Livestock Metabolome Database: Showing metabocard for 4-Hydroxycinnamic acid (LMDB00770)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-30 18:17:41 UTC

Update Date

2016-08-01 19:17:19 UTC

Lmdb

LMDB00770

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Hydroxycinnamic acid

Description

4-Hydroxycinnamic acid, also known as trans-p-hydroxycinnamate or p-coumaric acid, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. 4-Hydroxycinnamic acid exists in all living species, ranging from bacteria to plants to humans. 4-Hydroxycinnamic acid is found, on average, in the highest concentration within a few different foods, such as pepper (c. frutescens), pineapples (Ananas comosus), and sunflowers (Helianthus annuus) and in a lower concentration in robusta coffees (Coffea canephora), common buckwheats (Fagopyrum esculentum), and european plums (Prunus domestica). 4-Hydroxycinnamic acid has also been detected, but not quantified in, several different foods, such as cantaloupe melons (Cucumis melo var. cantalupensis), monk fruits (Siraitia grosvenorii), rapinis (Brassica ruvo), mugworts (Artemisia vulgaris), and black cabbages (Brassica oleracea var. viridis). This could make 4-hydroxycinnamic acid a potential biomarker for the consumption of these foods. 4-Hydroxycinnamic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 4-Hydroxycinnamic acid.

Structure

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

Synonyms

Value	Source
(2E)-3-(4-Hydroxyphenyl)acrylic acid	ChEBI
(e)-3-(4-Hydroxyphenyl)-2-propenoic acid	ChEBI
(e)-p-Coumaric acid	ChEBI
(e)-p-Hydroxycinnamic acid	ChEBI
4'-HYDROXYCINNAMIC ACID	ChEBI
Naringeninic acid	ChEBI
p-Coumaric acid	ChEBI
trans-p-Coumaric acid	ChEBI
trans-p-Coumarinic acid	ChEBI
trans-p-Hydroxycinnamate	ChEBI
trans-p-Hydroxycinnamic acid	ChEBI
trans-4-Hydroxycinnamate	Kegg
4-Hydroxycinnamate	Kegg
(2E)-3-(4-Hydroxyphenyl)acrylate	Generator
(e)-3-(4-Hydroxyphenyl)-2-propenoate	Generator
(e)-p-Coumarate	Generator
(e)-p-Hydroxycinnamate	Generator
4'-HYDROXYCINNAMate	Generator
Naringeninate	Generator
p-Coumarate	Generator
trans-p-Coumarate	Generator
trans-p-Coumarinate	Generator
4-Coumaric acid, (e)-isomer	MeSH
4-Coumaric acid, (Z)-isomer	MeSH
4-Coumaric acid, disodium salt	MeSH
p-Coumaryl alcohol	MeSH
p-Hydroxycinnamic acid	MeSH
Para-coumaric acid	MeSH
trans-3-(4'-Hydroxyphenyl)-2-propenoic acid	MeSH
trans-HPPA	MeSH
3-(4-Hydroxyphenyl)-2-propenoate	HMDB
3-(4-Hydroxyphenyl)-2-propenoic acid	HMDB
3-(4-Hydroxyphenyl)acrylate	HMDB
3-(4-Hydroxyphenyl)acrylic acid	HMDB
4-Coumarate	HMDB
4-Hydroxy cinnamate	HMDB
4-Hydroxy cinnamic acid	HMDB
4-Hydroxyphenylpropenoate	HMDB
4-Hydroxyphenylpropenoic acid	HMDB
b-[4-Hydroxyphenyl]acrylate	HMDB
b-[4-Hydroxyphenyl]acrylic acid	HMDB
beta-[4-Hydroxyphenyl]acrylate	HMDB
beta-[4-Hydroxyphenyl]acrylic acid	HMDB
cis-P-Coumarate	HMDB
Hydroxycinnamate	HMDB
Hydroxycinnamic acid	HMDB
P-Cumarate	HMDB
P-Cumaric acid	HMDB
P-Hydroxycinnamate	HMDB
P-Hydroxyphenylacrylate	HMDB
P-Hydroxyphenylacrylic acid	HMDB
Para coumarate	HMDB
Para coumaric acid	HMDB
Para-coumarate	HMDB
4-Hydroxycinnamic acid	ChEBI
trans-4-Coumarate	Generator, HMDB
(2E)-3-(4-Hydroxyphenyl)-2-propenoic acid	HMDB
(2E)-3-(4-Hydroxyphenyl)prop-2-enoic acid	HMDB
(E)-3-(4-Hydroxyphenyl)acrylic acid	HMDB
(E)-4-Hydroxycinnamic acid	HMDB
4’-Hydroxycinnamic acid	HMDB
p-Cumaric acid	HMDB
p-Hydroxy-trans-cinnamic acid	HMDB
p-Hydroxyphenylacrylic acid	HMDB
p-trans-Coumaric acid	HMDB
trans-3-(4-Hydroxyphenyl)-2-propenoic acid	HMDB
trans-4-Coumaric acid	HMDB
β-[4-Hydroxyphenyl]acrylic acid	HMDB

