Showing Compound Chlorogenic acid (FDB002582)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:26 UTC

Update date

2020-09-17 15:39:09 UTC

Primary ID

FDB002582

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Chlorogenic acid

Description

Chlorogenic acid, also known as chlorogenate or 3-caffeoylquinate, belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1. Chlorogenic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Chlorogenic acid has been detected, but not quantified in, several different foods, such as limes, cocoa beans, celery leaves, caraway, and epazotes. This could make chlorogenic acid a potential biomarker for the consumption of these foods.

CAS Number

327-97-9

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

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Synonym	Source
(-)-5-Caffeoyl quinic acid	PhytoBank
3 Caffeoylquinic acid	MeSH
3-(3,4-Dihydroxycinnamoyl)quinate	Generator
3-(3,4-Dihydroxycinnamoyl)quinic acid	ChEBI
3-Caffeoylquinate	Generator
3-Caffeoylquinic acid	ChEBI
3-O-(3,4-Dihydroxycinnamoyl)-D-quinic acid	PhytoBank
3-O-Caffeoylquinate	Generator
3-O-Caffeoylquinic acid	ChEBI
3-trans-Caffeoylquinic acid	HMDB

Showing 1 to 10 of 42 entries

Predicted Properties

Property	Value	Source
Water Solubility	3.44 g/L	ALOGPS
logP	0.17	ALOGPS
logP	-0.27	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.33	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.75 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	83.23 m³·mol⁻¹	ChemAxon
Polarizability	33.42 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C16H18O9

IUPAC name

(1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid

InChI Identifier

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

InChI Key

CWVRJTMFETXNAD-JUHZACGLSA-N

Isomeric 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

Average Molecular Weight

354.3087

Monoisotopic Molecular Weight

354.095082174

Classification

Description

Belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Quinic acids and derivatives

Alternative Parents

Substituents

Quinic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexanol
Fatty acid ester
Phenol
Fatty acyl
Hydroxy acid
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Alpha-hydroxy acid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Polyol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

cinnamate ester (CHEBI:16112 )
tannin (CHEBI:16112 )
Caffeate derivatives (C00852 )

Ontology

Foods

Fruits and vegetables:

Beverages:

Coffee products

Infusions:

Tea products

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 54.24%; H 5.12%; O 40.64%	DFC
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Chlorogenic acid, non-derivatized, GC-MS Spectrum	splash10-052b-0975000000-7ff0681e9983191145ac	Spectrum
GC-MS	Chlorogenic acid, non-derivatized, GC-MS Spectrum	splash10-052b-0975000000-25fbc0fd86e2102b1846	Spectrum
GC-MS	Chlorogenic acid, 6 TMS, GC-MS Spectrum	splash10-0a4j-1897000000-1bf40e61c8b016f6d1fe	Spectrum
GC-MS	Chlorogenic acid, non-derivatized, GC-MS Spectrum	splash10-052b-0975000000-7ff0681e9983191145ac	Spectrum
GC-MS	Chlorogenic acid, non-derivatized, GC-MS Spectrum	splash10-052b-0975000000-25fbc0fd86e2102b1846	Spectrum
GC-MS	Chlorogenic acid, non-derivatized, GC-MS Spectrum	splash10-0a4j-1897000000-1bf40e61c8b016f6d1fe	Spectrum
Predicted GC-MS	Chlorogenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000l-9424000000-5a5e7a151673f74acf94	Spectrum
Predicted GC-MS	Chlorogenic acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-3322039000-dccdea510eeadb723d61	Spectrum
Predicted GC-MS	Chlorogenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-0900000000-c967ed2de6bc445ffb02	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-03di-0900000000-4fb0aa23529c84f7e829	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-029j-1900000000-7ae6eafda8c4a3c22517	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - FD-B (Unknown) , Positive	splash10-0udi-0009000000-378f6298ca0416519525	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0009000000-0b3427977e0c1f9d6a75	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0006-0901000000-e3869338c5312cfd01a2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0006-0900000000-4f7df62a909594e8dabf	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-0900000000-4438cf2b7d3dd0ca06a4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-000f-3900000000-a7982b43b83d191b2651	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-08fr-0927000000-708aeb0e652c03f8b1db	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-03di-0900000000-ae6e117173e672cfa4e8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-03di-0900000000-9847301060b85490005a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-03di-0900000000-2bcf6303448c0b3ed50a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-00li-2900000000-0943d4e9b9fc1a7d947f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-03di-0900000000-6d376727bd1d633ce205	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-01ot-0900000000-8515e331dca6691469af	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-000i-0900000000-21182fce172fa6b497d0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-03di-2900000000-0cab1210002740e149b4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udl-0609000000-83c24cdc722253a22133	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0918000000-3ee17b66f5461b5349a2	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03g3-0902000000-adb0080c997613268656	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004j-1900000000-837dabfad86490278224	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfu-0519000000-d321b79970ee8839fc24	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06vm-1922000000-410b2ca167dfdb9d0a54	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-0900000000-090aec697972e64791aa	2017-07-26	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16112

Phenol-Explorer ID

948

DrugBank ID

Not Available

HMDB ID

HMDB03164

CRC / DFC (Dictionary of Food Compounds) ID

CMM44-X:CMM44-X

EAFUS ID

Not Available

Dr. Duke ID

3-O-CAFFEOYLQUINIC-ACID|CAFFEOYL-3-QUINIC-ACID|CHLOROGENIC-ACID|CAFFETANNIC-ACID

BIGG ID

Not Available

KNApSAcK ID

C00002724

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Chlorogenic_acid

Phenol-Explorer Metabolite ID

475

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
aldose reductase inhibitor	48550	An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).	DUKE
allelochemic			DUKE
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	DUKE
analgesic	35480	An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.	DUKE
anti atherosclerotic	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti cancer	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti carcinogenic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti diabetic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti Epstein-Barr virus	22587	A substance that destroys or inhibits replication of viruses.	DUKE