(S)-tert-butyl 2-(6-acrylamido-2-(benzyloxycarbonylamino)hexanamido)acetate

ID: ALA2203476

Chembl Id: CHEMBL2203476

PubChem CID: 71450343

Max Phase: Preclinical

Molecular Formula: C23H33N3O6

Molecular Weight: 447.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(=O)NCCCC[C@H](NC(=O)OCc1ccccc1)C(=O)NCC(=O)OC(C)(C)C

Standard InChI:  InChI=1S/C23H33N3O6/c1-5-19(27)24-14-10-9-13-18(21(29)25-15-20(28)32-23(2,3)4)26-22(30)31-16-17-11-7-6-8-12-17/h5-8,11-12,18H,1,9-10,13-16H2,2-4H3,(H,24,27)(H,25,29)(H,26,30)/t18-/m0/s1

Standard InChI Key:  OWDSSINHZRXMBO-SFHVURJKSA-N

Alternative Forms

1. Parent:

   

   ALA2203476

   tert-butyl 2-[[(2S)-2-(phenylmethoxycarbonylamino)-6-(prop-2-enoylamino)hexanoyl]amino]acetate

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: 447.53

Molecular Weight (Monoisotopic): 447.2369

AlogP: 2.21

#Rotatable Bonds: 12

Polar Surface Area: 122.83

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.39

CX Basic pKa: ┄

CX LogP: 2.12

CX LogD: 2.12

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.26

Np Likeness Score: -0.29

References

1. Wityak J, Prime ME, Brookfield FA, Courtney SM, Erfan S, Johnsen S, Johnson PD, Li M, Marston RW, Reed L, Vaidya D, Schaertl S, Pedret-Dunn A, Beconi M, Macdonald D, Muñoz-Sanjuan I, Dominguez C..  (2012)  SAR Development of Lysine-Based Irreversible Inhibitors of Transglutaminase 2 for Huntington's Disease.,  3  (12): [PMID:24900424] [10.1021/ml300241m]

Source

Source(1):

• Scientific Literature