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101490-85-1 molecular structure
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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 and InChIs

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

Cite this record

CBID:133346 http://www.chembase.cn/molecule-133346.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
101490-85-1
MDL Number
MFCD00037662
Beilstein Number
4335306
PubChem SID
162227623
24899374
PubChem CID
13558997

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 13558997 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 12.20014  H Acceptors
H Donor LogD (pH = 5.5) -0.4938789 
LogD (pH = 7.4) -0.49388558  Log P -0.4938787 
Molar Refractivity 94.069 cm3 Polarizability 35.23762 Å3
Polar Surface Area 138.04 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMF: soluble expand Show data source
DMSO: soluble expand Show data source
H2O: soluble expand Show data source
Fluorescence
λex 571 nm; λem 590 nm in 0.1 M phosphate pH 7.0 (β-glucosidase) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
Purity
≥90% expand Show data source
≥95% (HPLC) expand Show data source
Grade
for fluorescence expand Show data source
Empirical Formula (Hill Notation)
C18H17NO8 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 83639 external link
Application
suitable as fluorogenic substrate for β-glucosidase
Other Notes
Detection of β-glucosidase with fluorogenic probe1

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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