(R)-2-Amino-N-(3-methoxy-4-(thiazol-5-yl)phenyl)-4-methylpentanamide

ID: ALA4875628

PubChem CID: 117799665

Max Phase: Preclinical

Molecular Formula: C16H21N3O2S

Molecular Weight: 319.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(NC(=O)[C@H](N)CC(C)C)ccc1-c1cncs1

Standard InChI:  InChI=1S/C16H21N3O2S/c1-10(2)6-13(17)16(20)19-11-4-5-12(14(7-11)21-3)15-8-18-9-22-15/h4-5,7-10,13H,6,17H2,1-3H3,(H,19,20)/t13-/m1/s1

Standard InChI Key:  NOMYDZAHVHHVJY-CYBMUJFWSA-N

Molfile:  

 
     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   34.3124  -14.8786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3112  -15.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0193  -16.1071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7289  -15.6977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7261  -14.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0175  -14.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6045  -14.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5189  -13.6583    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   32.7195  -13.4886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3110  -14.1964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8581  -14.8035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6032  -16.1062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8958  -15.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4373  -16.1052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.1443  -15.6955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8527  -16.1029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1431  -14.8783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.5598  -15.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2681  -16.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8540  -16.9201    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.2694  -16.9179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9752  -15.6910    0.0000 C   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
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11  7  2  0
  1  7  1  0
  2 12  1  0
 12 13  1  0
  4 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 16 18  1  0
 18 19  1  0
 16 20  1  1
 19 21  1  0
 19 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4875628

   (R)-2-amino-N-(3-methoxy-4-(thiazol-5-yl)phenyl)-4-methylpentanamide

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: 319.43

Molecular Weight (Monoisotopic): 319.1354

AlogP: 3.13

#Rotatable Bonds: 6

Polar Surface Area: 77.24

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.86

CX Basic pKa: 8.27

CX LogP: 2.25

CX LogD: 1.33

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.86

Np Likeness Score: -0.62

References

1. Hartz RA, Ahuja VT, Nara SJ, Kumar CMV, Brown JM, Bristow LJ, Rajamani R, Muckelbauer JK, Camac D, Kiefer SE, Hunihan L, Gulianello M, Lewis M, Easton A, Lippy JS, Surti N, Pattipati SN, Dokania M, Elavazhagan S, Dandapani K, Hamman BD, Allen J, Kostich W, Bronson JJ, Macor JE, Dzierba CD..  (2021)  Discovery, Structure-Activity Relationships, and In Vivo Evaluation of Novel Aryl Amides as Brain Penetrant Adaptor Protein 2-Associated Kinase 1 (AAK1) Inhibitors for the Treatment of Neuropathic Pain.,  64  (15.0): [PMID:34270254] [10.1021/acs.jmedchem.1c00472]

Source

Source(1):

• Scientific Literature