4-NITROANILINE

ID: ALA14282

Max Phase: Preclinical

Molecular Formula: C6H6N2O2

Molecular Weight: 138.13

Molecule Type: Small molecule

Associated Items:

Representations

Synonyms (2): 1-Amino-4-nitrobenzene | p-Nitroaniline
Synonyms from Alternative Forms(2):

    Canonical SMILES:  Nc1ccc([N+](=O)[O-])cc1

    Standard InChI:  InChI=1S/C6H6N2O2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H,7H2

    Standard InChI Key:  TYMLOMAKGOJONV-UHFFFAOYSA-N

    Associated Targets(Human)

    Prolyl endopeptidase 1176 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Lymphoblastoid cell 5959 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Aldehyde dehydrogenase 1A1 77053 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Histone acetyltransferase GCN5 14285 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Bromodomain adjacent to zinc finger domain protein 2B 56204 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Estrogen receptor alpha 17718 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Androgen Receptor 11781 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Glucocorticoid receptor 14987 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Nuclear factor erythroid 2-related factor 2 95332 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Geminin 128009 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Ataxin-2 54410 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Glucagon-like peptide 1 receptor 111429 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Nuclear receptor ROR-gamma 8495 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Cytochrome P450 1A1 1169 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Cytochrome P450 1B1 1148 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Associated Targets(non-human)

    Rattus norvegicus 775804 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Thioredoxin glutathione reductase 28579 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Plasmodium falciparum 966862 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Colon 38 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Small intestine 70 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Molecule Features

    Natural Product: NoOral: NoChemical Probe: NoParenteral: No
    Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
    Chirality: NoAvailability: NoProdrug: No

    Drug Indications

    MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

    Mechanisms of Action

    Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

    Properties

    Molecular Weight: 138.13Molecular Weight (Monoisotopic): 138.0429AlogP: 1.18#Rotatable Bonds: 1
    Polar Surface Area: 69.16Molecular Species: NEUTRALHBA: 3HBD: 1
    #RO5 Violations: 0HBA (Lipinski): 4HBD (Lipinski): 2#RO5 Violations (Lipinski): 0
    CX Acidic pKa: CX Basic pKa: 2.13CX LogP: 1.08CX LogD: 1.08
    Aromatic Rings: 1Heavy Atoms: 10QED Weighted: 0.36Np Likeness Score: -1.21

    References

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    2. Zon G, Ludeman SM, Brandt JA, Boyd VL, Ozkan G, Egan W, Shao KL..  (1984)  NMR spectroscopic studies of intermediary metabolites of cyclophosphamide. A comprehensive kinetic analysis of the interconversion of cis- and trans-4-hydroxycyclophosphamide with aldophosphamide and the concomitant partitioning of aldophosphamide between irreversible fragmentation and reversible conjugation pathways.,  27  (4): [PMID:6708049] [10.1021/jm00370a008]
    3. Caron G, Ermondi G..  (2005)  Calculating virtual log P in the alkane/water system (log P(N)(alk)) and its derived parameters deltalog P(N)(oct-alk) and log D(pH)(alk).,  48  (9): [PMID:15857133] [10.1021/jm048980b]
    4. Fujikawa M, Nakao K, Shimizu R, Akamatsu M..  (2007)  QSAR study on permeability of hydrophobic compounds with artificial membranes.,  15  (11): [PMID:17418579] [10.1016/j.bmc.2007.03.040]
    5. Helguera AM, Cordeiro MN, Pérez MA, Combes RD, González MP..  (2008)  QSAR modeling of the rodent carcinogenicity of nitrocompounds.,  16  (6): [PMID:18295489] [10.1016/j.bmc.2007.11.029]
    6. Pérez-Garrido A, Morales Helguera A, Abellán Guillén A, Cordeiro MN, Garrido Escudero A..  (2009)  Convenient QSAR model for predicting the complexation of structurally diverse compounds with beta-cyclodextrins.,  17  (2): [PMID:19056282] [10.1016/j.bmc.2008.11.040]
    7. Racys DT, Rea D, Fülöp V, Wills M..  (2010)  Inhibition of prolyl oligopeptidase with a synthetic unnatural dipeptide.,  18  (13): [PMID:20627594] [10.1016/j.bmc.2010.05.012]
    8. PubChem BioAssay data set, 
    9. PubChem BioAssay data set, 
    10. PubChem BioAssay data set, 
    11. Nabuurs RJ, Kapoerchan VV, Metaxas A, de Jongh S, de Backer M, Welling MM, Jiskoot W, Windhorst AD, Overkleeft HS, van Buchem MA, Overhand M, van der Weerd L..  (2014)  Polyfluorinated bis-styrylbenzenes as amyloid-β plaque binding ligands.,  22  (8): [PMID:24657049] [10.1016/j.bmc.2014.02.054]
    12. Scherrer RA, Howard SM..  (1977)  Use of distribution coefficients in quantitative structure-activity relationships.,  20  (1): [PMID:13215] [10.1021/jm00211a010]
    13. Lee D, Perez P, Jackson W, Chin T, Galbreath M, Fronczek FR, Isovitsch R, Iimoto DS..  (2016)  Aryl morpholino triazenes inhibit cytochrome P450 1A1 and 1B1.,  26  (14): [PMID:27265259] [10.1016/j.bmcl.2016.05.064]
    14. Green KD, Fosso MY, Mayhoub AS, Garneau-Tsodikova S..  (2019)  Investigating the promiscuity of the chloramphenicol nitroreductase from Haemophilus influenzae towards the reduction of 4-nitrobenzene derivatives.,  29  (9): [PMID:30826292] [10.1016/j.bmcl.2019.02.025]