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
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 219.09
Logarithm of the Partition Coefficient (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
CHEMBL24231
CAS Number
330-13-2
UNII
59NF9TE3BA
DrugBank ID
DB04214
TTD ID
D0T0YI
INTEDE ID
DR2064
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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]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Alkaline phosphatase, placental type (ALPP) OTZU4G9W PPB1_HUMAN Biotransformations [3]
Dual specificity protein phosphatase 23 (DUSP23) OTE2PG54 DUS23_HUMAN Biotransformations [4]
Low molecular weight phosphotyrosine protein phosphatase (ACP1) OTJ9CKLU PPAC_HUMAN Biotransformations [5]
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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
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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 The in vitro enzymic labilities of chemically distinct phosphomonoester prodrugs. Pharm Res. 1992 Apr;9(4):497-503. doi: 10.1023/a:1015840329786.
4 Molecular cloning and characterization of a novel dual-specificity phosphatase 23 gene from human fetal brain. Int J Biochem Cell Biol. 2004 Aug;36(8):1542-53. doi: 10.1016/j.biocel.2003.12.014.
5 Synthesis, biological activity and structure-activity relationships of new benzoic acid-based protein tyrosine phosphatase inhibitors endowed with insulinomimetic effects in mouse C2C12 skeletal muscle cells. Eur J Med Chem. 2014 Jan;71:112-27. doi: 10.1016/j.ejmech.2013.11.001. Epub 2013 Nov 11.