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

General Information of Drug (ID: DR2078)
Drug Name
Cytidine
Synonyms
Cytidin; Cytosine riboside; Cytosine, 1-beta-D-ribofuranosyl-; Zytidin; beta-D-Ribofuranoside, cytosine-1; cytidine; 1-beta-D-Ribofuranosylcytosine; 1-beta-Ribofuranosylcytosine; 1beta-2'-Ribofuranosylcytosine, d-; 1beta-Ribofuranosylcytosine; 2(1H)-Pyrimidinone, 4-amino-1-beta-D-ribofuranosyl-; 4-Amino-1-beta-D-ribofuranosyl-2(1H)-pyrimidinone; 4-Amino-1beta-D-ribofuranosyl-2(1H)-pyrimidinone; 65-46-3; CHEBI:17562; Cyd; EINECS 200-610-9; MFCD00006545; NSC 20258; UNII-5CSZ8459RP
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 243.22 Topological Polar Surface Area 129
Heavy Atom Count 17 Rotatable Bond Count 2
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
6175
PubChem SID
2561 ; 3758 ; 610624 ; 833276 ; 841097 ; 3132638 ; 8144101 ; 8153876 ; 11110524 ; 12109173 ; 15342347 ; 24892387 ; 24892710 ; 25621293 ; 26754267 ; 29225173 ; 49684259 ; 49693276 ; 49834502 ; 50036797 ; 51092061 ; 56459360 ; 76890969 ; 81044585 ; 85098495 ; 85165010 ; 85230757 ; 87565639 ; 88211484 ; 92297505 ; 93576752 ; 99246698 ; 99381411 ; 99453898 ; 103313321 ; 103823300 ; 104223697 ; 104311310 ; 117588066 ; 124558522 ; 125264648 ; 126523004 ; 126635400 ; 127303743 ; 127303744 ; 127303745 ; 127303746 ; 127303747 ; 127303748 ; 127303749
ChEBI ID
CHEBI:17562
CAS Number
65-46-3
TTD Drug ID
D0E7ES
Formula
C9H13N3O5
Canonical SMILES
C1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)O)O
InChI
1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7-,8-/m1/s1
InChIKey
UHDGCWIWMRVCDJ-XVFCMESISA-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
Cytidine diphosphate DM004933
6132
Conjugation - Phosphorylation 1 [4] , [2]
Cytidine triphosphate DM003227
6176
Conjugation - Phosphorylation 2 [4] , [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005324 Cytidine Cytidine diphosphate Conjugation - Phosphorylation NRK1 ... [4], [2]
MR005325 Cytidine diphosphate Cytidine triphosphate Conjugation - Phosphorylation NRK1 ... [4], [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Nicotinamide riboside kinase 1 (NRK1) DME0479 Homo sapiens
NRK1_HUMAN
2.7.1.22
[2]
Nicotinamide riboside kinase 2 (NRK2) DME0478 Homo sapiens
NRK2_HUMAN
2.7.1.22
[2]
Uridine-cytidine kinase 1 (UCK1) DME0481 Homo sapiens
UCK1_HUMAN
2.7.1.48
[3]
Uridine-cytidine kinase 2 (UCK2) DME0480 Homo sapiens
UCK2_HUMAN
2.7.1.48
[3]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Nicotinamide riboside kinase 1 (NRK1) DME0479 Km = 15 microM
NRK1_HUMAN
[2]
Nicotinamide riboside kinase 2 (NRK2) DME0478 Km = 15 microM
NRK2_HUMAN
[2]
Uridine-cytidine kinase 1 (UCK1) DME0481 Km = 0.086 microM
UCK1_HUMAN
[3]
Uridine-cytidine kinase 2 (UCK2) DME0480 Km = 0.086 microM
UCK2_HUMAN
[3]
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: 4728).
2 Nicotinamide riboside kinase structures reveal new pathways to NAD+. PLoS Biol. 2007 Oct 2;5(10):e263.
3 Phosphorylation of uridine and cytidine nucleoside analogs by two human uridine-cytidine kinases. Mol Pharmacol. 2001 May;59(5):1181-6.
4 Metabolism of cytidine and uridine in bean leaves

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