Details
Stereochemistry | ACHIRAL |
Molecular Formula | C9H8O4 |
Molecular Weight | 180.1574 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)\C=C\C1=CC(O)=C(O)C=C1
InChI
InChIKey=QAIPRVGONGVQAS-DUXPYHPUSA-N
InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+
Molecular Formula | C9H8O4 |
Molecular Weight | 180.1574 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
Caffeic acid is an organic compound that is classified as a hydroxycinnamic acid. Caffeic acid is naturally found in many agricultural products, such as fruit, vegetables, wine, olive oil, and coffee, and therefore, significantly present in human diet. Caffeic acid has been reported to have a wide variety of biological activities, including antioxidants, antithrombosis, antihypertensive, antifibrosis, antiviral and anti-tumor properties. Caffeic acid can be effectively employed as a natural antioxidant in various food products such as oils. Caffeic acid exhibits potent anticancer effect in HT-1080 cell line and that it may be used as an anticancer agent. Caffeic acid showed neuroprotective action against oxidative and DNA damage produced in the kindling epilepsy model, although they did not produce antiepileptogenic effect in vivo. Caffeic acid was effective in patients with primary immune thrombocytopenia. Detected in clinical trial caffeic acid-related adverse events were: mild nausea and elevation of liver enzymes.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: WP254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21116690 |
|||
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Inhibition of HIV-1 proteinase by non-peptide carboxylates. | 1991 Apr 15 |
|
In vitro and in vivo reversible and irreversible inhibition of rat glutathione S-transferase isoenzymes by caffeic acid and its 2-S-glutathionyl conjugate. | 1993 Jul |
|
Inhibitors of HIV-1 replication [corrected; erratum to be published] that inhibit HIV integrase. | 1996 Jun 25 |
|
Dicaffeoylquinic acid inhibitors of human immunodeficiency virus integrase: inhibition of the core catalytic domain of human immunodeficiency virus integrase. | 1996 Oct |
|
Dicaffeoylquinic and dicaffeoyltartaric acids are selective inhibitors of human immunodeficiency virus type 1 integrase. | 1998 Jan |
|
Structure-activity relationships: analogues of the dicaffeoylquinic and dicaffeoyltartaric acids as potent inhibitors of human immunodeficiency virus type 1 integrase and replication. | 1999 Feb 11 |
|
Steroid hormone activity of flavonoids and related compounds. | 2000 Jul |
|
15-LOX-1: a novel molecular target of nonsteroidal anti-inflammatory drug-induced apoptosis in colorectal cancer cells. | 2000 Jul 19 |
|
Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase. | 2001 Feb |
|
Nonsteroidal anti-inflammatory drugs induce apoptosis in esophageal cancer cells by restoring 15-lipoxygenase-1 expression. | 2001 Jun 15 |
|
Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation. | 2004 Jul 2 |
|
Protective effect of Mesona procumbens against tert-butyl hydroperoxide-induced acute hepatic damage in rats. | 2004 Jun 30 |
|
Urinary flavonoids and phenolic acids as biomarkers of intake for polyphenol-rich foods. | 2006 Jul |
|
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
|
Anti-inflammatory and anti-atherogenic effects of cathechin, caffeic acid and trans-resveratrol in apolipoprotein E deficient mice. | 2007 Apr |
|
Transcriptional regulation of deoxynivalenol-induced IL-8 expression in human monocytes. | 2007 Oct |
|
Protection of mouse brain from aluminum-induced damage by caffeic acid. | 2008 Spring |
|
Oxygen-glucose deprivation activates 5-lipoxygenase mediated by oxidative stress through the p38 mitogen-activated protein kinase pathway in PC12 cells. | 2009 Mar |
|
Preventive effect of caffeic acid on lysosomal dysfunction in isoproterenol-induced myocardial infarcted rats. | 2010 Mar-Apr |
|
Caffeic acid protects rat heart mitochondria against isoproterenol-induced oxidative damage. | 2010 Nov |
|
Interaction of cinnamic acid derivatives with commercial hypoglycemic drugs on 2-deoxyglucose uptake in 3T3-L1 adipocytes. | 2011 Sep 28 |
|
Design, synthesis, and molecular hybrids of caudatin and cinnamic acids as novel anti-hepatitis B virus agents. | 2012 Aug |
|
Activity of caffeic acid derivatives against Candida albicans biofilm. | 2014 Mar 15 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT03070262
300mg three times a day
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21116690
Caffeic acid treatment significantly increased ROS level in HT-1080 cells. Among all the doses tested, 50 ug/ml of Caffeic acid showed the maximum generation of ROS (95%) in HT-1080 cells.
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 00:51:19 UTC 2023
by
admin
on
Thu Jul 06 00:51:19 UTC 2023
|
Record UNII |
U2S3A33KVM
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C68539
Created by
admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
|
||
|
DSLD |
1678 (Number of products:14)
Created by
admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
U2S3A33KVM
Created by
admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
|
PRIMARY | |||
|
16433
Created by
admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
|
PRIMARY | |||
|
C68540
Created by
admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
|
PRIMARY | |||
|
206-361-2
Created by
admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
|
PRIMARY | |||
|
C040048
Created by
admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
|
PRIMARY | |||
|
57197
Created by
admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
|
PRIMARY | |||
|
100000174372
Created by
admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
|
PRIMARY | |||
|
689043
Created by
admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
|
PRIMARY | |||
|
CAFFEIC ACID
Created by
admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
|
PRIMARY | |||
|
331-39-5
Created by
admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
|
NON-SPECIFIC STEREOCHEMISTRY | |||
|
1311397
Created by
admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
|
PRIMARY | RxNorm | ||
|
M2908
Created by
admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
|
PRIMARY | Merck Index | ||
|
331-39-5
Created by
admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
|
PRIMARY | |||
|
501-16-6
Created by
admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
|
PRIMARY | |||
|
U2S3A33KVM
Created by
admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
|
PRIMARY | |||
|
DB01880
Created by
admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
|
PRIMARY | |||
|
17395
Created by
admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
|
PRIMARY | |||
|
623438
Created by
admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
19.2% reaction on PG synthase w/10.0 mM conc. of compound
|
||
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE -> PARENT |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |