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

General Information of Drug (ID: DR2060)
Drug Name
Acetyl ethylene
Synonyms
Acetone, methylene-; 3-Buten-2-one; Butenone; Ketone, methyl vinyl; METHYL VINYL KETONE; Methyl ethenyl ketone; Methyl-vinyl-cetone; Methyl-vinyl-cetone [French]; Methylene acetone; Methylvinyl ketone; Methylvinylketon; Methylvinylketon [German]; Methylvinylketone; Vinyl methyl ketone; but-1-en-3-one; but-3-en-2-one; delta(sup 3)-2-Butenone; gamma-Oxo-alpha-butylene; methylvinylcetone; 1-Buten-3-one; 2-Butenone; 3-Butene-2-one; 3-Butenone-2; 3-oxo-1-butene; 78-94-4; CCRIS 3423; HSDB 716; NSC 4853; UNII-AR7642I1MP
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 70.09 Topological Polar Surface Area 17.1
Heavy Atom Count 5 Rotatable Bond Count 1
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
6570
ChEBI ID
CHEBI:48058
CAS Number
78-94-4
Formula
C4H6O
Canonical SMILES
CC(=O)C=C
InChI
1S/C4H6O/c1-3-4(2)5/h3H,1H2,2H3
InChIKey
FUSUHKVFWTUUBE-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
GSH-MVK DM001685 N. A. Unclear 1 [3]
Nepsilon-(3-formyl-3,4-dehydropiperidino)lysine DM001686 N. A. Other reaction - Dehydration 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000051 Acetyl ethylene GSH-MVK Unclear Unclear [3]
MR000052 Acetyl ethylene Nepsilon-(3-formyl-3,4-dehydropiperidino)lysine Other reaction - Dehydration Unclear [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
NADPH:quinone reductase (CRYZ) DME0468 Homo sapiens
QOR_HUMAN
1.6.5.5
[2]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
NADPH:quinone reductase (CRYZ) DME0468 Km = 0.035 microM
QOR_HUMAN
[2]
References
1 Identification of a fused-ring 2'-deoxyadenosine adduct formed in human cells incubated with 1-chloro-3-buten-2-one, a potential reactive metabolite of 1,3-butadiene. Chem Res Toxicol. 2016 Jun 20;29(6):1041-50.
2 Kinetic and structural evidence of the alkenal/one reductase specificity of human crystallin. Cell Mol Life Sci. 2011 Mar;68(6):1065-77.
3 Intracellular Metabolism of ,-Unsaturated Carbonyl Compounds, Acrolein, Crotonaldehyde and Methyl Vinyl Ketone, Active Toxicants in Cigarette Smoke: Participation of Glutathione Conjugation Ability and Aldehyde-Ketone Sensitive Reductase Activity Chem Pharm Bull (Tokyo). 2016;64(6):585-93. doi: 10.1248/cpb.c15-00986.
4 Differences in lysine adduction by acrolein and methyl vinyl ketone: implications for cytotoxicity in cultured hepatocytes Chem Res Toxicol. 2005 Nov;18(11):1627-33. doi: 10.1021/tx0502387.

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