Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 00:17:59 UTC
Update Date2021-09-26 22:56:54 UTC
HMDB IDHMDB0247291
Secondary Accession NumbersNone
Metabolite Identification
Common Namealpha-Naphthoflavone
Descriptionalpha-naphthoflavone, also known as 7,8-benzoflavone or 7,8-BF, 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). Based on a literature review a significant number of articles have been published on alpha-naphthoflavone. This compound has been identified in human blood as reported by (PMID: 31557052 ). Alpha-naphthoflavone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically alpha-Naphthoflavone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
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 Molecular Weight272.2974
Monoisotopic Molecular Weight272.083729628
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
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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-194.60130932474
DeepCCS[M+Na]+170.16630932474
AllCCS[M+H]+164.132859911
AllCCS[M+H-H2O]+160.132859911
AllCCS[M+NH4]+167.832859911
AllCCS[M+Na]+168.932859911
AllCCS[M-H]-164.032859911
AllCCS[M+Na-2H]-162.732859911
AllCCS[M+HCOO]-161.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
alpha-NaphthoflavoneO=C1C=C(OC2=C1C=CC1=CC=CC=C21)C1=CC=CC=C13795.3Standard polar33892256
alpha-NaphthoflavoneO=C1C=C(OC2=C1C=CC1=CC=CC=C21)C1=CC=CC=C12771.1Standard non polar33892256
alpha-NaphthoflavoneO=C1C=C(OC2=C1C=CC1=CC=CC=C21)C1=CC=CC=C12888.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - alpha-Naphthoflavone EI-B (Non-derivatized)splash10-00di-2950000000-3f3c0aa2d9b942a7e0fd2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Naphthoflavone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fkc-0690000000-d95b19eb4958254ecd162017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Naphthoflavone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Naphthoflavone LC-ESI-QTOF , positive-QTOFsplash10-00di-0190000000-aa43a8f9d0352725e6762017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Naphthoflavone LC-ESI-QTOF , positive-QTOFsplash10-00di-0090000000-f5d4d77da80ab36ad0232017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Naphthoflavone 10V, Positive-QTOFsplash10-00di-0190000000-aa43a8f9d0352725e6762021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Naphthoflavone 20V, Positive-QTOFsplash10-00di-0090000000-f5d4d77da80ab36ad0232021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Naphthoflavone 10V, Positive-QTOFsplash10-00di-0090000000-f8f5cbed6b1a04c986722017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Naphthoflavone 20V, Positive-QTOFsplash10-00di-0090000000-f2b100cfd0874fb816922017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Naphthoflavone 40V, Positive-QTOFsplash10-0uk9-3930000000-e1b30d3cc6f415020fad2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Naphthoflavone 10V, Negative-QTOFsplash10-00di-0090000000-8c730956d4df5d2c2df12017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Naphthoflavone 20V, Negative-QTOFsplash10-00di-0090000000-5390fc715752907dd7b72017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Naphthoflavone 40V, Negative-QTOFsplash10-0v4i-0940000000-e6c5d980a7f70c4493202017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Naphthoflavone 10V, Positive-QTOFsplash10-00di-0090000000-c145c134e7a1d3427f272021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Naphthoflavone 20V, Positive-QTOFsplash10-00di-0090000000-c145c134e7a1d3427f272021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Naphthoflavone 40V, Positive-QTOFsplash10-00dj-0290000000-44ff94d129c424a2b4122021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Naphthoflavone 10V, Negative-QTOFsplash10-00di-0090000000-61c6e7d71c517d8f72712021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Naphthoflavone 20V, Negative-QTOFsplash10-00di-0090000000-61c6e7d71c517d8f72712021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Naphthoflavone 40V, Negative-QTOFsplash10-00dl-0490000000-642128239715b00d34262021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID11297
KEGG Compound IDNot Available
BioCyc IDCPD-10550
BiGG IDNot Available
Wikipedia LinkAlpha-Naphthoflavone
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID76995
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1465221
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]