Identification

Name
Flavone
Accession Number
DB07776  (DB11139)
Type
Small Molecule
Groups
Approved, Experimental
Description
Not 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
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
BacminFlavone (50 mg/1) + Ascorbic acid (500 mg/1) + Biotin (150 ug/1) + Chromium Cr-51 chloride (0.1 mg/1) + Cupric oxide (3 mg/1) + Cyanocobalamin (50 ug/1) + Ferrous fumarate (27 mg/1) + Folic Acid (1 mg/1) + Magnesium oxide (50 mg/1) + Manganese gluconate (5 mg/1) + Nicotinamide (100 mg/1) + Calcium pantothenate (25 mg/1) + Pyridoxine hydrochloride (25 mg/1) + Riboflavin (20 mg/1) + Selenomethionine (50 ug/1) + Thiamine mononitrate (20 mg/1) + Vitamin A acetate (2000 [iU]/1) + Zinc oxide (22.5 mg/1) + alpha-Tocopherol acetate (30 [iU]/1)Tablet, coatedOralMarnel Pharmaceuticals, Llc2000-04-01Not applicableUs
Categories
UNII
S2V45N7G3B
CAS number
525-82-6
Weight
Average: 222.2387
Monoisotopic: 222.068079564
Chemical Formula
C15H10O2
InChI Key
VHBFFQKBGNRLFZ-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

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UNeocarzinostatinNot AvailableStreptomyces carzinostaticus
USteroid hormone receptor ERR1
agonist
Human
USteroid hormone receptor ERR2
agonist
Human
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

General References
Not Available
External Links
Human Metabolome Database
HMDB0003075
KEGG Compound
C15608
PubChem Compound
10680
PubChem Substance
99444247
ChemSpider
10230
BindingDB
50028962
ChEBI
42491
ChEMBL
CHEMBL275638
IUPHAR
409
Guide to Pharmacology
GtP Drug Page
HET
FLN
Wikipedia
Flavones
PDB Entries
2g0l / 4hki

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Tablet, coatedOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not 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
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MSGC-MSsplash10-00dl-8930000000-3944bcd59fd467475fe4
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-00dl-8930000000-3944bcd59fd467475fe4
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00dl-6930000000-af643d33c8bd90e12e34
Mass Spectrum (Electron Ionization)MSsplash10-00di-8980000000-8dd4180be084c0205fee
MS/MS Spectrum - Quattro_QQQ 10V, NegativeLC-MS/MSsplash10-00di-0190000000-c5dc113240ef2eddc9bc
MS/MS Spectrum - Quattro_QQQ 25V, NegativeLC-MS/MSsplash10-0udi-0900000000-cbc602f9fb305cfab2ad
MS/MS Spectrum - Quattro_QQQ 40V, NegativeLC-MS/MSsplash10-0udi-0900000000-1767db1ce89913542708
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0002-9610000000-8f6ea890ee174ff2cab9
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-00fr-0910000000-f99e5ea29982d8657bf3
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-03di-0390000000-1a1ab6620996a9ddc429
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-00di-0090000000-e8ad16adbd7e6c8dcc23
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-0950000000-94425655598eb5a5cfb4
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-0090000000-dd86946c50229a30d124
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-0490000000-5a3c393a8cf2ea0eac18
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-0090000000-fbeb1951905acd75fd95
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

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
Chromones / Pyranones and derivatives / Benzene and substituted derivatives / Heteroaromatic compounds / Oxacyclic compounds / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Flavone / Chromone / Benzopyran / 1-benzopyran / Pyranone / Benzenoid / Monocyclic benzene moiety / Pyran / Heteroaromatic compound / Oxacycle
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
flavones (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
Uniprot Name
Neocarzinostatin
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...
Gene Name
ESRRA
Uniprot ID
P11474
Uniprot Name
Steroid hormone receptor ERR1
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
Uniprot Name
Steroid hormone receptor ERR2
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 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]
  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 November 02, 2018 06:38