3-hydroxy-3-methyl-N-[(2R,3S,4S,5R)-4,5,6-trihydroxy-2-methyloxan-3-yl]butanamide

• ChemBase ID: 153975
• Molecular Formular: C11H21NO6
• Molecular Mass: 263.28754
• Monoisotopic Mass: 263.1368874
• SMILES: C[C@@H]1[C@H]([C@@H]([C@H](C(O1)O)O)O)NC(=O)CC(C)(C)O
• Canonical SMILES: O=C(CC(O)(C)C)N[C@@H]1[C@@H](C)OC([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C11H21NO6/c1-5-7(8(14)9(15)10(16)18-5)12-6(13)4-11(2,3)17/h5,7-10,14-17H,4H2,1-3H3,(H,12,13)/t5-,7-,8+,9-,10?/m1/s1
• InChIKey: UUVASJJCLBEXCO-QNRYFBKSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-hydroxy-3-methyl-N-[(2R,3S,4S,5R)-4,5,6-trihydroxy-2-methyloxan-3-yl]butanamide
• IUPAC Traditional name: 3-hydroxy-3-methyl-N-[(2R,3S,4S,5R)-4,5,6-trihydroxy-2-methyloxan-3-yl]butanamide
• Synonyms: 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-D-glucopyranose; Anthrose

Database IDs

• CAS Number: 769959-88-8
• PubChem SID: 162248114
• PubChem CID: 71311769

CALCULATED PROPERTIES

• Acid pKa: 11.311571
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -2.0567489
• LogD (pH = 7.4): -2.056801
• Log P: -2.0567482
• Molar Refractivity: 60.9396 cm^3
• Polarizability: 24.82753 Å^3
• Polar Surface Area: 119.25 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C12H23NO6

DETAILS

Sigma Aldrich - 49746

Application
Anthrose, a nonreducing dideoxy-glucopyranose, has recently been identified as a unique component of the bacillus anthracis exosporium and Bacillus cereus endospores. Anthrose is used in anthrax research.