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
| 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 |
DescriptionSources: http://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/17994537https://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/28393840
Sources: http://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/17994537https://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/28393840
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
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
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 |
|---|---|---|---|---|
| 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 |
|---|---|---|---|---|
0.6637 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 |
|
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 |
|
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 |
|
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 |
|---|---|---|---|---|
1.782 ng × h/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 |
|
1.135 ng × h/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 |
|
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 |
|---|---|---|---|---|
1.4 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 |
|
1.3 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 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 |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
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 [Inhibition 50 uM] | ||||
| no | ||||
| 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 |
|---|---|---|
| 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 |
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| Separation and Identification of Phenolic Acid and Flavonoids from Nerium indicum Flowers. | 2014-02-05 |
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| 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 |
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| Neuroprotective effects of chlorogenic acid on scopolamine-induced amnesia via anti-acetylcholinesterase and anti-oxidative activities in mice. | 2010-12-15 |
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| Antihyperlipidemic effect of chlorogenic acid and tetrahydrocurcumin in rats subjected to diabetogenic agents. | 2010-12-05 |
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| 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
| Substance Class |
Chemical
Created
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Mon Mar 31 20:24:08 GMT 2025
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Mon Mar 31 20:24:08 GMT 2025
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| Record UNII |
318ADP12RI
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| Record Status |
Validated (UNII)
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DSLD |
354 (Number of products:22)
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NCI_THESAURUS |
C28203
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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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70861
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DTXSID101318952
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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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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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ACTIVE MOIETY |