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

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H18O9
Molecular Weight 354.3087
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CHLOROGENIC ACID

SMILES

O[C@@H]1C[C@](O)(C[C@@H](OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@@H]1O)C(O)=O

InChI

InChIKey=CWVRJTMFETXNAD-JUHZACGLSA-N
InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1

HIDE SMILES / InChI
Z-Chlorogenic acid better known as cis-5-caffeoylquinic acid is a cinnamate ester formed by condensation fo the carboxy group of cis-caffeic acid with the 5-hydroxy group of (+)-quinic acid. It is a naturally occurring isomer of Chlorogenic acid and can be extracted from Nerium indicum flowers, coffee plant, Purpurascen leaves, Artemisia pectinata, and tobacco. In some but not all extractions cis-5caffeoylquinic content is increased after UV exposure of plant or cells.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q16665
Gene ID: 3091.0
Gene Symbol: HIF1A
Target Organism: Homo sapiens (Human)
Target ID: Q9NYA1
Gene ID: 8877.0
Gene Symbol: SPHK1
Target Organism: Homo sapiens (Human)
44.87 µM [EC50]
62.33 µM [EC50]
Conditions
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.7638 ng/mL
3.64 mg single, oral
dose: 3.64 mg
route of administration: Oral
experiment type: SINGLE
co-administered: TAUROCHOLIC ACID
CHLOROGENIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
0.6637 ng/mL
3.64 mg 3 times / day steady-state, oral
dose: 3.64 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: TAUROCHOLIC ACID
CHLOROGENIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
2376 ng/mL
3 mg/kg single, intramuscular
dose: 3 mg/kg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
CHLOROGENIC ACID plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2914 ng/mL
3 mg/kg 1 times / day multiple, intramuscular
dose: 3 mg/kg
route of administration: Intramuscular
experiment type: MULTIPLE
co-administered:
CHLOROGENIC ACID plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1.135 ng × h/L
3.64 mg single, oral
dose: 3.64 mg
route of administration: Oral
experiment type: SINGLE
co-administered: TAUROCHOLIC ACID
CHLOROGENIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1.782 ng × h/L
3.64 mg 3 times / day steady-state, oral
dose: 3.64 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: TAUROCHOLIC ACID
CHLOROGENIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
6124 ng × h/mL
3 mg/kg single, intramuscular
dose: 3 mg/kg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
CHLOROGENIC ACID plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
7199 ng × h/mL
3 mg/kg 1 times / day multiple, intramuscular
dose: 3 mg/kg
route of administration: Intramuscular
experiment type: MULTIPLE
co-administered:
CHLOROGENIC ACID plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.3 h
3.64 mg single, oral
dose: 3.64 mg
route of administration: Oral
experiment type: SINGLE
co-administered: TAUROCHOLIC ACID
CHLOROGENIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1.4 h
3.64 mg 3 times / day steady-state, oral
dose: 3.64 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: TAUROCHOLIC ACID
CHLOROGENIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1 h
3 mg/kg single, intramuscular
dose: 3 mg/kg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
CHLOROGENIC ACID plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.2 h
3 mg/kg 1 times / day multiple, intramuscular
dose: 3 mg/kg
route of administration: Intramuscular
experiment type: MULTIPLE
co-administered:
CHLOROGENIC ACID plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
OverviewDrug as perpetrator​Drug as victimTox targets
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Dietary effects on the uptake of benzo[a]pyrene.
1994 Aug
Action of chlorogenic acid on the complement system.
1999
LC/ES-MS detection of hydroxycinnamates in human plasma and urine.
2001 Apr
Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation.
2004 Jul 2
Inhibition of activator protein-1, NF-kappaB, and MAPKs and induction of phase 2 detoxifying enzyme activity by chlorogenic acid.
2005 Jul 29
Activation of rat liver microsomal glutathione S-transferase by gallic acid.
2005 Nov 19
Absorption and metabolism of caffeic acid and chlorogenic acid in the small intestine of rats.
2006 Jul
Chlorogenic acid is absorbed in its intact form in the stomach of rats.
2006 May
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Analysis of interaction property of bioactive components in Danggui Buxue Decoction with protein by microdialysis coupled with HPLC-DAD-MS.
2007 Jun 1
Examining the genomic influence of skin antioxidants in vitro.
2010
Antihyperlipidemic effect of chlorogenic acid and tetrahydrocurcumin in rats subjected to diabetogenic agents.
2010 Dec 5
Naturally occurring phenolic acids inhibit 12-O-tetradecanoylphorbol-13-acetate induced NF-kappaB, iNOS and COX-2 activation in mouse epidermis.
2010 Jan 31
Biochemical mechanism of caffeic acid phenylethyl ester (CAPE) selective toxicity towards melanoma cell lines.
2010 Oct 6
Looking for the physiological role of anthocyanins in the leaves of Coffea arabica.
2012 Jul-Aug
Chlorogenic acid reduces liver inflammation and fibrosis through inhibition of toll-like receptor 4 signaling pathway.
2013 Jan 7
The therapeutic detoxification of chlorogenic acid against acetaminophen-induced liver injury by ameliorating hepatic inflammation.
2015 Aug 5
Separation and Identification of Phenolic Acid and Flavonoids from Nerium indicum Flowers.
2015 Jan-Feb
Acetaminophen hepatotoxicity and sterile inflammation: The mechanism of protection of Chlorogenic acid.
2016 Jan 5
Patents

