ID: ALA331943

Max Phase: Preclinical

Molecular Formula: C22H24N4O4S2

Molecular Weight: 472.59

Molecule Type: Small molecule

Associated Items:

Representations

Synonyms (1): RPR-120844
Synonyms from Alternative Forms(1):

    Canonical SMILES:  COc1ccc2ccc(S(=O)(=O)N(C)[C@H]3CCN(Cc4csc(C(=N)N)c4)C3=O)cc2c1

    Standard InChI:  InChI=1S/C22H24N4O4S2/c1-25(19-7-8-26(22(19)27)12-14-9-20(21(23)24)31-13-14)32(28,29)18-6-4-15-3-5-17(30-2)10-16(15)11-18/h3-6,9-11,13,19H,7-8,12H2,1-2H3,(H3,23,24)/t19-/m0/s1

    Standard InChI Key:  YQYYTNCSSDRJHZ-IBGZPJMESA-N

    Associated Targets(Human)

    Coagulation factor X 9693 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Thrombin 11687 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Vitamin K-dependent protein C 491 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Plasminogen 2339 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Tissue-type plasminogen activator 1057 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Trypsin I 2306 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Kallikrein 6 143 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Associated Targets(non-human)

    Trypsin II 226 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Coagulation factor X 201 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: 472.59Molecular Weight (Monoisotopic): 472.1239AlogP: 2.62#Rotatable Bonds: 7
    Polar Surface Area: 116.79Molecular Species: BASEHBA: 6HBD: 2
    #RO5 Violations: 0HBA (Lipinski): 8HBD (Lipinski): 3#RO5 Violations (Lipinski): 0
    CX Acidic pKa: CX Basic pKa: 8.92CX LogP: 1.64CX LogD: 0.15
    Aromatic Rings: 3Heavy Atoms: 32QED Weighted: 0.40Np Likeness Score: -1.13

    References

    1. Choi-Sledeski YM, Becker MR, Green DM, Davis R, Ewing WR, Mason HJ, Ly C, Spada A, Liang G, Cheney D, Barton J, Chu V, Brown K, Colussi D, Bentley R, Leadley R, Dunwiddie C, Pauls HW..  (1999)  Aminoisoquinolines: design and synthesis of an orally active benzamidine isostere for the inhibition of factor XA.,  (17): [PMID:10498204] [10.1016/s0960-894x(99)00421-7]
    2. Ewing WR, Becker MR, Manetta VE, Davis RS, Pauls HW, Mason H, Choi-Sledeski YM, Green D, Cha D, Spada AP, Cheney DL, Mason JS, Maignan S, Guilloteau JP, Brown K, Colussi D, Bentley R, Bostwick J, Kasiewski CJ, Morgan SR, Leadley RJ, Dunwiddie CT, Perrone MH, Chu V..  (1999)  Design and structure-activity relationships of potent and selective inhibitors of blood coagulation factor Xa.,  42  (18): [PMID:10479288] [10.1021/jm990040h]
    3. Choi-Sledeski YM, McGarry DG, Green DM, Mason HJ, Becker MR, Davis RS, Ewing WR, Dankulich WP, Manetta VE, Morris RL, Spada AP, Cheney DL, Brown KD, Colussi DJ, Chu V, Heran CL, Morgan SR, Bentley RG, Leadley RJ, Maignan S, Guilloteau JP, Dunwiddie CT, Pauls HW..  (1999)  Sulfonamidopyrrolidinone factor Xa inhibitors: potency and selectivity enhancements via P-1 and P-4 optimization.,  42  (18): [PMID:10479289] [10.1021/jm990041+]
    4. Pinto DJ, Smallheer JM, Cheney DL, Knabb RM, Wexler RR..  (2010)  Factor Xa inhibitors: next-generation antithrombotic agents.,  53  (17): [PMID:20503967] [10.1021/jm100146h]
    5. Liang G, Chen X, Aldous S, Pu SF, Mehdi S, Powers E, Giovanni A, Kongsamut S, Xia T, Zhang Y, Wang R, Gao Z, Merriman G, McLean LR, Morize I..  (2012)  Virtual Screening and X-ray Crystallography for Human Kallikrein 6 Inhibitors with an Amidinothiophene P1 Group.,  (2): [PMID:24900446] [10.1021/ml200291e]

    Source