(2R,4R,5R,6S)-4-(hydroxymethyl)-10-imino-3,7-dioxa-1,9-diazatricyclo[6.4.0.02,6]dodeca-8,11-dien-5-ol hydrochloride

• ChemBase ID: 138922
• Molecular Formular: C9H12ClN3O4
• Molecular Mass: 261.66228
• Monoisotopic Mass: 261.05163356
• SMILES: c1cn2c(nc1=N)O[C@@H]1[C@H]2O[C@@H]([C@H]1O)CO.Cl
• Canonical SMILES: OC[C@H]1O[C@@H]2[C@H]([C@@H]1O)Oc1n2ccc(=N)n1.Cl
• InChI: InChI=1S/C9H11N3O4.ClH/c10-5-1-2-12-8-7(16-9(12)11-5)6(14)4(3-13)15-8;/h1-2,4,6-8,10,13-14H,3H2;1H/t4-,6-,7+,8-;/m1./s1
• InChIKey: KZOWNALBTMILAP-JBMRGDGGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R,5R,6S)-4-(hydroxymethyl)-10-imino-3,7-dioxa-1,9-diazatricyclo[6.4.0.0^2,^6]dodeca-8,11-dien-5-ol hydrochloride
• IUPAC Traditional name: (2R,4R,5R,6S)-4-(hydroxymethyl)-10-imino-3,7-dioxa-1,9-diazatricyclo[6.4.0.0^2,^6]dodeca-8,11-dien-5-ol hydrochloride
• Synonyms: 2,2′-Anhydro-(1-β-D-arabinofuranosyl)cytosine hydrochloride; 2,2′-Anhydro-1-β-D-arabinofuranosylcytosine hydrochloride; Ancitabine; O2,2′-Cyclocytidine; (-)-Cyclocytidine hydrochloride; Cyclo-C; Cyclocytidine; Ancitabine hydrochloride; 2,2′-脱水-(1-β-D-阿拉伯呋喃糖基)胞嘧啶 盐酸盐; 2,2′-脱水-1-β-D-阿糖呋喃胞嘧啶 盐酸盐; O2,2′-环胞苷; 安西他滨; (-)-环胞啶 盐酸盐; 安西他滨 盐酸盐

Database IDs

• CAS Number: 10212-25-6
• EC Number: 233-515-6
• MDL Number: MFCD00012636
• PubChem SID: 24278241; 162233173
• PubChem CID: 25050

CALCULATED PROPERTIES

• Acid pKa: 12.978742
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -1.1883035
• LogD (pH = 7.4): -1.1879807
• Log P: -1.1879754
• Molar Refractivity: 62.4472 cm^3
• Polarizability: 20.28107 Å^3
• Polar Surface Area: 98.37 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 269-270 °C (dec.)(lit.)
• Optical Rotation: [α]22/D -21.6°, c = 2 in H2O

Safety Information

• RTECS: LV2615000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 98%
• Salt Data: HCl
• Empirical Formula (Hill Notation): C9H11N3O4 · HCl
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Sigma Aldrich - A8598

Biochem/physiol Actions
Antineoplastic
Application
Ancitabine hydrochloride is an antineoplastic agent for the treatment of lymphatic leukemia and sinus acceleration.