(R)-3-((4-(2-chloroacetamido)-3,5-dimethyl-1H-pyrrol-2-yl)methylene)-2-oxo-N-(1-phenylethyl)indoline-5-carboxamide

ID: ALA4791260

PubChem CID: 162672001

Max Phase: Preclinical

Molecular Formula: C26H25ClN4O3

Molecular Weight: 476.96

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1[nH]c(/C=C2\C(=O)Nc3ccc(C(=O)N[C@H](C)c4ccccc4)cc32)c(C)c1NC(=O)CCl

Standard InChI:  InChI=1S/C26H25ClN4O3/c1-14-22(28-16(3)24(14)31-23(32)13-27)12-20-19-11-18(9-10-21(19)30-26(20)34)25(33)29-15(2)17-7-5-4-6-8-17/h4-12,15,28H,13H2,1-3H3,(H,29,33)(H,30,34)(H,31,32)/b20-12-/t15-/m1/s1

Standard InChI Key:  UWWMLSOJAKHPMN-GEYIUBJWSA-N

Molfile:  

 
     RDKit          2D

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    6.8457  -18.5023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8445  -19.3219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5526  -19.7308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5508  -18.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2594  -18.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2642  -19.3219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.0408  -18.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3458  -18.8981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2887  -17.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0870  -17.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6987  -17.8283    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4040  -17.4155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2294  -16.6171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4302  -18.5027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7224  -18.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0148  -18.5030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7222  -17.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3055  -18.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5983  -18.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5981  -19.3225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3109  -19.7308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0151  -19.3204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7725  -16.0066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5729  -16.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1161  -15.5612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8300  -16.9474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9164  -15.7263    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
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  5  6  1  0
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 14 18  1  0
  1 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  1
 23 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 23  1  0
 15 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
 32 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4791260

   ---

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: 476.96

Molecular Weight (Monoisotopic): 476.1615

AlogP: 4.79

#Rotatable Bonds: 6

Polar Surface Area: 103.09

Molecular Species: NEUTRAL

HBA: 3

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.92

CX Basic pKa: ┄

CX LogP: 3.97

CX LogD: 3.97

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.30

Np Likeness Score: -0.90

References

1. Rowlands RA,Chen Q,Bouley RA,Avramova LV,Tesmer JJG,White AD.  (2021)  Generation of Highly Selective, Potent, and Covalent G Protein-Coupled Receptor Kinase 5 Inhibitors.,  64  (1.0): [PMID:33393767] [10.1021/acs.jmedchem.0c01522]

2. Cho, Sung Yun SY and 9 more authors.  2013-12-15  Design and synthesis of novel 3-(benzo[d]oxazol-2-yl)-5-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)pyridin-2-amine derivatives as selective G-protein-coupled receptor kinase-2 and -5 inhibitors.  [PMID:24210504]

Source

Source(1):

• Scientific Literature