(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 (2H-tetrazol-5-ylmethyl)-amide

ID: ALA303944

PubChem CID: 44310088

Max Phase: Preclinical

Molecular Formula: C24H32N8O4

Molecular Weight: 496.57

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)NCc1nn[nH]n1)C3)N(C)C(C)=O

Standard InChI:  InChI=1S/C24H32N8O4/c1-5-13(2)20(31(4)14(3)33)23(35)26-17-10-9-15-7-6-8-16-11-18(32(21(15)16)24(17)36)22(34)25-12-19-27-29-30-28-19/h6-8,13,17-18,20H,5,9-12H2,1-4H3,(H,25,34)(H,26,35)(H,27,28,29,30)/t13-,17-,18-,20-/m0/s1

Standard InChI Key:  UVBOXTLBOKIXQQ-RMXWXBJUSA-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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 10  8  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA303944

   (2S,11S)-11-[[(2S,3S)-2-[acetyl(methyl)amino]-3-methylpentanoyl]amino]-12-oxo-N-(2H-tetrazol-5-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: 496.57

Molecular Weight (Monoisotopic): 496.2547

AlogP: 0.10

#Rotatable Bonds: 8

Polar Surface Area: 153.28

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.75

CX Basic pKa: ┄

CX LogP: 0.76

CX LogD: -0.76

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.47

Np Likeness Score: -0.48

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