CHLOROGENIC ACID, (Z)-

Investigational

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

Structure Search

SMILES

O[C@@H]1C[C@](O)(C[C@@H](OC(=O)\C=C/C2=CC=C(O)C(O)=C2)[C@@H]1O)C(O)=O

InChI

InChIKey=CWVRJTMFETXNAD-XYXZIBEBSA-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

HIDE SMILES / InChI

Description
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Hypoxia-inducible factor 1-alpha 10 Target ID: Q16665 Gene ID: 3091.0 Gene Symbol: HIF1A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/28165392	Modulator 828
Sphingosine kinase 1 6 Target ID: Q9NYA1 Gene ID: 8877.0 Gene Symbol: SPHK1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/28165392	Modulator 828
Neuraminidase 21 Target ID: CHEMBL2051 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28393840	Blocker 537	44.87 µM [EC50]
Neuraminidase 21 Target ID: CHEMBL1287607 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28393840	Blocker 537	62.33 µM [EC50]

Conditions

Condition	Modality	Highest Phase	Product
Hypertension 567 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24943289	Primary	Not Provided 504	Unknown Approved Use Unknown
Cancer 592 Sources: https://clinicaltrials.gov/ct2/show/NCT02245204	Primary	Phase I 428	Unknown Approved Use Unknown
Impaired glucose tolerance 2 Sources: https://clinicaltrials.gov/ct2/show/NCT02621060	Primary	Phase II 1132	Unknown Approved Use Unknown
Non-alcoholic fatty liver disease 30 Sources: https://clinicaltrials.gov/ct2/show/NCT02929901	Primary	Phase III 656	Unknown Approved Use Unknown
influenza A H1N1 virus infection 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28393840	Primary	Basic research	Unknown Approved Use Unknown
Influenza A H3N2 virus infection 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28393840	Primary	Basic research	Unknown Approved Use Unknown
Unknown 2578

C_max

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	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	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	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	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

T_1/2

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	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	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
inducer 781 substrate 1737 inhibitor 1587	substrate 1037 inhibitor 1767	substrate 1217 inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1461 OAT3 642 CYP2E1 882 CYP2C19 1478 OAT1 599 CYP1A2 1524 OATP1B3 706 OATP1B1 788	COMT 4 CYP1A2 1054 SULT1A1 29 CYP2C19 991 UGT1A6 307 CYP2E1 667 P-gp 1537 GST 4 UGT1A9 380	P-gp 257

Drug as perpetrator

Target	Modality	Activity
CYP2E1 970	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/26160718/	likely
CYP1A2 1692	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/10871299/	no [IC50 >100 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/10871299/	no [IC50 >100 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/10871299/	no [IC50 >100 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/10871299/	no [IC50 >100 uM]
CYP2C19 1553	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/10871299/	no [IC50 ND uM]
P-gp 1650	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/377#sid=10321213	no [Inhibition 50 uM]
OAT1 603	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/21697612/	no
P-gp 1650	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/20580705/	no
OAT3 644	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/21697612/	weak [Inhibition 100 uM]
CYP3A4 1925	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/20580705/	weak
OATP1B1 803	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes [Inhibition 10 uM]
OATP1B3 715	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes [Inhibition 10 uM]

Drug as victim

Target	Modality	Activity
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/22551521/	likely
CYP2E1 667	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/22551521/	major
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/22551521/	major
CYP1A2 1054	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/22551521/	minor
CYP2C19 991	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/22551521/	minor
CYP2D6 1217	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/22551521/	minor
UGT1A6 307	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10836148/	no
UGT1A9 380	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10836148/	no
COMT 4	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/22551521/	yes
GST 4	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/22551521/	yes
P-gp 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/32484174/	yes
SULT1A1 29	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12920175/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/720553#sid=56463713 \| https://pubchem.ncbi.nlm.nih.gov/bioassay/720551#sid=56463713

