Identification
NameFlavone
Accession NumberDB07776  (DB11139)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
Synonyms
2-Phenyl-4-benzopyron
2-Phenyl-4-chromone
2-phenyl-4H-1-benzopyran-4-one
2-phenyl-4H-benzopyran-4-one
2-phenyl-γ-benzopyrone
2-Phenylbenzopyran-4-one
2-phenylchromone
Flavon
External IDs NSC-19028
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNIIS2V45N7G3B
CAS number525-82-6
WeightAverage: 222.2387
Monoisotopic: 222.068079564
Chemical FormulaC15H10O2
InChI KeyVHBFFQKBGNRLFZ-UHFFFAOYSA-N
InChI
InChI=1S/C15H10O2/c16-13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14/h1-10H
IUPAC Name
2-phenyl-4H-chromen-4-one
SMILES
O=C1C=C(OC2=CC=CC=C12)C1=CC=CC=C1
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
NeocarzinostatinProteinunknownNot AvailableStreptomyces carzinostaticusP0A3R9 details
Steroid hormone receptor ERR1Proteinunknown
agonist
HumanP11474 details
Steroid hormone receptor ERR2Proteinunknown
agonist
HumanO95718 details
Cytochrome P450 1B1ProteinunknownNot AvailableHumanQ16678 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00819 mg/mLALOGPS
logP3.54ALOGPS
logP2.97ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)15.63ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity66.97 m3·mol-1ChemAxon
Polarizability23.79 Å3ChemAxon
Number of Rings3ChemAxon
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-00dl-8930000000-3944bcd59fd467475fe4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00dl-6930000000-af643d33c8bd90e12e34View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00dl-6930000000-af643d33c8bd90e12e34View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00di-0190000000-c5dc113240ef2eddc9bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0udi-0900000000-cbc602f9fb305cfab2adView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0udi-0900000000-1767db1ce89913542708View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-9610000000-8f6ea890ee174ff2cab9View in MoNA
MSMass Spectrum (Electron Ionization)splash10-00di-8980000000-8dd4180be084c0205feeView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
DescriptionThis 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).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavones
Alternative ParentsChromones / Pyranones and derivatives / Benzene and substituted derivatives / Heteroaromatic compounds / Oxacyclic compounds / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
SubstituentsFlavone / Chromone / Benzopyran / 1-benzopyran / Pyranone / Benzenoid / Monocyclic benzene moiety / Pyran / Heteroaromatic compound / Oxacycle
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptorsflavones (CHEBI:42491 ) / flavones (C15608 ) / Flavones and Flavonols (LMPK12110097 ) / a flavone (CPD-8485 )

Targets

Kind
Protein
Organism
Streptomyces carzinostaticus
Pharmacological action
unknown
General Function:
NCS has antibiotic activity (for Gram-positive bacteria) and antitumor activity (for certain mouse tumors). NCS binds non-covalently to a chromophore which is the cytotoxic and mutagenic component of the antibiotic. The chromophore binds to DNA as a weak intercalator and causes single- and double-strand breaks.
Specific Function:
Dna binding
Gene Name:
ncsA
Uniprot ID:
P0A3R9
Molecular Weight:
14455.08 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
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 may act as an important regulator of MCAD promoter. Binds to the C1 region of the lactoferrin gene promoter. Requires dimerization and the coactivator, PGC-1A, for full activity. The ERRalpha/PGC1alp...
Gene Name:
ESRRA
Uniprot ID:
P11474
Molecular Weight:
45509.11 Da
References
  1. Suetsugi M, Su L, Karlsberg K, Yuan YC, Chen S: Flavone and isoflavone phytoestrogens are agonists of estrogen-related receptors. Mol Cancer Res. 2003 Nov;1(13):981-91. [PubMed:14638870 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Nuclear receptor, may regulate ESR1 transcriptional activity. Induces the expression of PERM1 in the skeletal muscle.
Gene Name:
ESRRB
Uniprot ID:
O95718
Molecular Weight:
56207.085 Da
References
  1. Suetsugi M, Su L, Karlsberg K, Yuan YC, Chen S: Flavone and isoflavone phytoestrogens are agonists of estrogen-related receptors. Mol Cancer Res. 2003 Nov;1(13):981-91. [PubMed:14638870 ]
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 unrelated compounds, including steroids, fatty acids, retinoid and xenobiotics. Preferentially oxidizes 17beta-estradiol to the carcinogenic 4-hydroxy derivative, and a variety of procarcinogenic compou...
Gene Name:
CYP1B1
Uniprot ID:
Q16678
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 ]
  2. Shimada T, Tanaka K, Takenaka S, Murayama N, Martin MV, Foroozesh MK, Yamazaki H, Guengerich FP, Komori M: Structure-function relationships of inhibition of human cytochromes P450 1A1, 1A2, 1B1, 2C9, and 3A4 by 33 flavonoid derivatives. Chem Res Toxicol. 2010 Dec 20;23(12):1921-35. doi: 10.1021/tx100286d. [PubMed:21053930 ]
Drug created on September 15, 2010 15:25 / Updated on July 07, 2017 03:06