p-Nitrophenyl beta-D-glucuronide

HCID 82565

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Basic information

CAS: 10344-94-2
Standard SMILES: O=C(O)[C@H]1O[C@@H](Oc2ccc([N+](=O)[O-])cc2)[C@H](O)[C@@H](O)[C@@H]1O
InChIKey: QSUILVWOWLUOEU-GOVZDWNOSA-N
Molecular formula: C12H13NO9
Average molar mass: 315.23 g/mol
Monoisotopic mass: 315.059031

Overview

4-nitrophenyl beta-D-glucuronide is a beta-D-glucosiduronic acid having a 4-nitrophenyl substituent at the anomeric position. It has a role as a chromogenic compound. It is a beta-D-glucosiduronic acid and a C-nitro compound. It is functionally related to a 4-nitrophenol.

Names & identifiers

Preferred name: p-Nitrophenyl beta-D-glucuronide
IUPAC: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-nitrophenoxy)oxane-2-carboxylic acid
English name: 4-NITROPHENYL-BETA-D-GLUCURONIDE
Molecular formula: C12H13NO9
Molecular weight: 315.23

Names & synonyms

10344-94-24-Nitrophenyl beta-D-glucopyranosiduronic acid4-Nitrophenylglucuronidep-nitrophenyl beta-d-glucuronidep-nitrophenylglucuronidepara-nitrophenylglucuronideRefChem:928467233-753-04-Nitrophenyl beta-D-glucuronide4-Nitrophenyl b-D-glucosiduronic acid(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-nitrophenoxy)oxane-2-carboxylic acidMFCD00036210

Show more names

NPGp-Nitrophenyl-β-D-glucuronidepNPG-1PNP-GlcAGlcA-b-PNPPNP-BETA-D-GLCAp-nitrophenyl B24-Nitrophenyl βSynonym 4-Nitropheny-D-Galactofuranoside

p-Nitrophenyl beta-D-glucopyranosiduronic acid4-Nitrophenyl |A-D-glucuronide4-Nitrophenyl -D-glucuronide(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-nitrophenoxy)tetrahydro-2H-pyran-2-carboxylic acidC12H13NO9p-Nitrophenyl b-D-Glucuronide Sodium Salt60833-84-3EN04823

Database identifiers

CAS: 10344-94-2、60833-84-3
PubChem CID: 82565
DTXSID: DTXSID801356618
ChEMBL: CHEMBL495244
ChEBI: CHEBI:90146
EC Number: 233-753-0
Nikkaji: J236.780G

Properties

Computed structural properties

XLogP: -0.2
Topological polar surface area: 162 Å²
Hydrogen bond donors: 4
Hydrogen bond acceptors: 9
Rotatable bonds: 3
Heavy atoms: 22
Formal charge: 0
Complexity: 417

Experimental & physicochemical properties

LogP-0.75

Physicochemical properties

Melting point: 93 °C · 93°C
Boiling point: 644.4 · 644.4±55.0 °C(Predicted)
Density: 1.731 · 1.731±0.06 g/cm3(Predicted)
storage temp.: -20 °C · -20°C
solubility: 2 O: · H2O: 0.1 g/mL, clear, faintly yellow
pka: 2.69 · 2.69±0.70(Predicted)
form: Liquid
color: Clear colorless to light yellow
optical activity: 20 · [α]20/D 102±3°, c = 1% in ethanol
Water Solubility: 250 mg/mL · Water : 250 mg/mL (793.07 mM; Need ultrasonic)
BRN: 1438576 · 1438576
InChI: InChI=1/C12H13NO9/c14-7-8(15)10(11(17)18)22-12(9(7)16)21-6-3-1-5(2-4-6)13(19)20/h1-4,7-10,12,14-16H,(H,17,18)/t7-,8-,9+,10-,12+/s3
InChIKey: QSUILVWOWLUOEU-GOVZDWNOSA-N
SMILES: [C@H]1(OC2C=CC([N+]([O-])=O)=CC=2)[C@H](O)[C@H]([C@H](O)[C@@H](C(=O)O)O1)O |&1:0,11,13,14,16,r|
CAS DataBase Reference: 10344 · 10344-94-2(CAS DataBase Reference)
UNSPSC Code: 12352204 · 12352204
NACRES: 77 · NA.77
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P305+P351+P338
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Safety Statements: 22 · 22-24/25
WGK Germany: 3 · 3
F: 10 · 10-21
HS Code: 29329990 · 29329990
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

Hazard information

Regulatory Information.beta.-D-Glucopyranosiduronic acid, 4-nitrophenyl: Does not have an individual approval but may be used under an appropriate group standard

Safety data

F: 10-21
PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
hs_code: 29329990
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 22-24/25
Storage Class: 11 - Combustible Solids
Hazard statements: H302-H315-H319-H335
Precautionary statements: P261-P305+P351+P338

Chemistry & industry

Applications · 3 items

Uses4-Nitrophenyl β-D-glucuronide has been used for determining the β-glucuronidase activity in urine samples, β-glucuronidase activity of bacteria in caecum content digesta and bovine liver. It has also been used to study the inhibitory effect of Phyllanthus amarus extracts on β-glucuronidase.

Uses4-Nitrophenyl β-D-glucuronide has been used as substrate in acetate buffer to measure β-glucuronidase.

General DescriptionChromogenic substrate for β-glucuronidase (Km = ~0.22 mM).