N-((S)-1-amino-3-(2,4-dichlorophenyl)propan-2-yl)-5-(2-(methylamino)pyrimidin-4-yl)thiophene-2-carboxamide

ID: ALA213618

PubChem CID: 16043304

Max Phase: Preclinical

Molecular Formula: C19H19Cl2N5OS

Molecular Weight: 436.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNc1nccc(-c2ccc(C(=O)N[C@H](CN)Cc3ccc(Cl)cc3Cl)s2)n1

Standard InChI:  InChI=1S/C19H19Cl2N5OS/c1-23-19-24-7-6-15(26-19)16-4-5-17(28-16)18(27)25-13(10-22)8-11-2-3-12(20)9-14(11)21/h2-7,9,13H,8,10,22H2,1H3,(H,25,27)(H,23,24,26)/t13-/m0/s1

Standard InChI Key:  HHOVRZGUSBMKKU-ZDUSSCGKSA-N

Molfile:  

     RDKit          2D

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    0.3451   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3451    0.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3694    0.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1230    0.0792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4556    1.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2626    1.4068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6751    0.6923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4956    0.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9805    1.2735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8311   -0.1476    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6516   -0.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9871   -0.9875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8076   -1.0737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1365    0.4336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8010    1.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596    0.4148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7741    0.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7741   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596   -1.2352    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4885    0.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2030    0.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9175    0.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6319    0.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6319   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3464   -1.2352    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9175   -1.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2030   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4885   -1.2352    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  2 16  1  0
  3  4  1  0
  5  3  2  0
  7  4  1  0
  6  5  1  0
  7  6  2  0
  7  8  1  0
  9  8  2  0
  8 10  1  0
 15  9  1  0
 11 10  2  0
 11 12  1  0
 11 14  1  0
 13 12  1  0
 15 14  2  0
 17 16  1  1
 17 18  1  0
 17 20  1  0
 18 19  1  0
 20 21  1  0
 21 22  1  0
 21 27  2  0
 23 22  2  0
 24 23  1  0
 24 25  1  0
 26 24  2  0
 27 26  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA213618

   N-[(1s)-2-Amino-1-(2,4-Dichlorobenzyl)ethyl]-5-[2-(Methylamino)pyrimidin-4-Yl]thiophene-2-Carboxamide

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: 436.37

Molecular Weight (Monoisotopic): 435.0687

AlogP: 3.85

#Rotatable Bonds: 7

Polar Surface Area: 92.93

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.02

CX LogP: 3.70

CX LogD: 2.08

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.52

Np Likeness Score: -1.25

References

1. Lin X, Murray JM, Rico AC, Wang MX, Chu DT, Zhou Y, Del Rosario M, Kaufman S, Ma S, Fang E, Crawford K, Jefferson AB..  (2006)  Discovery of 2-pyrimidyl-5-amidothiophenes as potent inhibitors for AKT: synthesis and SAR studies.,  16  (16): [PMID:16765046] [10.1016/j.bmcl.2006.05.092]

Source

Source(1):

• Scientific Literature