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 |
---|---|---|---|---|
0.7638 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 |
|
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 |
|
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 |
---|---|---|
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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Steroid hormone activity of flavonoids and related compounds. | 2000 Jul |
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LC/ES-MS detection of hydroxycinnamates in human plasma and urine. | 2001 Apr |
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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 |
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Identification of isomeric dicaffeoylquinic acids from Eleutherococcus senticosus using HPLC-ESI/TOF/MS and 1H-NMR methods. | 2002 Nov-Dec |
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Effects of coffee components on the response of GABA(A) receptors expressed in Xenopus oocytes. | 2003 Dec 17 |
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Chlorogenic acid bioavailability largely depends on its metabolism by the gut microflora in rats. | 2003 Jun |
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Chlorogenic acid, quercetin-3-rutinoside and black tea phenols are extensively metabolized in humans. | 2003 Jun |
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Effect of antioxidants, oxidants, metals and saliva on cytotoxicity induction by sodium fluoride. | 2003 Sep-Oct |
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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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Apple phytochemicals and their health benefits. | 2004 May 12 |
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Interactions of human serum albumin with chlorogenic acid and ferulic acid. | 2004 Sep 24 |
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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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Novel screening assay for antioxidant protection against peroxyl radical-induced loss of protein function. | 2007 Nov |
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Profiling the phenolic compounds of Artemisia pectinata by HPLC-PAD-MSn. | 2008 Jul-Aug |
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Examining the genomic influence of skin antioxidants in vitro. | 2010 |
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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 |
|
Biochemical mechanism of caffeic acid phenylethyl ester (CAPE) selective toxicity towards melanoma cell lines. | 2010 Oct 6 |
|
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
Substance Class |
Chemical
Created
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admin
on
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Sat Dec 17 07:34:28 UTC 2022
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on
Sat Dec 17 07:34:28 UTC 2022
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Record UNII |
318ADP12RI
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Record Status |
Validated (UNII)
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Record Version |
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DSLD |
354 (Number of products:22)
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NCI_THESAURUS |
C28203
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Code System | Code | Type | Description | ||
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1794427
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D002726
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PRIMARY | |||
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M3413
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PRIMARY | Merck Index | ||
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318ADP12RI
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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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DTXSID3024786
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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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Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
ASSAY (HPLC)
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
The water-soluble fraction was repeatedly chromatographed
over MCI gel CHP20P, Sephadex LH-20, and YMC ODSA to yield the compound.
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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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Related Record | Type | Details | ||
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ACTIVE MOIETY |