7   11   19                                                  
CONECT   13   11   14   17                                                  
CONECT   14   13   15   18                                                  
CONECT   15    9   14   19                                                  
CONECT   16   10                                                            
CONECT   17   13                                                            
CONECT   18   14                                                            
CONECT   19   12   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
36-Dihydroxy-flavone	HMDB
36-Dihydroxyflavone	HMDB
6-Hydroxyflavonol	HMDB

Chemical Formula

C₁₅H₁₀O₄

Average Mass

254.2410 Da

Monoisotopic Mass

254.05791 Da

IUPAC Name

3,6-dihydroxy-2-phenyl-4H-chromen-4-one

Traditional Name

3,6-dihydroxy-2-phenylchromen-4-one

CAS Registry Number

108238-41-1

SMILES

OC1=CC2=C(OC(=C(O)C2=O)C2=CC=CC=C2)C=C1

InChI Identifier

InChI=1S/C15H10O4/c16-10-6-7-12-11(8-10)13(17)14(18)15(19-12)9-4-2-1-3-5-9/h1-8,16,18H

InChI Key

XHLOLFKZCUCROE-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
6-hydroxyflavonoid
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organic oxygen compound
Organooxygen 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	2.98	ALOGPS
logP	2.42	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.74	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.92 m³·mol⁻¹	ChemAxon
Polarizability	25.66 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

HMDB0134546

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

600072

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

688659

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3,6-Dihydroxyflavone (NP0138402)

MOL for NP0138402 (3,6-Dihydroxyflavone)

3D MOL for NP0138402 (3,6-Dihydroxyflavone)

3D SDF for NP0138402 (3,6-Dihydroxyflavone)

3D-SDF for NP0138402 (3,6-Dihydroxyflavone)

PDB for NP0138402 (3,6-Dihydroxyflavone)

3D PDB for NP0138402 (3,6-Dihydroxyflavone)

SMILES for NP0138402 (3,6-Dihydroxyflavone)

INCHI for NP0138402 (3,6-Dihydroxyflavone)

Structure for NP0138402 (3,6-Dihydroxyflavone)

3D Structure for NP0138402 (3,6-Dihydroxyflavone)