APIGENIN

Possibly Marketed Outside US

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 Search

SMILES

OC1=CC=C(C=C1)C2=CC(=O)C3=C(O)C=C(O)C=C3O2

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

Targets

Primary Target	Pharmacology	Potency
Central benzodiazepine receptor (bovine) 1 Target ID: Central benzodiazepine receptor (bovine) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7617761	Binding Agent 1064	3.0 µM [Ki]
Mu opioid receptor 221 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17685652	Antagonist 2778
Sigma opioid receptor 63 Target ID: CHEMBL287 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17685652	Antagonist 2778
Kappa opioid receptor 108 Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17685652	Antagonist 2778

PubMed

Title	Date	PubMed
Medicinal and ethnoveterinary remedies of hunters in Trinidad.	2001	11737880
Apigenin acts on the tumor cell invasion process and regulates protease production.	2001	11588896
Differential expression of two cytochrome P450s involved in the biosynthesis of flavones and anthocyanins in chemo-varietal forms of Perilla frutescens.	2001 Dec	11773526
Antioxidant capacity of a 3-deoxyanthocyanidin from soybean.	2001 Dec	11730874
Peroxidative metabolism of apigenin and naringenin versus luteolin and quercetin: glutathione oxidation and conjugation.	2001 Feb 15	11182292
A distinctive flavonoid chemistry for the anomalous genus Biebersteinia.	2001 Jan	11198823
Aquiledine and isoaquiledine, novel flavonoid alkaloids from Aquilegia ecalcarata.	2001 Jan	11170673
Apigenin inhibits growth and induces G2/M arrest by modulating cyclin-CDK regulators and ERK MAP kinase activation in breast carcinoma cells.	2001 Jan-Feb	11299771
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	11457914
Partial restoration of defective chloride conductance in DeltaF508 CF mice by trimethylamine oxide.	2001 Jul	11404245
Isovitexin o-glucosides from Aquilegia vulgaris L.	2001 Jul-Aug	11693732
Flavonoid (myricetin, quercetin, kaempferol, luteolin, and apigenin) content of edible tropical plants.	2001 Jun	11410016
Differing effects of endocrine-disrupting chemicals on basal and FSH-stimulated progesterone production in rat granulosa-luteal cells.	2001 Jun	11395928
Flavonoid characters contributing to the taxonomic revision of the Hebe parviflora complex.	2001 Mar	11261578
Flavonoid compounds in the flowers of Kitaibelia vitifolia Willd. (Malvaceae).	2001 Mar-Apr	11501790
Casein kinase II sites in the intracellular C-terminal domain of the thyrotropin-releasing hormone receptor and chimeric gonadotropin-releasing hormone receptors contribute to beta-arrestin-dependent internalization.	2001 May 25	11278484
Suppression of inducible cyclooxygenase and nitric oxide synthase through activation of peroxisome proliferator-activated receptor-gamma by flavonoids in mouse macrophages.	2001 May 4	11343698
Protein kinase CK2: signaling and tumorigenesis in the mammary gland.	2001 Nov	11827167
Cell-based assay for high-throughput quantitative screening of CFTR chloride transport agonists.	2001 Nov	11600438
Phosphorylation by the protein kinase CK2 promotes calpain-mediated degradation of IkappaBalpha.	2001 Nov 1	11673497
In vivo hepatoprotective activity of active fraction from ethanolic extract of Eclipta alba leaves.	2001 Oct	11883149
NF-kappaB and the MAP kinases/AP-1 pathways are both involved in interleukin-6 and interleukin-8 expression in fibroblast-like synoviocytes stimulated by protein I/II, a modulin from oral streptococci.	2001 Oct	11580755
Selective growth-inhibitory, cell-cycle deregulatory and apoptotic response of apigenin in normal versus human prostate carcinoma cells.	2001 Oct 5	11573952
Acylated flavone C-glycosides from Cucumis sativus.	2001 Sep	11524127
Cloning of parsley flavone synthase I.	2001 Sep	11524111
Hyaluronan enters keratinocytes by a novel endocytic route for catabolism.	2001 Sep 14	11451952
Induction of a dopaminergic phenotype in cultured striatal neurons by bone morphogenetic proteins.	2001 Sep 23	11557097
Qualitative and quantitative chromatographic investigation of flavonoids in Bellis perennis L.	2001 Sep-Oct	11876448
Effects of intrinsic fluorescence and quenching on fluorescence-based screening of natural products.	2002 Apr	12046870
Botanical antioxidants for chemoprevention of photocarcinogenesis.	2002 Apr 1	11897547
Dimerization and phosphorylation of thyrotropin-releasing hormone receptors are modulated by agonist stimulation.	2002 Aug 2	12023974
Functional interaction of protein kinase CK2 and c-Myc in lymphomagenesis.	2002 Aug 8	12149649
The role of UV-B radiation in aquatic and terrestrial ecosystems--an experimental and functional analysis of the evolution of UV-absorbing compounds.	2002 Feb	11849977
Effect of six flavonoid compounds from Ixeris sonchifolia on stimulus-induced superoxide generation and tyrosyl phosphorylation in human neutrophils.	2002 Feb	11750278
Effect of flavonoids on cell cycle progression in prostate cancer cells.	2002 Feb 8	11790449
Estrogenic and cholinergic properties of the methanol extract of Ruellia praetermissa Sceinf. ex. Lindau (Acanthaceae) in female rats.	2002 Jan	11924764
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 Jan	11807956
Flavonoids inhibit genetic toxicity produced by carcinogens in cells expressing CYP1A2 and CYP1A1.	2002 Jan	11752233
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	11841797
Effects of apigenin on the serum- and platelet derived growth factor-BB-induced proliferation of rat aortic vascular smooth muscle cells.	2002 Jul	12142993
In vitro properties of a recombinant flavonol synthase from Arabidopsis thaliana.	2002 Jul	12126705
Interactions of different phenolic acids and flavonoids with soy proteins.	2002 Jun 18	12063116
Flavonoids differentially regulate IFN gamma-induced ICAM-1 expression in human keratinocytes: molecular mechanisms of action.	2002 Jun 5	12044887
Effects of flavonoid phytochemicals on cortisol production and on activities of steroidogenic enzymes in human adrenocortical H295R cells.	2002 Mar	11948020
Flavonoids increase the intracellular glutathione level by transactivation of the gamma-glutamylcysteine synthetase catalytical subunit promoter.	2002 Mar 1	11864778
Rapid quantification of constituents in St. John's wort extracts by NIR spectroscopy.	2002 May 15	12008122
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	12032841
Molecular modeling of flavonoids that inhibits xanthine oxidase.	2002 May 31	12054758
Structural requirements of flavonoids for inhibition of antigen-Induced degranulation, TNF-alpha and IL-4 production from RBL-2H3 cells.	2002 Oct	12150856
High-affinity activators of cystic fibrosis transmembrane conductance regulator (CFTR) chloride conductance identified by high-throughput screening.	2002 Oct 4	12161441

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:08:17 GMT 2023` Edited by `admin` on `Fri Dec 15 18:08:17 GMT 2023`
Record UNII	7V515PI7F6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

APIGENIN

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

VERSULIN

Common Name

English

LY-080400

Code

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

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)