U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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(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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Central benzodiazepine receptor (bovine)
3.0 µM [Ki]
PubMed

PubMed

TitleDatePubMed
Inhibition of aromatase activity by flavonoids.
1999 Jun
Flavones and sesquiterpene lactones from Achillea atrata subsp. multifida: antimicrobial activity.
1999 Jun
Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines.
2000 Jul-Aug
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
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
Seasonal and population variation in flavonoid and alliarinoside content of Alliaria petiolata.
2001 Aug
Samioside, a new phenylethanoid glycoside with free-radical scavenging and antimicrobial activities from Phlomis samia.
2001 Aug
Phenolic constituents and antioxidant activity of an extract of Anthuriumversicolor leaves.
2001 Aug
[Investigation on method speliality in identifying Fructus Crataegi with vitexin rhamnoside].
2001 Dec
Differential expression of two cytochrome P450s involved in the biosynthesis of flavones and anthocyanins in chemo-varietal forms of Perilla frutescens.
2001 Dec
Inhibitory effect of decoction of Perilla frutescens on cultured murine mesangial cell proliferation and quantitative analysis of its active constituents.
2001 Feb
Alfalfa (Medicago sativa L.) flavonoids. 1. Apigenin and luteolin glycosides from aerial parts.
2001 Feb
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
LC coupled to ion-trap MS for the rapid screening and detection of polyphenol antioxidants from Helichrysum stoechas.
2001 Jan
A distinctive flavonoid chemistry for the anomalous genus Biebersteinia.
2001 Jan
Aquiledine and isoaquiledine, novel flavonoid alkaloids from Aquilegia ecalcarata.
2001 Jan
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
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 characters contributing to the taxonomic revision of the Hebe parviflora complex.
2001 Mar
Modulation of multidrug resistance protein 1 (MRP1/ABCC1) transport and atpase activities by interaction with dietary flavonoids.
2001 May
Effects of structurally related flavonoids on cell cycle progression of human melanoma cells: regulation of cyclin-dependent kinases CDK2 and CDK1.
2001 May 15
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
Suppression of inducible cyclooxygenase and nitric oxide synthase through activation of peroxisome proliferator-activated receptor-gamma by flavonoids in mouse macrophages.
2001 May 4
In vivo hepatoprotective activity of active fraction from ethanolic extract of Eclipta alba leaves.
2001 Oct
Effect of oral treatment of Perilla frutescens and its constituents on type-I allergy in mice.
2001 Oct
Selective growth-inhibitory, cell-cycle deregulatory and apoptotic response of apigenin in normal versus human prostate carcinoma cells.
2001 Oct 5
No evidence for the in vivo activity of aromatase-inhibiting flavonoids.
2001 Sep
Regeneration in avian hair cell epithelia: identification of intracellular signals required for S-phase entry.
2001 Sep
Induction of a dopaminergic phenotype in cultured striatal neurons by bone morphogenetic proteins.
2001 Sep 23
Dietary flavonoids: bioavailability, metabolic effects, and safety.
2002
Effects of intrinsic fluorescence and quenching on fluorescence-based screening of natural products.
2002 Apr
Scutellarein 4'-methyl ether glycosides as taxonomic markers in Teucridium and Tripora (Lamiaceae, Ajugoideae).
2002 Aug
Regulation of histone deacetylase 2 by protein kinase CK2.
2002 Aug 30
Flavonoids inhibit genetic toxicity produced by carcinogens in cells expressing CYP1A2 and CYP1A1.
2002 Jan
Oxidation of quercetin by salivary components. Quercetin-dependent reduction of salivary nitrite under acidic conditions producing nitric oxide.
2002 Jul 17
Interactions of different phenolic acids and flavonoids with soy proteins.
2002 Jun 18
Effects of flavonoid phytochemicals on cortisol production and on activities of steroidogenic enzymes in human adrenocortical H295R cells.
2002 Mar
Relationships of urinary phyto-oestrogen excretion to BMD in postmenopausal women.
2002 Mar
In vitro investigation of cytochrome P450-mediated metabolism of dietary flavonoids.
2002 May
Molecular modeling of flavonoids that inhibits xanthine oxidase.
2002 May 31
Flavonoids from Ficaria verna Huds.
