(2S,3S,4S,5R,6R)-6-{[({2-[(carbamoyloxy)methyl]-2-methylpentyl}oxy)carbonyl]amino}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 172757
• Molecular Formular: C15H26N2O10
• Molecular Mass: 394.37434
• Monoisotopic Mass: 394.15874504
• SMILES: C(=O)(OCC(COC(=O)N)(C)CCC)N[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: CCCC(COC(=O)N)(COC(=O)N[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)C
• InChI: InChI=1S/C15H26N2O10/c1-3-4-15(2,5-25-13(16)23)6-26-14(24)17-11-9(20)7(18)8(19)10(27-11)12(21)22/h7-11,18-20H,3-6H2,1-2H3,(H2,16,23)(H,17,24)(H,21,22)/t7-,8-,9+,10-,11+,15?/m0/s1
• InChIKey: JJNJNGDGGZSOLF-DQYDNALCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-{[({2-[(carbamoyloxy)methyl]-2-methylpentyl}oxy)carbonyl]amino}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-{[({2-[(carbamoyloxy)methyl]-2-methylpentyl}oxy)carbonyl]amino}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[[[[2-[[(Aminocarbonyl)oxy]methyl]-2-methylpentyl]oxy]carbonyl]amino]-1-deoxy-β-D-Glucopyranuronic Acid; 1-(Carboxyamino)-1-deoxyglucopyranuronic Acid N-[2-(Hydroxymethyl)-2-methylpentyl] Ester Carbamate; Meprobamate N-β-D-GlucuronideSee M227761

Database IDs

• CAS Number: 58569-76-9
• PubChem SID: 164228667
• PubChem CID: 71750010

CALCULATED PROPERTIES

• Acid pKa: 3.1294658
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -3.2860184
• LogD (pH = 7.4): -4.399812
• Log P: -0.9427587
• Molar Refractivity: 85.4629 cm^3
• Polarizability: 34.947647 Å^3
• Polar Surface Area: 197.87 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Low Melting Solid
• Melting Point: 28-30°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M227760

A metabolite of Meprobamate (M227750).

REFERENCES

• Tsukamoto, H., et al.: Life Sciences, 2, 382 (1963)
• Fenselau, C., et al.: J. Med. Chem., 19, 678 (1963)