Sample Use Guides

In a phase II trial Chlorogenic acid was administered to patients with impaired glucose tolerance. Chlorogenic acid was provided as three 400 mg capsules taken a half hour before meals for 90 days.
Route of Administration: Oral
DU145 cells were maintained in RPMI1640 medium supplemented with 10% fetal bovine serum and penicillin/streptomycin and incubated at 37 deg-C in an atmosphere with 5% CO2. Hypoxic conditions were established in an anaerobic chamber flushed with 1% oxygen, 5% CO2, and 94% nitrogen. Cells were incubated with 50 uM chlorogenic acid in hypoxic conditions for 4 hours to determine the effect of chlorogenic acid on HIF-1a. Chlorogenic acid significantly reduced the hypoxia-induced expression of HIF-1a and expression of Sphingosine Kinase 1 (SPHK-1) returned to normoxic levels. Cells were also treated with various concentrations of chlorogenic acid (0 - 100 uM) for 24 hours and cell viability was decreased by 20%.
Name Type Language
CHLOROGENIC ACID
MI  
Common Name English
5-O-(3,4-DIHYDROXYCINNAMOYL)-L-QUINIC ACID
Common Name English
CYCLOHEXANECARBOXYLIC ACID, 3-(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-1,4,5-TRIHYDROXY-, (1S,3R,4R,5R)-
Systematic Name English
HERIGUARD
Brand Name English
Chlorogenic acid [WHO-DD]
Common Name English
TRANS-CAFFEIC ACID 5-O-D-QUINATE
Common Name English
CYCLOHEXANECARBOXYLIC ACID, 3-((3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENYL)OXY)-1,4,5-TRIHYDROXY-, (1S-(1-.ALPHA.,3-.BETA.,4-.ALPHA.,5-.ALPHA.))-
Common Name English
(+)-CHLOROGENIC ACID
Common Name English
CP CHLOROGENIC ACID
Brand Name English
5-CQA
Common Name English
TRANS-5-O-CAFFEOYLQUINIC ACID
Common Name English
NSC-407296
Code English
NSC-70861
Code English
CHLOROGENIC ACID (CONSTITUENT OF ST. JOHN'S WORT) [DSC]
Common Name English
CYCLOHEXANECARBOXYLIC ACID, 3-((3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENYL)OXY)-1,4,5-TRIHYDROXY-, (1S,3R,4R,5R)-
Common Name English
CHLOROGENIC ACID [USP-RS]
Common Name English
CHLOROGENIC ACID [MI]
Common Name English
CHLOROGENIC ACID (CONSTITUENT OF ECHINACEA ANGUSTIFOLIA ROOT, ECHINACEA PALLIDA ROOT, ECHINACEA PURPUREA ROOT AND ECHINACEA PURPUREA AERIAL PARTS) [DSC]
Common Name English
TRANS-CHLOROGENIC ACID
Common Name English
Classification Tree Code System Code
DSLD 354 (Number of products:22)
Created by admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
NCI_THESAURUS C28203
Created by admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID3024786
Created by admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
PRIMARY
PUBCHEM
1794427
Created by admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
PRIMARY
MESH
D002726
Created by admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
PRIMARY
MERCK INDEX
m3413
Created by admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
PRIMARY Merck Index
DAILYMED
318ADP12RI
Created by admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
PRIMARY
SMS_ID
100000164346
Created by admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
PRIMARY
CAS
202650-88-2
Created by admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
PRIMARY
NSC
407296
Created by admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
PRIMARY
RXCUI
1311387
Created by admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
PRIMARY RxNorm
CAS
327-97-9
Created by admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
DRUG BANK
DB12029
Created by admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
PRIMARY
FDA UNII
318ADP12RI
Created by admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
PRIMARY
NCI_THESAURUS
C116073
Created by admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
PRIMARY NCIT
NSC
70861
Created by admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
PRIMARY
EVMPD
SUB178745
Created by admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
PRIMARY
RS_ITEM_NUM
1115545
Created by admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
PRIMARY
EVMPD
SUB114543
Created by admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
ALTERNATIVE
WIKIPEDIA
CHLOROGENIC ACID
Created by admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
PRIMARY
CHEBI
16112
Created by admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
PRIMARY
ECHA (EC/EINECS)
206-325-6
Created by admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
PRIMARY