Np mrd loader

Record Information
Version2.0
Created at2024-01-23 20:10:42 UTC
Updated at2024-09-03 04:19:09 UTC
NP-MRD IDNP0332427
Natural Product DOIhttps://doi.org/10.57994/1653
Secondary Accession NumbersNone
Natural Product Identification
Common Namealpha-Naphthoflavone
Description2-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). alpha-Naphthoflavone 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) (PMID: 6474163) (PMID: 6710497).
Structure
Thumb
Synonyms
ValueSource
2-Phenyl-4H-naphtho(1,2-b)pyran-4-oneChEBI
7,8-BenzoflavoneChEBI
7,8-BFChEBI
alpha-NaphthylflavoneChEBI
Benzo[H]flavoneChEBI
a-NaphthylflavoneGenerator
Α-naphthylflavoneGenerator
a-NaphthoflavoneGenerator
Α-naphthoflavoneGenerator
alpha-NaphthoflavoneMeSH
Chemical FormulaC19H12O2
Average Mass272.2974 Da
Monoisotopic Mass272.08373 Da
IUPAC Name2-phenyl-4H-benzo[h]chromen-4-one
Traditional Nameα-naphthoflavone
CAS Registry NumberNot 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 KeyVFMMPHCGEFXGIP-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-23View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-23View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-23View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-23View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-23View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavones
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.73ALOGPS
logP3.96ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)15.56ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity83.42 m³·mol⁻¹ChemAxon
Polarizability29.73 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB07453
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-10550
BiGG IDNot Available
Wikipedia LinkAlpha-Naphthoflavone
METLIN IDNot Available
PubChem Compound11790
PDB IDNot Available
ChEBI ID76995
Good Scents IDNot Available
References
General References
  1. Sloane NH: alpha-Naphthoflavone activation of 6-hydroxymethylbenzo(alpha)pyrene synthetase. Cancer Res. 1975 Dec;35(12):3731-4. [PubMed:143 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Diamond L, Gelboin HV: Alpha-naphthoflavone: an inhibitor of hydrocarbon cytotoxicity and microsomal hydroxylase. Science. 1969 Nov 21;166(3908):1023-5. doi: 10.1126/science.166.3908.1023. [PubMed:5347522 ]
  6. Kellis JT Jr, Vickery LE: Inhibition of human estrogen synthetase (aromatase) by flavones. Science. 1984 Sep 7;225(4666):1032-4. doi: 10.1126/science.6474163. [PubMed:6474163 ]
  7. Bergman HB, Bryant BJ, Nesnow S: Metabolism of alpha-naphthoflavone by rat, mouse, rabbit, and hamster liver microsomes. Toxicol Appl Pharmacol. 1984 Mar 15;72(3):469-75. doi: 10.1016/0041-008x(84)90123-6. [PubMed:6710497 ]
  8. Nesnow S, Bergman H: Metabolism of alpha-naphthoflavone by rat liver microsomes. Cancer Res. 1981 Jul;41(7):2621-6. [PubMed:7248934 ]
  9. Santostefano M, Merchant M, Arellano L, Morrison V, Denison MS, Safe S: alpha-Naphthoflavone-induced CYP1A1 gene expression and cytosolic aryl hydrocarbon receptor transformation. Mol Pharmacol. 1993 Feb;43(2):200-6. [PubMed:8381508 ]
  10. Campbell DR, Kurzer MS: Flavonoid inhibition of aromatase enzyme activity in human preadipocytes. J Steroid Biochem Mol Biol. 1993 Sep;46(3):381-8. doi: 10.1016/0960-0760(93)90228-o. [PubMed:9831487 ]