2-(1-(3-chlorophenyl)-2-hydroxyethyl)-6-(2-((2-hydroxyethyl)amino)pyrimidin-4-yl)isoindolin-1-one

ID: ALA4518783

PubChem CID: 146634740

Max Phase: Preclinical

Molecular Formula: C22H21ClN4O3

Molecular Weight: 424.89

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1c2cc(-c3ccnc(NCCO)n3)ccc2CN1C(CO)c1cccc(Cl)c1

Standard InChI:  InChI=1S/C22H21ClN4O3/c23-17-3-1-2-15(10-17)20(13-29)27-12-16-5-4-14(11-18(16)21(27)30)19-6-7-24-22(26-19)25-8-9-28/h1-7,10-11,20,28-29H,8-9,12-13H2,(H,24,25,26)

Standard InChI Key:  MXKZOOSGWALMQP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   27.6840   -1.1308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.6829   -1.9504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3909   -2.3593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.1006   -1.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0978   -1.1272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3891   -0.7220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8054   -2.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8054   -3.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5129   -3.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5089   -1.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9749   -2.3584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2170   -2.3511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2240   -3.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0046   -3.4160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4801   -2.7496    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.9933   -2.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2392   -1.3123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2973   -2.7426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7120   -3.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6998   -2.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5172   -2.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9197   -1.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5050   -0.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6836   -0.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2849   -1.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5291   -3.4398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9742   -3.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7368   -1.3112    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   26.2662   -3.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2655   -4.4008    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
  7  8  2  0
  8  9  1  0
  9 13  2  0
 12 10  2  0
 10  7  1  0
  4  7  1  0
  2 11  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  1  0
 16 17  2  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 19 26  1  0
 11 27  1  0
 22 28  1  0
 27 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4518783

   ---

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: 424.89

Molecular Weight (Monoisotopic): 424.1302

AlogP: 2.89

#Rotatable Bonds: 7

Polar Surface Area: 98.58

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.79

CX Basic pKa: 3.85

CX LogP: 2.29

CX LogD: 2.29

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.54

Np Likeness Score: -0.97

References

1. Ji D, Zhang L, Zhu Q, Bai Y, Wu Y, Xu Y..  (2019)  Discovery of potent, orally bioavailable ERK1/2 inhibitors with isoindolin-1-one structure by structure-based drug design.,  164  [PMID:30605831] [10.1016/j.ejmech.2018.12.040]

Source

Source(1):

• Scientific Literature