3-cyclopropyl-10-((S)-3-hydroxy-3-(5-methylisoxazol-3-yl)but-1-ynyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

ID: ALA3941082

PubChem CID: 134145793

Max Phase: Preclinical

Molecular Formula: C23H22N4O4

Molecular Weight: 418.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc([C@@](C)(O)C#Cc2ccc3c(c2)-c2nc(C(N)=O)c(C4CC4)n2CCO3)no1

Standard InChI:  InChI=1S/C23H22N4O4/c1-13-11-18(26-31-13)23(2,29)8-7-14-3-6-17-16(12-14)22-25-19(21(24)28)20(15-4-5-15)27(22)9-10-30-17/h3,6,11-12,15,29H,4-5,9-10H2,1-2H3,(H2,24,28)/t23-/m0/s1

Standard InChI Key:  YWHACELMMCHPDB-QHCPKHFHSA-N

Molfile:  

     RDKit          2D

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    4.6678   -2.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1678   -2.2142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9139   -3.5065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9217   -0.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9287    0.2032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4535   -1.2159    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2972   -0.4110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0900    1.6946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0851   -0.6017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1752   -1.6272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5003    2.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5073    3.3026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.3604   -0.8389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7326   -1.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7544   -2.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9665    0.5332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2882   -2.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5082   -3.5079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1358   -4.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5079   -4.6256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8390   -4.7734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  9  8  1  0
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 10 11  1  0
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 15 13  2  0
 13 16  1  0
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 15 18  1  0
 19 16  2  0
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 20 19  1  0
 21 22  3  0
 22 23  1  0
 23 24  1  6
 25 23  1  0
 23 26  1  0
 27 25  1  0
 25 28  2  0
 27 29  2  0
 28 30  1  0
 31 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3941082

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 418.45

Molecular Weight (Monoisotopic): 418.1641

AlogP: 2.47

#Rotatable Bonds: 3

Polar Surface Area: 116.40

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.68

CX Basic pKa: 2.77

CX LogP: 2.36

CX LogD: 2.36

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.63

Np Likeness Score: -1.00

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