ID: ALA289651

Max Phase: Preclinical

Molecular Formula: C19H26N2O2

Molecular Weight: 314.43

Molecule Type: Small molecule

Associated Items:

Representations

Synonyms (1): SUAM-1221
Synonyms from Alternative Forms(1):

    Canonical SMILES:  O=C([C@@H]1CCCN1C(=O)CCCc1ccccc1)N1CCCC1

    Standard InChI:  InChI=1S/C19H26N2O2/c22-18(12-6-10-16-8-2-1-3-9-16)21-15-7-11-17(21)19(23)20-13-4-5-14-20/h1-3,8-9,17H,4-7,10-15H2/t17-/m0/s1

    Standard InChI Key:  HDRSLHFTJYMQIL-KRWDZBQOSA-N

    Associated Targets(Human)

    Prolyl endopeptidase 1176 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Dipeptidyl peptidase II 2000 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Dipeptidyl peptidase IV 7109 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Associated Targets(non-human)

    Prolyl endopeptidase 113 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Prolyl endopeptidase 246 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Prolyl endopeptidase 14 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Prolyl endopeptidase 55 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Seprase 241 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: 314.43Molecular Weight (Monoisotopic): 314.1994AlogP: 2.62#Rotatable Bonds: 5
    Polar Surface Area: 40.62Molecular Species: NEUTRALHBA: 2HBD: 0
    #RO5 Violations: 0HBA (Lipinski): 4HBD (Lipinski): 0#RO5 Violations (Lipinski): 0
    CX Acidic pKa: CX Basic pKa: CX LogP: 2.28CX LogD: 2.28
    Aromatic Rings: 1Heavy Atoms: 23QED Weighted: 0.84Np Likeness Score: -0.98

    References

    1. Karoly K, Sandor E, Edit S, Miklos F, Judit S, Benjamin P, Andrea S, Istvan H.  (1997)  Prolyl endopeptidase inhibitors1: N-acyl derivatives of L-thioproline-pyrrolidine,  (13): [10.1016/S0960-894X(97)00295-3]
    2. Tanaka Y, Niwa S, Nishioka H, Yamanaka T, Torizuka M, Yoshinaga K, Kobayashi N, Ikeda Y, Arai H..  (1994)  New potent prolyl endopeptidase inhibitors: synthesis and structure-activity relationships of indan and tetralin derivatives and their analogues.,  37  (13): [PMID:8027988] [10.1021/jm00039a019]
    3. Portevin B, Benoist A, Rémond G, Hervé Y, Vincent M, Lepagnol J, De Nanteuil G..  (1996)  New prolyl endopeptidase inhibitors: in vitro and in vivo activities of azabicyclo[2.2.2]octane, azabicyclo[2.2.1]heptane, and perhydroindole derivatives.,  39  (12): [PMID:8691432] [10.1021/jm950858c]
    4. Vendeville S, Bourel L, Davioud-Charvet E, Grellier P, Deprez B, Sergheraert C..  (1999)  Automated parallel synthesis of a tetrahydroisoquinolin-based library: potential prolyl endopeptidase inhibitors.,  (3): [PMID:10091698] [10.1016/s0960-894x(99)00003-7]
    5. Wallén EA, Christiaans JA, Forsberg MM, Venäläinen JI, Männistö PT, Gynther J..  (2002)  Dicarboxylic acid bis(L-prolyl-pyrrolidine) amides as prolyl oligopeptidase inhibitors.,  45  (20): [PMID:12238937] [10.1021/jm020966g]
    6. Jarho EM, Venäläinen JI, Huuskonen J, Christiaans JA, Garcia-Horsman JA, Forsberg MM, Järvinen T, Gynther J, Männistö PT, Wallén EA..  (2004)  A cyclopent-2-enecarbonyl group mimics proline at the P2 position of prolyl oligopeptidase inhibitors.,  47  (23): [PMID:15509157] [10.1021/jm049503w]
    7. Jarho EM, Wallén EA, Christiaans JA, Forsberg MM, Venäläinen JI, Männistö PT, Gynther J, Poso A..  (2005)  Dicarboxylic acid azacycle l-prolyl-pyrrolidine amides as prolyl oligopeptidase inhibitors and three-dimensional quantitative structure-activity relationship of the enzyme-inhibitor interactions.,  48  (15): [PMID:16033257] [10.1021/jm0500020]
    8. Jarho EM, Venäläinen JI, Juntunen J, Yli-Kokko AL, Vepsäläinen J, Christiaans JA, Forsberg MM, Järvinen T, Männistö PT, Wallén EA..  (2006)  An introduction of a pyridine group into the structure of prolyl oligopeptidase inhibitors.,  16  (21): [PMID:16919454] [10.1016/j.bmcl.2006.08.029]
    9. Kánai K, Arányi P, Böcskei Z, Ferenczy G, Harmat V, Simon K, Bátori S, Náray-Szabo G, Hermecz I..  (2008)  Prolyl oligopeptidase inhibition by N-acyl-pro-pyrrolidine-type molecules.,  51  (23): [PMID:19006380] [10.1021/jm800944x]
    10. Lawandi J, Gerber-Lemaire S, Juillerat-Jeanneret L, Moitessier N..  (2010)  Inhibitors of prolyl oligopeptidases for the therapy of human diseases: defining diseases and inhibitors.,  53  (9): [PMID:20058865] [10.1021/jm901104g]
    11. Van der Veken P, Fülöp V, Rea D, Gerard M, Van Elzen R, Joossens J, Cheng JD, Baekelandt V, De Meester I, Lambeir AM, Augustyns K..  (2012)  P2-substituted N-acylprolylpyrrolidine inhibitors of prolyl oligopeptidase: biochemical evaluation, binding mode determination, and assessment in a cellular model of synucleinopathy.,  55  (22): [PMID:23121075] [10.1021/jm301060g]
    12. Kallinen A, Todorov B, Kallionpää R, Bäck S, Sarparanta M, Raki M, García-Horsman JA, Bergström KA, Wallén EA, Männistö PT, Airaksinen AJ..  (2014)  Synthesis and biological evaluation of novel (123)I-labeled 4-(4-iodophenyl)butanoyl-L-prolyl-(2S)-pyrrolidines for imaging prolyl oligopeptidase in vivo.,  79  [PMID:24763264] [10.1016/j.ejmech.2014.04.014]
    13. Kilpeläinen TP, Tyni JK, Lahtela-Kakkonen MK, Eteläinen TS, Myöhänen TT, Wallén EAA..  (2019)  Tetrazole as a Replacement of the Electrophilic Group in Characteristic Prolyl Oligopeptidase Inhibitors.,  10  (12): [PMID:31857839] [10.1021/acsmedchemlett.9b00394]

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