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 1059	3.0 µM [Ki]
Mu opioid receptor 221 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17685652	Antagonist 2760
Sigma opioid receptor 63 Target ID: CHEMBL287 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17685652	Antagonist 2760
Kappa opioid receptor 108 Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17685652	Antagonist 2760

PubMed

Title	Date	PubMed
Study of biochemical prevalence indicators for the assessment of iodine deficiency disorders in adults at field conditions in Gujarat (India).	2001	11708609
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
A new flavone derivative from Ehretia ovalifolia leaves.	2001 Aug	11534347
Acylated apigenin glycosides from alfalfa (Medicago sativa L.) var. Artal.	2001 Aug	11454348
[Investigation on method speliality in identifying Fructus Crataegi with vitexin rhamnoside].	2001 Dec	11917841
Alfalfa (Medicago sativa L.) flavonoids. 1. Apigenin and luteolin glycosides from aerial parts.	2001 Feb	11262024
Peroxidative metabolism of apigenin and naringenin versus luteolin and quercetin: glutathione oxidation and conjugation.	2001 Feb 15	11182292
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
Inhibition of inducible nitric oxide synthase and cyclooxygenase-2 expression by flavonoids in macrophage J774A.1.	2001 Jan 12	11213362
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
[Comparison of photometric, electrochemical and post-column fluorescence detection for the determination of flavonoids by HPLC].	2001 Jun	11577389
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
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
Flavonoids differentially inhibit guinea pig epidermal cytosolic phospholipase A2.	2001 Nov-Dec	11993721
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
Cloning of parsley flavone synthase I.	2001 Sep	11524111
Identification and determination of glucuronides and their aglycones in Erigeron breviscapus by liquid chromatography-tandem mass spectrometry.	2001 Sep 14	11587333
Hyaluronan enters keratinocytes by a novel endocytic route for catabolism.	2001 Sep 14	11451952
Absorption and metabolism of flavonoids in the caco-2 cell culture model and a perused rat intestinal model.	2002 Apr	11901089
Botanical antioxidants for chemoprevention of photocarcinogenesis.	2002 Apr 1	11897547
Functional interaction of protein kinase CK2 and c-Myc in lymphomagenesis.	2002 Aug 8	12149649
Effect of six flavonoid compounds from Ixeris sonchifolia on stimulus-induced superoxide generation and tyrosyl phosphorylation in human neutrophils.	2002 Feb	11750278
Flavonoids inhibit genetic toxicity produced by carcinogens in cells expressing CYP1A2 and CYP1A1.	2002 Jan	11752233
Effects of apigenin on the serum- and platelet derived growth factor-BB-induced proliferation of rat aortic vascular smooth muscle cells.	2002 Jul	12142993
Antiproliferative constituents in plants 10. Flavones from the leaves of Lantana montevidensis Briq. and consideration of structure-activity relationship.	2002 Jul	12132661
In vitro properties of a recombinant flavonol synthase from Arabidopsis thaliana.	2002 Jul	12126705
Phytochemical constituents from the herba of Artemisia apiacea.	2002 Jun	12135098
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
Induction of human UDP-glucuronosyltransferase UGT1A1 by flavonoids-structural requirements.	2002 May	11950788
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
Flavonoids from Ficaria verna Huds.	2002 May-Jun	12132681
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 `Thu Jul 06 01:24:19 UTC 2023` Edited by `admin` on `Thu Jul 06 01:24:19 UTC 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)