3-({(S)-(S)-5-[(S)-2-((S)-Acetyl-methyl-amino)-3-methyl-pentanoylamino]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indole-2-carbonyl}-amino)-propionic acid

ID: ALA306449

PubChem CID: 44310111

Max Phase: Preclinical

Molecular Formula: C25H34N4O6

Molecular Weight: 486.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@@H](C(=O)N[C@H]1CCc2cccc3c2N(C1=O)[C@H](C(=O)NCCC(=O)O)C3)N(C)C(C)=O

Standard InChI:  InChI=1S/C25H34N4O6/c1-5-14(2)21(28(4)15(3)30)24(34)27-18-10-9-16-7-6-8-17-13-19(29(22(16)17)25(18)35)23(33)26-12-11-20(31)32/h6-8,14,18-19,21H,5,9-13H2,1-4H3,(H,26,33)(H,27,34)(H,31,32)/t14-,18-,19-,21-/m0/s1

Standard InChI Key:  JGCKCYSHUODELU-KKTRPPJXSA-N

Molfile:  

     RDKit          2D

 35 37  0  0  1  0  0  0  0  0999 V2000
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    7.5042   -3.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0667   -3.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167   -3.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125   -2.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8292   -2.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6667   -3.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3292   -3.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -3.7167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542   -4.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5375   -4.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417   -4.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6292   -3.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8292   -2.7375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0542   -4.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9292   -5.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.2625   -5.0792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7000   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3500   -4.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9542   -4.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6000   -2.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1500   -1.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4125   -2.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0917   -3.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6542   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8292   -1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6875   -5.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0917   -5.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6792   -6.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  7  1  0
  5  1  1  0
  6  5  1  0
  9  7  1  1
  8  2  1  0
  9  3  1  0
 11 10  1  6
 11  4  1  0
  2 12  1  1
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 14 18  1  0
 15  4  2  0
 16  3  2  0
 17  5  2  0
 26 18  1  0
 19 12  2  0
 20  9  1  0
 21 13  2  0
 22 14  2  0
 23 12  1  0
 24 17  1  0
 25 11  1  0
 26 23  1  0
 27 14  1  0
 28  6  2  0
 29 10  1  0
 30 13  1  0
 31 32  2  0
 32 17  1  0
 33 25  1  0
 25 34  1  1
 35 33  1  0
  6  8  1  0
 24 20  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA306449

   3-[[(2S,11S)-11-[[(2S,3S)-2-[acetyl(methyl)amino]-3-methylpentanoyl]amino]-12-oxo-1-azatricyclo[6.4.1.04,13]trideca-4,6,8(13)-triene-2-carbonyl]amino]propanoic acid

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: 486.57

Molecular Weight (Monoisotopic): 486.2478

AlogP: 0.86

#Rotatable Bonds: 9

Polar Surface Area: 136.12

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.79

CX Basic pKa: ┄

CX LogP: 0.55

CX LogD: -2.72

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.47

Np Likeness Score: 0.01

References

1. Willoughby CA, Bull HG, Garcia-Calvo M, Jiang J, Chapman KT, Thornberry NA..  (2002)  Discovery of potent, selective human granzyme B inhibitors that inhibit CTL mediated apoptosis.,  12  (16): [PMID:12127536] [10.1016/s0960-894x(02)00363-3]

Source

Source(1):

• Scientific Literature