5-Bromo-4-(4-bromo-1-methyl-1H-pyrazol-5-yl)-N-((3S,4S)-4-(4-chlorophenyl)piperidin-3-yl)-1-methyl-1H-pyrrole-2-carboxamide

ID: ALA4560290

PubChem CID: 155558294

Max Phase: Preclinical

Molecular Formula: C21H22Br2ClN5O

Molecular Weight: 555.70

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1ncc(Br)c1-c1cc(C(=O)N[C@@H]2CNCC[C@H]2c2ccc(Cl)cc2)n(C)c1Br

Standard InChI:  InChI=1S/C21H22Br2ClN5O/c1-28-18(9-15(20(28)23)19-16(22)10-26-29(19)2)21(30)27-17-11-25-8-7-14(17)12-3-5-13(24)6-4-12/h3-6,9-10,14,17,25H,7-8,11H2,1-2H3,(H,27,30)/t14-,17+/m0/s1

Standard InChI Key:  FPWXDJFRNZVCBT-WMLDXEAASA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   20.1271   -3.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1259   -4.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8340   -4.6706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5436   -4.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5408   -3.4385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8322   -3.0332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8304   -5.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1208   -5.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1186   -6.7059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8244   -7.1185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.5340   -6.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5379   -5.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4142   -5.4818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7054   -5.8885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9988   -5.4781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7032   -6.7057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9146   -4.6697    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1157   -4.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7052   -5.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2505   -5.8130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8923   -5.2877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3452   -4.6783    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5978   -5.0087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6811   -5.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4800   -5.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5167   -3.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8097   -6.7413    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   20.8297   -2.2160    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.5229   -4.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7853   -3.7503    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  1  0
  7 12  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  7  3  1  6
  8 13  1  1
 13 14  1  0
 14 15  1  0
 14 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 15  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 21  2  0
 22 26  1  0
 25 27  1  0
  6 28  1  0
 17 29  1  0
 18 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4560290

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 555.70

Molecular Weight (Monoisotopic): 552.9880

AlogP: 4.48

#Rotatable Bonds: 4

Polar Surface Area: 63.88

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.21

CX LogP: 3.71

CX LogD: 1.91

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.50

Np Likeness Score: -0.69

References

1. Dong X, Zhan W, Zhao M, Che J, Dai X, Wu Y, Xu L, Zhou Y, Zhao Y, Tian T, Cheng G, Jin Z, Li J, Shao Y, He Q, Yang B, Weng Q, Hu Y..  (2019)  Discovery of 3,4,6-Trisubstituted Piperidine Derivatives as Orally Active, Low hERG Blocking Akt Inhibitors via Conformational Restriction and Structure-Based Design.,  62  (15): [PMID:31298542] [10.1021/acs.jmedchem.9b00891]

Source

Source(1):

• Scientific Literature