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

• ChemBase ID: 132583
• Molecular Formular: C17H18O9
• Molecular Mass: 366.31942
• Monoisotopic Mass: 366.09508216
• SMILES: CC(=O)c1cc2ccc(cc2oc1=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2ccc3c(c2)oc(=O)c(c3)C(=O)C)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C17H18O9/c1-7(19)10-4-8-2-3-9(5-11(8)25-16(10)23)24-17-15(22)14(21)13(20)12(6-18)26-17/h2-5,12-15,17-18,20-22H,6H2,1H3/t12-,13-,14+,15-,17-/m1/s1
• InChIKey: KYVGMGQCZKBVDT-OWVAZHOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-acetyl-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one
• IUPAC Traditional name: 3-acetyl-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-2-one
• Synonyms: 3-Acetyl-7-coumarinyl-β-D-glucopyranoside; 3-Acetyl-7-(β-D-glucopyranosyloxy)coumarin; 3-Acetylumbelliferyl β-D-glucopyranoside

Database IDs

• CAS Number: 20943-16-2
• MDL Number: MFCD00037378
• Beilstein Number: 1268871
• PubChem SID: 24890787; 162226860
• PubChem CID: 16218898

CALCULATED PROPERTIES

• Acid pKa: 12.20014
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.8714053
• LogD (pH = 7.4): -0.87141204
• Log P: -0.8714052
• Molar Refractivity: 85.2993 cm^3
• Polarizability: 33.847836 Å^3
• Polar Surface Area: 142.75 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95%

DETAILS

Sigma Aldrich - A3582

Substrates
Fluorogenic substrate for β-glucosidase.