4-methyl-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one

• ChemBase ID: 2365
• Molecular Formular: C16H18O8
• Molecular Mass: 338.30932
• Monoisotopic Mass: 338.10016754
• SMILES: Cc1cc(=O)oc2cc(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)ccc12
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2ccc3c(c2)oc(=O)cc3C)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C16H18O8/c1-7-4-12(18)23-10-5-8(2-3-9(7)10)22-16-15(21)14(20)13(19)11(6-17)24-16/h2-5,11,13-17,19-21H,6H2,1H3/t11-,13-,14+,15-,16-/m1/s1
• InChIKey: YUDPTGPSBJVHCN-YMILTQATSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-methyl-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one
• IUPAC Traditional name: 4-methyl-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-2-one
• Synonyms: MUD; 4-Methylumbelliferyl β-D-glucopyranoside; 4-METHYLUMBELLIFERYL-β-D-GLUCOSIDE; 4-Methylumbelliferyl-Alpha-D-Glucose

Database IDs

• CAS Number: 18997-57-4; 17833-43-1
• EC Number: 242-736-7
• MDL Number: MFCD00063694
• Beilstein Number: 94672
• PubChem SID: 46507226; 160965816; 24885955; 24896859
• PubChem CID: 2733779

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.20014
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -0.4888793
• LogD (pH = 7.4): -0.48888606
• Log P: -0.4888792
• Molar Refractivity: 79.9559 cm^3
• Polarizability: 31.877827 Å^3
• Polar Surface Area: 125.68 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.34
• LOG S: -1.82
• Solubility (Water): 5.11e+00 g/l

PROPERTIES

Physical Property

• Melting Point: 210-212 °C; 212-215°C
• Optical Rotation: [α]20/D -99±4°, c = 0.3% in H2O
• Fluorescence: λex 316 nm; λem 372 nm (pH 9.1); λex 360 nm; λem 449 nm (Reaction product); λex 365 nm; λem 445 nm in 0.1 M sodium acetate pH 5.0 (after cleavage by β-glucosidase)

Safety Information

• Storage Condition: 0°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥99.0% (HPLC)
• Suitability: suitable for fluorescence
• Empirical Formula (Hill Notation): C16H18O8
• Classification: Rare Derivatives of Natural Compounds

DETAILS

MP Biomedicals - 02102352

Crystalline

DrugBank - DB02639

Drug information: experimental

Sigma Aldrich - 69600

Other Notes
Substrate for β-glucosidase1