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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

Targets

Targets

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

PubMed

TitleDatePubMed
Study of biochemical prevalence indicators for the assessment of iodine deficiency disorders in adults at field conditions in Gujarat (India).
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
A new flavone derivative from Ehretia ovalifolia leaves.
2001 Aug
Acylated apigenin glycosides from alfalfa (Medicago sativa L.) var. Artal.
2001 Aug
[Investigation on method speliality in identifying Fructus Crataegi with vitexin rhamnoside].
2001 Dec
Alfalfa (Medicago sativa L.) flavonoids. 1. Apigenin and luteolin glycosides from aerial parts.
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
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
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
[Comparison of photometric, electrochemical and post-column fluorescence detection for the determination of flavonoids by HPLC].
2001 Jun
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
Phosphorylation by the protein kinase CK2 promotes calpain-mediated degradation of IkappaBalpha.
2001 Nov 1
Flavonoids differentially inhibit guinea pig epidermal cytosolic phospholipase A2.
2001 Nov-Dec
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
Cloning of parsley flavone synthase I.
2001 Sep
Identification and determination of glucuronides and their aglycones in Erigeron breviscapus by liquid chromatography-tandem mass spectrometry.
2001 Sep 14
Hyaluronan enters keratinocytes by a novel endocytic route for catabolism.
2001 Sep 14
Absorption and metabolism of flavonoids in the caco-2 cell culture model and a perused rat intestinal model.
2002 Apr
Botanical antioxidants for chemoprevention of photocarcinogenesis.
2002 Apr 1
Functional interaction of protein kinase CK2 and c-Myc in lymphomagenesis.
2002 Aug 8
Effect of six flavonoid compounds from Ixeris sonchifolia on stimulus-induced superoxide generation and tyrosyl phosphorylation in human neutrophils.
2002 Feb
Flavonoids inhibit genetic toxicity produced by carcinogens in cells expressing CYP1A2 and CYP1A1.
2002 Jan
Effects of apigenin on the serum- and platelet derived growth factor-BB-induced proliferation of rat aortic vascular smooth muscle cells.
2002 Jul
Antiproliferative constituents in plants 10. Flavones from the leaves of Lantana montevidensis Briq. and consideration of structure-activity relationship.
2002 Jul
In vitro properties of a recombinant flavonol synthase from Arabidopsis thaliana.
2002 Jul
Phytochemical constituents from the herba of Artemisia apiacea.
2002 Jun
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
Induction of human UDP-glucuronosyltransferase UGT1A1 by flavonoids-structural requirements.
2002 May
Rapid quantification of constituents in St. John's wort extracts by NIR spectroscopy.
2002 May 15
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
Flavonoids from Ficaria verna Huds.
2002 May-Jun
Structural requirements of flavonoids for inhibition of antigen-Induced degranulation, TNF-alpha and IL-4 production from RBL-2H3 cells.
2002 Oct
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 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
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 Thu Jul 06 01:24:19 UTC 2023 , Edited by admin on Thu Jul 06 01:24:19 UTC 2023
DSLD 1394 (Number of products:104)
Created by admin on Thu Jul 06 01:24:19 UTC 2023 , Edited by admin on Thu Jul 06 01:24:19 UTC 2023
NCI_THESAURUS C68464
Created by admin on Thu Jul 06 01:24:19 UTC 2023 , Edited by admin on Thu Jul 06 01:24:19 UTC 2023
Code System Code Type Description
MERCK INDEX
M1987
Created by admin on Thu Jul 06 01:24:19 UTC 2023 , Edited by admin on Thu Jul 06 01:24:19 UTC 2023
PRIMARY Merck Index
RS_ITEM_NUM
1040683
Created by admin on Thu Jul 06 01:24:19 UTC 2023 , Edited by admin on Thu Jul 06 01:24:19 UTC 2023
PRIMARY
HSDB
7573
Created by admin on Thu Jul 06 01:24:19 UTC 2023 , Edited by admin on Thu Jul 06 01:24:19 UTC 2023
PRIMARY
ECHA (EC/EINECS)
208-292-3
Created by admin on Thu Jul 06 01:24:19 UTC 2023 , Edited by admin on Thu Jul 06 01:24:19 UTC 2023
PRIMARY
MESH
D047310
Created by admin on Thu Jul 06 01:24:19 UTC 2023 , Edited by admin on Thu Jul 06 01:24:19 UTC 2023
PRIMARY
SMS_ID
100000183496
Created by admin on Thu Jul 06 01:24:19 UTC 2023 , Edited by admin on Thu Jul 06 01:24:19 UTC 2023
PRIMARY
CAS
520-36-5
Created by admin on Thu Jul 06 01:24:19 UTC 2023 , Edited by admin on Thu Jul 06 01:24:19 UTC 2023
PRIMARY
DAILYMED
7V515PI7F6
Created by admin on Thu Jul 06 01:24:19 UTC 2023 , Edited by admin on Thu Jul 06 01:24:19 UTC 2023
PRIMARY
NSC
83244
Created by admin on Thu Jul 06 01:24:19 UTC 2023 , Edited by admin on Thu Jul 06 01:24:19 UTC 2023
PRIMARY
DRUG BANK
DB07352
Created by admin on Thu Jul 06 01:24:19 UTC 2023 , Edited by admin on Thu Jul 06 01:24:19 UTC 2023
PRIMARY
WIKIPEDIA
APIGENIN
Created by admin on Thu Jul 06 01:24:19 UTC 2023 , Edited by admin on Thu Jul 06 01:24:19 UTC 2023
PRIMARY
PUBCHEM
5280443
Created by admin on Thu Jul 06 01:24:19 UTC 2023 , Edited by admin on Thu Jul 06 01:24:19 UTC 2023
PRIMARY
FDA UNII
7V515PI7F6
Created by admin on Thu Jul 06 01:24:19 UTC 2023 , Edited by admin on Thu Jul 06 01:24:19 UTC 2023
PRIMARY
EPA CompTox
DTXSID6022391
Created by admin on Thu Jul 06 01:24:19 UTC 2023 , Edited by admin on Thu Jul 06 01:24:19 UTC 2023
PRIMARY
RXCUI
1368130
Created by admin on Thu Jul 06 01:24:19 UTC 2023 , Edited by admin on Thu Jul 06 01:24:19 UTC 2023
PRIMARY RxNorm
CHEBI
18388
Created by admin on Thu Jul 06 01:24:19 UTC 2023 , Edited by admin on Thu Jul 06 01:24:19 UTC 2023
PRIMARY
NCI_THESAURUS
C68466
Created by admin on Thu Jul 06 01:24:19 UTC 2023 , Edited by admin on Thu Jul 06 01:24:19 UTC 2023
PRIMARY
CHEBI
58470
Created by admin on Thu Jul 06 01:24:19 UTC 2023 , Edited by admin on Thu Jul 06 01:24:19 UTC 2023
PRIMARY
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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.
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53% Cell growth rate of human acute promyelocytic leukemia HL-60 cells at 50 uM of compound vs control
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