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

• ChemBase ID: 133346
• Molecular Formular: C18H17NO8
• Molecular Mass: 375.32948
• Monoisotopic Mass: 375.09541651
• SMILES: c1cc2nc3ccc(cc3oc2cc1=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)oc2c(n3)ccc(=O)c2)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C18H17NO8/c20-7-14-15(22)16(23)17(24)18(27-14)25-9-2-4-11-13(6-9)26-12-5-8(21)1-3-10(12)19-11/h1-6,14-18,20,22-24H,7H2/t14-,15-,16+,17-,18-/m1/s1
• InChIKey: QULZFZMEBOATFS-UYTYNIKBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3H-phenoxazin-3-one
• IUPAC Traditional name: 7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenoxazin-3-one
• Synonyms: 3-Phenoxazone 7-(β-D-glucopyranoside); Resorufin β-D-glucopyranoside

Database IDs

• CAS Number: 101490-85-1
• MDL Number: MFCD00037662
• Beilstein Number: 4335306
• PubChem SID: 162227623; 24899374
• PubChem CID: 13558997

CALCULATED PROPERTIES

• Acid pKa: 12.20014
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -0.4938789
• LogD (pH = 7.4): -0.49388558
• Log P: -0.4938787
• Molar Refractivity: 94.069 cm^3
• Polarizability: 35.23762 Å^3
• Polar Surface Area: 138.04 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF: soluble; DMSO: soluble; H2O: soluble
• Fluorescence: λex 571 nm; λem 590 nm in 0.1 M phosphate pH 7.0 (β-glucosidase)

Safety Information

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

Product Information

• Purity: ≥90%; ≥95% (HPLC)
• Grade: for fluorescence
• Empirical Formula (Hill Notation): C18H17NO8

DETAILS

Sigma Aldrich - 83639

Application
suitable as fluorogenic substrate for β-glucosidase
Other Notes
Detection of β-glucosidase with fluorogenic probe1