Cannabis Compound Database: Showing Compound Card for (E)-p-Coumaric acid (CDB000177)

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Record Information

Version

1.0

Created at

2020-03-18 23:27:38 UTC

Updated at

2022-12-13 19:31:28 UTC

CannabisDB ID

CDB000177

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

(E)-p-Coumaric acid

Description

trans-4-Coumaric acid or (e)-p-Coumaric acid, the trans-isomer of 4-coumaric acid, also known as 4-hydroxycinnamic acid, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing a cinnamic acid where the benzene ring is hydroxylated. 4-Hydroxycinnamic acid is a neutral compound. 4-Hydroxycinnamic acid exists in all living species, from bacteria to humans. 4-Hydroxycinnamic acid is found in highest concentrations in pepper (c. frutescens), pineapples, and sunflowers and in lower concentration in spinachs, kiwis, and sweet oranges. 4-Hydroxycinnamic acid has also been detected in wild rices, soursops, garden onions, hyssops, and avocado. This could make 4-hydroxycinnamic acid a potential biomarker for the consumption of these foods. 4-Hydroxycinnamic acid is also found in cannabis plants reported by Paris in 1973 ¬†(PMID: 6991645 ).

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

164.16

Monoisotopic Molecular Weight

164.0473

IUPAC Name

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

Traditional Name

coumaric acid

CAS Registry Number

501-98-4

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

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Microbe

Plant:

Biological location:

Cell and elements:

Extracellular

Cell:

Fibroblast

Subcellular:

Biofluid and excreta:

Role

Biological role:

Nutrient

Industrial application:

Pharmaceutical industry:

Pharmaceutical

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	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-03xr-6900000000-348f5c7c030570e0612f	2015-03-01	View Spectrum
GC-MS	(E)-p-Coumaric acid, non-derivatized, GC-MS Spectrum	splash10-014m-1981000000-e7648e85764a445a919c	Spectrum
GC-MS	(E)-p-Coumaric acid, 2 TMS, GC-MS Spectrum	splash10-066v-3791000000-a5712bbe8401ef499b5a	Spectrum
GC-MS	(E)-p-Coumaric acid, non-derivatized, GC-MS Spectrum	splash10-03di-8900000000-3bb023f80c1f54a16adc	Spectrum
GC-MS	(E)-p-Coumaric acid, non-derivatized, GC-MS Spectrum	splash10-03xr-5900000000-a364c62c9122c0fbe6de	Spectrum
GC-MS	(E)-p-Coumaric acid, non-derivatized, GC-MS Spectrum	splash10-014m-1981000000-e7648e85764a445a919c	Spectrum
GC-MS	(E)-p-Coumaric acid, non-derivatized, GC-MS Spectrum	splash10-066v-3791000000-a5712bbe8401ef499b5a	Spectrum
GC-MS	(E)-p-Coumaric acid, non-derivatized, GC-MS Spectrum	splash10-014m-1891000000-d8804981d3918cac534d	Spectrum
Predicted GC-MS	(E)-p-Coumaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014j-2900000000-7075c3e10f9df528109e	Spectrum
Predicted GC-MS	(E)-p-Coumaric acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00xu-6390000000-3110f0f6eb462a38bb64	Spectrum
Predicted GC-MS	(E)-p-Coumaric 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 - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-03di-0900000000-b58aab08954c973df04e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-014i-0900000000-3ddb41572ba36a950e37	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-014i-0900000000-ccac7f071084bc660095	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-014i-3900000000-5dc8af06da0120779cff	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-00kf-9500000000-9187edc4498ab4345e5a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-014i-0900000000-3d831c6acd9d3188de2f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-03di-0900000000-fbb6439b7d012045f3a8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative	splash10-0002-0900000000-9e18d43a8d86f9b9e72b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-014i-0900000000-c45397049a7ba500b332	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-03di-0900000000-b58aab08954c973df04e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-3ddb41572ba36a950e37	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-ccac7f071084bc660095	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-3900000000-5dc8af06da0120779cff	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00kf-9500000000-9187edc4498ab4345e5a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0900000000-3d831c6acd9d3188de2f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-03di-0900000000-fbb6439b7d012045f3a8	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0002-0900000000-9e18d43a8d86f9b9e72b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-c6491d0aaba639e3ae07	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0002-0900000000-9e18d43a8d86f9b9e72b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-014i-0900000000-a183cce49af676c95d4e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-1f13fa0e7a24be298cfb	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9200000000-206402014014906dbe29	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	splash10-03di-8900000000-3bb023f80c1f54a16adc	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00kb-3900000000-1118928776a5a6e213db	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-0002-0900000000-c5faa58d353ca1466c3c	2017-09-14	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, DMSO, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, DMSO, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Tyrosinase	TYR	11q14-q21	P14679	details
UDP-glucuronosyltransferase 1-1	UGT1A1	2q37	P22309	details
Cytosolic beta-glucosidase	GBA3		Q9H227	details
Sulfotransferase 1A3	SULT1A3		P0DMM9	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
Alien Dawg	Detected and Quantified	0.0168 mg/g dry wt	David S. Wishart,...	details
Gabriola	Detected and Quantified	0.00253 mg/g dry wt	David S. Wishart,...	details
Island Honey	Detected and Quantified	0.00608 mg/g dry wt	David S. Wishart,...	details
Quadra	Detected and Quantified	0.00965 mg/g dry wt	David S. Wishart,...	details
Sensi Star	Detected and Quantified	0.0184 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream	Detected and Quantified	0.0367 mg/g dry wt	David S. Wishart,...	details

External Links

HMDB ID

HMDB0002035

DrugBank ID

DB04066

Phenol Explorer Compound ID

FoodDB 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

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]

Enzymes

Enzyme Details

1. Tyrosinase

General function:: Involved in oxidoreductase activity
Specific function:: This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:: TYR
Uniprot ID:: P14679
Molecular weight:: 60392.69

Enzyme Details

2. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Enzyme Details

3. Cytosolic beta-glucosidase

General function:: Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:: Glycosidase probably involved in the intestinal absorption and metabolism of dietary flavonoid glycosides. Able to hydrolyze a broad variety of glycosides including phytoestrogens, flavonols, flavones, flavanones and cyanogens. Possesses beta-glycosylceramidase activity and may be involved in a nonlysosomal catabolic pathway of glycosylceramide.
Gene Name:: GBA3
Uniprot ID:: Q9H227
Molecular weight:: Not Available

Enzyme Details

4. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Showing Compound Card for (E)-p-Coumaric acid (CDB000177)

Structure for CDB000177 ((E)-p-Coumaric acid)

Enzymes