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY427037	https://www.001chemical.com/chem/search?q=DY427037
1PlusChem LLC	1P003PAI	https://www.1pchem.com/search?query=1P003PAI
1PlusChem LLC	1P00I6OP	https://www.1pchem.com/search?query=1P00I6OP
A2B Chem	AI47673	http://a2bchem.com/prod/AI47673
AA Blocks	AA00I659	http://aablocks.com/goods/Goods/detail?id=AA00I659
AK Scientific	E748	https://aksci.com/item_detail.php?cat=E748
AK Scientific	J10338	https://aksci.com/item_detail.php?cat=J10338
AK Scientific	O675	https://aksci.com/item_detail.php?cat=O675
Alfa Chemistry	ACM327979	http://www.alfa-chemistry.com/search.aspx?q=ACM327979
Alinda	ALBB-030169	http://alinda.ru/finechem_en_.html?i=ALBB-030169
Ambeed	A163338	http://www.ambeed.com/search/Search.html?keyword=A163338
Angene	AGN-PC-0R86P1	http://www.angenechemical.com/productshow/AGN-PC-0R86P1.html
ApexBio Technology	N1769	https://www.apexbt.com/catalogsearch/result/?q=N1769
ApexBio Technology	N1857	https://www.apexbt.com/catalogsearch/result/?q=N1857
Apollo Scientific	BIB6027	http://www.apolloscientific.co.uk/chemical_results.php?qstext=BIB6027&product_group=%25&search_fieldname=header_search
Apollo Scientific	OR1166	http://www.apolloscientific.co.uk/chemical_results.php?qstext=OR1166&product_group=%25&search_fieldname=header_search
AstaTech	F16266	http://astatechinc.com/CPSResult.php?CRNO=F16266
BOC Sciences	327-97-9	http://www.bocsci.com/description.asp?cas=327-97-9
BOC Sciences	6001-76-9	http://www.bocsci.com/description.asp?cas=6001-76-9
Biopurify Phytochemicals	BP0345	https://www.phytopurify.com/search.do?a=s&searchtype=3&psize=10&q=BP0345&searchhtmp=simplesearch&t=1
Capot Chemical	13036	https://www.capotchem.com/search.do?q=13036
Cayman Chemical	70930	http://www.caymanchem.com/app/template/Product.vm/catalog/70930
Chem Scene	CS-3766	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-3766
Chem-Impex International	21877	http://www.chemimpex.com/category/search/21877/2?filter=&search=21877&type=q&keywordoption=ANY&cid=2&fltrdesc=
Chem4Pharma	C4PN2	https://www.chem4pharma.com/product-page/C4PN2
ChemDiv	BB58-3170	http://chemistryondemand.com:8080/eShop/search_results.jsp?idnumber=BB58-3170
ChemShuttle	151614	https://www.chemshuttle.com/catalogsearch/result/?q=151614
Combi-Blocks	QA-8481	http://www.combi-blocks.com/cgi-bin/find.cgi?QA-8481
Combi-Blocks	QC-9619	http://www.combi-blocks.com/cgi-bin/find.cgi?QC-9619
Frontier Scientific Services	501003455	http://orders.frontierssi.com/fssionline32/public/product.aspx?cat=501003455&type=hts
Hairui	HR123597	http://www.hairuichem.com/en/product/search.do?q=HR123597
Indofine	024991S	https://indofinechemical.com/details.aspx?Sku=024991S
Indofine	06-040	https://indofinechemical.com/details.aspx?Sku=06-040
Indofine	C-002	https://indofinechemical.com/details.aspx?Sku=C-002
KeyOrganics	AS-12284	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-12284
KeyOrganics	VS-08670	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=VS-08670
Lab Network	LN01830864	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01830864
Lab Seeker	SC-13943	http://www.labseeker.com/search.php?keywords=SC-13943&category=0
LabSeeker	SC-13943	http://www.labseeker.com/search.php?keywords=SC-13943&category=0
Matrix Scientific	90566	http://www.matrixscientific.com/090566.html
MedChem Express	HY-N0055	https://www.medchemexpress.com/search.html?q=HY-N0055&ft=&fa=&fp=
MolPort	MolPort-001-740-212	https://www.molport.com/shop/molecule-link/MolPort-001-740-212
MolPort	MolPort-001-759-169	https://www.molport.com/shop/molecule-link/MolPort-001-759-169
MolPort	MolPort-004-955-158	https://www.molport.com/shop/molecule-link/MolPort-004-955-158
MolPort	MolPort-020-392-495	https://www.molport.com/shop/molecule-link/MolPort-020-392-495
Molcore	MC427037	http://www.molcore.com/CatMC427037.html
Molnova	M19253	https://www.molnova.com/en/serch-list.html?keywords=M19253
MuseChem	I003163	https://www.musechem.com/product/I003163.html
Oakwood	213614	http://www.oakwoodchemical.com/ProductsList.aspx?txtSearch=213614
Princeton BioMolecular Research	OSSL_298285	http://www.princetonbio.com/order_online?common_id=OSSL_298285
Ryan Scientific	Nicotine	https://ryansci.com/products?q=Nicotine&list_q=&search_type=exact
Selleck Chemicals	S2280	http://www.selleckchem.com/search.html?searchDTO.searchParam=S2280
Specs	AP-163/40806917	http://www.specs.net/enter.php?specsid=AP-163/40806917
SynQuest	375840	http://www.synquestlabs.com/search-result.html?q=2929-1-04
TargetMol	BBP03169	https://www.targetmol.com/search?keyword=BBP03169
TargetMol	T2805	https://www.targetmol.com/search?keyword=T2805
TargetMol	T6S1538	https://www.targetmol.com/search?keyword=T6S1538
Tetrahedron	TS32681	http://www.thsci.com/search.do?q=TS32681
TimTec	ST056308	http://www.echemstore.com/catalogsearch/result/?q=ST056308
Toronto Research Chemicals	C366540	https://www.trc-canada.com/product-detail/?CatNum=C366540
Vitas-M Laboratory	BBL028113	http://www.vitasmlab.biz/search/BBL028113
Vitas-M Laboratory	STL377917	http://www.vitasmlab.biz/search/STL377917
W&J PharmaChem	50A211812	http://wjpharmachem.com/new/searcht.php?keyword=50A211812
eMolecules	29541115	https://orderbb.emolecules.com/search/#?query=29541115
eMolecules	44842269	https://orderbb.emolecules.com/search/#?query=44842269
eMolecules	492483	https://orderbb.emolecules.com/search/#?query=492483
eMolecules	49777957	https://orderbb.emolecules.com/search/#?query=49777957
eMolecules	50523144	https://orderbb.emolecules.com/search/#?query=50523144
eNovation Chemicals	D401658	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D401658&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-5282788280	https://mcule.com/MCULE-5282788280/
mcule	MCULE-8135887819	https://mcule.com/MCULE-8135887819/
mcule	MCULE-8331698684	https://mcule.com/MCULE-8331698684/

