Details of the Drug

General Information of Drug (ID: DMBX4UJ)

• Drug Name: 4-nitrophenyl phosphate
• Synonyms: 4-nitrophenyl phosphate; 4-Nitrophenyl dihydrogen phosphate; 330-13-2; Nitrophenylphosphate; Phosphoric acid, mono(4-nitrophenyl) ester; p-nitrophenyl phosphate; p-Nitrophenyl dihydrogen phosphate; p-Nitrophenol phosphate; p-Nitrophenylphosphate; (4-nitrophenyl) dihydrogen phosphate; PNPP; NSC 404086; Phenol, p-nitro-, dihydrogen phosphate; CHEMBL24231; (4-nitrophenoxy)phosphonic acid; CHEBI:17440; XZKIHKMTEMTJQX-UHFFFAOYSA-N; pNPP Alkaline Phosphatase Substrate; Phosphoric acid, mono(p-nitrophenyl) ester (8CI); Phosphoric ac

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]

• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 219.09
  Topological Polar Surface Area (xlogp); 0.3
  Rotatable Bond Count (rotbonds); 2
  Hydrogen Bond Donor Count (hbonddonor); 2
  Hydrogen Bond Acceptor Count (hbondacc); 6
• Chemical Identifiers:
  Formula: C6H6NO6P
  IUPAC Name: (4-nitrophenyl) dihydrogen phosphate
  Canonical SMILES: C1=CC(=CC=C1[N+](=O)[O-])OP(=O)(O)O
  InChI: 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
• Cross-matching ID:
  PubChem CID: 378
  ChEBI ID: CHEBI:17440
  CAS Number: 330-13-2
  DrugBank ID: DB04214
  TTD ID: D0T0YI
  INTEDE ID: DR2064

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Carbonic anhydrase (CA)	TTUNARX	NOUNIPROTAC	Inhibitor	[1]
Carbonic anhydrase I (CA-I)	TTHQPL7	CAH1_HUMAN	Inhibitor	[1]
Carbonic anhydrase II (CA-II)	TTANPDJ	CAH2_HUMAN	Inhibitor	[1]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Tyrosine-protein phosphatase non-receptor 1 (PTP1B) Main DME	DE6TFXV	PTN1_HUMAN	Substrate	[2]

Molecular Expression Atlas of This Drug

• The Studied Disease: Discovery agent
• ICD Disease Classification: N.A.

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Carbonic anhydrase I (CA-I)	DTT	CA1	5.23E-14	-0.11	-0.41
Carbonic anhydrase II (CA-II)	DTT	CA2	7.95E-08	0.52	0.33
Tyrosine-protein phosphatase non-receptor 1 (PTP1B)	DME	PTPN1	1.51E-03	2.25E-02	1.26E-01

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] Residues distant from the active site influence protein-tyrosine phosphatase 1B inhibitor binding. J Biol Chem. 2006 Feb 24;281(8):5258-66.
• [3] Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8.
• [4] Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
• [5] URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 2597).
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• [15] Inhibition of carbonic anhydrases I and II by N-unsubstituted carbamate esters. J Biol Chem. 1992 Dec 15;267(35):25044-50.
• [16] Nature of the inhibition of carbonic anhydrase by acetazolamide and benzthiazide. J Pharmacol Exp Ther. 1961 Mar;131:271-4.
• [17] Carbonic anhydrase inhibitors: Inhibition of the new membrane-associated isoform XV with phenols. Bioorg Med Chem Lett. 2008 Jun 15;18(12):3593-6.
• [18] Cloning, expression, post-translational modifications and inhibition studies on the latest mammalian carbonic anhydrase isoform, CA XV. J Med Chem. 2009 Feb 12;52(3):646-54.
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