4-amino-N-cyclopropyl-8-(2,5-dimethoxyphenyl)-7-fluorocinnoline-3-carboxamide

ID: ALA1783271

PubChem CID: 54584292

Max Phase: Preclinical

Molecular Formula: C20H19FN4O3

Molecular Weight: 382.40

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  COc1ccc(OC)c(-c2c(F)ccc3c(N)c(C(=O)NC4CC4)nnc23)c1

Standard InChI:  InChI=1S/C20H19FN4O3/c1-27-11-5-8-15(28-2)13(9-11)16-14(21)7-6-12-17(22)19(25-24-18(12)16)20(26)23-10-3-4-10/h5-10H,3-4H2,1-2H3,(H2,22,24)(H,23,26)

Standard InChI Key:  WEFRNUXPTYTOEU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   10.5194    1.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5182    0.7685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2331    0.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2313    2.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9466    1.5995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9501    0.7664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6692    0.3551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6624    2.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6579    2.8463    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2316   -0.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5152   -0.8753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5134   -1.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2277   -2.1141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9453   -1.6984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9436   -0.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6605   -2.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6619   -2.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8029   -0.4591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3894    1.6087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3879    0.7701    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0863   -0.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8034    0.3566    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.1028    2.0231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8184    1.6126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1005    2.8481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5317    2.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3539    2.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9394    2.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  2  0
  3  6  2  0
 13 14  1  0
  1  2  2  0
 14 15  2  0
 15 10  1  0
  5  8  1  0
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  6  7  1  0
 16 17  1  0
  7 20  2  0
 11 18  1  0
 19 20  1  0
 19  8  2  0
  5  4  2  0
  8  9  1  0
 18 21  1  0
  4  1  1  0
  2 22  1  0
  3 10  1  0
 19 23  1  0
  5  6  1  0
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 10 11  2  0
 23 25  2  0
 24 26  1  0
 27 26  1  0
 28 27  1  0
 26 28  1  0
 11 12  1  0
  2  3  1  0
M  END

Associated Targets(Human)

GABRG2 Tclin GABA-A receptor; alpha-2/beta-3/gamma-2 (949 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Liver microsomes (16955 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GABRA1 Tclin GABA-A receptor; alpha-1/beta-2/gamma-2 (1171 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GABRG2 Tclin GABA-A receptor; alpha-3/beta-3/gamma-2 (1250 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

Biocomponents

Calculated Properties

Molecular Weight: 382.40Molecular Weight (Monoisotopic): 382.1441AlogP: 2.93#Rotatable Bonds: 5
Polar Surface Area: 99.36Molecular Species: NEUTRALHBA: 6HBD: 2
#RO5 Violations: HBA (Lipinski): 7HBD (Lipinski): 3#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 3.36CX LogP: 2.37CX LogD: 2.37
Aromatic Rings: 3Heavy Atoms: 28QED Weighted: 0.70Np Likeness Score: -0.96

References

1. Alhambra C, Becker C, Blake T, Chang AH, Damewood JR, Daniels T, Dembofsky BT, Gurley DA, Hall JE, Herzog KJ, Horchler CL, Ohnmacht CJ, Schmiesing RJ, Dudley A, Ribadeneira MD, Knappenberger KS, Maciag C, Stein MM, Chopra M, Liu XF, Christian EP, Arriza JL, Chapdelaine MJ..  (2011)  Development and SAR of functionally selective allosteric modulators of GABAA receptors.,  19  (9): [PMID:21498079] [10.1016/j.bmc.2011.03.035]
2. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]