General Information of the Compound
Compound ID
CP0066824
Compound Name
AZACITIDINE
    Show/Hide
Synonyms
2-(beta-D-Ribofuranosyl)-4-amino-1,3,5-triazin-2-one
4-Amino-1-(beta-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one
4-Amino-1-beta-D-ribofuranosyl-1,3,5-traizin-2(1H)-one
4-Amino-1-beta-D-ribofuranosyl-1,3,5-triazine-2(1H)-one
4-Amino-1-beta-D-ribofuranosyl-s-triazin-2(1H)-one
4-Amino-1-beta-d-ribofuranosyl-1,3,5-triazin-2(1H)-one
4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triaz
4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
4-amino-1-beta-L-ribofuranosyl-1,3,5-triazin-2(1H)-one
5 AZC
5 Azacytidine
5-AC
5-AZAC
5-AZCR
5-aza-CR
5-azacitidine
5-azacytidine
5-azacytidine, Mylosar, Ladakamycin, Vidaza, Azacitidine
5AzaC
Antibiotic U 18496
Azacitidina
Azacitidina [INN-Spanish]
Azacitidine
Azacitidine (JAN/USAN/INN)
Azacitidine [USAN:INN]
Azacitidinum
Azacitidinum [INN-Latin]
Azacytidine
Ladakamycin
Mylo sar
Mylosar
NS-17
Pharmion Brand of Azacitidine;A 2385
Pyrimidine antimetabolite: inhibits nucleic acid replication
S-Triazin-2(1H)-one, 4-amino-1-beta-D-ribofuranosyl-(8CI)
U 18496
U-18496
Vidaz (TN)
Vidaza
Vidaza (TN)
WR-183027
Wr 183027
    Show/Hide
Structure
Formula
C8H12N4O5
Molecular Weight
244.207
Canonical SMILES
Nc1ncn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)n1
    Show/Hide
InChI
InChI=1S/C8H12N4O5/c9-7-10-2-12(8(16)11-7)6-5(15)4(14)3(1-13)17-6/h2-6,13-15H,1H2,(H2,9,11,16)/t3-,4-,5-,6-/m1/s1
    Show/Hide
InChIKey
NMUSYJAQQFHJEW-KVTDHHQDSA-N
CAS
320-67-2
Physicochemical Property
logP
-3.168
Rotatable Bonds
2
Heavy Atom Count
17
Polar Areas
143.72
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
9
Complexity
17

"RO5" indicates the cutoff set by lipinski's rule of five:

(1) Molecular weight less than 500 Dalton;

(2) xlogp less than 5;

(3) No more than 5 hbonddonor (Hydrogen Bond Donor Count);

(4) No more than 10 hbondacc (Hydrogen Bond Acceptor Count);

(5) No more than 10 rotbonds (Rotatable Bond Count).

    Show/Hide
Click to Show/Hide the External Link(s) of This Compound
PubChem ID
CID: 9444
SID: 12013374
ChEMBL ID
CHEMBL1489
DrugBank ID
DB00928
Map of Molecular Bioactivity Related to the Compound
Map of Molecular Bioactivity Related to the Compound

Compound
Cell Line
Protein

Bioactivity Value:

<= 0.1 μM
> 0.1 μM and <= 10 μM
> 10 μM
Imprecise Activity
Table of Molecular Bioactivities Related to the Compound
Protein ID: PT06109, Geminin
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000015 SW480 Homo sapiens (Human)  2
1
Potency ~ 115.8 nM
   TI
   LI
   LO
   TS
2
Potency ~ 2909.3 nM
   TI
   LI
   LO
   TS
Protein ID: PT02997, Isocitrate dehydrogenase [NADP] cytoplasmic
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000156 HT-1080 Homo sapiens (Human)  1
1
Potency ~ 1636 nM
   TI
   LI
   LO
   TS
Protein ID: PT01065, Serine/threonine-protein kinase mTOR
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL001056 MEF-1 [Mouse fibroblast] Mus musculus (Mouse)  1
1
Potency = 14689.2 nM
   TI
   LI
   LO
   TS
Clinical Information about the Compound
Drug 1 ( Azacitidine )
Drug Name Azacitidine
Company Celgene
Indication
Myelodysplastic syndrome
Phase 1