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

ID: ALA4870048

PubChem CID: 117799755

Max Phase: Preclinical

Molecular Formula: C18H23N3O2

Molecular Weight: 313.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(NC(=O)[C@H](N)CC(C)C)ccc1-c1ccncc1

Standard InChI:  InChI=1S/C18H23N3O2/c1-12(2)10-16(19)18(22)21-14-4-5-15(17(11-14)23-3)13-6-8-20-9-7-13/h4-9,11-12,16H,10,19H2,1-3H3,(H,21,22)/t16-/m1/s1

Standard InChI Key:  DMAAWLGYWQNKGD-MRXNPFEDSA-N

Molfile:  

 
     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   23.3587  -20.2977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3576  -21.1172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0656  -21.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7753  -21.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7724  -20.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0638  -19.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6509  -19.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6495  -21.5252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9421  -21.1161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4836  -21.5242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.1907  -21.1145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8990  -21.5220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1894  -20.2973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6061  -21.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3144  -21.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9003  -22.3392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.3157  -22.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0215  -21.1101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6534  -19.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9464  -18.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2384  -19.0747    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2419  -19.8957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9495  -20.2996    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
  1  7  1  0
  2  8  1  0
  8  9  1  0
  4 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
 14 15  1  0
 12 16  1  1
 15 17  1  0
 15 18  1  0
  7 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23  7  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4870048

   (R)-2-amino-N-(3-methoxy-4-(pyridin-4-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: 313.40

Molecular Weight (Monoisotopic): 313.1790

AlogP: 3.07

#Rotatable Bonds: 6

Polar Surface Area: 77.24

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.06

CX Basic pKa: 8.27

CX LogP: 2.38

CX LogD: 1.46

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.86

Np Likeness Score: -0.56

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]

2. Zarrinkar, Patrick P PP and 15 more authors.  2009-10-01  AC220 is a uniquely potent and selective inhibitor of FLT3 for the treatment of acute myeloid leukemia (AML).  [PMID:19654408]

3. and Abdel-Magid, Ahmed F AF.  2017-06-08  Inhibitors of Adaptor-Associated Kinase 1 (AAK1) May Treat Neuropathic Pain, Schizophrenia, Parkinson's Disease, and Other Disorders.  [PMID:28626516]

4. Klaeger, Susan S and 47 more authors.  2017-12-01  The target landscape of clinical kinase drugs.  [PMID:29191878]

Source

Source(1):

• Scientific Literature