beta-Naphthoflavone

Identification

Name
beta-Naphthoflavone
Accession Number
DB06732
Type
Small Molecule
Groups
Experimental
Description

beta-Naphthoflavone, also known as 5,6-benzoflavone, is a potent agonist of the aryl hydrocarbon receptor and as such is an inducer of such detoxification enzymes as cytochromes P450 (CYPs) and uridine 5'-diphospho-glucuronosyltransferases (UGTs). β-Naphthoflavone is a putative chemopreventive agent.

Structure
Thumb
Synonyms
  • 5,6-benzoflavone
  • beta-NF
External IDs
NSC-136015
Product Ingredients
Not Available
Approved Prescription Products
Not Available
Approved Generic Prescription Products
Not Available
Approved Over the Counter Products
Not Available
Unapproved/Other Products
Not Available
International/Other Brands
Not Available
Brand mixtures
Not Available
Categories
UNII
1BT0256Y8O
CAS number
6051-87-2
Weight
Average: 272.2974
Monoisotopic: 272.083729628
Chemical Formula
C19H12O2
InChI Key
OUGIDAPQYNCXRA-UHFFFAOYSA-N
InChI
InChI=1S/C19H12O2/c20-16-12-18(14-7-2-1-3-8-14)21-17-11-10-13-6-4-5-9-15(13)19(16)17/h1-12H
IUPAC Name
3-phenyl-1H-benzo[f]chromen-1-one
SMILES
O=C1C=C(OC2=C1C1=CC=CC=C1C=C2)C1=CC=CC=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UEstrogen receptor alphaNot AvailableHuman
USteroid hormone receptor ERR1Not AvailableHuman
UCOUP transcription factor 1Not AvailableHuman
UAryl hydrocarbon receptorNot AvailableHuman
UCytochrome P450 1B1Not AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference
Not Available
General References
  1. Chlouchi A, Girard C, Bonet A, Viollon-Abadie C, Heyd B, Mantion G, Martin H, Richert L: Effect of chrysin and natural coumarins on UGT1A1 and 1A6 activities in rat and human hepatocytes in primary culture. Planta Med. 2007 Jul;73(8):742-7. Epub 2007 Jun 28. [PubMed:17599282 ]
  2. Izzotti A, Bagnasco M, Cartiglia C, Longobardi M, Camoirano A, Tampa E, Lubet RA, De Flora S: Modulation of multigene expression and proteome profiles by chemopreventive agents. Mutat Res. 2005 Dec 11;591(1-2):212-23. Epub 2005 Aug 3. [PubMed:16083920 ]
External Links
PubChem Compound
2361
PubChem Substance
99443278
ChemSpider
2271
BindingDB
50028963
ChEBI
77013
ChEMBL
CHEMBL26260
Wikipedia
Beta-Naphthoflavone
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
Not Available
FDA label
Not Available
MSDS
Download (46.9 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00101 mg/mLALOGPS
logP4.72ALOGPS
logP3.96ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)15.42ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity83.42 m3·mol-1ChemAxon
Polarizability29.9 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9641
Caco-2 permeable+0.8868
P-glycoprotein substrateNon-substrate0.6558
P-glycoprotein inhibitor INon-inhibitor0.7379
P-glycoprotein inhibitor IINon-inhibitor0.5145
Renal organic cation transporterNon-inhibitor0.837
CYP450 2C9 substrateNon-substrate0.809
CYP450 2D6 substrateNon-substrate0.9124
CYP450 3A4 substrateNon-substrate0.7084
CYP450 1A2 substrateInhibitor0.9644
CYP450 2C9 inhibitorNon-inhibitor0.5201
CYP450 2D6 inhibitorNon-inhibitor0.9372
CYP450 2C19 inhibitorInhibitor0.8993
CYP450 3A4 inhibitorInhibitor0.6321
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5396
Ames testNon AMES toxic0.731
CarcinogenicityNon-carcinogens0.9114
BiodegradationNot ready biodegradable0.7247
Rat acute toxicity2.8447 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8858
hERG inhibition (predictor II)Non-inhibitor0.935
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - EI-BGC-MSsplash10-00di-3790000000-c4fd2800aec22c1db180
Predicted LC-MS/MS Spectrum - 10V, PositivePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 20V, PositivePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 40V, PositivePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 10V, NegativePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 20V, NegativePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 40V, NegativePredicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of chemical entities 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
