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
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
DescriptionSources: https://www.drugbank.ca/drugs/DB12029 | https://www.ncbi.nlm.nih.gov/pubmed/11401245 | https://clinicaltrials.gov/ct2/show/NCT02621060 | https://www.ncbi.nlm.nih.gov/pubmed/28393840 | https://www.ncbi.nlm.nih.gov/pubmed/28393840http://www.hmdb.ca/metabolites/HMDB29278 | http://phenol-explorer.eu/compounds/521 | https://www.ncbi.nlm.nih.gov/pubmed/25767323 | https://www.ncbi.nlm.nih.gov/pubmed/25214217 | https://www.ncbi.nlm.nih.gov/pubmed/22372995 | https://www.ncbi.nlm.nih.gov/pubmed/17994537
Sources: https://www.drugbank.ca/drugs/DB12029 | https://www.ncbi.nlm.nih.gov/pubmed/11401245 | https://clinicaltrials.gov/ct2/show/NCT02621060 | https://www.ncbi.nlm.nih.gov/pubmed/28393840 | https://www.ncbi.nlm.nih.gov/pubmed/28393840http://www.hmdb.ca/metabolites/HMDB29278 | http://phenol-explorer.eu/compounds/521 | https://www.ncbi.nlm.nih.gov/pubmed/25767323 | https://www.ncbi.nlm.nih.gov/pubmed/25214217 | https://www.ncbi.nlm.nih.gov/pubmed/22372995 | https://www.ncbi.nlm.nih.gov/pubmed/17994537
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
Primary Target | Pharmacology | Condition | Potency |
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Target ID: Q16665 Gene ID: 3091.0 Gene Symbol: HIF1A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/28165392 |
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Target ID: Q9NYA1 Gene ID: 8877.0 Gene Symbol: SPHK1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/28165392 |
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Target ID: CHEMBL2051 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28393840 |
44.87 µM [EC50] | ||
Target ID: CHEMBL1287607 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28393840 |
62.33 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.7638 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27114321 |
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 |
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0.6637 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27114321 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31541942 |
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 |
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2914 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31541942 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.135 ng × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27114321 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27114321 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31541942 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31541942 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27114321 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27114321 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31541942 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31541942 |
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 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
likely | ||||
no [IC50 >100 uM] | ||||
no [IC50 >100 uM] | ||||
no [IC50 >100 uM] | ||||
no [IC50 >100 uM] | ||||
no [IC50 ND uM] | ||||
no [Inhibition 50 uM] | ||||
no | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/20580705/ |
no | |||
weak [Inhibition 100 uM] | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/20580705/ |
weak | |||
yes [Inhibition 10 uM] | ||||
yes [Inhibition 10 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
likely | ||||
major | ||||
major | ||||
minor | ||||
minor | ||||
minor | ||||
no | ||||
no | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
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Dietary effects on the uptake of benzo[a]pyrene. | 1994 Aug |
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Action of chlorogenic acid on the complement system. | 1999 |
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LC/ES-MS detection of hydroxycinnamates in human plasma and urine. | 2001 Apr |
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Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation. | 2004 Jul 2 |
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Inhibition of activator protein-1, NF-kappaB, and MAPKs and induction of phase 2 detoxifying enzyme activity by chlorogenic acid. | 2005 Jul 29 |
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Activation of rat liver microsomal glutathione S-transferase by gallic acid. | 2005 Nov 19 |
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Absorption and metabolism of caffeic acid and chlorogenic acid in the small intestine of rats. | 2006 Jul |
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Chlorogenic acid is absorbed in its intact form in the stomach of rats. | 2006 May |
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Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
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Analysis of interaction property of bioactive components in Danggui Buxue Decoction with protein by microdialysis coupled with HPLC-DAD-MS. | 2007 Jun 1 |
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Examining the genomic influence of skin antioxidants in vitro. | 2010 |
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Antihyperlipidemic effect of chlorogenic acid and tetrahydrocurcumin in rats subjected to diabetogenic agents. | 2010 Dec 5 |
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Naturally occurring phenolic acids inhibit 12-O-tetradecanoylphorbol-13-acetate induced NF-kappaB, iNOS and COX-2 activation in mouse epidermis. | 2010 Jan 31 |
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Biochemical mechanism of caffeic acid phenylethyl ester (CAPE) selective toxicity towards melanoma cell lines. | 2010 Oct 6 |
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Looking for the physiological role of anthocyanins in the leaves of Coffea arabica. | 2012 Jul-Aug |
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Chlorogenic acid reduces liver inflammation and fibrosis through inhibition of toll-like receptor 4 signaling pathway. | 2013 Jan 7 |
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The therapeutic detoxification of chlorogenic acid against acetaminophen-induced liver injury by ameliorating hepatic inflammation. | 2015 Aug 5 |
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Separation and Identification of Phenolic Acid and Flavonoids from Nerium indicum Flowers. | 2015 Jan-Feb |
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Acetaminophen hepatotoxicity and sterile inflammation: The mechanism of protection of Chlorogenic acid. | 2016 Jan 5 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT02621060
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28165392
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%.
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Classification Tree | Code System | Code | ||
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DSLD |
354 (Number of products:22)
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NCI_THESAURUS |
C28203
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DTXSID3024786
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1794427
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D002726
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m3413
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318ADP12RI
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100000164346
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202650-88-2
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407296
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1311387
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327-97-9
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NON-SPECIFIC STEREOCHEMISTRY | |||
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DB12029
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318ADP12RI
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C116073
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PRIMARY | NCIT | ||
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70861
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SUB178745
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1115545
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SUB114543
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ALTERNATIVE | |||
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CHLOROGENIC ACID
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16112
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206-325-6
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ACTIVE MOIETY