PubMed

Title	Date	PubMed
Dietary effects on the uptake of benzo[a]pyrene.	1994 Aug	8070737
Action of chlorogenic acid on the complement system.	1999	10412494
Steroid hormone activity of flavonoids and related compounds.	2000 Jul	10989984
LC/ES-MS detection of hydroxycinnamates in human plasma and urine.	2001 Apr	11308321
Effect of antioxidants, oxidants, metals and saliva on cytotoxicity induction by sodium fluoride.	2003 Sep-Oct	14666669
Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation.	2004 Jul 2	15117964
Apple phytochemicals and their health benefits.	2004 May 12	15140261
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Profiling the phenolic compounds of Artemisia pectinata by HPLC-PAD-MSn.	2008 Jul-Aug	17994537
Interaction of cinnamic acid derivatives with commercial hypoglycemic drugs on 2-deoxyglucose uptake in 3T3-L1 adipocytes.	2011 Sep 28	21870829
Looking for the physiological role of anthocyanins in the leaves of Coffea arabica.	2012 Jul-Aug	22372995
Chlorogenic acid reduces liver inflammation and fibrosis through inhibition of toll-like receptor 4 signaling pathway.	2013 Jan 7	23146752
Separation and Identification of Phenolic Acid and Flavonoids from Nerium indicum Flowers.	2015 Jan-Feb	25767323
Acetaminophen hepatotoxicity and sterile inflammation: The mechanism of protection of Chlorogenic acid.	2016 Jan 5	26363200

Patents

Sample Use Guides

In Vivo Use Guide

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

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%.

Name

Type

Language

CHLOROGENIC ACID, (Z)-

Common Name

English

CHLOROGENIC ACID Z-FORM [MI]

Common Name

English

CIS-CHLOROGENIC ACID

Common Name

English

CYCLOHEXANECARBOXYLIC ACID, 3-(((2Z)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-1,4,5-TRIHYDROXY-, (1S,3R,4R,5R)-

Systematic Name

English

Code System Code Type Description

CAS

15016-60-1