Chemical entities
Super Class
Organic compounds
Class
Phenylpropanoids and polyketides
Sub Class
Flavonoids
Direct Parent
Flavones
Alternative Parents
Naphthopyrans / Chromones / Naphthalenes / Pyranones and derivatives / Benzene and substituted derivatives / Heteroaromatic compounds / Oxacyclic compounds / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Flavone / Naphthopyran / Chromone / Benzopyran / Naphthalene / 1-benzopyran / Pyranone / Monocyclic benzene moiety / Pyran / Benzenoid
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organic heterotricyclic compound, extended flavonoid (CHEBI:77013 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 Da
References
  1. Klinge CM, Kaur K, Swanson HI: The aryl hydrocarbon receptor interacts with estrogen receptor alpha and orphan receptors COUP-TFI and ERRalpha1. Arch Biochem Biophys. 2000 Jan 1;373(1):163-74. [PubMed:10620335 ]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Binds to an ERR-alpha response element (ERRE) containing a single consensus half-site, 5'-TNAAGGTCA-3'. Can bind to the medium-chain acyl coenzyme A dehydrogenase (MCAD) response element NRRE-1 and...
Gene Name
ESRRA
Uniprot ID
P11474
Uniprot Name
Steroid hormone receptor ERR1
Molecular Weight
45509.11 Da
References
  1. Klinge CM, Kaur K, Swanson HI: The aryl hydrocarbon receptor interacts with estrogen receptor alpha and orphan receptors COUP-TFI and ERRalpha1. Arch Biochem Biophys. 2000 Jan 1;373(1):163-74. [PubMed:10620335 ]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Coup (chicken ovalbumin upstream promoter) transcription factor binds to the ovalbumin promoter and, in conjunction with another protein (S300-II) stimulates initiation of transcription. Binds to both direct repeats and palindromes of the 5'-AGGTCA-3' motif. Represses transcriptional activity of LHCG.
Specific Function
Retinoic acid-responsive element binding
Gene Name
NR2F1
Uniprot ID
P10589
Uniprot Name
COUP transcription factor 1
Molecular Weight
46155.24 Da
References
  1. Klinge CM, Kaur K, Swanson HI: The aryl hydrocarbon receptor interacts with estrogen receptor alpha and orphan receptors COUP-TFI and ERRalpha1. Arch Biochem Biophys. 2000 Jan 1;373(1):163-74. [PubMed:10620335 ]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transcription regulatory region dna binding
Specific Function
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes...
Gene Name
AHR
Uniprot ID
P35869
Uniprot Name
Aryl hydrocarbon receptor
Molecular Weight
96146.705 Da
References
  1. Klinge CM, Kaur K, Swanson HI: The aryl hydrocarbon receptor interacts with estrogen receptor alpha and orphan receptors COUP-TFI and ERRalpha1. Arch Biochem Biophys. 2000 Jan 1;373(1):163-74. [PubMed:10620335 ]
  2. Gasiewicz TA, Rucci G: Alpha-naphthoflavone acts as an antagonist of 2,3,7, 8-tetrachlorodibenzo-p-dioxin by forming an inactive complex with the Ah receptor. Mol Pharmacol. 1991 Nov;40(5):607-12. [PubMed:1658599 ]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1B1
Uniprot ID
Q16678
Uniprot Name
Cytochrome P450 1B1
Molecular Weight
60845.33 Da
References
  1. Shimada T, Tanaka K, Takenaka S, Foroozesh MK, Murayama N, Yamazaki H, Guengerich FP, Komori M: Reverse type I binding spectra of human cytochrome P450 1B1 induced by flavonoid, stilbene, pyrene, naphthalene, phenanthrene, and biphenyl derivatives that inhibit catalytic activity: a structure-function relationship study. Chem Res Toxicol. 2009 Jul;22(7):1325-33. doi: 10.1021/tx900127s. [PubMed:19563207 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Drug created on August 18, 2010 15:03 / Updated on September 01, 2017 11:30