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Details

Stereochemistry ACHIRAL
Molecular Formula C15H10O5
Molecular Weight 270.2369
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of APIGENIN

SMILES

OC1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C=C(O)C=C3O

InChI

InChIKey=KZNIFHPLKGYRTM-UHFFFAOYSA-N
InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H

HIDE SMILES / InChI
Molecular Formula C15H10O5
Molecular Weight 270.2369
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

2012
608
Targets

Targets

Primary TargetPharmacologyConditionPotency
Central benzodiazepine receptor (bovine)
1
Target ID: Central benzodiazepine receptor (bovine)
Binding Agent
1076
 3.0 µM [Ki]
Antagonist
2849
Antagonist
2849
Antagonist
2849
PubMed

PubMed

TitleDatePubMed
High-affinity activators of cystic fibrosis transmembrane conductance regulator (CFTR) chloride conductance identified by high-throughput screening.
2002-10-04
Structural requirements of flavonoids for inhibition of antigen-Induced degranulation, TNF-alpha and IL-4 production from RBL-2H3 cells.
2002-10
Regulation of histone deacetylase 2 by protein kinase CK2.
2002-08-30
Functional interaction of protein kinase CK2 and c-Myc in lymphomagenesis.
2002-08-08
Dimerization and phosphorylation of thyrotropin-releasing hormone receptors are modulated by agonist stimulation.
2002-08-02
Scutellarein 4'-methyl ether glycosides as taxonomic markers in Teucridium and Tripora (Lamiaceae, Ajugoideae).
2002-08
Flavonoids from Ficaria verna Huds.
2002-07-23
Oxidation of quercetin by salivary components. Quercetin-dependent reduction of salivary nitrite under acidic conditions producing nitric oxide.
2002-07-17
Effects of apigenin on the serum- and platelet derived growth factor-BB-induced proliferation of rat aortic vascular smooth muscle cells.
2002-07
Antiproliferative constituents in plants 10. Flavones from the leaves of Lantana montevidensis Briq. and consideration of structure-activity relationship.
2002-07
In vitro properties of a recombinant flavonol synthase from Arabidopsis thaliana.
2002-07
Interactions of different phenolic acids and flavonoids with soy proteins.
2002-06-18
Flavonoids differentially regulate IFN gamma-induced ICAM-1 expression in human keratinocytes: molecular mechanisms of action.
2002-06-05
Phytochemical constituents from the herba of Artemisia apiacea.
2002-06
Molecular modeling of flavonoids that inhibits xanthine oxidase.
2002-05-31
Involvement of nuclear factor-kappa B, Bax and Bcl-2 in induction of cell cycle arrest and apoptosis by apigenin in human prostate carcinoma cells.
2002-05-23
Rapid quantification of constituents in St. John's wort extracts by NIR spectroscopy.
2002-05-15
Flavonoids differentially inhibit guinea pig epidermal cytosolic phospholipase A2.
2002-05-08
In vitro investigation of cytochrome P450-mediated metabolism of dietary flavonoids.
2002-05
Induction of human UDP-glucuronosyltransferase UGT1A1 by flavonoids-structural requirements.
2002-05
Botanical antioxidants for chemoprevention of photocarcinogenesis.
2002-04-01
Effects of intrinsic fluorescence and quenching on fluorescence-based screening of natural products.
2002-04
Prevention of cellular ROS damage by isovitexin and related flavonoids.
2002-04
Absorption and metabolism of flavonoids in the caco-2 cell culture model and a perused rat intestinal model.
