4-((4-Ethoxy-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)-N-(2-hydroxy-2-methylpropyl)-3-methoxybenzamide

ID: ALA4741733

PubChem CID: 118286449

Max Phase: Preclinical

Molecular Formula: C20H25N5O4

Molecular Weight: 399.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOc1nc(Nc2ccc(C(=O)NCC(C)(C)O)cc2OC)nc2[nH]ccc12

Standard InChI:  InChI=1S/C20H25N5O4/c1-5-29-18-13-8-9-21-16(13)24-19(25-18)23-14-7-6-12(10-15(14)28-4)17(26)22-11-20(2,3)27/h6-10,27H,5,11H2,1-4H3,(H,22,26)(H2,21,23,24,25)

Standard InChI Key:  PBUIMZPVMYITCU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   17.3288   -3.6443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3277   -4.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0357   -4.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7454   -4.4634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7425   -3.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0339   -3.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4487   -3.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4456   -2.4123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6196   -4.8719    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9123   -4.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9174   -3.6457    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2109   -3.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2110   -4.8715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5039   -4.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5016   -3.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7184   -3.3913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2366   -4.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7221   -4.7224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2126   -2.4194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5057   -2.0093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5074   -1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1580   -3.6354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0355   -5.6900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7431   -6.0988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8641   -3.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5734   -3.6300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2795   -3.2188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5764   -4.4472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2788   -4.0364    0.0000 O   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
  5  7  1  0
  7  8  2  0
  2  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 15  2  0
 14 13  2  0
 13 10  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 14  1  0
 12 19  1  0
 19 20  1  0
 20 21  1  0
  7 22  1  0
  3 23  1  0
 23 24  1  0
 22 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4741733

   4-[(4-ethoxy-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino]-N-(2-hydroxy-2-methylpropyl)-3-methoxybenzamide

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: 399.45

Molecular Weight (Monoisotopic): 399.1907

AlogP: 2.61

#Rotatable Bonds: 8

Polar Surface Area: 121.39

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.85

CX Basic pKa: 4.71

CX LogP: 2.35

CX LogD: 2.35

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.46

Np Likeness Score: -0.98

References

1. Ding X,Stasi LP,Ho MH,Zhao B,Wang H,Long K,Xu Q,Sang Y,Sun C,Hu H,Yu H,Wan Z,Wang L,Edge C,Liu Q,Li Y,Dong K,Guan X,Tattersall FD,Reith AD,Ren F.  (2018)  Discovery of 4-ethoxy-7H-pyrrolo[2,3-d]pyrimidin-2-amines as potent, selective and orally bioavailable LRRK2 inhibitors.,  28  (9.0): [PMID:29588215] [10.1016/j.bmcl.2018.03.045]

Source

Source(1):

• Scientific Literature