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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

Molecular Formula C16H18O9
Molecular Weight 354.3087
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 1
Optical Activity UNSPECIFIED

Chlorogenic acid is the ester of caffeic acid and (-)-quinic acid. Chlorogenic acid is a naturally occurring plant metabolite and can be found with the related compounds cryptochlorgenic acid and neochlorogenic acid in the leaves of Hibiscus sabdariffa, coffee, potato, eggplant, peaches, and prunes. Chlorogenic acid has been investigated as a dietary supplement to improve glucose intolerant hypoglycemia and non-alcoholic fatty liver disease. It has also been identified as a potential anticancer agent by reducing the expression of HIF-1a and Sphingosine Kinase-1. Chlorogenic acid was also identified as a neuraminidase blocker effective against influenza A virus (H1N1 and H3N2).

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
0.6637 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
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
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
1.782 ng × h/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
1.135 ng × h/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
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
1.4 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
1.3 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 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
Acetaminophen hepatotoxicity and sterile inflammation: The mechanism of protection of Chlorogenic acid.
2016-01-05
The therapeutic detoxification of chlorogenic acid against acetaminophen-induced liver injury by ameliorating hepatic inflammation.
2015-08-05
Renoprotective mechanisms of chlorogenic acid in cisplatin-induced kidney injury.
2014-10-03
Separation and Identification of Phenolic Acid and Flavonoids from Nerium indicum Flowers.
2014-02-05
Chlorogenic acid reduces liver inflammation and fibrosis through inhibition of toll-like receptor 4 signaling pathway.
2013-01-07
Inhibitory effects of caffeic acid phenethyl ester derivatives on replication of hepatitis C virus.
2013
Looking for the physiological role of anthocyanins in the leaves of Coffea arabica.
2012-03-01
Interaction of cinnamic acid derivatives with commercial hypoglycemic drugs on 2-deoxyglucose uptake in 3T3-L1 adipocytes.
2011-09-28
Neuroprotective effects of chlorogenic acid on scopolamine-induced amnesia via anti-acetylcholinesterase and anti-oxidative activities in mice.
2010-12-15
Antihyperlipidemic effect of chlorogenic acid and tetrahydrocurcumin in rats subjected to diabetogenic agents.
2010-12-05
Biochemical mechanism of caffeic acid phenylethyl ester (CAPE) selective toxicity towards melanoma cell lines.
2010-10-06
Naturally occurring phenolic acids inhibit 12-O-tetradecanoylphorbol-13-acetate induced NF-kappaB, iNOS and COX-2 activation in mouse epidermis.
2010-01-31
Examining the genomic influence of skin antioxidants in vitro.
2010
Profiling the phenolic compounds of Artemisia pectinata by HPLC-PAD-MSn.
2007-11-13
Novel screening assay for antioxidant protection against peroxyl radical-induced loss of protein function.
2007-11
Analysis of interaction property of bioactive components in Danggui Buxue Decoction with protein by microdialysis coupled with HPLC-DAD-MS.
2007-06-01
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006-11
Absorption and metabolism of caffeic acid and chlorogenic acid in the small intestine of rats.
2006-07
Chlorogenic acid is absorbed in its intact form in the stomach of rats.
2006-05
Activation of rat liver microsomal glutathione S-transferase by gallic acid.
2005-11-19
Inhibition of activator protein-1, NF-kappaB, and MAPKs and induction of phase 2 detoxifying enzyme activity by chlorogenic acid.
2005-07-29
Interactions of human serum albumin with chlorogenic acid and ferulic acid.
2004-09-24
Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation.
2004-07-02
Apple phytochemicals and their health benefits.
2004-05-12
Effects of coffee components on the response of GABA(A) receptors expressed in Xenopus oocytes.
2003-12-17
Effect of antioxidants, oxidants, metals and saliva on cytotoxicity induction by sodium fluoride.
