Cannabis Compound Database: Showing Compound Card for Eugenol (CDB000055)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (4)transporters (1) Show 6 proteins XML

Record Information

Version

1.0

Created at

2020-03-18 23:23:07 UTC

Updated at

2020-12-07 19:07:01 UTC

CannabisDB ID

CDB000055

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Eugenol

Description

Eugenol or 4-allyl-2-methoxyphenol is classified as a phenylpropanoid, formally derived from¬†guaiacol,¬†with an allyl chain substituted para to the¬†hydroxy¬†group. It is soluble in water, alcohol,¬†chloroform, ether and oils. Eugenol is a neutral compound. It is biosynthesized from tyrosine. Eugenol exists in all eukaryotes, from yeast to humans. It is a clear to pale yellow oily liquid extracted from clove oil, nutmeg, cinnamon, basil and bay leaf. It has a pleasant, spicy, clove-like odor with a spicy pungent taste. Eugenol is found in highest concentrations in cloves, allspices, and carrots and in lower concentrations in walnuts, ceylon cinnamons, and wild carrots. Eugenol has also been detected in shea tree, passion fruits, winged beans, fireweeds, and gingers, making it a potential biomarker for the consumption of these foods. It is a noncannabinoid phenol compound found in cannabis plants (PMID: 6991645 ). Eugenol is used in perfumeries, flavorings and essential oils. It was first used for the manufacture of vanillin (https://doi.org/10.1021/ed054p776), though most vanillin is now produced from petrochemicals or from by-products of paper manufacture. Eugenol is hepatotoxic, meaning it may cause damage to the¬†liver, if consumed in high doses. Eugenol has local antiseptic and anaesthetic properties (PMID: 15089054 ; PMID: 935250 ) and acts as positive allosteric modulators of the GABAA¬†receptor. It has high antioxidant, anti-proliferative, and anti-inflammatory activities with potential roles in alleviating and preventing cancer and inflammatory reactions (PMID: 27771920 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,3,4-Eugenol	ChEBI
1-Allyl-3-methoxy-4-hydroxybenzene	ChEBI
1-Allyl-4-hydroxy-3-methoxybenzene	ChEBI
1-Hydroxy-2-methoxy-4-allylbenzene	ChEBI
1-Hydroxy-2-methoxy-4-prop-2-enylbenzene	ChEBI
1-Hydroxy-2-methoxy-4-propenylbenzene	ChEBI
2-Hydroxy-5-allylanisole	ChEBI
2-Methoxy-1-hydroxy-4-allylbenzene	ChEBI
2-Methoxy-4-(2-propen-1-yl)phenol	ChEBI
2-Methoxy-4-(2-propenyl)phenol	ChEBI
2-Methoxy-4-allylphenol	ChEBI
2-Methoxy-4-prop-2-enyl-phenol	ChEBI
2-Methoxy-4-prop-2-enylphenol	ChEBI
4-Allyl-1-hydroxy-2-methoxybenzene	ChEBI
4-Allyl-2-methoxyphenol	ChEBI
4-Allylcatechol-2-methyl ether	ChEBI
4-Allylguaiacol	ChEBI
4-Hydroxy-3-methoxy-1-allylbenzene	ChEBI
Allylguaiacol	ChEBI
Caryophyllic acid	ChEBI
Eugenic acid	ChEBI
p-Allylguaiacol	ChEBI
p-Eugenol	ChEBI
Caryophyllate	Generator
Eugenate	Generator
2-Methoxy-4-(3-propenyl)phenol	HMDB
2-Methoxy-4-(prop-2-en-1-yl)phenol	HMDB
4-Allyl-2-methoxy-phenol	HMDB
4-Allylcatechol 2-methyl ether	HMDB
4-Hydroxy-3-methoxyallylbenzene	HMDB
5-Allylguaiacol	HMDB
Engenol	HMDB
Eugenol (natural)	HMDB
Synthetic eugenol	HMDB
2-Methoxy-4-(2'-propenyl)phenol	PhytoBank
2-Methoxy-4-(2’-propenyl)phenol	PhytoBank
2-Methoxy-4-[2-allyl]phenol	PhytoBank
3-(3-Methoxy-4-hydroxyphenyl)propene	PhytoBank
3-(4-Hydroxy-3-methoxyphenyl)-1-propene	PhytoBank
4-Allenylguaiacol	PhytoBank

Chemical Formula

C₁₀H₁₂O₂

Average Molecular Weight

164.2

Monoisotopic Molecular Weight

164.0837

IUPAC Name

2-methoxy-4-(prop-2-en-1-yl)phenol

Traditional Name

eugenol

CAS Registry Number

97-53-0

SMILES

COC1=C(O)C=CC(CC=C)=C1

InChI Identifier

InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3

InChI Key

RRAFCDWBNXTKKO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:4917 )
phenylpropanoid (CHEBI:4917 )
monomethoxybenzene (CHEBI:4917 )
Monolignols (C10453 )
a monoterpenol (CPD-6481 )
a phenol (CPD-6481 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Synthetic:

Personal care product

Environmental:

Tobacco smoke

Biological:

Animal

Plant:

Biological location:

Subcellular:

Biofluid and excreta:

Role

Environmental role:

