(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]oxane-2-carboxylic acid; cyclohexanamine

• ChemBase ID: 174522
• Molecular Formular: C22H29NO9
• Molecular Mass: 451.46696
• Monoisotopic Mass: 451.18423151
• SMILES: Cc1cc(=O)oc2cc(ccc12)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](C(=O)O)O1)O)O)O.C1CCC(CC1)N
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](Oc2ccc3c(c2)oc(=O)cc3C)[C@@H]([C@H]([C@@H]1O)O)O.NC1CCCCC1
• InChI: InChI=1S/C16H16O9.C6H13N/c1-6-4-10(17)24-9-5-7(2-3-8(6)9)23-16-13(20)11(18)12(19)14(25-16)15(21)22;7-6-4-2-1-3-5-6/h2-5,11-14,16,18-20H,1H3,(H,21,22);6H,1-5,7H2/t11-,12-,13+,14+,16+;/m0./s1
• InChIKey: GTQICDDVIGZFCZ-OMZMBYLHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]oxane-2-carboxylic acid; cyclohexanamine
• IUPAC Traditional name: (2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(4-methyl-2-oxochromen-7-yl)oxy]oxane-2-carboxylic acid; cyclohexylamine
• Synonyms: 4-Methylumbelliferyl α-L-Iduronic Acid Cyclohexylammonium Salt; 4-Methylumbelliferyl α-L-Idopyranosiduronic Acid Cyclohexylammonium Salt

Database IDs

• CAS Number: 66895-33-8
• PubChem SID: 164230432
• PubChem CID: 71307169

CALCULATED PROPERTIES

• Acid pKa: 2.9729717
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -2.6557503
• LogD (pH = 7.4): -3.6463246
• Log P: -0.16860466
• Molar Refractivity: 79.8233 cm^3
• Polarizability: 31.865303 Å^3
• Polar Surface Area: 142.75 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 145-148°C

Safety Information

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

DETAILS

Toronto Research Chemicals - M334700

4-Methylumbelliferyl α-L-Idopyranosiduronic Acid is a fluorogenic substrate in the assay of α-L-Iduronidase. It is useful for the detection of Hurlers syndrome.

REFERENCES

• Matalon, R., et al.: Biochem. Biophys. Res. Commun., 47, 959 (1972)
• Srivastava, R.M., et al.: Carbohydr. Res., 60, 315 (1972)