2003-12-12
Chlorogenic acid bioavailability largely depends on its metabolism by the gut microflora in rats.
2003-06
Chlorogenic acid, quercetin-3-rutinoside and black tea phenols are extensively metabolized in humans.
2003-06
Identification of isomeric dicaffeoylquinic acids from Eleutherococcus senticosus using HPLC-ESI/TOF/MS and 1H-NMR methods.
2002-12-24
Glucose 6-phosphate transport in fibroblast microsomes from glycogen storage disease type 1b patients: evidence for multiple glucose 6-phosphate transport systems.
2001-07-15
LC/ES-MS detection of hydroxycinnamates in human plasma and urine.
2001-04
Steroid hormone activity of flavonoids and related compounds.
2000-07
Action of chlorogenic acid on the complement system.
1999
Dietary effects on the uptake of benzo[a]pyrene.
1994-08
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 20:24:08 GMT 2025
Edited
by admin
on Mon Mar 31 20:24:08 GMT 2025
Record UNII
318ADP12RI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CHLOROGENIC ACID
MI  
Common Name English
CP CHLOROGENIC ACID
Preferred 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
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 Mon Mar 31 20:24:08 GMT 2025 , Edited by admin on Mon Mar 31 20:24:08 GMT 2025
NCI_THESAURUS C28203
Created by admin on Mon Mar 31 20:24:08 GMT 2025 , Edited by admin on Mon Mar 31 20:24:08 GMT 2025
Code System Code Type Description
PUBCHEM
1794427
Created by admin on Mon Mar 31 20:24:08 GMT 2025 , Edited by admin on Mon Mar 31 20:24:08 GMT 2025
PRIMARY
MESH
D002726
Created by admin on Mon Mar 31 20:24:08 GMT 2025 , Edited by admin on Mon Mar 31 20:24:08 GMT 2025
PRIMARY
MERCK INDEX
m3413
Created by admin on Mon Mar 31 20:24:08 GMT 2025 , Edited by admin on Mon Mar 31 20:24:08 GMT 2025
PRIMARY Merck Index
DAILYMED
318ADP12RI
Created by admin on Mon Mar 31 20:24:08 GMT 2025 , Edited by admin on Mon Mar 31 20:24:08 GMT 2025
PRIMARY
SMS_ID
100000164346
Created by admin on Mon Mar 31 20:24:08 GMT 2025 , Edited by admin on Mon Mar 31 20:24:08 GMT 2025
PRIMARY
CAS
202650-88-2
Created by admin on Mon Mar 31 20:24:08 GMT 2025 , Edited by admin on Mon Mar 31 20:24:08 GMT 2025
PRIMARY
NSC
407296
Created by admin on Mon Mar 31 20:24:08 GMT 2025 , Edited by admin on Mon Mar 31 20:24:08 GMT 2025
PRIMARY
RXCUI
1311387
Created by admin on Mon Mar 31 20:24:08 GMT 2025 , Edited by admin on Mon Mar 31 20:24:08 GMT 2025
PRIMARY RxNorm
CAS
327-97-9
Created by admin on Mon Mar 31 20:24:08 GMT 2025 , Edited by admin on Mon Mar 31 20:24:08 GMT 2025
NON-SPECIFIC STEREOCHEMISTRY
DRUG BANK
DB12029
Created by admin on Mon Mar 31 20:24:08 GMT 2025 , Edited by admin on Mon Mar 31 20:24:08 GMT 2025
PRIMARY
FDA UNII
318ADP12RI
Created by admin on Mon Mar 31 20:24:08 GMT 2025 , Edited by admin on Mon Mar 31 20:24:08 GMT 2025
PRIMARY
NCI_THESAURUS
C116073
Created by admin on Mon Mar 31 20:24:08 GMT 2025 , Edited by admin on Mon Mar 31 20:24:08 GMT 2025
PRIMARY NCIT
NSC
70861
Created by admin on Mon Mar 31 20:24:08 GMT 2025 , Edited by admin on Mon Mar 31 20:24:08 GMT 2025
PRIMARY
EPA CompTox
DTXSID101318952
Created by admin on Mon Mar 31 20:24:08 GMT 2025 , Edited by admin on Mon Mar 31 20:24:08 GMT 2025
PRIMARY
EVMPD
SUB178745
Created by admin on Mon Mar 31 20:24:08 GMT 2025 , Edited by admin on Mon Mar 31 20:24:08 GMT 2025
PRIMARY
RS_ITEM_NUM
1115545
Created by admin on Mon Mar 31 20:24:08 GMT 2025 , Edited by admin on Mon Mar 31 20:24:08 GMT 2025
PRIMARY
EVMPD
SUB114543
Created by admin on Mon Mar 31 20:24:08 GMT 2025 , Edited by admin on Mon Mar 31 20:24:08 GMT 2025
ALTERNATIVE
WIKIPEDIA
CHLOROGENIC ACID
Created by admin on Mon Mar 31 20:24:08 GMT 2025 , Edited by admin on Mon Mar 31 20:24:08 GMT 2025
PRIMARY
CHEBI
16112
Created by admin on Mon Mar 31 20:24:08 GMT 2025 , Edited by admin on Mon Mar 31 20:24:08 GMT 2025
PRIMARY
ECHA (EC/EINECS)
206-325-6
Created by admin on Mon Mar 31 20:24:08 GMT 2025 , Edited by admin on Mon Mar 31 20:24:08 GMT 2025
PRIMARY
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Methanol extracts of stevia dry leaves were directly used for LC-MS analysis. Efficient separation and resolution were achieved with diphenyl packing and acetonitrile/water as solvent in the HPLC method. Negative ion mode was used for all MS measurements.
Related Record Type Details
ACTIVE MOIETY