(S)-4-(1-(2-aminopyrimidin-4-yl)-2-ethoxy-1H-benzo[d]imidazol-6-yl)-2-(5-methyloxazol-2-yl)but-3-yn-2-ol

ID: ALA4546659

PubChem CID: 155552645

Max Phase: Preclinical

Molecular Formula: C21H20N6O3

Molecular Weight: 404.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOc1nc2ccc(C#C[C@](C)(O)c3ncc(C)o3)cc2n1-c1ccnc(N)n1

Standard InChI:  InChI=1S/C21H20N6O3/c1-4-29-20-25-15-6-5-14(7-9-21(3,28)18-24-12-13(2)30-18)11-16(15)27(20)17-8-10-23-19(22)26-17/h5-6,8,10-12,28H,4H2,1-3H3,(H2,22,23,26)/t21-/m0/s1

Standard InChI Key:  HZWIAHGTTPPVAC-NRFANRHFSA-N

Molfile:  

 
     RDKit          2D

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   28.6651  -10.6259    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0000  -11.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3344  -11.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0759  -11.8944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6229  -12.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4288  -12.3395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6846  -11.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1358  -10.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2152  -10.8582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6023  -11.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   29.3795   -9.3880    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.3786   -8.5637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6628   -8.1514    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9466   -8.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   30.0927   -8.1505    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.4916  -11.3823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2969  -11.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1035  -11.0355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6571  -11.6472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8864  -10.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8157  -10.6177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5721  -10.9481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.1202  -10.3307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7024   -9.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8961   -9.7960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.9414  -10.4113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0
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  2  3  1  0
  3  1  2  0
  4  5  2  0
  5  6  1  0
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  7  8  1  0
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 13 14  2  0
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 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  2 13  1  0
 15 19  1  0
  8 20  1  0
 20 21  3  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  1
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 25  2  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4546659

   ---

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: 404.43

Molecular Weight (Monoisotopic): 404.1597

AlogP: 2.35

#Rotatable Bonds: 4

Polar Surface Area: 125.11

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.14

CX Basic pKa: 5.62

CX LogP: 2.84

CX LogD: 2.83

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.50

Np Likeness Score: -0.90

References

1. Feng JA, Lee P, Alaoui MH, Barrett K, Castanedo G, Godemann R, McEwan P, Wang X, Wu P, Zhang Y, Harris SF, Staben ST..  (2019)  Structure Based Design of Potent Selective Inhibitors of Protein Kinase D1 (PKD1).,  10  (9): [PMID:31531194] [10.1021/acsmedchemlett.8b00658]

Source

Source(1):

• Scientific Literature