5-hydroxy-1-(4-(1-methyl-1H-pyrazol-4-yl)benzyl)-4-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid

ID: ALA1092977

PubChem CID: 46886452

Max Phase: Preclinical

Molecular Formula: C21H21N3O4

Molecular Weight: 379.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1cc(-c2ccc(Cn3cc(C(=O)O)c(=O)c4c3CCCC4O)cc2)cn1

Standard InChI:  InChI=1S/C21H21N3O4/c1-23-11-15(9-22-23)14-7-5-13(6-8-14)10-24-12-16(21(27)28)20(26)19-17(24)3-2-4-18(19)25/h5-9,11-12,18,25H,2-4,10H2,1H3,(H,27,28)

Standard InChI Key:  SKYMJGOQOIAXMW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    4.7181  -23.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7169  -24.0913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4316  -24.5040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4298  -22.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1448  -23.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1437  -24.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8603  -24.5085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5828  -24.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5840  -23.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8627  -22.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8580  -25.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5711  -25.7477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8628  -22.0181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2994  -22.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0127  -23.2655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3014  -22.0266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5635  -26.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2758  -26.9870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9922  -26.5765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9919  -25.7476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2790  -25.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7036  -26.9884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4273  -22.0267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7005  -27.8077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4802  -28.0690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9698  -27.4083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4925  -26.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7944  -27.4159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  6  1  0
  1  2  1  0
  5  4  1  0
 14 15  1  0
 14 16  2  0
  9 14  1  0
  4  1  1  0
 12 17  2  0
  5 10  1  0
 17 18  1  0
  6  7  1  0
 18 19  2  0
  7  8  1  0
 19 20  1  0
  8  9  2  0
 20 21  2  0
 21 12  1  0
  9 10  1  0
 19 22  1  0
  5  6  2  0
  4 23  1  0
 22 24  1  0
  7 11  1  0
 11 12  1  0
  2  3  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 22  2  0
 10 13  2  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1092977

   5-Hydroxy-1-[[4-(1-methylpyrazol-4-yl)phenyl]methyl]-4-oxo-5,6,7,8-tetrahydroquinoline-3-carboxylic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 379.42

Molecular Weight (Monoisotopic): 379.1532

AlogP: 2.37

#Rotatable Bonds: 4

Polar Surface Area: 97.35

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.97

CX Basic pKa: 1.82

CX LogP: 1.91

CX LogD: -1.27

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.73

Np Likeness Score: -0.71

References

1. Kuduk SD, DiPardo RM, Beshore DC, Ray WJ, Ma L, Wittmann M, Seager MA, Koeplinger KA, Thompson CD, Hartman GD, Bilodeau MT..  (2010)  Hydroxy cycloalkyl fused pyridone carboxylic acid M(1) positive allosteric modulators.,  20  (8): [PMID:20346667] [10.1016/j.bmcl.2010.02.095]

Source

Source(1):

• Scientific Literature