5-Chloro-1-(2-{4-[2,4-dioxo-4-(4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-butyl]-piperazin-1-yl}-2-oxo-ethyl)-1H-indole-2,3-dione

ID: ALA84975

PubChem CID: 44462328

Max Phase: Preclinical

Molecular Formula: C27H26ClN5O6

Molecular Weight: 551.99

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CC(=O)N1CCC(=O)Nc2ccccc21)CN1CCN(C(=O)CN2C(=O)C(=O)c3cc(Cl)ccc32)CC1

Standard InChI:  InChI=1S/C27H26ClN5O6/c28-17-5-6-21-19(13-17)26(38)27(39)33(21)16-25(37)31-11-9-30(10-12-31)15-18(34)14-24(36)32-8-7-23(35)29-20-3-1-2-4-22(20)32/h1-6,13H,7-12,14-16H2,(H,29,35)

Standard InChI Key:  GVBRCHUSUCAKKX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    1.6042   -9.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4000   -8.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9792   -9.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4000   -7.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167   -7.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250   -0.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0292   -5.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4542   -5.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125   -7.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2292   -6.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8208  -11.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8208  -10.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5333  -11.4750    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4167   -3.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4542   -2.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7250   -4.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375   -3.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  6  1  0
  4  7  1  0
  5  2  1  0
  6  1  1  0
  7 13  1  0
  8  1  1  0
  9  8  1  0
 10 14  1  0
 11  4  1  0
 12  9  1  0
 13 20  1  0
 14 11  2  0
 15 18  1  0
 16  4  1  0
 17 32  1  0
 18 16  1  0
 19  6  2  0
 20 29  1  0
 21  3  2  0
 22  2  2  0
 23  5  2  0
 24  7  2  0
 25  9  2  0
 26 12  1  0
 27 12  1  0
 28 15  2  0
 29 17  1  0
 30 20  2  0
 31 26  1  0
 32 27  1  0
 33 34  2  0
 34 19  1  0
 35 33  1  0
 36 11  1  0
 37 14  1  0
 38 36  2  0
 39 38  1  0
  3  5  1  0
 21 33  1  0
 31 17  1  0
 15 10  1  0
 37 39  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA84975

   5-chloro-1-[2-[4-[2,4-dioxo-4-(2-oxo-3,4-dihydro-1H-1,5-benzodiazepin-5-yl)butyl]piperazin-1-yl]-2-oxoethyl]indole-2,3-dione

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: 551.99

Molecular Weight (Monoisotopic): 551.1572

AlogP: 1.35

#Rotatable Bonds: 6

Polar Surface Area: 127.41

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.77

CX Basic pKa: 4.31

CX LogP: 0.56

CX LogD: 0.56

Aromatic Rings: 2

Heavy Atoms: 39

QED Weighted: 0.42

Np Likeness Score: -1.08

References

1. Shuttleworth SJ, Nasturica D, Gervais C, Siddiqui MA, Rando RF, Lee N..  (2000)  Parallel synthesis of isatin-based serine protease inhibitors.,  10  (22): [PMID:11086715] [10.1016/s0960-894x(00)00523-0]

Source

Source(1):

• Scientific Literature