N-[(2R,3R,4S,5S,6R)-2-{[(3aR,4R,5R,6S,6aS)-2-(dimethylamino)-4-hydroxy-6-(hydroxymethyl)-3aH,4H,5H,6H,6aH-cyclopenta[d][1,3]oxazol-5-yl]oxy}-5-{[(2S,3R,4S,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

• ChemBase ID: 4189
• Molecular Formular: C25H42N4O14
• Molecular Mass: 622.61938
• Monoisotopic Mass: 622.26975204
• SMILES: CN(C)C1=N[C@@H]2[C@@H](O)[C@H](O[C@@H]3O[C@H](CO)[C@@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@@H](O)[C@H]4NC(=O)C)[C@@H](O)[C@H]3NC(=O)C)[C@@H](CO)[C@@H]2O1
• Canonical SMILES: OC[C@H]1O[C@@H](O[C@@H]2[C@@H](CO)[C@H]3[C@@H]([C@H]2O)N=C(O3)N(C)C)[C@@H]([C@@H]([C@@H]1O[C@@H]1O[C@H](CO)[C@H]([C@H]([C@H]1NC(=O)C)O)O)O)NC(=O)C
• InChI: InChI=1S/C25H42N4O14/c1-8(33)26-14-17(36)16(35)11(6-31)39-23(14)42-22-12(7-32)40-24(15(19(22)38)27-9(2)34)41-21-10(5-30)20-13(18(21)37)28-25(43-20)29(3)4/h10-24,30-32,35-38H,5-7H2,1-4H3,(H,26,33)(H,27,34)/t10-,11+,12+,13+,14+,15+,16+,17-,18+,19-,20-,21+,22+,23-,24-/m0/s1
• InChIKey: MDWNFWDBQGOKNZ-XYUDZHFQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2R,3R,4S,5S,6R)-2-{[(3aR,4R,5R,6S,6aS)-2-(dimethylamino)-4-hydroxy-6-(hydroxymethyl)-3aH,4H,5H,6H,6aH-cyclopenta[d][1,3]oxazol-5-yl]oxy}-5-{[(2S,3R,4S,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: @allosamidin
• Synonyms: Allosamidine; NAA-(1-4)NAA-(1-4)AMI; Allosamidin

Database IDs

• CAS Number: 103782-08-7
• PubChem SID: 160967621; 46506500
• PubChem CID: 119339

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.806896
• H Acceptors: 16
• H Donor: 9
• LogD (pH = 5.5): -7.148352
• LogD (pH = 7.4): -5.9484215
• Log P: -5.8492174
• Molar Refractivity: 138.7099 cm^3
• Polarizability: 56.523228 Å^3
• Polar Surface Area: 261.56 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.34
• LOG S: -1.2
• Solubility (Water): 3.94e+01 g/l

DETAILS

DrugBank - DB04628

• Drug Groups: experimental
• Description: Allosamidin exhibits extremely potent inhibitory activity against chitinases from a number of sources, particularly from Candida albicans, and can be utilized as potent antifungal agent.