N-[(2R,3S,4S,5R)-4,6-dihydroxy-5-methoxy-2-methyloxan-3-yl]-3-hydroxy-3-methylbutanamide

• ChemBase ID: 160732
• Molecular Formular: C12H23NO6
• Molecular Mass: 277.31412
• Monoisotopic Mass: 277.15253746
• SMILES: O1C([C@H]([C@H]([C@@H]([C@@H]1C)NC(=O)CC(O)(C)C)O)OC)O
• Canonical SMILES: CO[C@@H]1C(O)O[C@H]([C@H]([C@@H]1O)NC(=O)CC(O)(C)C)C
• InChI: InChI=1S/C12H23NO6/c1-6-8(13-7(14)5-12(2,3)17)9(15)10(18-4)11(16)19-6/h6,8-11,15-17H,5H2,1-4H3,(H,13,14)/t6-,8-,9+,10-,11?/m1/s1
• InChIKey: XXOSQKWOPXPGQY-YKVPTUPCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2R,3S,4S,5R)-4,6-dihydroxy-5-methoxy-2-methyloxan-3-yl]-3-hydroxy-3-methylbutanamide
• IUPAC Traditional name: N-[(2R,3S,4S,5R)-4,6-dihydroxy-5-methoxy-2-methyloxan-3-yl]-3-hydroxy-3-methylbutanamide
• Synonyms: 1,5-Dihydroxyanthraquinone; 1,5-Dihydroxy-9,10-anthraquinone; NSC 646570; NSC 7211; Anthrarufin 85%

Database IDs

• CAS Number: 117-12-4
• PubChem SID: 162254867
• PubChem CID: 50906606

CALCULATED PROPERTIES

• Acid pKa: 11.339628
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -1.4136224
• LogD (pH = 7.4): -1.4136714
• Log P: -1.4136215
• Molar Refractivity: 65.6908 cm^3
• Polarizability: 26.7126 Å^3
• Polar Surface Area: 108.25 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Poor solubility in all solvents tested. DMSO (Sparingly)
• Apperance: Yellow to Green Solid
• Melting Point: 279-280°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A679300

An anthraquinone derivative with suppressive effects against nitric oxide (NO) synthase. Potential antimalarial agent. Used in studies as a potential competitive non-peptidic inhibitor of HIV-1 proteinase.

REFERENCES

• Lee, H. et al.: J. Kor. Soc. App. Biolog. Chem., 53, 831 (2010)
• Winter, R.W. et al.: Bioorg. Med. Chem. Lett., 5, 1927 (2010)
• Brinkworth, R.I. et al.: Biochim. Biophys. Acta, Prot. Struct. Mol. Enzymol., 1253, 5 (2010)