(2S,5S)-5-((R)-3-Methyl-2-pyridin-2-yl-butyrylamino)-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indole-2-carboxylic acid (1H-[1,2,3]triazol-4-ylmethyl)-amide

ID: ALA304727

PubChem CID: 44310015

Max Phase: Preclinical

Molecular Formula: C26H29N7O3

Molecular Weight: 487.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)[C@@H](C(=O)N[C@H]1CCc2cccc3c2N(C1=O)[C@H](C(=O)NCc1cn[nH]n1)C3)c1ccccn1

Standard InChI:  InChI=1S/C26H29N7O3/c1-15(2)22(19-8-3-4-11-27-19)25(35)30-20-10-9-16-6-5-7-17-12-21(33(23(16)17)26(20)36)24(34)28-13-18-14-29-32-31-18/h3-8,11,14-15,20-22H,9-10,12-13H2,1-2H3,(H,28,34)(H,30,35)(H,29,31,32)/t20-,21-,22+/m0/s1

Standard InChI Key:  BTLKDBNKGRJVJE-FDFHNCONSA-N

Molfile:  

     RDKit          2D

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    7.5875   -6.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.7042   -6.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4542   -3.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917   -6.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9042   -3.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4125   -2.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8500   -4.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2750   -6.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  0
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  2 14  1  1
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 10 18  1  6
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 28  7  2  0
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 35 36  2  0
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  7 12  1  0
 26 24  1  0
 28 29  1  0
 15  6  1  0
 31 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA304727

   (2S,11S)-11-[[(2R)-3-methyl-2-pyridin-2-ylbutanoyl]amino]-12-oxo-N-(2H-triazol-4-ylmethyl)-1-azatricyclo[6.4.1.04,13]trideca-4,6,8(13)-triene-2-carboxamide

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: 487.56

Molecular Weight (Monoisotopic): 487.2332

AlogP: 1.64

#Rotatable Bonds: 7

Polar Surface Area: 132.97

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.20

CX Basic pKa: 4.23

CX LogP: 1.42

CX LogD: 1.42

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.46

Np Likeness Score: -0.84

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