Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1942)
Drug Name
Eugenol
Synonyms
Allylguaiacol; Caryophyllic acid; Engenol; Eugenic acid; Phenol, 2-methoxy-4-(2-propenyl)-; Synthetic eugenol; eugenol; p-Allylguaiacol; p-Eugenol; 1,3,4-Eugenol; 1-Hydroxy-2-methoxy-4-allylbenzene; 1-Hydroxy-2-methoxy-4-prop-2-enylbenzene; 2-Methoxy-1-hydroxy-4-allylbenzene; 2-Methoxy-4-(2-propenyl)phenol; 2-Methoxy-4-allylphenol; 2-Methoxy-4-prop-2-enylphenol; 4-Allyl-1-hydroxy-2-methoxybenzene; 4-Allyl-2-methoxyphenol; 4-Allylcatechol-2-methyl ether; 4-Allylguaiacol; 5-Allylguaiacol; 97-53-0
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 164.2 Topological Polar Surface Area 29.5
Heavy Atom Count 12 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
3314
PubChem SID
12636 ; 74509 ; 125977 ; 588506 ; 597975 ; 866329 ; 3133265 ; 5268443 ; 8139909 ; 8146418 ; 8149344 ; 8152109 ; 10538901 ; 11335867 ; 11361106 ; 11371571 ; 11375463 ; 11462078 ; 11484964 ; 11489080 ; 11490462 ; 11493597 ; 11528359 ; 11537592 ; 15321782 ; 17389879 ; 24862128 ; 24869788 ; 24894609 ; 24901114 ; 24901115 ; 26611744 ; 26679332 ; 26747361 ; 26747362 ; 26753011 ; 29204126 ; 37904874 ; 47206065 ; 47365196 ; 47515328 ; 47959753 ; 48413772 ; 48421969 ; 48423424 ; 48425142 ; 50105594 ; 50105595 ; 50800114 ; 53787078
ChEBI ID
CHEBI:4917
CAS Number
97-53-0
TTD Drug ID
D0O4QB
Formula
C10H12O2
Canonical SMILES
COC1=C(C=CC(=C1)CC=C)O
InChI
1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3
InChIKey
RRAFCDWBNXTKKO-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
3-piperidyl-1-(3'-methoxy-4'-hydroxyphenyl)-1-propanone DM005872 N. A. Unclear 1 [3]
3-pyrrolidinyl-1-(3'-methoxy-4'-hydroxyphenyl)-1-propanone DM005873 N. A. Unclear 1 [3]
Glucuronic acid conjugate DM005871 N. A. Unclear 1 [4]
Quinone methide DM003429 N. A. Unclear 1 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006292 Eugenol Quinone methide Unclear Unclear [5]
MR006293 Eugenol Glucuronic acid conjugate Unclear Unclear [4]
MR006294 Eugenol 3-piperidyl-1-(3'-methoxy-4'-hydroxyphenyl)-1-propanone Unclear Unclear [3]
MR006295 Eugenol 3-pyrrolidinyl-1-(3'-methoxy-4'-hydroxyphenyl)-1-propanone Unclear Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A7 (UGT1A7) DME0065 Homo sapiens
UD17_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A8 (UGT1A8) DME0064 Homo sapiens
UD18_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[2]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Km = 0.0084 microM
UD11_HUMAN
[2]
UDP-glucuronosyltransferase 1A7 (UGT1A7) DME0065 Km = 0.0084 microM
UD17_HUMAN
[2]
UDP-glucuronosyltransferase 1A8 (UGT1A8) DME0064 Km = 0.0084 microM
UD18_HUMAN
[2]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Km = 0.0084 microM
UD19_HUMAN
[2]
References
1 The IUPHAR/BPS Guide to PHARMACOLOGY in 2020: extending immunopharmacology content and introducing the IUPHAR/MMV Guide to MALARIA PHARMACOLOGY. Nucleic Acids Res. 2020 Jan 8;48(D1):D1006-D1021. (Ligand id: 2425).
2 Differential and special properties of the major human UGT1-encoded gastrointestinal UDP-glucuronosyltransferases enhance potential to control chemical uptake. J Biol Chem. 2004 Jan 9;279(2):1429-41.
3 PubChem:Eugenol
4 Metabolism and cytotoxicity of eugenol in isolated rat hepatocytes
5 Applying sputum as a diagnostic tool in pneumonia: limited yield, minimal impact on treatment decisions

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