Bovine Metabolome Database: Showing metabocard for 4-Hydroxycinnamic acid (BMDB0002035)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:50:14 UTC

Update Date

2020-05-11 20:02:33 UTC

BMDB ID

BMDB0002035

Secondary Accession Numbers

BMDB02035

Metabolite Identification

Common Name

4-Hydroxycinnamic acid

Description

trans-4-Coumaric acid, also known as 4-hydroxycinnamic acid or trans-p-hydroxycinnamate, 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. trans-4-Coumaric acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. trans-4-Coumaric acid exists in all living species, ranging from bacteria to humans.

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

7400-08-0

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

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Mitochondria

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	211.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	1.79	SANGSTER (1994)

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
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-014m-1981000000-e7648e85764a445a919c	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-066v-3791000000-a5712bbe8401ef499b5a	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-8900000000-3bb023f80c1f54a16adc	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03xr-5900000000-a364c62c9122c0fbe6de	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014m-1981000000-e7648e85764a445a919c	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-066v-3791000000-a5712bbe8401ef499b5a	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014m-1891000000-d8804981d3918cac534d	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-014j-2900000000-7075c3e10f9df528109e	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00xu-6390000000-3110f0f6eb462a38bb64	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-03di-0900000000-b58aab08954c973df04e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-014i-0900000000-3ddb41572ba36a950e37	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-014i-0900000000-ccac7f071084bc660095	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-014i-3900000000-5dc8af06da0120779cff	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-00kf-9500000000-9187edc4498ab4345e5a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-014i-0900000000-3d831c6acd9d3188de2f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-03di-0900000000-fbb6439b7d012045f3a8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative	splash10-0002-0900000000-9e18d43a8d86f9b9e72b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-014i-0900000000-c45397049a7ba500b332	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-03di-0900000000-b58aab08954c973df04e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-3ddb41572ba36a950e37	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-ccac7f071084bc660095	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-3900000000-5dc8af06da0120779cff	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00kf-9500000000-9187edc4498ab4345e5a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0900000000-3d831c6acd9d3188de2f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-03di-0900000000-fbb6439b7d012045f3a8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0002-0900000000-9e18d43a8d86f9b9e72b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-c6491d0aaba639e3ae07	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0002-0900000000-9e18d43a8d86f9b9e72b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-014i-0900000000-a183cce49af676c95d4e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-1f13fa0e7a24be298cfb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9200000000-206402014014906dbe29	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	splash10-03di-8900000000-3bb023f80c1f54a16adc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00kb-3900000000-1118928776a5a6e213db	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-0002-0900000000-c5faa58d353ca1466c3c	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-03xr-6900000000-348f5c7c030570e0612f	View in MoNA
1D NMR	¹H NMR Spectrum (1D, DMSO, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, DMSO, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Fibroblasts
Milk

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 14168161	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 23438684	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0002035

DrugBank ID

DB04066

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

32374

References

Synthesis Reference

Ben-Bassat, Arie; Sariaslani, Fateme Sima; Huang, Lisa L.; Patnaik, Ranjan; Lowe, David J. Fermentative preparation of para-hydroxycinnamic acid and cinnamic acid at alkaline ph. U.S. Pat. Appl. Publ. (2005), 23 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54. [PubMed:14168161 ]

Showing metabocard for 4-Hydroxycinnamic acid (BMDB0002035)

Structure for BMDB0002035 (4-Hydroxycinnamic acid)