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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

2012
595
Targets

Targets

Primary TargetPharmacologyConditionPotency
Central benzodiazepine receptor (bovine)
1
Target ID: Central benzodiazepine receptor (bovine)
Binding Agent
1064
 3.0 µM [Ki]
Antagonist
2778
Antagonist
2778
Antagonist
2778
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
Medicinal and ethnoveterinary remedies of hunters in Trinidad.
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
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
Acylated apigenin glycosides from alfalfa (Medicago sativa L.) var. Artal.
2001 Aug
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
Flavonoids as peroxynitrite scavengers: the role of the hydroxyl groups.
2001 Feb
Peroxidative metabolism of apigenin and naringenin versus luteolin and quercetin: glutathione oxidation and conjugation.
2001 Feb 15
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
Inhibition of inducible nitric oxide synthase and cyclooxygenase-2 expression by flavonoids in macrophage J774A.1.
2001 Jan 12
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
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
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
Cell-based assay for high-throughput quantitative screening of CFTR chloride transport agonists.
2001 Nov
Radiation protection of human lymphocyte chromosomes in vitro by orientin and vicenin.
2001 Nov 15
Flavonoids differentially inhibit guinea pig epidermal cytosolic phospholipase A2.
2001 Nov-Dec
Selective growth-inhibitory, cell-cycle deregulatory and apoptotic response of apigenin in normal versus human prostate carcinoma cells.
2001 Oct 5
Dietary flavonoids: bioavailability, metabolic effects, and safety.
2002
Prevention of cellular ROS damage by isovitexin and related flavonoids.
2002 Apr
Dimerization and phosphorylation of thyrotropin-releasing hormone receptors are modulated by agonist stimulation.
2002 Aug 2
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
Regulatory effects of stem cell factor and interleukin-4 on adhesion of human mast cells to extracellular matrix proteins.
2002 Feb 1
Intracellular flavonoids as electron donors for extracellular ferricyanide reduction in human erythrocytes.
2002 Jan 1
Apigenin and LY294002 prolong EGF-stimulated ERK1/2 activation in PC12 cells but are unable to induce full differentiation.
2002 Jan 16
Rapid quantification of constituents in St. John's wort extracts by NIR spectroscopy.
2002 May 15
Flavonoids from Ficaria verna Huds.
2002 May-Jun
Patents

Patents

05863728
3
JP2000086510A
3
JP2001114675A
7
JP2002528464A
9
JP2003504327A
27
JP2003527441A
7
JP2003532634A
65
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
7
JP2011512798A
9
JP2013539792A
2
JP2014201529A
1
JP4370072B2
48
JP4777515B2
5
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 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
  • 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 15 18:08:18 GMT 2023 , Edited by admin on Fri Dec 15 18:08:18 GMT 2023
DSLD 1394 (Number of products:104)
Created by admin on Fri Dec 15 18:08:18 GMT 2023 , Edited by admin on Fri Dec 15 18:08:18 GMT 2023
NCI_THESAURUS C68464
Created by admin on Fri Dec 15 18:08:18 GMT 2023 , Edited by admin on Fri Dec 15 18:08:18 GMT 2023
Code System Code Type Description
MERCK INDEX
m1987
Created by admin on Fri Dec 15 18:08:18 GMT 2023 , Edited by admin on Fri Dec 15 18:08:18 GMT 2023
PRIMARY Merck Index
RS_ITEM_NUM
1040683
Created by admin on Fri Dec 15 18:08:18 GMT 2023 , Edited by admin on Fri Dec 15 18:08:18 GMT 2023
PRIMARY
HSDB
7573
Created by admin on Fri Dec 15 18:08:18 GMT 2023 , Edited by admin on Fri Dec 15 18:08:18 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-292-3
Created by admin on Fri Dec 15 18:08:18 GMT 2023 , Edited by admin on Fri Dec 15 18:08:18 GMT 2023
PRIMARY
MESH
D047310
Created by admin on Fri Dec 15 18:08:18 GMT 2023 , Edited by admin on Fri Dec 15 18:08:18 GMT 2023
PRIMARY
SMS_ID
100000183496
Created by admin on Fri Dec 15 18:08:18 GMT 2023 , Edited by admin on Fri Dec 15 18:08:18 GMT 2023
PRIMARY
CAS
520-36-5
Created by admin on Fri Dec 15 18:08:18 GMT 2023 , Edited by admin on Fri Dec 15 18:08:18 GMT 2023
PRIMARY
DAILYMED
7V515PI7F6
Created by admin on Fri Dec 15 18:08:18 GMT 2023 , Edited by admin on Fri Dec 15 18:08:18 GMT 2023
PRIMARY
NSC
83244
Created by admin on Fri Dec 15 18:08:18 GMT 2023 , Edited by admin on Fri Dec 15 18:08:18 GMT 2023
PRIMARY
DRUG BANK
DB07352
Created by admin on Fri Dec 15 18:08:18 GMT 2023 , Edited by admin on Fri Dec 15 18:08:18 GMT 2023
PRIMARY
WIKIPEDIA
APIGENIN
Created by admin on Fri Dec 15 18:08:18 GMT 2023 , Edited by admin on Fri Dec 15 18:08:18 GMT 2023
PRIMARY
PUBCHEM
5280443
Created by admin on Fri Dec 15 18:08:18 GMT 2023 , Edited by admin on Fri Dec 15 18:08:18 GMT 2023
PRIMARY
FDA UNII
7V515PI7F6
Created by admin on Fri Dec 15 18:08:18 GMT 2023 , Edited by admin on Fri Dec 15 18:08:18 GMT 2023
PRIMARY
EPA CompTox
DTXSID6022391
Created by admin on Fri Dec 15 18:08:18 GMT 2023 , Edited by admin on Fri Dec 15 18:08:18 GMT 2023
PRIMARY
RXCUI
1368130
Created by admin on Fri Dec 15 18:08:18 GMT 2023 , Edited by admin on Fri Dec 15 18:08:18 GMT 2023
PRIMARY RxNorm
CHEBI
18388
Created by admin on Fri Dec 15 18:08:18 GMT 2023 , Edited by admin on Fri Dec 15 18:08:18 GMT 2023
PRIMARY
NCI_THESAURUS
C68466
Created by admin on Fri Dec 15 18:08:18 GMT 2023 , Edited by admin on Fri Dec 15 18:08:18 GMT 2023
PRIMARY
CHEBI
58470
Created by admin on Fri Dec 15 18:08:18 GMT 2023 , Edited by admin on Fri Dec 15 18:08:18 GMT 2023
PRIMARY
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Related Record Type Details
Structure of APIGENIN
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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