CHEBI:4917 - eugenol

ChEBI IDCHEBI:4917
ChEBI Nameeugenol
Stars
DefinitionA phenylpropanoid formally derived from guaiacol with an allyl chain substituted para to the hydroxy group. It is a major component of clove essential oil, and exhibits antibacterial, analgesic and antioxidant properties. It has been widely used in dentistry to treat toothache and pulpitis.
Last Modified24 May 2023
DownloadsMolfile
FormulaC10H12O2
Net Charge0
Average Mass164.204
Monoisotopic Mass164.08373
SMILESC=CCc1ccc(O)c(OC)c1
InChIInChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3
InChIKeyRRAFCDWBNXTKKO-UHFFFAOYSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Homo sapiens (ncbitaxon:9606)
blood (UBERON:0000178) PubMed (2329164)
saliva (UBERON:0001836) PubMed (20809147)
Syzygium aromaticum (ncbitaxon:219868) - DOI (10.1080/1040841X.2017.1295225)
Roles Classification
Chemical Roles:
radical scavenger  A role played by a substance that can react readily with, and thereby eliminate, radicals.
flavouring agent  A food additive that is used to added improve the taste or odour of a food.
Biological Roles:
EC 1.4.3.4 (monoamine oxidase) inhibitor  An EC 1.4.3.* (oxidoreductase acting on donor CH-NH2 group, oxygen as acceptor) inhibitor that interferes with the action of monoamine oxidase (EC 1.4.3.4).
voltage-gated sodium channel blocker  Any sodium channel blocker that interferes with the activity of voltage-gated sodium channels.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
flavouring agent  A food additive that is used to added improve the taste or odour of a food.
sensitiser  A chemical compound that causes a substantial proportion of exposed people or animals to develop an allergic reaction in normal tissue after repeated exposure to the compound.
human blood serum metabolite  Any metabolite (endogenous or exogenous) found in human blood serum samples.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
volatile oil component  Any plant metabolite that is found naturally as a component of a volatile oil.
allergen  A chemical compound, or part thereof, which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.
NF-kappaB inhibitor  An inhibitor of NF-κB (nuclear factor κ-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Applications:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
flavouring agent  A food additive that is used to added improve the taste or odour of a food.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
anaesthetic  Substance which produces loss of feeling or sensation.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
ChEBI Ontology
Outgoing Relation(s)
eugenol (CHEBI:4917) has functional parent guaiacol (CHEBI:28591)
eugenol (CHEBI:4917) has role allergen (CHEBI:50904)
eugenol (CHEBI:4917) has role anaesthetic (CHEBI:38867)
eugenol (CHEBI:4917) has role analgesic (CHEBI:35480)
eugenol (CHEBI:4917) has role anti-inflammatory agent (CHEBI:67079)
eugenol (CHEBI:4917) has role antibacterial agent (CHEBI:33282)
eugenol (CHEBI:4917) has role antineoplastic agent (CHEBI:35610)
eugenol (CHEBI:4917) has role apoptosis inducer (CHEBI:68495)
eugenol (CHEBI:4917) has role EC 1.4.3.4 (monoamine oxidase) inhibitor (CHEBI:38623)
eugenol (CHEBI:4917) has role flavouring agent (CHEBI:35617)
eugenol (CHEBI:4917) has role human blood serum metabolite (CHEBI:85234)
eugenol (CHEBI:4917) has role NF-κB inhibitor (CHEBI:73240)
eugenol (CHEBI:4917) has role radical scavenger (CHEBI:48578)
eugenol (CHEBI:4917) has role sensitiser (CHEBI:139492)
eugenol (CHEBI:4917) has role volatile oil component (CHEBI:27311)
eugenol (CHEBI:4917) has role voltage-gated sodium channel blocker (CHEBI:38634)
eugenol (CHEBI:4917) is a alkenylbenzene (CHEBI:195237)
eugenol (CHEBI:4917) is a monomethoxybenzene (CHEBI:25235)
eugenol (CHEBI:4917) is a phenols (CHEBI:33853)
eugenol (CHEBI:4917) is a phenylpropanoid (CHEBI:26004)
Incoming Relation(s)
O-methyleugenol (CHEBI:4918) has functional parent eugenol (CHEBI:4917)
1'-acetoxyeugenol acetate (CHEBI:470) has functional parent eugenol (CHEBI:4917)
3-methyleugenol (CHEBI:59074) has functional parent eugenol (CHEBI:4917)
3,5,6-trimethyleugenol (CHEBI:59096) has functional parent eugenol (CHEBI:4917)
5-methyleugenol (CHEBI:59072) has functional parent eugenol (CHEBI:4917)
6-methyleugenol (CHEBI:59060) has functional parent eugenol (CHEBI:4917)
eugenol sulfate (CHEBI:133570) has functional parent eugenol (CHEBI:4917)
dihydroconiferyl alcohol (CHEBI:4559) is a eugenol (CHEBI:4917)
IUPAC Name 
2-methoxy-4-(prop-2-en-1-yl)phenol
Synonyms  Source
1,3,4-EugenolNIST Chemistry WebBook
1-allyl-3-methoxy-4-hydroxybenzeneChEBI
1-allyl-4-hydroxy-3-methoxybenzeneChEBI
1-Hydroxy-2-methoxy-4-allylbenzeneChemIDplus
1-Hydroxy-2-methoxy-4-prop-2-enylbenzeneChemIDplus
1-Hydroxy-2-methoxy-4-propenylbenzeneChemIDplus
UniProt Name  Source
eugenolUniProt
Manual XrefsDatabases
13876103ChemSpider
2008BPDB
4648DrugCentral
C00000619KNApSAcK
C10453KEGG COMPOUND
CPD-6481MetaCyc
D04117KEGG DRUG
EOLPDBeChem
EugenolWikipedia
FDB012171FooDB
HMDB0005809HMDB
LSM-2720LINCS
Registry NumbersSources
Reaxys:1366759Reaxys
CAS:97-53-0NIST Chemistry WebBook
CAS:97-53-0ChemIDplus
Citations