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
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
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 |
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
Cmax
AUC
T1/2
Overview
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Drug as victim
Tox targets
Sourcing
PubMed
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%.