1-(6-fluoro-3-(4-(methylsulfonyl)piperazine-1-carbonyl)quinolin-4-yl)-4-methylpiperidine-4-carbonitrile

ID: ALA4216370

PubChem CID: 142581496

Max Phase: Preclinical

Molecular Formula: C22H26FN5O3S

Molecular Weight: 459.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C#N)CCN(c2c(C(=O)N3CCN(S(C)(=O)=O)CC3)cnc3ccc(F)cc23)CC1

Standard InChI:  InChI=1S/C22H26FN5O3S/c1-22(15-24)5-7-26(8-6-22)20-17-13-16(23)3-4-19(17)25-14-18(20)21(29)27-9-11-28(12-10-27)32(2,30)31/h3-4,13-14H,5-12H2,1-2H3

Standard InChI Key:  SIGXVLVHXOJBCM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   15.0396  -10.0374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6352   -9.3317    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.2262  -10.0348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4693   -4.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8821   -5.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2905   -4.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1790   -8.1182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1779   -8.9378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8859   -9.3467    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8841   -7.7094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5928   -8.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5935   -8.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3021   -9.3407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0103   -8.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0056   -8.1077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2965   -7.7044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8817   -6.8922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5923   -6.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5919   -5.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1764   -5.6716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1753   -6.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4712   -7.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7108   -7.6949    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.0566   -3.8383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4710   -6.8926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7636   -8.1186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0579   -7.7053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3524   -8.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3483   -8.9282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0560   -9.3388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7677   -8.9318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9329   -8.9232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  5  4  1  0
  6  5  1  0
  7  8  2  0
  8  9  1  0
  9 12  2  0
 11 10  2  0
 10  7  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 10 17  1  0
 17 18  1  0
 17 21  1  0
 18 19  1  0
 19  5  1  0
  5 20  1  0
 20 21  1  0
  7 22  1  0
 15 23  1  0
  4 24  3  0
 22 25  2  0
 22 26  1  0
 26 27  1  0
 26 31  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 29  2  1  0
  2 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4216370

   ---

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: 459.55

Molecular Weight (Monoisotopic): 459.1740

AlogP: 2.22

#Rotatable Bonds: 3

Polar Surface Area: 97.61

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.88

CX LogP: 0.94

CX LogD: 0.92

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.70

Np Likeness Score: -1.50

References

1. Yang SM, Martinez NJ, Yasgar A, Danchik C, Johansson C, Wang Y, Baljinnyam B, Wang AQ, Xu X, Shah P, Cheff D, Wang XS, Roth J, Lal-Nag M, Dunford JE, Oppermann U, Vasiliou V, Simeonov A, Jadhav A, Maloney DJ..  (2018)  Discovery of Orally Bioavailable, Quinoline-Based Aldehyde Dehydrogenase 1A1 (ALDH1A1) Inhibitors with Potent Cellular Activity.,  61  (11): [PMID:29767973] [10.1021/acs.jmedchem.8b00270]

Source

Source(1):

• Scientific Literature