ContaminantDB: Neochlorogenic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 21:50:57 UTC

Update Date

2016-11-09 01:17:56 UTC

Accession Number

CHEM024668

Identification

Common Name

Neochlorogenic acid

Class

Small Molecule

Description

A cinnamate ester obtained by formal condensation of the carboxy group of trans-caffeic acid with the 5-hydroxy group of quinic acid.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(1R,3R,4S,5R)-3-[(2E)-3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxycyclohexanecarboxylic acid	ChEBI
Caffeoyl quinic acid	ChEBI
Neochlorogenate	ChEBI
Neochlorogenic acid	ChEBI
trans-5-O-Caffeoyl-D-quinate	ChEBI
trans-Neochlorogenic acid	ChEBI
(1R,3R,4S,5R)-3-[(2E)-3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxycyclohexanecarboxylate	Generator
Caffeoyl quinate	Generator
trans-5-O-Caffeoyl-D-quinic acid	Generator
trans-Neochlorogenate	Generator
5-Caffeoylquinate	Generator
5-O-Caffeoylquinic acid	HMDB
5'-O-Caffeoylquinic acid	HMDB

Chemical Formula

C₁₆H₁₈O₉

Average Molecular Mass

354.309 g/mol

Monoisotopic Mass

354.095 g/mol

CAS Registry Number

906-33-2

IUPAC Name

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

Traditional Name

neochlorogenic acid

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 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-NXLLHMKUSA-N

Chemical Taxonomy

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:16384 )
cyclitol carboxylic acid (CHEBI:16384 )
Caffeate derivatives (C17147 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

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	33.12 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (6 TMS)	splash10-0a4i-2779000000-05b2fc59f56f79049968	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Negative	splash10-000l-0900000000-5ab6455873264462bceb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-000f-0900000000-cda19179fe6c6b526bab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-002f-0901000000-893cb76037debb93b2ad	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-002f-0900000000-ca261c56261936391ff5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0109000000-5de1931e7418f0c537ac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-03dr-0900000000-de7078adddab10dc09ac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-105a6e539cf0d57bb256	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0900000000-1b705a6715ed1c6c3c4e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-03di-0900000000-8c0991eea696d59be2f6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-03di-0900000000-06335c33e4d64583bd46	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0918000000-3ee17b66f5461b5349a2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03g3-0902000000-adb0080c997613268656	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004j-1900000000-837dabfad86490278224	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfu-0519000000-d321b79970ee8839fc24	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06vm-1922000000-410b2ca167dfdb9d0a54	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-0900000000-090aec697972e64791aa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udl-0907000000-7552557c59dc3f71d17e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f76-0912000000-2007c2339d38311de146	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000l-2901000000-8f60dc3d397918e40c71	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0905000000-558b49c195cd84c2bb62	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0900000000-a3bfaab2ee36f5805f06	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02ib-2900000000-d93b9afe7d5384280f4d	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum