4-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide hydrate

• ChemBase ID: 133375
• Molecular Formular: C12H17N5O6
• Molecular Mass: 327.29328
• Monoisotopic Mass: 327.11788329
• SMILES: c1c(c2c(ncnc2n1[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O)N)C(=O)N.O
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cc(c2c1ncnc2N)C(=O)N.O
• InChI: InChI=1S/C12H15N5O5.H2O/c13-9-6-4(10(14)21)1-17(11(6)16-3-15-9)12-8(20)7(19)5(2-18)22-12;/h1,3,5,7-8,12,18-20H,2H2,(H2,14,21)(H2,13,15,16);1H2/t5-,7-,8-,12-;/m1./s1
• InChIKey: QTYUIEDCERYPNJ-CCUUNMJDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide hydrate
• IUPAC Traditional name: 4-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carboxamide hydrate
• Synonyms: 7-Deaza-7-carbamoyladenosine hydrate; Sangivamycin hydrate from Streptomyces rimosus

Database IDs

• CAS Number: 18417-89-5
• MDL Number: MFCD00214391
• PubChem SID: 162227652; 24899678
• PubChem CID: 16219974

CALCULATED PROPERTIES

• Acid pKa: 12.449252
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -3.4930182
• LogD (pH = 7.4): -2.4886172
• Log P: -2.4278197
• Molar Refractivity: 74.45 cm^3
• Polarizability: 28.303923 Å^3
• Polar Surface Area: 169.74 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: UY9355000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 26/27/28
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330
• GHS Precautionary statements: P260-P264-P280-P284-P302 + P350-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: 2-8°C

DETAILS

Sigma Aldrich - S5895

Biochem/physiol Actions
A cytotoxic purine nucleoside, active against human cytomegalovirus (HCMV); inhibits protein kinase C.