2002-04
Qualitative and quantitative chromatographic investigation of flavonoids in Bellis perennis L.
2002-03-06
Flavonoids increase the intracellular glutathione level by transactivation of the gamma-glutamylcysteine synthetase catalytical subunit promoter.
2002-03-01
Effects of flavonoid phytochemicals on cortisol production and on activities of steroidogenic enzymes in human adrenocortical H295R cells.
2002-03
Relationships of urinary phyto-oestrogen excretion to BMD in postmenopausal women.
2002-03
Effect of flavonoids on cell cycle progression in prostate cancer cells.
2002-02-08
Regulatory effects of stem cell factor and interleukin-4 on adhesion of human mast cells to extracellular matrix proteins.
2002-02-01
Chemotaxonomic features associated with flavonoids of cannabinoid-free cannabis (Cannabis sativa subsp. sativa L.) in relation to hops (Humulus lupulus L.).
2002-02
The role of UV-B radiation in aquatic and terrestrial ecosystems--an experimental and functional analysis of the evolution of UV-absorbing compounds.
2002-02
Flavone glucoside uptake into barley mesophyll and Arabidopsis cell culture vacuoles. Energization occurs by H(+)-antiport and ATP-binding cassette-type mechanisms.
2002-02
Effect of six flavonoid compounds from Ixeris sonchifolia on stimulus-induced superoxide generation and tyrosyl phosphorylation in human neutrophils.
2002-02
Apigenin and LY294002 prolong EGF-stimulated ERK1/2 activation in PC12 cells but are unable to induce full differentiation.
2002-01-16
Wogonin and fisetin induce apoptosis in human promyeloleukemic cells, accompanied by a decrease of reactive oxygen species, and activation of caspase 3 and Ca(2+)-dependent endonuclease.
2002-01-15
Intracellular flavonoids as electron donors for extracellular ferricyanide reduction in human erythrocytes.
2002-01-01
Estrogenic and cholinergic properties of the methanol extract of Ruellia praetermissa Sceinf. ex. Lindau (Acanthaceae) in female rats.
2002-01
A p21(waf1)-independent pathway for inhibitory phosphorylation of cyclin-dependent kinase p34(cdc2) and concomitant G(2)/M arrest by the chemopreventive flavonoid apigenin.
2002-01
Flavonoids inhibit genetic toxicity produced by carcinogens in cells expressing CYP1A2 and CYP1A1.
2002-01
HET-CAM bioassay as in vitro alternative to the croton oil test for investigating steroidal and non-steroidal compounds.
2002
Dietary flavonoids: bioavailability, metabolic effects, and safety.
2002
[Investigation on method speliality in identifying Fructus Crataegi with vitexin rhamnoside].
2001-12
Differential expression of two cytochrome P450s involved in the biosynthesis of flavones and anthocyanins in chemo-varietal forms of Perilla frutescens.
2001-12
Antioxidant capacity of a 3-deoxyanthocyanidin from soybean.
2001-12
Protein kinase CK2: signaling and tumorigenesis in the mammary gland.
2001-11
In vivo hepatoprotective activity of active fraction from ethanolic extract of Eclipta alba leaves.
2001-10
Antioxidant ability of various flavonoids against DPPH radicals and LDL oxidation.
2001-10
Medicinal and ethnoveterinary remedies of hunters in Trinidad.
2001
Study of biochemical prevalence indicators for the assessment of iodine deficiency disorders in adults at field conditions in Gujarat (India).
2001
Patents

