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Details

Stereochemistry ACHIRAL
Molecular Formula C15H10O5
Molecular Weight 270.2375
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of APIGENIN

SMILES

c1cc(ccc1-c2cc(=O)c3c(cc(cc3o2)O)O)O

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 270.2375
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

2012
611
Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Central benzodiazepine receptor (bovine)
Binding Agent
996
 3.0 µM [Ki]
Antagonist
2575
Antagonist
2575
Antagonist
2575
PubMed

PubMed

TitleDatePubMed
Study of biochemical prevalence indicators for the assessment of iodine deficiency disorders in adults at field conditions in Gujarat (India).
2001
Apigenin acts on the tumor cell invasion process and regulates protease production.
2001
Study of antioxidant effect of apigenin, luteolin and quercetin by DNA protective method.
2001
A new flavone derivative from Ehretia ovalifolia leaves.
2001 Aug
Seasonal and population variation in flavonoid and alliarinoside content of Alliaria petiolata.
2001 Aug
In vitro binding studies with two hypericum perforatum extracts--hyperforin, hypericin and biapigenin--on 5-HT6, 5-HT7, GABA(A)/benzodiazepine, sigma, NPY-Y1/Y2 receptors and dopamine transporters.
2001 Jul
Specific flavonoids induced nod gene expression and pre-activated nod genes of Rhizobium leguminosarum increased pea (Pisum sativum L.) and lentil (Lens culinaris L.) nodulation in controlled growth chamber environments.
2001 Jul
[Comparison of photometric, electrochemical and post-column fluorescence detection for the determination of flavonoids by HPLC].
2001 Jun
Common phytochemicals are ecdysteroid agonists and antagonists: a possible evolutionary link between vertebrate and invertebrate steroid hormones.
2001 Jun
Differing effects of endocrine-disrupting chemicals on basal and FSH-stimulated progesterone production in rat granulosa-luteal cells.
2001 Jun
Flavonoid compounds in the flowers of Kitaibelia vitifolia Willd. (Malvaceae).
2001 Mar-Apr
Effects of structurally related flavonoids on cell cycle progression of human melanoma cells: regulation of cyclin-dependent kinases CDK2 and CDK1.
2001 May 15
Suppression of inducible cyclooxygenase and nitric oxide synthase through activation of peroxisome proliferator-activated receptor-gamma by flavonoids in mouse macrophages.
2001 May 4
Cell-based assay for high-throughput quantitative screening of CFTR chloride transport agonists.
2001 Nov
Flavonoids differentially inhibit guinea pig epidermal cytosolic phospholipase A2.
2001 Nov-Dec
In vivo hepatoprotective activity of active fraction from ethanolic extract of Eclipta alba leaves.
2001 Oct
Antioxidant ability of various flavonoids against DPPH radicals and LDL oxidation.
2001 Oct
No evidence for the in vivo activity of aromatase-inhibiting flavonoids.
2001 Sep
Acylated flavone C-glycosides from Cucumis sativus.
2001 Sep
Cloning of parsley flavone synthase I.
2001 Sep
Induction of a dopaminergic phenotype in cultured striatal neurons by bone morphogenetic proteins.
2001 Sep 23
Qualitative and quantitative chromatographic investigation of flavonoids in Bellis perennis L.
2001 Sep-Oct
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
Effects of intrinsic fluorescence and quenching on fluorescence-based screening of natural products.
2002 Apr
Prevention of cellular ROS damage by isovitexin and related flavonoids.
2002 Apr
Absorption and metabolism of flavonoids in the caco-2 cell culture model and a perused rat intestinal model.
2002 Apr
Scutellarein 4'-methyl ether glycosides as taxonomic markers in Teucridium and Tripora (Lamiaceae, Ajugoideae).
2002 Aug
Dimerization and phosphorylation of thyrotropin-releasing hormone receptors are modulated by agonist stimulation.
2002 Aug 2
Regulation of histone deacetylase 2 by protein kinase CK2.
2002 Aug 30
Functional interaction of protein kinase CK2 and c-Myc in lymphomagenesis.
2002 Aug 8
Chemotaxonomic features associated with flavonoids of cannabinoid-free cannabis (Cannabis sativa subsp. sativa L.) in relation to hops (Humulus lupulus L.).
2002 Feb
Flavonoids inhibit genetic toxicity produced by carcinogens in cells expressing CYP1A2 and CYP1A1.
2002 Jan
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 Jan 15
Effects of apigenin on the serum- and platelet derived growth factor-BB-induced proliferation of rat aortic vascular smooth muscle cells.
2002 Jul
Antiproliferative constituents in plants 10. Flavones from the leaves of Lantana montevidensis Briq. and consideration of structure-activity relationship.
2002 Jul
In vitro properties of a recombinant flavonol synthase from Arabidopsis thaliana.
2002 Jul
Oxidation of quercetin by salivary components. Quercetin-dependent reduction of salivary nitrite under acidic conditions producing nitric oxide.
2002 Jul 17
Phytochemical constituents from the herba of Artemisia apiacea.
2002 Jun
Interactions of different phenolic acids and flavonoids with soy proteins.
2002 Jun 18
Flavonoids differentially regulate IFN gamma-induced ICAM-1 expression in human keratinocytes: molecular mechanisms of action.
2002 Jun 5
Effects of flavonoid phytochemicals on cortisol production and on activities of steroidogenic enzymes in human adrenocortical H295R cells.
2002 Mar
In vitro investigation of cytochrome P450-mediated metabolism of dietary flavonoids.
2002 May
Induction of human UDP-glucuronosyltransferase UGT1A1 by flavonoids-structural requirements.
2002 May
Rapid quantification of constituents in St. John's wort extracts by NIR spectroscopy.
2002 May 15
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 May 23
Molecular modeling of flavonoids that inhibits xanthine oxidase.
2002 May 31
Flavonoids from Ficaria verna Huds.
2002 May-Jun
Structural requirements of flavonoids for inhibition of antigen-Induced degranulation, TNF-alpha and IL-4 production from RBL-2H3 cells.
2002 Oct
High-affinity activators of cystic fibrosis transmembrane conductance regulator (CFTR) chloride conductance identified by high-throughput screening.
2002 Oct 4
Patents

