NAV

beta-Naphthoflavone

Identification

Generic Name
beta-Naphthoflavone
DrugBank Accession Number
DB06732
Background

β-Naphthoflavone, also known as 5,6-benzoflavone, is a potent agonist of the aryl hydrocarbon receptor and induces cytochromes P450 (CYPs) and uridine 5'-diphospho-glucuronosyltransferases (UGTs). It may be a chemopreventive agent.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 272.2974
Monoisotopic: 272.083729628
Chemical Formula
C19H12O2
Synonyms
  • 3-phenyl-1H-naphtho(2,1-b)pyran-1-one
  • 5,6-benzoflavone
  • beta-NF
  • β-NF
External IDs
  • NSC-136015
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UEstrogen receptor alphaNot AvailableHumans
USteroid hormone receptor ERR1Not AvailableHumans
UCOUP transcription factor 1Not AvailableHumans
UAryl hydrocarbon receptor
agonist
Humans
UCytochrome P450 1B1Not AvailableHumans
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
AcenocoumarolThe metabolism of Acenocoumarol can be increased when combined with beta-Naphthoflavone.
AcetaminophenThe metabolism of Acetaminophen can be increased when combined with beta-Naphthoflavone.
AcyclovirThe metabolism of Acyclovir can be increased when combined with beta-Naphthoflavone.
AgomelatineThe metabolism of Agomelatine can be increased when combined with beta-Naphthoflavone.
AlbendazoleThe metabolism of Albendazole can be increased when combined with beta-Naphthoflavone.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound 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
Naphthopyrans / Chromones / Naphthalenes / Pyranones and derivatives / Benzene and substituted derivatives / Heteroaromatic compounds / Oxacyclic compounds / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
1-benzopyran / Aromatic heteropolycyclic compound / Benzenoid / Benzopyran / Chromone / Flavone / Heteroaromatic compound / Hydrocarbon derivative / Monocyclic benzene moiety / Naphthalene
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organic heterotricyclic compound, extended flavonoid (CHEBI:77013)
Affected organisms
Not Available

Chemical Identifiers

UNII
1BT0256Y8O
CAS number
6051-87-2
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

References

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. [Article]
  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. [Article]
PubChem Compound
2361
PubChem Substance
99443278
ChemSpider
2271
BindingDB
50028963
ChEBI
77013
ChEMBL
CHEMBL26260
ZINC
ZINC000000057645
Wikipedia
Beta-Naphthoflavone
MSDS
Download (46.9 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

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 Basic)-5.4Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area26.3 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity83.42 m3·mol-1Chemaxon
Polarizability29.91 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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-a043bc7619f943cda8f6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-afa59ac3b0620e1294b3
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-8ede12615bcafefbb44d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-803358c5460967fbd359
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0290000000-2affb46db9b50f0bb9c7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014l-0390000000-b315f4d4c1e793b087d8
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-163.1511357
predicted
DarkChem Lite v0.1.0
[M-H]-173.2313081
predicted
DarkChem Lite v0.1.0
[M-H]-161.62941
predicted
DeepCCS 1.0 (2019)
[M+H]+173.8847081
predicted
DarkChem Lite v0.1.0
[M+H]+173.8156081
predicted
DarkChem Lite v0.1.0
[M+H]+163.98741
predicted
DeepCCS 1.0 (2019)
[M+Na]+176.5900219
predicted
DarkChem Lite v0.1.0
[M+Na]+170.08055
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Estrogen receptor alpha
Kind
Protein
Organism
Humans
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. [Article]
Details2. Steroid hormone receptor ERR1
Kind
Protein
Organism
Humans
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. [Article]
Details3. COUP transcription factor 1
Kind
Protein
Organism
Humans
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. [Article]
Details4. Aryl hydrocarbon receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
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. [Article]
  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. [Article]
  3. Wei KL, Chen FY, Lin CY, Gao GL, Kao WY, Yeh CH, Chen CR, Huang HC, Tsai WR, Jong KJ, Li WJ, Su JG: Activation of aryl hydrocarbon receptor reduces carbendazim-induced cell death. Toxicol Appl Pharmacol. 2016 Sep 1;306:86-97. doi: 10.1016/j.taap.2016.06.004. Epub 2016 Jun 7. [Article]
Details5. Cytochrome P450 1B1
Kind
Protein
Organism
Humans
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. [Article]

Enzymes

Details1. Cytochrome P450 1A2
Kind
Protein
Organism
Humans
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. Shoda T, Mitsumori K, Onodera H, Toyoda K, Uneyama C, Takada K, Hirose M: Liver tumor-promoting effect of beta-naphthoflavone, a strong CYP 1A1/2 inducer, and the relationship between CYP 1A1/2 induction and Cx32 decrease in its hepatocarcinogenesis in the rat. Toxicol Pathol. 2000 Jul-Aug;28(4):540-7. doi: 10.1177/019262330002800406. [Article]

Drug created at August 18, 2010 21:03 / Updated at June 30, 2022 20:56