Patents

05863728
3
JP2000086510A
3
JP2001114675A
7
JP2002528464A
9
JP2003504327A
27
JP2003527441A
7
JP2003532634A
66
JP2004091338A
5
JP2004131500A
1
JP2004196833A
3
JP2004506656A
8
JP2006327967A
3
JP2007106718A
3
JP2007314472A
3
JP2007504443A
9
JP2007508371A
1
JP2008513378A
16
JP2009024023A
3
JP2010163363A
1
JP2010260818A
1
JP2011001283A
1
JP2011001284A
1
JP2011231058A
7
JP2011512798A
9
JP2013539792A
2
JP2014201529A
1
JP4370072B2
48
JP4777515B2
5
JPH02101013A
5
JPH02121998A
1
JPH0231660A
1
JPH04154805A
5
JPH04266809A
3
JPH04266903A
1
JPH04342516A
3
JPH0585934A
7
JPH0761927A
2
JPH08104628A
10
JPH09121829A
1
JPH09263534A
1
JPH10298098A
3
JPH1095732A
3
JPH11180867A
2
JPH11228407A
1
JPS5513771A
4
JPS5557583A
1
JPS60199817A
2
JPS6219068A
3
JPS62243655A
2
JPS6253923A
2
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:04:20 GMT 2025
Edited
by admin
on Mon Mar 31 19:04:20 GMT 2025
Record UNII
7V515PI7F6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
APIGENIN
HSDB   INCI   MI   USP-RS   WHO-DD  
INCI  
Official Name English
LY-080400
Preferred Name English
APIGENINE
Common Name English
APIGENOL
Common Name English
CI NATURAL YELLOW 1
Common Name English
APIGENIN [USP-RS]
Common Name English
APIGENIN [HSDB]
Common Name English
4',5,7-TRIHYDROXYFLAVONE
Systematic Name English
UCCF-031
Code English
APEGENIN
Common Name English
VERSULIN
Common Name English
FLAVONE, 4',5,7-TRIHYDROXY-
Systematic Name English
APIGENIN [MI]
Common Name English
Apigenin [WHO-DD]
Common Name English
5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
Systematic Name English
NSC-83244
Code English
APIGENIN (CONSTITUENT OF CHAMOMILE) [DSC]
Common Name English
PELARGIDENON-1449
Common Name English
4H-1-BENZOPYRAN-4-ONE, 5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-
Systematic Name English
2-(P-HYDROXYPHENYL)-5,7-DIHYDROXYCHROMONE
Common Name English
Classification Tree Code System Code
DSLD 222 (Number of products:60)
Created by admin on Mon Mar 31 19:04:20 GMT 2025 , Edited by admin on Mon Mar 31 19:04:20 GMT 2025
DSLD 1394 (Number of products:104)
Created by admin on Mon Mar 31 19:04:20 GMT 2025 , Edited by admin on Mon Mar 31 19:04:20 GMT 2025
NCI_THESAURUS C68464
Created by admin on Mon Mar 31 19:04:20 GMT 2025 , Edited by admin on Mon Mar 31 19:04:20 GMT 2025
Code System Code Type Description
MERCK INDEX
m1987
Created by admin on Mon Mar 31 19:04:20 GMT 2025 , Edited by admin on Mon Mar 31 19:04:20 GMT 2025
PRIMARY Merck Index
RS_ITEM_NUM
1040683
Created by admin on Mon Mar 31 19:04:20 GMT 2025 , Edited by admin on Mon Mar 31 19:04:20 GMT 2025
PRIMARY
HSDB
7573
Created by admin on Mon Mar 31 19:04:20 GMT 2025 , Edited by admin on Mon Mar 31 19:04:20 GMT 2025
PRIMARY
ECHA (EC/EINECS)
208-292-3
Created by admin on Mon Mar 31 19:04:20 GMT 2025 , Edited by admin on Mon Mar 31 19:04:20 GMT 2025
PRIMARY
MESH
D047310
Created by admin on Mon Mar 31 19:04:20 GMT 2025 , Edited by admin on Mon Mar 31 19:04:20 GMT 2025
PRIMARY
SMS_ID
100000183496
Created by admin on Mon Mar 31 19:04:20 GMT 2025 , Edited by admin on Mon Mar 31 19:04:20 GMT 2025
PRIMARY
CAS
520-36-5
Created by admin on Mon Mar 31 19:04:20 GMT 2025 , Edited by admin on Mon Mar 31 19:04:20 GMT 2025
PRIMARY
DAILYMED
7V515PI7F6
Created by admin on Mon Mar 31 19:04:20 GMT 2025 , Edited by admin on Mon Mar 31 19:04:20 GMT 2025
PRIMARY
NSC
83244
Created by admin on Mon Mar 31 19:04:20 GMT 2025 , Edited by admin on Mon Mar 31 19:04:20 GMT 2025
PRIMARY
DRUG BANK
DB07352
Created by admin on Mon Mar 31 19:04:20 GMT 2025 , Edited by admin on Mon Mar 31 19:04:20 GMT 2025
PRIMARY
WIKIPEDIA
APIGENIN
Created by admin on Mon Mar 31 19:04:20 GMT 2025 , Edited by admin on Mon Mar 31 19:04:20 GMT 2025
PRIMARY
PUBCHEM
5280443
Created by admin on Mon Mar 31 19:04:20 GMT 2025 , Edited by admin on Mon Mar 31 19:04:20 GMT 2025
PRIMARY
FDA UNII
7V515PI7F6
Created by admin on Mon Mar 31 19:04:20 GMT 2025 , Edited by admin on Mon Mar 31 19:04:20 GMT 2025
PRIMARY
EPA CompTox
DTXSID6022391
Created by admin on Mon Mar 31 19:04:20 GMT 2025 , Edited by admin on Mon Mar 31 19:04:20 GMT 2025
PRIMARY
RXCUI
1368130
Created by admin on Mon Mar 31 19:04:20 GMT 2025 , Edited by admin on Mon Mar 31 19:04:20 GMT 2025
PRIMARY RxNorm
CHEBI
18388
Created by admin on Mon Mar 31 19:04:20 GMT 2025 , Edited by admin on Mon Mar 31 19:04:20 GMT 2025
PRIMARY
NCI_THESAURUS
C68466
Created by admin on Mon Mar 31 19:04:20 GMT 2025 , Edited by admin on Mon Mar 31 19:04:20 GMT 2025
PRIMARY
CHEBI
58470
Created by admin on Mon Mar 31 19:04:20 GMT 2025 , Edited by admin on Mon Mar 31 19:04:20 GMT 2025
PRIMARY
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Related Record Type Details
Structure of APIGENIN
ACTIVE MOIETY
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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