sodium (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(quinolin-8-yloxy)oxane-2-carboxylate

• ChemBase ID: 153898
• Molecular Formular: C15H14NNaO7
• Molecular Mass: 343.26393
• Monoisotopic Mass: 343.06679607
• SMILES: c1cc2cccnc2c(c1)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)C(=O)[O-])O)O)O.[Na+]
• Canonical SMILES: [O-]C(=O)[C@H]1O[C@@H](Oc2cccc3c2nccc3)[C@@H]([C@H]([C@@H]1O)O)O.[Na+]
• InChI: InChI=1S/C15H15NO7.Na/c17-10-11(18)13(14(20)21)23-15(12(10)19)22-8-5-1-3-7-4-2-6-16-9(7)8;/h1-6,10-13,15,17-19H,(H,20,21);/q;+1/p-1/t10-,11-,12+,13-,15+;/m0./s1
• InChIKey: QYRMLNFJXNJXLO-KSOKONAESA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(quinolin-8-yloxy)oxane-2-carboxylate
• IUPAC Traditional name: sodium (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(quinolin-8-yloxy)oxane-2-carboxylate
• Synonyms: 8-Hydroxyquinoline-β-D-glucuronic acid sodium salt; 8-Quinolyl-β-D-glucopyranosiduronic acid sodium salt; 8-Hydroxyquinoline-β-D-glucuronide sodium salt; 8-Hydroxyquinoline-β-D-glucuronic acid 钠盐; 8-Quinolyl-β-D-glucopyranosiduronic acid 钠盐; 8-Hydroxyquinoline-β-D-glucuronide

Database IDs

• CAS Number: 207728-71-0
• MDL Number: MFCD02683911
• PubChem SID: 162248037
• PubChem CID: 66848758

CALCULATED PROPERTIES

• Acid pKa: 3.5529647
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -2.2442186
• LogD (pH = 7.4): -3.5322528
• Log P: -0.51977324
• Molar Refractivity: 84.8091 cm^3
• Polarizability: 30.985659 Å^3
• Polar Surface Area: 132.17 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]/D -84.0±4.0°, c = 1 in H2O

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (HPLC)
• Impurities: ≤12% water
• Empirical Formula (Hill Notation): C15H14NNaO7

DETAILS

Sigma Aldrich - 38153

Application
Substrate for detection of β-D-glucuronidase, yields a brown precipitate upon cleavage; E. coli detection1,2