(4-((4-Ethoxy-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-isopropoxyphenyl)(morpholino)methanone

ID: ALA4743843

PubChem CID: 118286352

Max Phase: Preclinical

Molecular Formula: C22H27N5O4

Molecular Weight: 425.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOc1nc(Nc2ccc(C(=O)N3CCOCC3)cc2OC(C)C)nc2[nH]ccc12

Standard InChI:  InChI=1S/C22H27N5O4/c1-4-30-20-16-7-8-23-19(16)25-22(26-20)24-17-6-5-15(13-18(17)31-14(2)3)21(28)27-9-11-29-12-10-27/h5-8,13-14H,4,9-12H2,1-3H3,(H2,23,24,25,26)

Standard InChI Key:  JNEYRGCOLYRABZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   29.8838  -24.4951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8827  -25.3146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5907  -25.7236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3004  -25.3141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2976  -24.4915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5890  -24.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0037  -24.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0007  -23.2630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1747  -25.7226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.4673  -25.3135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4725  -24.4964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.7659  -24.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7660  -25.7222    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.0589  -25.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0566  -24.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2734  -24.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7916  -24.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2771  -25.5732    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.7676  -23.2701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0607  -22.8601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0624  -22.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7130  -24.4861    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.7135  -25.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4186  -25.7064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1272  -25.2986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.1261  -24.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4164  -24.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5905  -26.5408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2982  -26.9495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2980  -27.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0060  -26.5411    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
  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
 22 23  1  0
 22 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  3 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4743843

   [4-[(4-ethoxy-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino]-3-propan-2-yloxyphenyl]-morpholin-4-ylmethanone

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: 425.49

Molecular Weight (Monoisotopic): 425.2063

AlogP: 3.36

#Rotatable Bonds: 7

Polar Surface Area: 101.60

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.81

CX Basic pKa: 4.69

CX LogP: 3.12

CX LogD: 3.12

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.60

Np Likeness Score: -1.56

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