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

General Information of Drug (ID: DR1763)
Drug Name
Decitabine
Synonyms
Dacogen; Decitabine; Dezocitidine; 2'-Deoxy-5-azacytidine; 2353-33-5; 4-Amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-1,3,5-triazin-2(1H)-one; 4-amino-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,3,5-triazin-2(1H)-one; 5-Aza-2′-Deoxycytidine; 5-Aza-2'-deoxycytidine; 5-Azadeoxycytidine; 5-Deoxy-2′-azacytidine; 5-aza-2-deoxycytidine; 5-aza-CdR; 5-aza-dC; 5A2dc; AzadC; CHEBI:50131; Dac; MLS001332587; NSC 127716; UNII-776B62CQ27
Indication Myelodysplastic syndrome [ICD11: 2A36] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 228.21 Topological Polar Surface Area 121
Heavy Atom Count 16 Rotatable Bond Count 2
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
451668
PubChem SID
596457 ; 10300747 ; 12013916 ; 14749266 ; 14798099 ; 17397761 ; 24890797 ; 26758275 ; 46505657 ; 47211573 ; 47515034 ; 48422583 ; 49831907 ; 49836662 ; 53789316 ; 56310803 ; 56310829 ; 56310991 ; 56311079 ; 56311138 ; 56311371 ; 56311372 ; 56311435 ; 56311466 ; 56311472 ; 56311487 ; 56311581 ; 56311739 ; 56311918 ; 56312280 ; 56312302 ; 56312939 ; 56313048 ; 56313052 ; 56313366 ; 56313487 ; 56313832 ; 56313833 ; 56313869 ; 56314010 ; 56324652 ; 57260149 ; 57288417 ; 57288447 ; 57288645 ; 57405281 ; 78597402 ; 92719107 ; 103771112 ; 104253166
ChEBI ID
ChEBI:50131
CAS Number
2353-33-5
TTD Drug ID
D0X5XU
Formula
C8H12N4O4
Canonical SMILES
C1C(C(OC1N2C=NC(=NC2=O)N)CO)O
InChI
1S/C8H12N4O4/c9-7-10-3-12(8(15)11-7)6-1-4(14)5(2-13)16-6/h3-6,13-14H,1-2H2,(H2,9,11,15)/t4-,5+,6+/m0/s1
InChIKey
XAUDJQYHKZQPEU-KVQBGUIXSA-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
5-aza-2'-deoxycytidine-monophosphate DM001940
125632
Other reaction - Phosphorylation 1 [5]
5-aza-2'-deoxyuridine DM001943
68517003
Oxidation - Deamination 1 [6]
5-aza-2'-deoxycytidine-diphosphate DM001941
129711299
Oxidation - Deamination 2 [4]
5-aza-2'-deoxycytidine-triphosphate DM001942
126357
Other reaction - Phosphorylation 3 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000751 Decitabine 5-aza-2'-deoxycytidine-monophosphate Other reaction - Phosphorylation DCK [5]
MR000752 Decitabine 5-aza-2'-deoxyuridine Oxidation - Deamination cdd [6]
MR000749 5-aza-2'-deoxycytidine-monophosphate 5-aza-2'-deoxycytidine-diphosphate Oxidation - Deamination CMPK1 [4]
MR000750 5-aza-2'-deoxycytidine-diphosphate 5-aza-2'-deoxycytidine-triphosphate Other reaction - Phosphorylation ndk [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytidine aminohydrolase (CDA) DME0080 Homo sapiens
CDD_HUMAN
3.5.4.5
[2]
Cytidine deaminase (cdd) DME1196 Mycoplasma hyorhinis
E0TLJ6_MYCHH
3.5.4.5
[3]
Nucleoside diphosphate kinase (ndk) DMEN041 Escherichia coli
NDK_ECOLI
4.2.1.77
[4]
References
1 Decitabine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Tracking decitabine incorporation into malignant myeloid cell DNA in vitro and in vivo by LC-MS/MS with enzymatic digestion. Sci Rep. 2019 Mar 14;9(1):4558.
3 Mycoplasma hyorhinis-encoded cytidine deaminase efficiently inactivates cytosine-based anticancer drugs. FEBS Open Bio. 2015 Aug 3;5:634-9.
4 Kinetic interaction of 5-AZA-2'-deoxycytidine-5'-monophosphate and its 5'-triphosphate with deoxycytidylate deaminase Mol Pharmacol. 1984 May;25(3):436-40.
5 Kinetics of phosphorylation of 5-aza-2'-deoxyycytidine by deoxycytidine kinase Biochem Pharmacol. 1979 Apr 15;28(8):1443-4. doi: 10.1016/0006-2952(79)90454-4.
6 Kinetics of deamination of 5-aza-2'-deoxycytidine and cytosine arabinoside by human liver cytidine deaminase and its inhibition by 3-deazauridine, thymidine or uracil arabinoside Biochem Pharmacol. 1983 Apr 1;32(7):1327-8. doi: 10.1016/0006-2952(83)90293-9.

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