(S)-N-((3S,4S)-5-Acetyl-7-cyano-1-((2-methoxynaphthalen-1-yl)-methyl)-4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]-diazepin-3-yl)-2-(methylamino)propanamide Hydrochloride

ID: ALA2436225

PubChem CID: 72714054

Max Phase: Preclinical

Molecular Formula: C29H32ClN5O4

Molecular Weight: 513.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN[C@@H](C)C(=O)N[C@@H]1C(=O)N(Cc2c(OC)ccc3ccccc23)c2ccc(C#N)cc2N(C(C)=O)[C@H]1C.Cl

Standard InChI:  InChI=1S/C29H31N5O4.ClH/c1-17(31-4)28(36)32-27-18(2)34(19(3)35)25-14-20(15-30)10-12-24(25)33(29(27)37)16-23-22-9-7-6-8-21(22)11-13-26(23)38-5;/h6-14,17-18,27,31H,16H2,1-5H3,(H,32,36);1H/t17-,18-,27-;/m0./s1

Standard InChI Key:  JHUGQHSVPSEAPO-FXXKCHFVSA-N

Molfile:  

     RDKit          2D

 39 41  0  0  0  0  0  0  0  0999 V2000
   13.0488   -4.5964    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.4127   -4.9572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7447   -5.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7501   -6.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1380   -6.6720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3623   -6.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2102   -5.1606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5400   -5.9189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3600   -6.0113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8509   -5.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5162   -4.5865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6973   -4.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1462   -7.6097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0383   -6.7053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3203   -6.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6089   -6.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8909   -6.3094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6153   -7.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1794   -6.7277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3585   -7.4671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3138   -5.4729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3871   -4.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0890   -3.6980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6601   -3.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0019   -5.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1576   -7.6736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7529   -8.0846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5286   -7.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7308   -7.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1735   -8.6736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3787   -8.4646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8024   -9.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0196   -9.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8185  -10.0460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3914   -9.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9994   -3.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4868   -3.2561    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5061   -6.2887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0816   -5.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  2  7  1  0
  8  5  1  0
  5  6  1  0
  6  4  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  6 13  2  0
  4 14  1  1
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  6
 17 19  1  0
  5 20  1  0
 15 21  2  0
  2 22  1  0
 22 23  2  0
 22 24  1  0
  3 25  1  6
 20 26  1  0
 26 31  2  0
 30 27  2  0
 27 28  1  0
 28 29  2  0
 29 26  1  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 30  1  0
 36 37  3  0
 11 36  1  0
 29 38  1  0
 38 39  1  0
M  END

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: 513.60

Molecular Weight (Monoisotopic): 513.2376

AlogP: 3.10

#Rotatable Bonds: 6

Polar Surface Area: 114.77

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.85

CX Basic pKa: 8.60

CX LogP: 2.02

CX LogD: 0.79

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.52

Np Likeness Score: -0.50

References

1. Kester RF, Donnell AF, Lou Y, Remiszewski SW, Lombardo LJ, Chen S, Le NT, Lo J, Moliterni JA, Han X, Hogg JH, Liang W, Michoud C, Rupert KC, Mischke S, Le K, Weisel M, Janson CA, Lukacs CM, Fretland AJ, Hong K, Polonskaia A, Gao L, Li S, Solis DS, Aguilar D, Tardell C, Dvorozniak M, Tannu S, Lee EC, Schutt AD, Goggin B..  (2013)  Optimization of benzodiazepinones as selective inhibitors of the X-linked inhibitor of apoptosis protein (XIAP) second baculovirus IAP repeat (BIR2) domain.,  56  (20): [PMID:24093940] [10.1021/jm400732v]

Source

Source(1):

• Scientific Literature