NP-MRD: Showing NP-Card for Œ±-Naphthoflavone (NP0137174)

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Record Information

Version

1.0

Created at

2022-05-30 16:43:59 UTC

Updated at

2022-05-30 16:43:59 UTC

NP-MRD ID

NP0137174

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Œ±-Naphthoflavone

Description

2-PHENYL-4H-BENZO[H]CHROMEN-4-ONE, also known as alpha-naphthylflavone or 2-phenyl-4H-naphtho(1,2-b)pyran-4-one, belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Œ±-Naphthoflavone is found in Rhaponticum repens. It was first documented in 1969 (PMID: 5347522). 2-PHENYL-4H-BENZO[H]CHROMEN-4-ONE is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 143) (PMID: 14564451) (PMID: 17889503) (PMID: 22716253).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 36  0  0  0  0  0  0  0  0999 V2000
   -0.2107    3.7373   -1.3261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0891    2.5427   -0.9078 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1482    1.9742   -0.6876 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3028    0.6844   -0.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6289    0.0758    0.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8129    0.7345   -0.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0432    0.1197    0.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1043   -1.1690    0.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9203   -1.8560    0.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7051   -1.2303    0.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2068   -0.0053   -0.0148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0000    0.4682   -0.2014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1931    1.7571   -0.6539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4680    2.2604   -0.8520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5424    1.4368   -0.5843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3798    0.1414   -0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4600   -0.6789    0.1363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3217   -1.9562    0.5838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0516   -2.4564    0.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9452   -1.6417    0.5167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1059   -0.3489    0.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0017    2.5998   -0.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7915    1.7602   -0.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9658    0.6778   -0.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0564   -1.6564    0.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9541   -2.8763    1.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7601   -1.7638    0.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5908    3.2744   -1.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5625    1.7809   -0.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4404   -0.2814   -0.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1651   -2.6176    0.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9196   -3.4779    1.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9562   -2.0098    0.6627 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 13  2  1  0
 21 16  1  0
 10  5  1  0
 21 12  1  0
  3 22  1  0
 14 28  1  0
 15 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 20 33  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
M  END

BHF
  Mrv0541 02241213262D          

 21 24  0  0  0  0            999 V2000
   -1.2475    0.6721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8350    1.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2475    2.1010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0100    1.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4025    2.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2275    2.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6400    1.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4650    1.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8775    0.6721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4650   -0.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6400   -0.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2275    0.6721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4025    0.6721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0100   -0.0424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8350   -0.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2475   -0.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8350   -1.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2475   -2.1858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0725   -2.1858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4850   -1.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0725   -0.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 15  2  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 13  2  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0137174

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1C=C(OC2=C1C=CC1=CC=CC=C21)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H12O2/c20-17-12-18(14-7-2-1-3-8-14)21-19-15-9-5-4-6-13(15)10-11-16(17)19/h1-12H

> <INCHI_KEY>
VFMMPHCGEFXGIP-UHFFFAOYSA-N

> <FORMULA>
C19H12O2

> <MOLECULAR_WEIGHT>
272.2974

> <EXACT_MASS>
272.083729628

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
29.73054105393158

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-phenyl-4H-benzo[h]chromen-4-one

> <ALOGPS_LOGP>
4.73

> <JCHEM_LOGP>
3.956861855333333

> <ALOGPS_LOGS>
-5.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.55625270461061

> <JCHEM_PKA_STRONGEST_BASIC>
-5.381708808182734

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
83.42140000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.71e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-naphthoflavone

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: BHF                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.329   1.255   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.559   2.588   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.329   3.922   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.019   2.588   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.751   3.922   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.291   3.922   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.061   2.588   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.601   2.588   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.371   1.255   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.601  -0.079   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.061  -0.079   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.291   1.255   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.751   1.255   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.019  -0.079   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.559  -0.079   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.329  -1.413   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.559  -2.746   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.329  -4.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.869  -4.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.639  -2.746   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.869  -1.413   0.000  0.00  0.00           C+0
CONECT    1    2   15                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12    7   11   13                                                  
CONECT   13    4   12   14                                                  
CONECT   14   13   15                                                       
CONECT   15    1   14   16                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   16   20                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Value	Source
2-Phenyl-4H-naphtho(1,2-b)pyran-4-one	ChEBI
7,8-Benzoflavone	ChEBI
7,8-BF	ChEBI
alpha-Naphthylflavone	ChEBI
Benzo[H]flavone	ChEBI
a-Naphthylflavone	Generator
Α-naphthylflavone	Generator
a-Naphthoflavone	Generator
Α-naphthoflavone	Generator
alpha-Naphthoflavone	MeSH

