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: 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 |
---|---|---|---|
Target ID: Q16665 Gene ID: 3091.0 Gene Symbol: HIF1A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/28165392 |
|||
Target ID: Q9NYA1 Gene ID: 8877.0 Gene Symbol: SPHK1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/28165392 |
|||
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 |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
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 |
---|---|---|---|
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 [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 |
---|---|---|
Action of chlorogenic acid on the complement system. | 1999 |
|
Steroid hormone activity of flavonoids and related compounds. | 2000 Jul |
|
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 |
|
Chlorogenic acid bioavailability largely depends on its metabolism by the gut microflora in rats. | 2003 Jun |
|
Chlorogenic acid, quercetin-3-rutinoside and black tea phenols are extensively metabolized in humans. | 2003 Jun |
|
Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation. | 2004 Jul 2 |
|
Apple phytochemicals and their health benefits. | 2004 May 12 |
|
Interactions of human serum albumin with chlorogenic acid and ferulic acid. | 2004 Sep 24 |
|
Inhibition of activator protein-1, NF-kappaB, and MAPKs and induction of phase 2 detoxifying enzyme activity by chlorogenic acid. | 2005 Jul 29 |
|
Activation of rat liver microsomal glutathione S-transferase by gallic acid. | 2005 Nov 19 |
|
Absorption and metabolism of caffeic acid and chlorogenic acid in the small intestine of rats. | 2006 Jul |
|
Chlorogenic acid is absorbed in its intact form in the stomach of rats. | 2006 May |
|
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
|
Profiling the phenolic compounds of Artemisia pectinata by HPLC-PAD-MSn. | 2008 Jul-Aug |
|
Examining the genomic influence of skin antioxidants in vitro. | 2010 |
|
Antihyperlipidemic effect of chlorogenic acid and tetrahydrocurcumin in rats subjected to diabetogenic agents. | 2010 Dec 5 |
|
Biochemical mechanism of caffeic acid phenylethyl ester (CAPE) selective toxicity towards melanoma cell lines. | 2010 Oct 6 |
|
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 |
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%.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 22:07:22 GMT 2023
by
admin
on
Fri Dec 15 22:07:22 GMT 2023
|
Record UNII |
318ADP12RI
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
DSLD |
354 (Number of products:22)
Created by
admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
|
||
|
NCI_THESAURUS |
C28203
Created by
admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
DTXSID3024786
Created by
admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
|
PRIMARY | |||
|
1794427
Created by
admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
|
PRIMARY | |||
|
D002726
Created by
admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
|
PRIMARY | |||
|
m3413
Created by
admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
|
PRIMARY | Merck Index | ||
|
318ADP12RI
Created by
admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
|
PRIMARY | |||
|
100000164346
Created by
admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
|
PRIMARY | |||
|
202650-88-2
Created by
admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
|
PRIMARY | |||
|
407296
Created by
admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
|
PRIMARY | |||
|
1311387
Created by
admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
|
PRIMARY | RxNorm | ||
|
327-97-9
Created by
admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
|
NON-SPECIFIC STEREOCHEMISTRY | |||
|
DB12029
Created by
admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
|
PRIMARY | |||
|
318ADP12RI
Created by
admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
|
PRIMARY | |||
|
C116073
Created by
admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
|
PRIMARY | NCIT | ||
|
70861
Created by
admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
|
PRIMARY | |||
|
SUB178745
Created by
admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
|
PRIMARY | |||
|
1115545
Created by
admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
|
PRIMARY | |||
|
SUB114543
Created by
admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
|
ALTERNATIVE | |||
|
CHLOROGENIC ACID
Created by
admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
|
PRIMARY | |||
|
16112
Created by
admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
|
PRIMARY | |||
|
206-325-6
Created by
admin on Fri Dec 15 22:07:22 GMT 2023 , Edited by admin on Fri Dec 15 22:07:22 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
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.
|
||
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
ASSAY (HPLC)
|
||
|
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.
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |