(S)-tert-Butyl 3-(2-chloro-5-ethyl-8-fluoro-5H-dibenzo[b,e][1,4]diazepin-11-ylamino)pyrrolidine-1-carboxylate

ID: ALA3609370

PubChem CID: 137125257

Max Phase: Preclinical

Molecular Formula: C24H28ClFN4O2

Molecular Weight: 458.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1c2ccc(F)cc2N=C(N[C@H]2CCN(C(=O)OC(C)(C)C)C2)c2cc(Cl)ccc21

Standard InChI:  InChI=1S/C24H28ClFN4O2/c1-5-30-20-8-6-15(25)12-18(20)22(28-19-13-16(26)7-9-21(19)30)27-17-10-11-29(14-17)23(31)32-24(2,3)4/h6-9,12-13,17H,5,10-11,14H2,1-4H3,(H,27,28)/t17-/m0/s1

Standard InChI Key:  GKEGWJJRPYLMOW-KRWDZBQOSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    4.7970   -1.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1241    0.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0183    1.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3486   -1.7444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6509    1.9313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1246    1.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5854    0.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2272   -0.7320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8722   -1.3706    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4672   -0.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7943    0.7632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2272    1.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3330    0.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0215   -1.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5730   -1.7444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2718    0.4439    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4802    0.5079    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.8563   -2.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1889   -3.4630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5406    3.2787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    4.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382    5.9172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9407    6.8447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1871    6.0101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7785    4.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5943    6.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8007    7.7065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7459    5.5620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1555    6.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0763    5.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2824    6.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3619    7.2592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  7  2  0
  8  4  2  0
  4  1  1  0
  5  6  2  0
  6 11  1  0
  5  7  1  0
  8  9  1  0
  9 10  1  0
  7  8  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  2 16  1  0
 13 17  1  0
  9 18  1  0
 18 19  1  0
  6 20  1  0
 21 20  1  1
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 21  1  0
 24 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3609370

   ---

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: 458.97

Molecular Weight (Monoisotopic): 458.1885

AlogP: 5.63

#Rotatable Bonds: 2

Polar Surface Area: 57.17

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.30

CX LogP: 4.88

CX LogD: 4.88

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.63

Np Likeness Score: -1.45

References

1. Karpov AS, Amiri P, Bellamacina C, Bellance MH, Breitenstein W, Daniel D, Denay R, Fabbro D, Fernandez C, Galuba I, Guerro-Lagasse S, Gutmann S, Hinh L, Jahnke W, Klopp J, Lai A, Lindvall MK, Ma S, Möbitz H, Pecchi S, Rummel G, Shoemaker K, Trappe J, Voliva C, Cowan-Jacob SW, Marzinzik AL..  (2015)  Optimization of a Dibenzodiazepine Hit to a Potent and Selective Allosteric PAK1 Inhibitor.,  6  (7): [PMID:26191365] [10.1021/acsmedchemlett.5b00102]

Source

Source(1):

• Scientific Literature