Environmental contaminant

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	−7.5 °C	Wikipedia
Boiling Point	254 °C	Wikipedia
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.66	ALOGPS
logP	2.61	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	9.94	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	48.79 m³·mol⁻¹	ChemAxon
Polarizability	17.9 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	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0il0-6900000000-ff0dc492bab70317bb2a	2014-09-20	View Spectrum
GC-MS	Eugenol, non-derivatized, GC-MS Spectrum	splash10-0ik9-5900000000-3d3a9e4f250074741003	Spectrum
GC-MS	Eugenol, non-derivatized, GC-MS Spectrum	splash10-03di-2900000000-395df8510f0db4933abe	Spectrum
GC-MS	Eugenol, non-derivatized, GC-MS Spectrum	splash10-03di-6900000000-1afdd3b83f6832b11f70	Spectrum
GC-MS	Eugenol, non-derivatized, GC-MS Spectrum	splash10-03di-4900000000-1d96ae8b031e47e13112	Spectrum
GC-MS	Eugenol, non-derivatized, GC-MS Spectrum	splash10-0ik9-6900000000-def0c646d72c040b58da	Spectrum
GC-MS	Eugenol, non-derivatized, GC-MS Spectrum	splash10-03di-0900000000-dfa64951eb648f5c9df1	Spectrum
GC-MS	Eugenol, non-derivatized, GC-MS Spectrum	splash10-0ik9-5900000000-3d3a9e4f250074741003	Spectrum
GC-MS	Eugenol, non-derivatized, GC-MS Spectrum	splash10-03di-2900000000-395df8510f0db4933abe	Spectrum
GC-MS	Eugenol, non-derivatized, GC-MS Spectrum	splash10-03di-6900000000-1afdd3b83f6832b11f70	Spectrum
GC-MS	Eugenol, non-derivatized, GC-MS Spectrum	splash10-03di-4900000000-1d96ae8b031e47e13112	Spectrum
GC-MS	Eugenol, non-derivatized, GC-MS Spectrum	splash10-0ik9-6900000000-def0c646d72c040b58da	Spectrum
GC-MS	Eugenol, non-derivatized, GC-MS Spectrum	splash10-03di-0900000000-dfa64951eb648f5c9df1	Spectrum
Predicted GC-MS	Eugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03ms-1900000000-da27a86009649c155318	Spectrum
Predicted GC-MS	Eugenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-8790000000-0d0c6f0e58d7dc3e5620	Spectrum
Predicted GC-MS	Eugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Eugenol, 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-QTOF , positive	splash10-014i-0900000000-4541582e8f6395e2fa87	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0900000000-84f950d2fc0742e324d5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0ab9-0900000000-4c037643a10913a70f5e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-0900000000-83f8f32dfd9b94fb1d24	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-2900000000-c65a2dab49b8ebb431da	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-001i-0900000000-65a67ccd1df0d2f1796f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0900000000-83f8f32dfd9b94fb1d24	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0ab9-0900000000-4c037643a10913a70f5e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-4541582e8f6395e2fa87	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0900000000-84f950d2fc0742e324d5	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-f5092971e88a27de65e9	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0a4i-2900000000-c65a2dab49b8ebb431da	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0900000000-7beab8e102e0252d1a87	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-9d2a857e8a482a061127	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-2900000000-9c846765367542bf4db1	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fr6-9500000000-98fcaf3ccca850c34bd3	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-835320dc79855273af7f	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-3a70eb9601589d9108a1	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052e-4900000000-1c4834945c53d64bab3b	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-8db47caa9667c101bd0f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03ka-0900000000-ab5855c31f23e61c7f54	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03k9-3900000000-868b72d9162a6b307829	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0900000000-63a94aabae02f360ee77	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05nr-1900000000-ce4d363c5e701cb34dfd	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9000000000-8e444a7d43baeb4d68f0	2021-09-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, 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
UDP-glucuronosyltransferase 2B28	UGT2B28	4q13.2	Q9BY64	details
UDP-glucuronosyltransferase 1-1	UGT1A1	2q37	P22309	details
UDP-glucuronosyltransferase 2B17	UGT2B17	4q13	O75795	details
Sulfotransferase 1A3	SULT1A3		P0DMM9	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Gamma-aminobutyric acid receptor subunit alpha-1	GABRA1	5q34-q35	P14867	details

Metal Bindings

Not Available

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Gamma-aminobutyric acid receptor subunit alpha-1	GABRA1	5q34-q35	P14867	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0005809

DrugBank ID

DB09086

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

ChEBI ID

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 ]
Jadhav BK, Khandelwal KR, Ketkar AR, Pisal SS: Formulation and evaluation of mucoadhesive tablets containing eugenol for the treatment of periodontal diseases. Drug Dev Ind Pharm. 2004 Feb;30(2):195-203. doi: 10.1081/ddc-120028715. [PubMed:15089054 ]
Sell AB, Carlini EA: Anesthetic action of methyleugenol and other eugenol derivatives. Pharmacology. 1976;14(4):367-77. doi: 10.1159/000136617. [PubMed:935250 ]
Fujisawa S, Murakami Y: Eugenol and Its Role in Chronic Diseases. Adv Exp Med Biol. 2016;929:45-66. doi: 10.1007/978-3-319-41342-6_3. [PubMed:27771920 ]

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 2B28

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
Gene Name:: UGT2B28
Uniprot ID:: Q9BY64
Molecular weight:: 38742.9

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. UDP-glucuronosyltransferase 2B17

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. The major substrates of this isozyme are eugenol > 4-methylumbelliferone > dihydrotestosterone (DHT) > androstane-3-alpha,17-beta-diol (3-alpha-diol) > testosterone > androsterone (ADT).
Gene Name:: UGT2B17
Uniprot ID:: O75795
Molecular weight:: 61094.915

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

Transporters

Enzyme Details

1. Gamma-aminobutyric acid receptor subunit alpha-1

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA1
Uniprot ID:: P14867
Molecular weight:: 51801.4

Showing Compound Card for Eugenol (CDB000055)

Structure for CDB000055 (Eugenol)

Enzymes

Transporters