(2S,3R,4S,5S,6R)-5-amino-2-(aminomethyl)-6-{[(1S,2S,3R,4S,6R)-4,6-diamino-2-{[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxycyclohexyl]oxy}oxane-3,4-diol

• ChemBase ID: 3274
• Molecular Formular: C17H34N4O10
• Molecular Mass: 454.47266
• Monoisotopic Mass: 454.22749331
• SMILES: NC[C@@H]1O[C@H](O[C@H]2[C@H](N)C[C@H](N)[C@@H](O)[C@@H]2O[C@@H]2O[C@@H](CO)[C@H](O)[C@H]2O)[C@@H](N)[C@H](O)[C@H]1O
• Canonical SMILES: OC[C@@H]1O[C@H]([C@@H]([C@H]1O)O)O[C@@H]1[C@@H](O[C@H]2O[C@@H](CN)[C@@H]([C@H]([C@@H]2N)O)O)[C@H](N)C[C@@H]([C@H]1O)N
• InChI: InChI=1S/C17H34N4O10/c18-2-6-10(24)12(26)8(21)16(28-6)30-14-5(20)1-4(19)9(23)15(14)31-17-13(27)11(25)7(3-22)29-17/h4-17,22-27H,1-3,18-21H2/t4-,5+,6-,7-,8-,9+,10-,11-,12-,13+,14-,15-,16+,17-/m0/s1
• InChIKey: NSKGQURZWSPSBC-NLZFXWNVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5S,6R)-5-amino-2-(aminomethyl)-6-{[(1S,2S,3R,4S,6R)-4,6-diamino-2-{[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxycyclohexyl]oxy}oxane-3,4-diol
• IUPAC Traditional name: ribastamin
• Synonyms: 5-Amino-2-Aminomethyl-6-[4,6-Diamino-2-(3,4-Dihydroxy-5-Hydroxymethyl-Tetrahydro-Furan-2-Yloxy)-3-Hydroxy-Cyclohexyloxy]-Tetrahydro-Pyran-3,4-Diol; Antibiotic SF 733; RIO; Ribastamin; Vistamycin; Xylostacin; Xylostasin; SF-733; Ribostamycin

Database IDs

• CAS Number: 25546-65-0
• PubChem SID: 46505351; 160966716
• PubChem CID: 46936732

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.193866
• H Acceptors: 14
• H Donor: 10
• LogD (pH = 5.5): -17.199512
• LogD (pH = 7.4): -11.747448
• Log P: -6.4305787
• Molar Refractivity: 100.172 cm^3
• Polarizability: 42.763172 Å^3
• Polar Surface Area: 262.38 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.92
• LOG S: -0.71
• Solubility (Water): 8.87e+01 g/l

DETAILS

DrugBank - DB03615

• Drug Groups: experimental
• Description: A broad-spectrum antimicrobial isolated from Streptomyces ribosifidicus. [PubChem]
• Affected Organisms: Humans and other mammals; Enteric bacteria and other eubacteria