Chemical Formula

C₁₉H₁₂O₂

Average Mass

272.2974 Da

Monoisotopic Mass

272.08373 Da

IUPAC Name

2-phenyl-4H-benzo[h]chromen-4-one

Traditional Name

α-naphthoflavone

CAS Registry Number

Not Available

SMILES

O=C1C=C(OC2=C1C=CC1=CC=CC=C21)C1=CC=CC=C1

InChI Identifier

InChI=1S/C19H12O2/c20-17-12-18(14-7-2-1-3-8-14)21-19-15-9-5-4-6-13(15)10-11-16(17)19/h1-12H

InChI Key

VFMMPHCGEFXGIP-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 201.216488466 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.133705802 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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

Species Name	Source	Reference
Acroptilon repens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavones

Alternative Parents

Substituents

Flavone
Naphthopyranone
Naphthopyran
Chromone
Benzopyran
Naphthalene
1-benzopyran
Pyranone
Pyran
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotricyclic compound (CHEBI:76995 )
extended flavonoid (CHEBI:76995 )
a small molecule (CPD-10550 )

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	4.73	ALOGPS
logP	3.96	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	15.56	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	83.42 m³·mol⁻¹	ChemAxon
Polarizability	29.73 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB07453

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-10550

BiGG ID

Not Available

Wikipedia Link

Alpha-Naphthoflavone

METLIN ID

Not Available

PubChem Compound

11790

PDB ID

Not Available

ChEBI ID

76995

Good Scents ID

Not Available

References

General References

Sloane NH: alpha-Naphthoflavone activation of 6-hydroxymethylbenzo(alpha)pyrene synthetase. Cancer Res. 1975 Dec;35(12):3731-4. [PubMed:143 ]
Cheng YW, Li CH, Lee CC, Kang JJ: Alpha-naphthoflavone induces vasorelaxation through the induction of extracellular calcium influx and NO formation in endothelium. Naunyn Schmiedebergs Arch Pharmacol. 2003 Nov;368(5):377-85. doi: 10.1007/s00210-003-0820-6. Epub 2003 Oct 15. [PubMed:14564451 ]
Jang JY, Shin S, Choi BI, Park D, Jeon JH, Hwang SY, Kim JC, Kim YB, Nahm SS: Antiteratogenic effects of alpha-naphthoflavone on 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) exposed mice in utero. Reprod Toxicol. 2007 Nov-Dec;24(3-4):303-9. doi: 10.1016/j.reprotox.2007.08.002. Epub 2007 Aug 19. [PubMed:17889503 ]
Liao PL, Li CH, Chang CY, Lu SR, Lin CH, Tse LS, Cheng YW: Anti-ageing effects of alpha-naphthoflavone on normal and UVB-irradiated human skin fibroblasts. Exp Dermatol. 2012 Jul;21(7):546-8. doi: 10.1111/j.1600-0625.2012.01517.x. [PubMed:22716253 ]
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Showing NP-Card for Œ±-Naphthoflavone (NP0137174)

MOL for NP0137174 (Œ±-Naphthoflavone)

3D MOL for NP0137174 (Œ±-Naphthoflavone)

3D SDF for NP0137174 (Œ±-Naphthoflavone)

3D-SDF for NP0137174 (Œ±-Naphthoflavone)

PDB for NP0137174 (Œ±-Naphthoflavone)

3D PDB for NP0137174 (Œ±-Naphthoflavone)

SMILES for NP0137174 (Œ±-Naphthoflavone)

INCHI for NP0137174 (Œ±-Naphthoflavone)

Structure for NP0137174 (Œ±-Naphthoflavone)

3D Structure for NP0137174 (Œ±-Naphthoflavone)