Azacitidine

Details

• Internal ID: 9ccbbf32-72f3-4212-8608-4e9c48a7a25e
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Glycosylamines
• IUPAC Name: 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
• SMILES (Canonical): C1=NC(=NC(=O)N1C2C(C(C(O2)CO)O)O)N
• SMILES (Isomeric): C1=NC(=NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)N
• 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
• InChI Key: NMUSYJAQQFHJEW-KVTDHHQDSA-N
• Popularity: 10,272 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₁₂N₄O₅
• Molecular Weight: 244.20 g/mol
• Exact Mass: 244.08076950 g/mol
• Topological Polar Surface Area (TPSA): 141.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -3.17
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• Azacitidine
• 320-67-2
• Ladakamycin
• Azacytidine
• Vidaza
• Mylosar
• 5-azacitidine
• Azacitidina
• Azacitidinum
• Azacitidinum [INN-Latin]
• 5-AZAC
• Azacitidina [INN-Spanish]
• Antibiotic U 18496
• C8H12N4O5
• Onureg
• NSC-102816
• U-18496
• CCRIS 60
• 4-Amino-1-beta-D-ribofuranosyl-s-triazin-2(1H)-one
• NSC 102816
• HSDB 6879
• 4-Amino-1-beta-d-ribofuranosyl-1,3,5-triazin-2(1H)-one
• WR-183027
• EINECS 206-280-2
• UNII-M801H13NRU
• 5-AZCR
• 5AzaC
• 5 AZC
• BRN 0620461
• CHEBI:2038
• M801H13NRU
• U 18496
• DTXSID9020116
• 5-AC
• 4-Amino-1-beta-D-ribofuranosyl-1,3,5-traizin-2(1H)-one
• NSC102816
• 4-amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,3,5-triazin-2(1H)-one
• U-18,496
• DTXCID10116
• NCI-C01569
• 4-Amino-1-(beta-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one
• Onureg (CC-486; oral azacitidine)
• 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro-1,3,5-triazin-2-one
• s-Triazin-2(1H)-one, 4-amino-1-beta-D-ribofuranosyl-
• NCGC00090851-04
• 5 Azacytidine
• AZACITIDINE (IARC)
• AZACITIDINE [IARC]
• Azacitidinum (INN-Latin)
• Azacitidina (INN-Spanish)
• AZACITIDINE (MART.)
• AZACITIDINE [MART.]
• AZACITIDINE (USP-RS)
• AZACITIDINE [USP-RS]
• 1,3,5-Triazin-2(1H)-one, 4-amino-1-beta-D-ribofuranosyl-
• 1,3,5-Triazin-2(1H)-one, 4-amino-1-.beta.-D-ribofuranosyl-
• MFCD00006539
• SMR000857239
• Vidaza (TN)
• 5-aza-CR
• SR-01000075662
• wr 183027
• Azacitidine;5-AzaC;Ladakamycin
• azacitidine for
• Azacitidine (JAN/USAN/INN)
• Azacitidine [USAN:INN:BAN]
• NS-17
• 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,3,5-triazin-2-one
• CAS-320-67-2
• Azacitidine (Vidaza)
• 2-(beta-D-Ribofuranosyl)-4-amino-1,3,5-triazin-2-one
• Spectrum_001262
• 4-Amino-1-beta-D-ribofuranosyl-1,3,5-triazine-2(1H)-one
• AZACITIDINE [MI]
• Spectrum2_000786
• Spectrum3_001509
• Spectrum4_000922
• Spectrum5_001166
• AZACITIDINE [INN]
• AZACITIDINE [JAN]
• AZACITIDINE [HSDB]
• AZACITIDINE [USAN]
• MolMap_000062
• 4-Amino-1-.beta.-D-ribofuranosyl-s-triazin-2(1H)-one
• A 2385
• AZACITIDINE [VANDF]
• AZACITIDINEAZACITIDINE
• SCHEMBL3741
• 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
• 5-ACZ
• CHEMBL1489
• Azacitidine (5-Azacytidine)
• Lopac0_000035
• AZACITIDINE [WHO-DD]
• BSPBio_003157
• KBioGR_001444
• KBioGR_002556
• KBioSS_001742
• KBioSS_002565
• MLS001333121
• MLS001333122
• MLS002153249
• MLS002548894
• DivK1c_000125
• SPECTRUM1502111
• SPBio_000892
• AZACITIDINE [EMA EPAR]
• GTPL6796
• BCBcMAP01_000083
• HMS500G07
• KBio1_000125
• KBio2_001742
• KBio2_002556
• KBio2_004310
• KBio2_005124
• KBio2_006878
• KBio2_007692
• KBio3_002657
• KBio3_003034
• NMUSYJAQQFHJEW-KVTDHHQDSA-
• AZACITIDINE [ORANGE BOOK]
• L01BC07
• pyrimidine antimetabolite: inhibits nucleic acid replication
• cMAP_000082
• NINDS_000125
• NMUSYJAQQFHJEW-KVTDHHQDSA-N
• HMS1921J22
• HMS2092D08
• HMS2231F15
• HMS3259D19
• HMS3260G11
• Pharmakon1600-01502111
• 5-Azacytidine, >=98% (HPLC)
• Tox21_111032
• Tox21_302985
• Tox21_500035
• BDBM50424715
• CCG-39046
• HB1374
• NSC758186
• s1782
• AKOS015896938
• Tox21_111032_1
• AM83944
• CS-1287
• DB00928
• LP00035
• NC00672
• NSC-758186
• 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triaz
• IDI1_000125
• NSC 103-627
• NCGC00090851-01
• NCGC00090851-02
