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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
44.87 µM [EC50]
62.33 µM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
0.7638 ng/mL
3.64 mg single, oral
CHLOROGENIC ACID plasma
Homo sapiens
0.6637 ng/mL
3.64 mg 3 times / day steady-state, oral
CHLOROGENIC ACID plasma
Homo sapiens
2376 ng/mL
3 mg/kg single, intramuscular
CHLOROGENIC ACID plasma
Homo sapiens
2914 ng/mL
3 mg/kg 1 times / day multiple, intramuscular
CHLOROGENIC ACID plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1.135 ng × h/L
3.64 mg single, oral
CHLOROGENIC ACID plasma
Homo sapiens
1.782 ng × h/L
3.64 mg 3 times / day steady-state, oral
CHLOROGENIC ACID plasma
Homo sapiens
6124 ng × h/mL
3 mg/kg single, intramuscular
CHLOROGENIC ACID plasma
Homo sapiens
7199 ng × h/mL
3 mg/kg 1 times / day multiple, intramuscular
CHLOROGENIC ACID plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.3 h
3.64 mg single, oral
CHLOROGENIC ACID plasma
Homo sapiens
1.4 h
3.64 mg 3 times / day steady-state, oral
CHLOROGENIC ACID plasma
Homo sapiens
1 h
3 mg/kg single, intramuscular
CHLOROGENIC ACID plasma
Homo sapiens
1.2 h
3 mg/kg 1 times / day multiple, intramuscular
CHLOROGENIC ACID plasma
Homo sapiens

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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
Record UNII
318ADP12RI
Record Status Validated (UNII)
Record Version