3-[(2S,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1H-pyrazole-5-carboxamide

• ChemBase ID: 177125
• Molecular Formular: C9H13N3O6
• Molecular Mass: 259.21602
• Monoisotopic Mass: 259.08043515
• SMILES: [C@H]1(C([C@@H]([C@@H](O1)c1n[nH]c(c1O)C(=O)N)O)O)CO
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)c1n[nH]c(c1O)C(=O)N
• InChI: InChI=1S/C9H13N3O6/c10-9(17)4-6(15)3(11-12-4)8-7(16)5(14)2(1-13)18-8/h2,5,7-8,13-16H,1H2,(H2,10,17)(H,11,12)/t2-,5?,7+,8+/m1/s1
• InChIKey: XESARGFCSKSFID-UPPIBNIFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(2S,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1H-pyrazole-5-carboxamide
• IUPAC Traditional name: 5-[(2S,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2H-pyrazole-3-carboxamide
• Synonyms: 4-Hydroxy-3-β-D-ribofuranosyl-1H-pyrazole-5-carboxamide; Antibiotic A 23813; NSC 143095; Pirazofurin; Przf; Pyrazofurin; Pyrazomycin; Pyrozofurin; β-Pyrazomycin; β-Pyrazofurin

Database IDs

• CAS Number: 30868-30-5
• PubChem SID: 164233035
• PubChem CID: 59991293

CALCULATED PROPERTIES

• LogD (pH = 7.4): -3.5251954
• Log P: -2.4988189
• Molar Refractivity: 57.3909 cm^3
• Polarizability: 21.981976 Å^3
• Polar Surface Area: 161.92 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false
• Acid pKa: 6.159365
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -2.5809014

DETAILS

Toronto Research Chemicals - P841750

Geldanamycin (G304500) derivative.

REFERENCES

• Smee, D., et al.: Antimicrob. Agents Chemother., 31, 1535 (1987)
• Krungkrai, J., et al.: Biochem. Pharmacol., 43, 1295 (1987)