Patents

05863728
3
JP2000086510A
3
JP2001114675A
7
JP2002528464A
4
JP2003504327A
27
JP2003527441A
7
JP2003532634A
63
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
6
JP2011512798A
9
JP2013539792A
2
JP2014201529A
1
JP4370072B2
48
JP4777515B2
4
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 Sat Jun 26 09:11:37 UTC 2021
Edited
by admin
on Sat Jun 26 09:11:37 UTC 2021
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
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
APIGENIN [WHO-DD]
Common Name English
VERSULIN
Common Name English
LY-080400
Code English
FLAVONE, 4',5,7-TRIHYDROXY-
Systematic Name English
APIGENIN [MI]
Common Name English
5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
Systematic Name English
APIGENIN [INCI]
Common 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 Sat Jun 26 09:11:37 UTC 2021 , Edited by admin on Sat Jun 26 09:11:37 UTC 2021
DSLD 1394 (Number of products:104)
Created by admin on Sat Jun 26 09:11:37 UTC 2021 , Edited by admin on Sat Jun 26 09:11:37 UTC 2021
NCI_THESAURUS C68464
Created by admin on Sat Jun 26 09:11:37 UTC 2021 , Edited by admin on Sat Jun 26 09:11:37 UTC 2021
Code System Code Type Description
MERCK INDEX
M1987
Created by admin on Sat Jun 26 09:11:37 UTC 2021 , Edited by admin on Sat Jun 26 09:11:37 UTC 2021
PRIMARY Merck Index
HSDB
7573
Created by admin on Sat Jun 26 09:11:37 UTC 2021 , Edited by admin on Sat Jun 26 09:11:37 UTC 2021
PRIMARY
ECHA (EC/EINECS)
208-292-3
Created by admin on Sat Jun 26 09:11:37 UTC 2021 , Edited by admin on Sat Jun 26 09:11:37 UTC 2021
PRIMARY
MESH
D047310
Created by admin on Sat Jun 26 09:11:37 UTC 2021 , Edited by admin on Sat Jun 26 09:11:37 UTC 2021
PRIMARY
CAS
520-36-5
Created by admin on Sat Jun 26 09:11:37 UTC 2021 , Edited by admin on Sat Jun 26 09:11:37 UTC 2021
PRIMARY
DRUG BANK
DB07352
Created by admin on Sat Jun 26 09:11:37 UTC 2021 , Edited by admin on Sat Jun 26 09:11:37 UTC 2021
PRIMARY
WIKIPEDIA
APIGENIN
Created by admin on Sat Jun 26 09:11:37 UTC 2021 , Edited by admin on Sat Jun 26 09:11:37 UTC 2021
PRIMARY
USP_CATALOG
1040683
Created by admin on Sat Jun 26 09:11:37 UTC 2021 , Edited by admin on Sat Jun 26 09:11:37 UTC 2021
PRIMARY USP-RS
PUBCHEM
5280443
Created by admin on Sat Jun 26 09:11:37 UTC 2021 , Edited by admin on Sat Jun 26 09:11:37 UTC 2021
PRIMARY
FDA UNII
7V515PI7F6
Created by admin on Sat Jun 26 09:11:37 UTC 2021 , Edited by admin on Sat Jun 26 09:11:37 UTC 2021
PRIMARY
EPA CompTox
520-36-5
Created by admin on Sat Jun 26 09:11:37 UTC 2021 , Edited by admin on Sat Jun 26 09:11:37 UTC 2021
PRIMARY
RXCUI
1368130
Created by admin on Sat Jun 26 09:11:37 UTC 2021 , Edited by admin on Sat Jun 26 09:11:37 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C68466
Created by admin on Sat Jun 26 09:11:37 UTC 2021 , Edited by admin on Sat Jun 26 09:11:37 UTC 2021
PRIMARY
Related Record Type Details
CHAMAEMELUM NOBILE FLOWER
PARENT -> CONSTITUENT ALWAYS PRESENT
ACAI FRUIT PULP
PARENT -> CONSTITUENT ALWAYS PRESENT
1,1-Diphenyl-2-picrylhydrazyl radical scavenging assay(DPPH) IC50 expressed as ug/mL was not tested due to the limited samples available. In vitro hydroxyl radical scavenging assay(Hydroxy Radical) IC50 expressed as ug/mL >5.
CANNABIS SATIVA SUBSP. INDICA TOP
PARENT -> CONSTITUENT ALWAYS PRESENT
CITRUS AURANTIUM FRUIT RIND
PARENT -> CONSTITUENT ALWAYS PRESENT
53% Cell growth rate of human acute promyelocytic leukemia HL-60 cells at 50 uM of compound vs control
PRIMULA VERIS FLOWER
PARENT -> CONSTITUENT ALWAYS PRESENT
FENUGREEK SEED
PARENT -> CONSTITUENT ALWAYS PRESENT
CHAMOMILE
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
Structure of APIGENIN
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
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