(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 (3-hydroxy-isoxazol-5-ylmethyl)-amide

ID: ALA305418

PubChem CID: 44310108

Max Phase: Preclinical

Molecular Formula: C26H33N5O6

Molecular Weight: 511.58

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)NCc1cc(O)no1)C3)N(C)C(C)=O

Standard InChI:  InChI=1S/C26H33N5O6/c1-5-14(2)22(30(4)15(3)32)25(35)28-19-10-9-16-7-6-8-17-11-20(31(23(16)17)26(19)36)24(34)27-13-18-12-21(33)29-37-18/h6-8,12,14,19-20,22H,5,9-11,13H2,1-4H3,(H,27,34)(H,28,35)(H,29,33)/t14-,19-,20-,22-/m0/s1

Standard InChI Key:  DEDSPRJAOZIWFP-YXXMBDFVSA-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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    6.2750   -2.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.2792   -4.8167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 34 22  1  0
 35 28  1  0
 28 36  1  1
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  8 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA305418

   (2S,11S)-11-[[(2S,3S)-2-[acetyl(methyl)amino]-3-methylpentanoyl]amino]-12-oxo-N-[(3-oxo-1,2-oxazol-5-yl)methyl]-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: 511.58

Molecular Weight (Monoisotopic): 511.2431

AlogP: 1.28

#Rotatable Bonds: 8

Polar Surface Area: 145.08

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.91

CX Basic pKa: ┄

CX LogP: 1.13

CX LogD: -0.82

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.48

Np Likeness Score: -0.33

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