(2S,5S)-5-[(S)-2-(Acetyl-methyl-amino)-3-(S)-methyl-pentanoylamino]-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: ALA306381

PubChem CID: 44309748

Max Phase: Preclinical

Molecular Formula: C25H33N7O4

Molecular Weight: 495.58

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)NCc1cn[nH]n1)C3)N(C)C(C)=O

Standard InChI:  InChI=1S/C25H33N7O4/c1-5-14(2)21(31(4)15(3)33)24(35)28-19-10-9-16-7-6-8-17-11-20(32(22(16)17)25(19)36)23(34)26-12-18-13-27-30-29-18/h6-8,13-14,19-21H,5,9-12H2,1-4H3,(H,26,34)(H,28,35)(H,27,29,30)/t14-,19-,20-,21-/m0/s1

Standard InChI Key:  PRNAJBBNAVROIQ-CXTHYWKRSA-N

Molfile:  

     RDKit          2D

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    2.5042   -5.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  0
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 32 33  2  0
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 29 32  1  0
 16  6  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA306381

   (2S,11S)-11-[[(2S,3S)-2-[acetyl(methyl)amino]-3-methylpentanoyl]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: 495.58

Molecular Weight (Monoisotopic): 495.2594

AlogP: 0.70

#Rotatable Bonds: 8

Polar Surface Area: 140.39

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.20

CX Basic pKa: ┄

CX LogP: 0.17

CX LogD: 0.16

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.49

Np Likeness Score: -0.42

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