(2S,5S)-5-[(S)-2-(2-Benzo[b]thiophen-3-yl-acetylamino)-3-(S)-methyl-pentanoylamino]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indole-2-carboxylic acid (1H-pyrazol-4-ylmethyl)-amide

ID: ALA306860

PubChem CID: 44310147

Max Phase: Preclinical

Molecular Formula: C33H36N6O4S

Molecular Weight: 612.76

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@H](NC(=O)Cc1csc2ccccc12)C(=O)N[C@H]1CCc2cccc3c2N(C1=O)[C@H](C(=O)NCc1cn[nH]c1)C3

Standard InChI:  InChI=1S/C33H36N6O4S/c1-3-19(2)29(38-28(40)14-23-18-44-27-10-5-4-9-24(23)27)32(42)37-25-12-11-21-7-6-8-22-13-26(39(30(21)22)33(25)43)31(41)34-15-20-16-35-36-17-20/h4-10,16-19,25-26,29H,3,11-15H2,1-2H3,(H,34,41)(H,35,36)(H,37,42)(H,38,40)/t19-,25-,26-,29-/m0/s1

Standard InChI Key:  MEIJZDBFAKTZAL-QVICYHPESA-N

Molfile:  

     RDKit          2D

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M  END

Alternative Forms

1. Parent:

   

   ALA306860

   (2S,11S)-11-[[(2S,3S)-2-[[2-(1-benzothiophen-3-yl)acetyl]amino]-3-methylpentanoyl]amino]-12-oxo-N-(1H-pyrazol-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: 612.76

Molecular Weight (Monoisotopic): 612.2519

AlogP: 3.40

#Rotatable Bonds: 10

Polar Surface Area: 136.29

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.05

CX Basic pKa: 2.41

CX LogP: 3.35

CX LogD: 3.35

Aromatic Rings: 4

Heavy Atoms: 44

QED Weighted: 0.22

Np Likeness Score: -0.99

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