Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR2064)
Drug Name
Nitrophenylphosphate
Synonyms
NSC 404086; Phenol, p-nitro-, dihydrogen phosphate; Phosphoric acid, mono(4-nitrophenyl) ester; Phosphoric acid, mono(p-nitrophenyl) ester (8CI); 4-Nitrophenyl phosphate; XZKIHKMTEMTJQX-UHFFFAOYSA-N; p-Nitrophenol phosphate; p-Nitrophenylphosphate; p-nitrophenyl phosphate; (4-nitrophenoxy)phosphonic acid; (4-nitrophenyl) dihydrogen phosphate; 330-13-2; 4-Nitrophenyl dihydrogen phosphate; 4-nitrophenyl phosphate; CHEBI:17440; CHEMBL24231; p-Nitrophenyl dihydrogen phosphate; pNPP Alkaline Phosphatase Substrate
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 219.09 Topological Polar Surface Area 113
Heavy Atom Count 14 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
378
ChEBI ID
CHEBI:17440
CAS Number
330-13-2
TTD Drug ID
D0T0YI
Formula
C6H6NO6P
Canonical SMILES
C1=CC(=CC=C1[N+](=O)[O-])OP(=O)(O)O
InChI
1S/C6H6NO6P/c8-7(9)5-1-3-6(4-2-5)13-14(10,11)12/h1-4H,(H2,10,11,12)
InChIKey
XZKIHKMTEMTJQX-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
1-amino-2-naphthyl phosphate (ANP) DM004007 N. A. Oxidation - Dephosphorylation 1 [3]
4-nitrophenolate DM004006
644235
Oxidation - Hydrolyzationn 1 [2]
p-nitrophenol DM004005
980
Oxidation - Hydrolyzationn 1 [1]
Ascorbic acid phosphate DM004008
129664751
Oxidation - Dephosphorylation 2 [3]
4-aminophenyl phosphate DM004009
122271
Oxidation - Dephosphorylation 3 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004380 Nitrophenylphosphate p-nitrophenol Oxidation - Hydrolyzationn CA2 [1]
MR004381 Nitrophenylphosphate 4-nitrophenolate Oxidation - Hydrolyzationn ALPL [2]
MR004382 Nitrophenylphosphate 1-amino-2-naphthyl phosphate (ANP) Oxidation - Dephosphorylation NQO1 [3]
MR004383 Nitrophenylphosphate Ascorbic acid phosphate Oxidation - Dephosphorylation NQO1 [3]
MR004384 Nitrophenylphosphate 4-aminophenyl phosphate Oxidation - Dephosphorylation NQO1 [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Alkaline phosphatase (ALPL) DME0079 Homo sapiens
PPBT_HUMAN
3.1.3.1
[2]
Carbonic anhydrase II (CA2) DME0409 Homo sapiens
CAH2_HUMAN
4.2.1.1
[1]
Quinone reductase 1 (NQO1) DME0097 Homo sapiens
NQO1_HUMAN
1.6.5.2
[3]
Tyrosine-protein phosphatase non-receptor 1 (PTP1B) DME0495 Homo sapiens
PTN1_HUMAN
3.1.3.48
[4]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Tyrosine-protein phosphatase non-receptor 1 (PTP1B) DME0495 Km = 0.38 microM
PTN1_HUMAN
[4]
References
1 Paraoxon, 4-nitrophenyl phosphate and acetate are substrates of - but not of -, - and -carbonic anhydrases. Bioorg Med Chem Lett. 2010 Nov 1;20(21):6208-12.
2 Capillary Electrophoresis/Dynamic Frontal Analysis for the Enzyme Assay of 4-Nitrophenyl Phosphate with Alkaline Phosphatase
3 Use of a Phosphatase-Like DT-Diaphorase Label for the Detection of Outer Membrane Vesicles
4 Residues distant from the active site influence protein-tyrosine phosphatase 1B inhibitor binding. J Biol Chem. 2006 Feb 24;281(8):5258-66.

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