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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H18O9
Molecular Weight 354.3094
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CHLOROGENIC ACID

SMILES

c1cc(c(cc1/C(/[H])=C(\[H])/C(=O)O[C@]2([H])C[C@@](C[C@]([H])([C@@]2([H])O)O)(C(=O)O)O)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 354.3094
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 1
Optical Activity UNSPECIFIED

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
Steroid hormone activity of flavonoids and related compounds.
2000 Jul
LC/ES-MS detection of hydroxycinnamates in human plasma and urine.
2001 Apr
Glucose 6-phosphate transport in fibroblast microsomes from glycogen storage disease type 1b patients: evidence for multiple glucose 6-phosphate transport systems.
2001 Jul 15
Identification of isomeric dicaffeoylquinic acids from Eleutherococcus senticosus using HPLC-ESI/TOF/MS and 1H-NMR methods.
2002 Nov-Dec
Effects of coffee components on the response of GABA(A) receptors expressed in Xenopus oocytes.
2003 Dec 17
Chlorogenic acid bioavailability largely depends on its metabolism by the gut microflora in rats.
2003 Jun
Chlorogenic acid, quercetin-3-rutinoside and black tea phenols are extensively metabolized in humans.
2003 Jun
Effect of antioxidants, oxidants, metals and saliva on cytotoxicity induction by sodium fluoride.
2003 Sep-Oct
Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation.
2004 Jul 2
Apple phytochemicals and their health benefits.
2004 May 12
Interactions of human serum albumin with chlorogenic acid and ferulic acid.
2004 Sep 24
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
Neuroprotective effects of chlorogenic acid on scopolamine-induced amnesia via anti-acetylcholinesterase and anti-oxidative activities in mice.
2010 Dec 15
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
Interaction of cinnamic acid derivatives with commercial hypoglycemic drugs on 2-deoxyglucose uptake in 3T3-L1 adipocytes.
2011 Sep 28
Looking for the physiological role of anthocyanins in the leaves of Coffea arabica.
2012 Jul-Aug
Inhibitory effects of caffeic acid phenethyl ester derivatives on replication of hepatitis C virus.
2013
Chlorogenic acid reduces liver inflammation and fibrosis through inhibition of toll-like receptor 4 signaling pathway.
2013 Jan 7
Renoprotective mechanisms of chlorogenic acid in cisplatin-induced kidney injury.
2014 Oct 3
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%.
Substance Class Chemical
Created
by admin
on Sat Jun 26 14:39:22 UTC 2021
Edited
by admin
on Sat Jun 26 14:39:22 UTC 2021
Record UNII
318ADP12RI
Record Status Validated (UNII)
Record Version
  • Download
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
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
CHLOROGENIC ACID [WHO-DD]
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 Sat Jun 26 14:39:22 UTC 2021 , Edited by admin on Sat Jun 26 14:39:22 UTC 2021
NCI_THESAURUS C28203
Created by admin on Sat Jun 26 14:39:22 UTC 2021 , Edited by admin on Sat Jun 26 14:39:22 UTC 2021
Code System Code Type Description
PUBCHEM
1794427
Created by admin on Sat Jun 26 14:39:22 UTC 2021 , Edited by admin on Sat Jun 26 14:39:22 UTC 2021
PRIMARY
USP_CATALOG
1115545
Created by admin on Sat Jun 26 14:39:22 UTC 2021 , Edited by admin on Sat Jun 26 14:39:22 UTC 2021
PRIMARY USP-RS
MESH
D002726
Created by admin on Sat Jun 26 14:39:22 UTC 2021 , Edited by admin on Sat Jun 26 14:39:22 UTC 2021
PRIMARY
MERCK INDEX
M3413
Created by admin on Sat Jun 26 14:39:22 UTC 2021 , Edited by admin on Sat Jun 26 14:39:22 UTC 2021
PRIMARY Merck Index
CAS
202650-88-2
Created by admin on Sat Jun 26 14:39:22 UTC 2021 , Edited by admin on Sat Jun 26 14:39:22 UTC 2021
PRIMARY
RXCUI
1311387
Created by admin on Sat Jun 26 14:39:22 UTC 2021 , Edited by admin on Sat Jun 26 14:39:22 UTC 2021
PRIMARY RxNorm
CAS
327-97-9
Created by admin on Sat Jun 26 14:39:22 UTC 2021 , Edited by admin on Sat Jun 26 14:39:22 UTC 2021
NON-SPECIFIC STEREOCHEMISTRY
DRUG BANK
DB12029
Created by admin on Sat Jun 26 14:39:22 UTC 2021 , Edited by admin on Sat Jun 26 14:39:22 UTC 2021
PRIMARY
FDA UNII
318ADP12RI
Created by admin on Sat Jun 26 14:39:22 UTC 2021 , Edited by admin on Sat Jun 26 14:39:22 UTC 2021
PRIMARY
NCI_THESAURUS
C116073
Created by admin on Sat Jun 26 14:39:22 UTC 2021 , Edited by admin on Sat Jun 26 14:39:22 UTC 2021
PRIMARY NCIT
EPA CompTox
327-97-9
Created by admin on Sat Jun 26 14:39:22 UTC 2021 , Edited by admin on Sat Jun 26 14:39:22 UTC 2021
PRIMARY
EVMPD
SUB178745
Created by admin on Sat Jun 26 14:39:22 UTC 2021 , Edited by admin on Sat Jun 26 14:39:22 UTC 2021
PRIMARY
EVMPD
SUB114543
Created by admin on Sat Jun 26 14:39:22 UTC 2021 , Edited by admin on Sat Jun 26 14:39:22 UTC 2021
ALTERNATIVE
WIKIPEDIA
CHLOROGENIC ACID
Created by admin on Sat Jun 26 14:39:22 UTC 2021 , Edited by admin on Sat Jun 26 14:39:22 UTC 2021
PRIMARY
ECHA (EC/EINECS)
206-325-6
Created by admin on Sat Jun 26 14:39:22 UTC 2021 , Edited by admin on Sat Jun 26 14:39:22 UTC 2021
PRIMARY
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The water-soluble fraction was repeatedly chromatographed over MCI gel CHP20P, Sephadex LH-20, and YMC ODSA to yield the compound.
PARENT -> CONSTITUENT ALWAYS PRESENT
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.
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ASSAY (HPLC)
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ACTIVE MOIETY