4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one hydrochloride

• ChemBase ID: 102079
• Molecular Formular: C9H14ClN3O5
• Molecular Mass: 279.67756
• Monoisotopic Mass: 279.06219824
• SMILES: O=c1nc(N)ccn1[C@@H]1O[C@@H]([C@@H](O)[C@@H]1O)CO.Cl
• Canonical SMILES: OC[C@H]1O[C@H]([C@H]([C@@H]1O)O)n1ccc(nc1=O)N.Cl
• InChI: InChI=1S/C9H13N3O5.ClH/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);1H/t4-,6-,7+,8-;/m1./s1
• InChIKey: KCURWTAZOZXKSJ-JBMRGDGGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one hydrochloride
• IUPAC Traditional name: cytarabine hydrochloride
• Synonyms: 1-(β-D-Arabino-furanosyl)-cytosine hydrochloride; Ara-C hydrochloride; Arabinocytidine hydrochloride; Arabinosylcytosine hydrochloride; Cytosine β-D-arabinofuranoside hydrochloride; 1-beta-D-Arabinofuranosylcytosine Hydrochloride; Cylocide; Cytarabine Hydrochloride; Cytosar Hydrochloride; Cytosine Arabinoside Hydrochloride; Iretin; Spongocytidine Hydrochloride; CYTOSINE-β-D-ARABINOFURANOSIDE HYDROCHLORIDE; 1-(β-D-呋喃阿拉伯糖苷)-胞嘧啶 盐酸盐; Ara-C 盐酸盐; 胞嘧啶阿拉伯糖苷 盐酸盐; 阿拉伯糖胞嘧啶 盐酸盐; 阿糖胞嘧啶 盐酸盐; 阿糖胞苷 盐酸盐; 胞嘧啶β-D-呋喃阿拉伯糖苷 盐酸盐

Database IDs

• CAS Number: 69-74-9
• EC Number: 200-713-9
• MDL Number: MFCD00012839
• PubChem SID: 24278329; 162088732
• PubChem CID: 6252

CALCULATED PROPERTIES

• Acid pKa: 12.553241
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -2.7975185
• LogD (pH = 7.4): -2.7975204
• Log P: -2.7975173
• Molar Refractivity: 54.5448 cm^3
• Polarizability: 21.48729 Å^3
• Polar Surface Area: 128.61 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: crystalline
• Melting Point: 197-198 °C(lit.); 197-198°C
• Optical Rotation: [α]25/D +130°, c = 1 in H2O

Safety Information

• Storage Condition: 2-8°C
• RTECS: HA5500000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 36-43-63; 63-36-43; R:22
• Safety Statements: 26-36/37; S:36/37/39
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H317-H319-H341-H361
• GHS Precautionary statements: P280-P305 + P351 + P338
• Storage Temperature: 2-8°C

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C9H13N3O5 · HCl

DETAILS

MP Biomedicals - 02100071

Hydrochloride
Crystalline
Inhibits incorporation of labeled thymidine into DNA.

Sigma Aldrich - C6645

Biochem/physiol Actions
Ara-C is phosphorylated to Ara-CTP and is incorporatee into DNA. It inhibits DNA replication by forming cleavage complexes with topoisomerase I resulting in DNA fragmentation, and ultimately induces apoptosis via the PKC signaling pathway.1 Does not inhibit RNA synthesis. Anti-leukemia agent.

Sigma Aldrich - 855855

Biochem/physiol Actions
Ara-C is phosphorylated to Ara-CTP and is incorporatee into DNA. It inhibits DNA replication by forming cleavage complexes with topoisomerase I resulting in DNA fragmentation, and ultimately induces apoptosis via the PKC signaling pathway.1 Does not inhibit RNA synthesis. Anti-leukemia agent.