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

ID: ALA4781735

PubChem CID: 162665966

Max Phase: Preclinical

Molecular Formula: C28H28N4O3

Molecular Weight: 468.56

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CCNC(=O)c1c(C)[nH]c(/C=C2\C(=O)Nc3ccc(C(=O)N[C@H](C)c4ccccc4)cc32)c1C

Standard InChI:  InChI=1S/C28H28N4O3/c1-5-13-29-28(35)25-16(2)24(30-18(25)4)15-22-21-14-20(11-12-23(21)32-27(22)34)26(33)31-17(3)19-9-7-6-8-10-19/h5-12,14-15,17,30H,1,13H2,2-4H3,(H,29,35)(H,31,33)(H,32,34)/b22-15-/t17-/m1/s1

Standard InChI Key:  NKNVDNYKAWGIGX-JVDNRXPZSA-N

Molfile:  

 
     RDKit          2D

 35 38  0  0  0  0  0  0  0  0999 V2000
   21.3735  -10.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3724  -11.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0804  -11.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0786  -10.2930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7872  -10.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7921  -11.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5764  -11.7712    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.0564  -11.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5686  -10.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8736  -11.0976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8166   -9.6607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6149   -9.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2265  -10.0278    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.9318   -9.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7572   -8.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9440   -8.7362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5314   -8.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6803   -9.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6657  -10.2934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6655   -9.4762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9581  -10.7022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2503  -10.2938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5427  -10.7025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2501   -9.4766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8333  -10.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1262  -10.7040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1259  -11.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8387  -11.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5429  -11.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3004   -8.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1007   -8.3713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.6439   -7.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4442   -7.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0432   -7.4305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9874   -7.3153    0.0000 C   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
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  8 10  2  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 12  2  0
 16 17  1  0
 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
 32 33  1  0
 30 34  2  0
 33 35  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4781735

   ---

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: 468.56

Molecular Weight (Monoisotopic): 468.2161

AlogP: 4.53

#Rotatable Bonds: 7

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: 4.00

CX LogD: 4.00

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.30

Np Likeness Score: -0.87

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