trans-5S-(2'S-Benzyloxycarbonylamino-3'phenylpropanamido)-7-(phenylsulfonyl)hept-6-en-1-(1-naphthalene)-sulfonamide

ID: ALA2419135

Chembl Id: CHEMBL2419135

PubChem CID: 73293367

Max Phase: Preclinical

Molecular Formula: C40H41N3O7S2

Molecular Weight: 739.92

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H](Cc1ccccc1)C(=O)N[C@H](/C=C/S(=O)(=O)c1ccccc1)CCCCNS(=O)(=O)c1cccc2ccccc12)OCc1ccccc1

Standard InChI:  InChI=1S/C40H41N3O7S2/c44-39(37(29-31-15-4-1-5-16-31)43-40(45)50-30-32-17-6-2-7-18-32)42-34(26-28-51(46,47)35-22-8-3-9-23-35)21-12-13-27-41-52(48,49)38-25-14-20-33-19-10-11-24-36(33)38/h1-11,14-20,22-26,28,34,37,41H,12-13,21,27,29-30H2,(H,42,44)(H,43,45)/b28-26+/t34-,37-/m0/s1

Standard InChI Key:  SSRGITLSUITMFB-JAISHVMPSA-N

Alternative Forms

1. Parent:

   

   ALA2419135

   benzyl N-[(2S)-1-[[(E,3S)-1-(benzenesulfonyl)-7-(naphthalen-1-ylsulfonylamino)hept-1-en-3-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate

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: 739.92

Molecular Weight (Monoisotopic): 739.2386

AlogP: 6.30

#Rotatable Bonds: 17

Polar Surface Area: 147.74

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.92

CX Basic pKa:

CX LogP: 6.53

CX LogD: 6.53

Aromatic Rings: 5

Heavy Atoms: 52

QED Weighted: 0.09

Np Likeness Score: -0.45

References

1. Dunny E, Doherty W, Evans P, Malthouse JP, Nolan D, Knox AJ..  (2013)  Vinyl sulfone-based peptidomimetics as anti-trypanosomal agents: design, synthesis, biological and computational evaluation.,  56  (17): [PMID:23952916] [10.1021/jm400294w]

2. Doherty W, Adler N, Butler TJ, Knox AJS, Evans P..  (2020)  Synthesis and optimisation of P₃ substituted vinyl sulfone-based inhibitors as anti-trypanosomal agents.,  28  (23.0): [PMID:32992251] [10.1016/j.bmc.2020.115774]

3. Rocha DA, Silva EB, Fortes IS, Lopes MS, Ferreira RS, Andrade SF..  (2018)  Synthesis and structure-activity relationship studies of cruzain and rhodesain inhibitors.,  157  [PMID:30282318] [10.1016/j.ejmech.2018.08.079]

Source

Source(1):

• Scientific Literature