2002 May-Jun
High-affinity activators of cystic fibrosis transmembrane conductance regulator (CFTR) chloride conductance identified by high-throughput screening.
2002 Oct 4
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
  • 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
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)
Created by admin on Fri Dec 16 23:49:07 UTC 2022 , Edited by admin on Fri Dec 16 23:49:07 UTC 2022
DSLD 1394 (Number of products:104)
Created by admin on Fri Dec 16 23:49:07 UTC 2022 , Edited by admin on Fri Dec 16 23:49:07 UTC 2022
NCI_THESAURUS C68464
Created by admin on Fri Dec 16 23:49:07 UTC 2022 , Edited by admin on Fri Dec 16 23:49:07 UTC 2022
Code System Code Type Description
MERCK INDEX
M1987
Created by admin on Fri Dec 16 23:49:07 UTC 2022 , Edited by admin on Fri Dec 16 23:49:07 UTC 2022
PRIMARY Merck Index
RS_ITEM_NUM
1040683
Created by admin on Fri Dec 16 23:49:07 UTC 2022 , Edited by admin on Fri Dec 16 23:49:07 UTC 2022
PRIMARY
HSDB
7573
Created by admin on Fri Dec 16 23:49:07 UTC 2022 , Edited by admin on Fri Dec 16 23:49:07 UTC 2022
PRIMARY
ECHA (EC/EINECS)
208-292-3
Created by admin on Fri Dec 16 23:49:07 UTC 2022 , Edited by admin on Fri Dec 16 23:49:07 UTC 2022
PRIMARY
MESH
D047310
Created by admin on Fri Dec 16 23:49:07 UTC 2022 , Edited by admin on Fri Dec 16 23:49:07 UTC 2022
PRIMARY
CAS
520-36-5
Created by admin on Fri Dec 16 23:49:07 UTC 2022 , Edited by admin on Fri Dec 16 23:49:07 UTC 2022
PRIMARY
DAILYMED
7V515PI7F6
Created by admin on Fri Dec 16 23:49:07 UTC 2022 , Edited by admin on Fri Dec 16 23:49:07 UTC 2022
PRIMARY
NSC
83244
Created by admin on Fri Dec 16 23:49:07 UTC 2022 , Edited by admin on Fri Dec 16 23:49:07 UTC 2022
PRIMARY
DRUG BANK
DB07352
Created by admin on Fri Dec 16 23:49:07 UTC 2022 , Edited by admin on Fri Dec 16 23:49:07 UTC 2022
PRIMARY
WIKIPEDIA
APIGENIN
Created by admin on Fri Dec 16 23:49:07 UTC 2022 , Edited by admin on Fri Dec 16 23:49:07 UTC 2022
PRIMARY
PUBCHEM
5280443
Created by admin on Fri Dec 16 23:49:07 UTC 2022 , Edited by admin on Fri Dec 16 23:49:07 UTC 2022
PRIMARY
FDA UNII
7V515PI7F6
Created by admin on Fri Dec 16 23:49:07 UTC 2022 , Edited by admin on Fri Dec 16 23:49:07 UTC 2022
PRIMARY
EPA CompTox
DTXSID6022391
Created by admin on Fri Dec 16 23:49:07 UTC 2022 , Edited by admin on Fri Dec 16 23:49:07 UTC 2022
PRIMARY
RXCUI
1368130
Created by admin on Fri Dec 16 23:49:07 UTC 2022 , Edited by admin on Fri Dec 16 23:49:07 UTC 2022
PRIMARY RxNorm
CHEBI
18388
Created by admin on Fri Dec 16 23:49:07 UTC 2022 , Edited by admin on Fri Dec 16 23:49:07 UTC 2022
PRIMARY
NCI_THESAURUS
C68466
Created by admin on Fri Dec 16 23:49:07 UTC 2022 , Edited by admin on Fri Dec 16 23:49:07 UTC 2022
PRIMARY
CHEBI
58470
Created by admin on Fri Dec 16 23:49:07 UTC 2022 , Edited by admin on Fri Dec 16 23:49:07 UTC 2022
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
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.
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
53% Cell growth rate of human acute promyelocytic leukemia HL-60 cells at 50 uM of compound vs control
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
ACTIVE MOIETY