APIGENIN

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
Target ID: Central benzodiazepine receptor (bovine) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7617761	Binding Agent 1037	3.0 µM [Ki]
Mu opioid receptor 221 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17685652	Antagonist 2737
Sigma opioid receptor 63 Target ID: CHEMBL287 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17685652	Antagonist 2737
Kappa opioid receptor 108 Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17685652	Antagonist 2737

PubMed

Title	Date	PubMed
Inhibition of aromatase activity by flavonoids.	1999 Jun	10403137
Flavones and sesquiterpene lactones from Achillea atrata subsp. multifida: antimicrobial activity.	1999 Jun	10395518
Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines.	2000 Jul-Aug	10953322
Study of biochemical prevalence indicators for the assessment of iodine deficiency disorders in adults at field conditions in Gujarat (India).	2001	11708609
Apigenin acts on the tumor cell invasion process and regulates protease production.	2001	11588896
Improved methods for the extraction and analysis of isoflavones from soy-containing foods and nutritional supplements by reversed-phase high-performance liquid chromatography and liquid chromatography-mass spectrometry.	2001 Apr 13	11355838
Seasonal and population variation in flavonoid and alliarinoside content of Alliaria petiolata.	2001 Aug	11521398
Samioside, a new phenylethanoid glycoside with free-radical scavenging and antimicrobial activities from Phlomis samia.	2001 Aug	11520237
Phenolic constituents and antioxidant activity of an extract of Anthuriumversicolor leaves.	2001 Aug	11520218
[Investigation on method speliality in identifying Fructus Crataegi with vitexin rhamnoside].	2001 Dec	11917841
Differential expression of two cytochrome P450s involved in the biosynthesis of flavones and anthocyanins in chemo-varietal forms of Perilla frutescens.	2001 Dec	11773526
Inhibitory effect of decoction of Perilla frutescens on cultured murine mesangial cell proliferation and quantitative analysis of its active constituents.	2001 Feb	11270716
Alfalfa (Medicago sativa L.) flavonoids. 1. Apigenin and luteolin glycosides from aerial parts.	2001 Feb	11262024
The neuroprotective effects of phytoestrogens on amyloid beta protein-induced toxicity are mediated by abrogating the activation of caspase cascade in rat cortical neurons.	2001 Feb 16	11083861
LC coupled to ion-trap MS for the rapid screening and detection of polyphenol antioxidants from Helichrysum stoechas.	2001 Jan	11199231
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
Common phytochemicals are ecdysteroid agonists and antagonists: a possible evolutionary link between vertebrate and invertebrate steroid hormones.	2001 Jun	11457661
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
Modulation of multidrug resistance protein 1 (MRP1/ABCC1) transport and atpase activities by interaction with dietary flavonoids.	2001 May	11306701
Effects of structurally related flavonoids on cell cycle progression of human melanoma cells: regulation of cyclin-dependent kinases CDK2 and CDK1.	2001 May 15	11322924
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
In vivo hepatoprotective activity of active fraction from ethanolic extract of Eclipta alba leaves.	2001 Oct	11883149
Effect of oral treatment of Perilla frutescens and its constituents on type-I allergy in mice.	2001 Oct	11642335
Selective growth-inhibitory, cell-cycle deregulatory and apoptotic response of apigenin in normal versus human prostate carcinoma cells.	2001 Oct 5	11573952
No evidence for the in vivo activity of aromatase-inhibiting flavonoids.	2001 Sep	11595503
Regeneration in avian hair cell epithelia: identification of intracellular signals required for S-phase entry.	2001 Sep	11576187
Induction of a dopaminergic phenotype in cultured striatal neurons by bone morphogenetic proteins.	2001 Sep 23	11557097
Dietary flavonoids: bioavailability, metabolic effects, and safety.	2002	12055336
Effects of intrinsic fluorescence and quenching on fluorescence-based screening of natural products.	2002 Apr	12046870
Scutellarein 4'-methyl ether glycosides as taxonomic markers in Teucridium and Tripora (Lamiaceae, Ajugoideae).	2002 Aug	12127590
Regulation of histone deacetylase 2 by protein kinase CK2.	2002 Aug 30	12082111
Flavonoids inhibit genetic toxicity produced by carcinogens in cells expressing CYP1A2 and CYP1A1.	2002 Jan	11752233
Oxidation of quercetin by salivary components. Quercetin-dependent reduction of salivary nitrite under acidic conditions producing nitric oxide.	2002 Jul 17	12105964
Interactions of different phenolic acids and flavonoids with soy proteins.	2002 Jun 18	12063116
Effects of flavonoid phytochemicals on cortisol production and on activities of steroidogenic enzymes in human adrenocortical H295R cells.	2002 Mar	11948020
Relationships of urinary phyto-oestrogen excretion to BMD in postmenopausal women.	2002 Mar	11940043
In vitro investigation of cytochrome P450-mediated metabolism of dietary flavonoids.	2002 May	11955666
Molecular modeling of flavonoids that inhibits xanthine oxidase.	2002 May 31	12054758
Flavonoids from Ficaria verna Huds.	2002 May-Jun	12132681
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 16 23:49:07 UTC 2022` Edited by `admin` on `Fri Dec 16 23:49:07 UTC 2022`
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)