Details of the Drug

General Information of Drug (ID: DMFIWAN)

Drug Name
NPPB
Synonyms
5-Nitro-2-(3-phenylpropylamino)benzoic acid; 107254-86-4; UNII-3A35O9G3YZ; 5-nitro-2-[(3-phenylpropyl)amino]benzoic acid; 3A35O9G3YZ; CHEBI:34457; Benzoic acid,5-nitro-2-[(3-phenylpropyl)amino]-; Benzoic acid, 5-nitro-2-((3-phenylpropyl)amino)-; 5-NITRO-2-PHENYLPROPYLAMINOBENZOIC ACID [NPPB]; 5-NITRO-2-(3-PHENYLPROPYLAMINO)-BENZOIC ACID; 5-Nitro-2-(3-phenylpropylamino)benzoic Acid (NPPB); SR-01000075336; HOE-144; HOE 144; Tocris-0593; Spectrum_001814; ACMC-20c9kv; AC1L1IEV; Spectrum4_000338; Spectrum2_001477; HOE 144; 5-nitro-2-(3-phenylpropylamino) benzoic acid
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1], [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 300.31
Topological Polar Surface Area (xlogp) 4.1
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C16H16N2O4
IUPAC Name
5-nitro-2-(3-phenylpropylamino)benzoic acid
Canonical SMILES
C1=CC=C(C=C1)CCCNC2=C(C=C(C=C2)[N+](=O)[O-])C(=O)O
InChI
InChI=1S/C16H16N2O4/c19-16(20)14-11-13(18(21)22)8-9-15(14)17-10-4-7-12-5-2-1-3-6-12/h1-3,5-6,8-9,11,17H,4,7,10H2,(H,19,20)
InChIKey
WBSMIPAMAXNXFS-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
4549
ChEBI ID
CHEBI:34457
CAS Number
107254-86-4
TTD ID
D08DQL

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Calcium-dependent chloride channel anoctamin (ANO) TTOJI4S ANO1_HUMAN Blocker (channel blocker) [3]
Chloride channel protein 2 (CLC-2) TT30NW6 CLCN2_HUMAN Blocker (channel blocker) [4]
Chloride channel protein 7 (ClC-7) TTST1AJ CLCN7_HUMAN Blocker (channel blocker) [5]
Permeability pathway (NP pathway) TTT1MCF NOUNIPROTAC Inhibitor [1]
Transformation-sensitive protein p120 (TRPA1) TTELV3W TRPA1_HUMAN Activator [6]
Volume regulated chloride channel (VRAC) TT0FC1V NOUNIPROTAC Blocker (channel blocker) [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

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
Chloride channel protein 2 (CLC-2) DTT CLCN2 8.78E-02 -0.01 -0.06
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Novel molecular targets for antimalarial drug development. Chem Biol Drug Des. 2008 Apr;71(4):287-97.
2 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. (Ligand id: 4270).
3 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: 708).
4 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: 699).
5 The G215R mutation in the Cl-/H+-antiporter ClC-7 found in ADO II osteopetrosis does not abolish function but causes a severe trafficking defect. PLoS One. 2010 Sep 7;5(9):e12585.
6 NPPB structure-specifically activates TRPA1 channels. Biochem Pharmacol. 2010 Jul 1;80(1):113-21.
7 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: 710).
8 Anoctamin Channels in Human Myometrium: A Novel Target for Tocolysis.Reprod Sci. 2018 Nov;25(11):1589-1600.
9 Nat Rev Drug Discov. 2013 Feb;12(2):87-90.
10 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: 709).
11 Lubiprostone stimulates secretion from tracheal submucosal glands of sheep, pigs, and humans. Am J Physiol Lung Cell Mol Physiol. 2009 May;296(5):L811-24.
12 Interpreting expression profiles of cancers by genome-wide survey of breadth of expression in normal tissues. Genomics 2005 Aug;86(2):127-41.
13 ClC-2 Cl- channels in human lung epithelia: activation by arachidonic acid, amidation, and acid-activated omeprazole. Am J Physiol Cell Physiol. 2001 Jul;281(1):C46-54.
14 TRPV1-mediated itch in seasonal allergic rhinitis. Allergy. 2009 May;64(5):807-10.
15 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
16 Transient receptor potential A1 mediates acetaldehyde-evoked pain sensation. Eur J Neurosci. 2007 Nov;26(9):2516-23.
17 Resolvin D1 attenuates activation of sensory transient receptor potential channels leading to multiple anti-nociception. Br J Pharmacol. 2010 Oct;161(3):707-20.
18 An ion channel essential for sensing chemical damage. J Neurosci. 2007 Oct 17;27(42):11412-5.
19 ANKTM1, a TRP-like channel expressed in nociceptive neurons, is activated by cold temperatures. Cell. 2003 Mar 21;112(6):819-29.
20 Transient receptor potential A1 is a sensory receptor for multiple products of oxidative stress. J Neurosci. 2008 Mar 5;28(10):2485-94.
21 TRPA1 and TRPV1 activation is a novel adjuvant effect mechanism in contact hypersensitivity. J Neuroimmunol. 2009 Feb 15;207(1-2):66-74.
22 Cox-dependent fatty acid metabolites cause pain through activation of the irritant receptor TRPA1. Proc Natl Acad Sci U S A. 2008 Aug 19;105(33):12045-50.
23 Cigarette smoke-induced neurogenic inflammation is mediated by alpha,beta-unsaturated aldehydes and the TRPA1 receptor in rodents. J Clin Invest. 2008 Jul;118(7):2574-82.