Chemical Formula

C₉H₈O₃

Average Molecular Weight

164.158

Monoisotopic Molecular Weight

164.047344122

IUPAC Name

(2E)-3-(4-hydroxyphenyl)prop-2-enoic acid

Traditional Name

coumaric acid

CAS Registry Number

Not Available

SMILES

OC(=O)\C=C\C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+

InChI Key

NGSWKAQJJWESNS-ZZXKWVIFSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids

Alternative Parents

Substituents

Cinnamic acid
Coumaric acid
Coumaric acid or derivatives
Hydroxycinnamic acid
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

4-coumaric acid (CHEBI:32374 )
Paracoumaryl alcohol derivatives (C00811 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.74	ALOGPS
logP	1.83	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	45.04 m³·mol⁻¹	ChemAxon
Polarizability	16.43 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-014m-1981000000-e7648e85764a445a919c	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-066v-3791000000-a5712bbe8401ef499b5a	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-8900000000-3bb023f80c1f54a16adc	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03xr-5900000000-a364c62c9122c0fbe6de	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014m-1981000000-e7648e85764a445a919c	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-066v-3791000000-a5712bbe8401ef499b5a	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014m-1891000000-d8804981d3918cac534d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-014j-2900000000-7075c3e10f9df528109e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00xu-6390000000-3110f0f6eb462a38bb64	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-03di-0900000000-b58aab08954c973df04e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-014i-0900000000-3ddb41572ba36a950e37	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-014i-0900000000-ccac7f071084bc660095	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-014i-3900000000-5dc8af06da0120779cff	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-00kf-9500000000-9187edc4498ab4345e5a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-014i-0900000000-3d831c6acd9d3188de2f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-03di-0900000000-fbb6439b7d012045f3a8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative	splash10-0002-0900000000-9e18d43a8d86f9b9e72b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-014i-0900000000-c45397049a7ba500b332	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-03di-0900000000-b58aab08954c973df04e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-3ddb41572ba36a950e37	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-ccac7f071084bc660095	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-3900000000-5dc8af06da0120779cff	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00kf-9500000000-9187edc4498ab4345e5a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0900000000-3d831c6acd9d3188de2f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-03di-0900000000-fbb6439b7d012045f3a8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0002-0900000000-9e18d43a8d86f9b9e72b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-c6491d0aaba639e3ae07	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0002-0900000000-9e18d43a8d86f9b9e72b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-014i-0900000000-a183cce49af676c95d4e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-1f13fa0e7a24be298cfb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9200000000-206402014014906dbe29	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	splash10-03di-8900000000-3bb023f80c1f54a16adc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00kb-3900000000-1118928776a5a6e213db	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-0002-0900000000-c5faa58d353ca1466c3c	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03xr-6900000000-348f5c7c030570e0612f	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C 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
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum