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

Details

Stereochemistry ACHIRAL
Molecular Formula C10H10O4
Molecular Weight 194.184
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of FERULIC ACID

SMILES

COC1=CC(\C=C\C(O)=O)=CC=C1O

InChI

InChIKey=KSEBMYQBYZTDHS-HWKANZROSA-N
InChI=1S/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+

HIDE SMILES / InChI
Molecular Formula C10H10O4
Molecular Weight 194.184
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Approval Year

2009
359
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 9.78 µM [Ki]
Inhibitor
8297
 9.87 µM [Ki]
Inhibitor
8297
 7.41 µM [Ki]
Inhibitor
8297
 9.43 µM [Ki]
Inhibitor
8297
 7.04 µM [Ki]
Inhibitor
8297
 2.89 µM [Ki]
Inhibitor
8297
 2.4 µM [Ki]
Inhibitor
8297
 3.78 µM [IC50]
PubMed

PubMed

TitleDatePubMed
Isolation and quantitation of steroids from normal human amniotic fluid.
1968 Aug
Curcumin and curcumin derivatives inhibit Tat-mediated transactivation of type 1 human immunodeficiency virus long terminal repeat.
1998 Jan-Feb
Investigation of the potential of capillary electrophoresis with off-line matrix-assisted laser desorption/ionization time-of-flight mass spectrometry for clinical analysis: examination of a glycoprotein factor associated with cancer cachexia.
1999 Feb 15
Bioactive constituents of the bark of Parkia biglobosa.
2000 Apr
In vitro and in vivo evaluation of caffeic and ferulic acids as topical photoprotective agents.
2000 Apr 10
Metabolites of orally administered Perilla frutescens extract in rats and humans.
2000 Jan
Antioxidant effect of ferulic acid in isolated membranes and intact cells: synergistic interactions with alpha-tocopherol, beta-carotene, and ascorbic acid.
2004 Apr 21
Rye bran bread intake elevates urinary excretion of ferulic acid in humans, but does not affect the susceptibility of LDL to oxidation ex vivo.
2004 Aug
Ferulic acid inhibits endothelial cell proliferation through NO down-regulating ERK1/2 pathway.
2004 Dec 15
Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation.
2004 Jul 2
Antitubercular constituents of Valeriana laxiflora.
2004 Jun
Influence of ferulic acid on circulatory prooxidant-antioxidant status during alcohol and PUFA induced toxicity.
2004 Sep
Ferulic acid inhibits vascular smooth muscle cell proliferation induced by angiotensin II.
2004 Sep 19
Interactions of human serum albumin with chlorogenic acid and ferulic acid.
2004 Sep 24
Ferulic acid, a natural protector against carbon tetrachloride-induced toxicity.
2005 Aug
Absorption, metabolism, degradation and urinary excretion of rosmarinic acid after intake of Perilla frutescens extract in humans.
2005 Feb
Antioxidant and antigenotoxic effects of plant cell wall hydroxycinnamic acids in cultured HT-29 cells.
2005 Jun
Modulation of hepatic phase II phenol sulfotransferase and antioxidant status by phenolic acids in rats.
2006 Aug
Synergistic salubrious effect of ferulic acid and ascorbic acid on membrane-bound phosphatases and lysosomal hydrolases during experimental myocardial infarction in rats.
2006 Dec 23
Synergistic interactions of ferulic acid with ascorbic acid: its cardioprotective role during isoproterenol induced myocardial infarction in rats.
2006 Feb
Attenuation of abnormalities in the lipid metabolism during experimental myocardial infarction induced by isoproterenol in rats: beneficial effect of ferulic acid and ascorbic acid.
2006 May
Analysis of interaction property of bioactive components in Danggui Buxue Decoction with protein by microdialysis coupled with HPLC-DAD-MS.
2007 Jun 1
Predicting the biological activities of 2-methoxyphenol antioxidants: effects of dimers.
2007 Mar-Apr
Exposure to metal ions regulates mRNA levels of APP and BACE1 in PC12 cells: blockage by curcumin.
2008 Aug 8
Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines.
2008 Dec 15
Influence of ferulic acid on nicotine-induced lipid peroxidation, DNA damage and inflammation in experimental rats as compared to N-acetylcysteine.
2008 Jan 20
Anti-atherogenic property of ferulic acid in apolipoprotein E-deficient mice fed Western diet: comparison with clofibrate.
2010 Aug-Sep
Restoration of altered microRNA expression in the ischemic heart with resveratrol.
2010 Dec 23
Anti-inflammatory effects of dietary phenolic compounds in an in vitro model of inflamed human intestinal epithelium.
2010 Dec 5
Biochemical mechanism of caffeic acid phenylethyl ester (CAPE) selective toxicity towards melanoma cell lines.
2010 Oct 6
Ferulic acid protects against carbon tetrachloride-induced liver injury in mice.
2011 Apr 11
Celastrol inhibits Tat-mediated human immunodeficiency virus (HIV) transcription and replication.
2011 Jul 29
Interaction of cinnamic acid derivatives with commercial hypoglycemic drugs on 2-deoxyglucose uptake in 3T3-L1 adipocytes.
2011 Sep 28
Inhibitory effects of caffeic acid phenethyl ester derivatives on replication of hepatitis C virus.
2013
Anticonvulsant and behavioral effects observed in mice following treatment with an ester derivative of ferulic acid: Isopentyl ferulate.
2015 Dec 5
Patents

Patents

JP1013016A
2
JP2000041622A
2
JP2000125840A
2
JP2000129257A
2
JP2000229913A
2
JP2000247900A
4
JP2000273019A
3
JP2000308477A
4
JP2000325015A
2
JP2000325049A
2
JP2001161314A
2
JP2001253863A
2
JP2001354556A
2
JP2002003386A
2
JP2002030039A
2
JP2002053464A
4
JP2002080354A
4
JP2002080355A
4
JP2002080356A
4
JP2002080357A
4
JP2002080381A
4
JP2002145765A
4
JP2002145766A
2
JP2002145767A
2
JP2002154977A
4
JP2002180081A
7
JP2002255778A
10
JP2002291406A
4
JP2002291437A
2
JP2002363075A
2
JP2002371002A
2
JP2002533379A
53
JP2002541233A
400
JP2003033196A
7
JP2003038144A
2
JP2003040709A
2
JP2003055182A
2
JP2003081824A
4
JP2003128632A
2
JP2003128633A
2
JP2003212774A
2
JP2003261444A
4
JP2003292410A
2
JP2003515526A
462
JP2003516112A
4
JP2003531246A
4
JP2003531247A
7
JP2004026657A
2
JP2004049186A
2
JP2004065156A
2
JP2004137287A
4
Substance Class Chemical
Created
by admin
on Sat Dec 16 20:00:10 GMT 2023
Edited
by admin
on Sat Dec 16 20:00:10 GMT 2023
Record UNII
AVM951ZWST
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FERULIC ACID
HSDB   INCI   MI   USP-RS   WHO-DD  
INCI  
Official Name English
FERULIC ACID [INCI]
Common Name English
Ferulic acid [WHO-DD]
Common Name English
NSC-51986
Code English
4-HYDROXY-3-METHOXYCINNAMIC ACID
Systematic Name English
(E)-3-(4-HYDROXY-3-METHOXY-PHENYL)PROP-2-ENOIC ACID
Systematic Name English
(E)-FERULIC ACID
Common Name English
FERULIC ACID [USP-RS]
Common Name English
CONIFERIC ACID
Systematic Name English
Trans-Ferulic acid [WHO-DD]
Common Name English
FERULIC ACID (CONSTITUENT OF BLACK COHOSH) [DSC]
Common Name English
NSC-674320
Code English
TRANS-FERULIC ACID
Common Name English
FERULIC ACID [MI]
Common Name English
FERULIC ACID [HSDB]
Common Name English
NSC-2821
Code English
2-PROPENOIC ACID, 3-(4-HYDROXY-3-METHOXYPHENYL)-, (2E)-
Systematic Name English
Classification Tree Code System Code
DSLD 1643 (Number of products:16)
Created by admin on Sat Dec 16 20:00:10 GMT 2023 , Edited by admin on Sat Dec 16 20:00:10 GMT 2023
FDA ORPHAN DRUG 886422
Created by admin on Sat Dec 16 20:00:10 GMT 2023 , Edited by admin on Sat Dec 16 20:00:10 GMT 2023
Code System Code Type Description
PUBCHEM
445858
Created by admin on Sat Dec 16 20:00:10 GMT 2023 , Edited by admin on Sat Dec 16 20:00:10 GMT 2023
PRIMARY
CAS
537-98-4
Created by admin on Sat Dec 16 20:00:10 GMT 2023 , Edited by admin on Sat Dec 16 20:00:10 GMT 2023
PRIMARY
NSC
2821
Created by admin on Sat Dec 16 20:00:10 GMT 2023 , Edited by admin on Sat Dec 16 20:00:10 GMT 2023
PRIMARY
SMS_ID
100000125953
Created by admin on Sat Dec 16 20:00:10 GMT 2023 , Edited by admin on Sat Dec 16 20:00:10 GMT 2023
PRIMARY
RS_ITEM_NUM
1270311
Created by admin on Sat Dec 16 20:00:10 GMT 2023 , Edited by admin on Sat Dec 16 20:00:10 GMT 2023
PRIMARY
FDA UNII
AVM951ZWST
Created by admin on Sat Dec 16 20:00:10 GMT 2023 , Edited by admin on Sat Dec 16 20:00:10 GMT 2023
PRIMARY
NSC
674320
Created by admin on Sat Dec 16 20:00:10 GMT 2023 , Edited by admin on Sat Dec 16 20:00:10 GMT 2023
PRIMARY
ECHA (EC/EINECS)
214-490-0
Created by admin on Sat Dec 16 20:00:10 GMT 2023 , Edited by admin on Sat Dec 16 20:00:10 GMT 2023
PRIMARY
CAS
1135-24-6
Created by admin on Sat Dec 16 20:00:10 GMT 2023 , Edited by admin on Sat Dec 16 20:00:10 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
NSC
51986
Created by admin on Sat Dec 16 20:00:10 GMT 2023 , Edited by admin on Sat Dec 16 20:00:10 GMT 2023
PRIMARY
DRUG BANK
DB07767
Created by admin on Sat Dec 16 20:00:10 GMT 2023 , Edited by admin on Sat Dec 16 20:00:10 GMT 2023
PRIMARY
WIKIPEDIA
FERULIC ACID
Created by admin on Sat Dec 16 20:00:10 GMT 2023 , Edited by admin on Sat Dec 16 20:00:10 GMT 2023
PRIMARY
CHEBI
17620
Created by admin on Sat Dec 16 20:00:10 GMT 2023 , Edited by admin on Sat Dec 16 20:00:10 GMT 2023
PRIMARY
RXCUI
1368647
Created by admin on Sat Dec 16 20:00:10 GMT 2023 , Edited by admin on Sat Dec 16 20:00:10 GMT 2023
PRIMARY RxNorm
DAILYMED
AVM951ZWST
Created by admin on Sat Dec 16 20:00:10 GMT 2023 , Edited by admin on Sat Dec 16 20:00:10 GMT 2023
PRIMARY
MESH
C004999
Created by admin on Sat Dec 16 20:00:10 GMT 2023 , Edited by admin on Sat Dec 16 20:00:10 GMT 2023
PRIMARY
HSDB
7663
Created by admin on Sat Dec 16 20:00:10 GMT 2023 , Edited by admin on Sat Dec 16 20:00:10 GMT 2023
PRIMARY
MERCK INDEX
m5359
Created by admin on Sat Dec 16 20:00:10 GMT 2023 , Edited by admin on Sat Dec 16 20:00:10 GMT 2023
PRIMARY Merck Index
EVMPD
SUB32804
Created by admin on Sat Dec 16 20:00:10 GMT 2023 , Edited by admin on Sat Dec 16 20:00:10 GMT 2023
PRIMARY
Related Record Type Details
MENYANTHES TRIFOLIATA LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
BLACK COHOSH
PARENT -> CONSTITUENT ALWAYS PRESENT
Structure of PIPERAZINE BISFERULATE
SALT/SOLVATE -> PARENT
FERULA ASSA-FOETIDA RESIN
PARENT -> CONSTITUENT ALWAYS PRESENT
ANGELICA SINENSIS ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
ASSAY (HPLC)
Structure of SODIUM FERULATE
SALT/SOLVATE -> PARENT
IPOMOEA AQUATICA LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
98.1% reaction on PG synthase w/10.0 mM conc. of compound
CENTAURIUM ERYTHRAEA WHOLE
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
Structure of FERULIC ACID
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966