• NCGC00090851-03
• NCGC00090851-05
• NCGC00090851-06
• NCGC00090851-07
• NCGC00090851-08
• NCGC00090851-10
• NCGC00090851-14
• NCGC00090851-22
• NCGC00178234-01
• NCGC00256541-01
• NCGC00260720-01
• AS-13697
• HY-10586
• SRI-10756_10
• SRI-10756_12
• SL-000003
• EU-0100035
• D03021
• EN300-118700
• F10504
• A821115
• Q416451
• J-700085
• SR-01000075662-1
• SR-01000075662-3
• SR-01000075662-7
• 4-Amino-1-beta-D-ribofuranosyl-D-triazin-2(1H)-one
• BRD-K03406345-001-02-1
• BRD-K03406345-001-27-8
• 4-Amino-1-?-D-ribofuranosyl-1,3,5-triazin-2(1H)-one
• Z1515383340
• 4-Amino-1-beta-D-ribofuranosyl-1,3,5-tr iazin-2(1H)-one
• Azacitidine, United States Pharmacopeia (USP) Reference Standard
• 4-Amino-1-(beta-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one; Ladakamycin
• Azacitidine, Pharmaceutical Secondary Standard; Certified Reference Material
• 1401238-97-8
• 5-Azacytidine, Hybri-Max(TM), gamma-irradiated, lyophilized powder, BioXtra, suitable for hybridoma
• 5AE
• 6-amino-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-1,3,5-triazin-3-ium-2-one
• InChI=1/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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7128	71.28%
Caco-2	-	0.9531	95.31%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Nucleus	0.4321	43.21%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9564	95.64%
OATP1B3 inhibitior	+	0.9495	94.95%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9812	98.12%
P-glycoprotein inhibitior	-	0.9451	94.51%
P-glycoprotein substrate	-	0.9306	93.06%
CYP3A4 substrate	-	0.6318	63.18%
CYP2C9 substrate	-	0.8090	80.90%
CYP2D6 substrate	-	0.8743	87.43%
CYP3A4 inhibition	-	0.9617	96.17%
CYP2C9 inhibition	-	0.9436	94.36%
CYP2C19 inhibition	-	0.9329	93.29%
CYP2D6 inhibition	-	0.9438	94.38%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9742	97.42%
CYP inhibitory promiscuity	-	0.9839	98.39%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Danger	0.7496	74.96%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9739	97.39%
Skin irritation	-	0.7886	78.86%
Skin corrosion	-	0.9426	94.26%
Ames mutagenesis	-	0.5529	55.29%
Human Ether-a-go-go-Related Gene inhibition	-	0.7689	76.89%
Micronuclear	+	1.0000	100.00%
Hepatotoxicity	-	0.5530	55.30%
skin sensitisation	-	0.8610	86.10%
Respiratory toxicity	+	0.9222	92.22%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.6279	62.79%
Acute Oral Toxicity (c)	III	0.7646	76.46%
Estrogen receptor binding	-	0.6964	69.64%
Androgen receptor binding	+	0.8130	81.30%
Thyroid receptor binding	+	0.6493	64.93%
Glucocorticoid receptor binding	+	0.7795	77.95%
Aromatase binding	+	0.6082	60.82%
PPAR gamma	+	0.6729	67.29%
Honey bee toxicity	-	0.9131	91.31%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	-	0.8959	89.59%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293237	P54132	Bloom syndrome protein	1.6 nM	Potency	via Super-PRED
CHEMBL1993	P26358	DNA (cytosine-5)-methyltransferase 1	300 nM	IC50	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	446.7 nM	Potency	via Super-PRED
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	116.7 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.01%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	91.26%	95.93%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.77%	94.00%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	89.51%	100.00%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	87.10%	98.46%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.30%	86.33%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	85.63%	80.33%
CHEMBL3401	O75469	Pregnane X receptor	83.41%	94.73%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	82.75%	93.10%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.71%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.44%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.39%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.32%	99.23%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 9444
• LOTUS: LTS0159153
• wikiData: Q416451