(5S,8S,11S,14S)-5-(carboxymethyl)-14-(3-ethoxy-3-oxoprop-1-enyl)-11-isopropyl-3,6,9,12-tetraoxo-1,8-diphenyl-2-oxa-4,7,10,13-tetraazahexadecan-16-oic acid

ID: ALA2324341

Chembl Id: CHEMBL2324341

PubChem CID: 71471109

Max Phase: Preclinical

Molecular Formula: C33H40N4O11

Molecular Weight: 668.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)/C=C/[C@H](CC(=O)O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CC(=O)O)NC(=O)OCc1ccccc1)c1ccccc1)C(C)C

Standard InChI:  InChI=1S/C33H40N4O11/c1-4-47-27(42)16-15-23(17-25(38)39)34-31(44)28(20(2)3)36-32(45)29(22-13-9-6-10-14-22)37-30(43)24(18-26(40)41)35-33(46)48-19-21-11-7-5-8-12-21/h5-16,20,23-24,28-29H,4,17-19H2,1-3H3,(H,34,44)(H,35,46)(H,36,45)(H,37,43)(H,38,39)(H,40,41)/b16-15+/t23-,24+,28+,29+/m1/s1

Standard InChI Key:  YPVHLSJXDPMUQA-FXWAWSABSA-N

Alternative Forms

1. Parent:

   

   ALA2324341

   (E,3S)-3-[[(2S)-2-[[(2S)-2-[[(2S)-3-carboxy-2-(phenylmethoxycarbonylamino)propanoyl]amino]-2-phenylacetyl]amino]-3-methylbutanoyl]amino]-6-ethoxy-6-oxohex-4-enoic acid

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: 668.70

Molecular Weight (Monoisotopic): 668.2694

AlogP: 1.83

#Rotatable Bonds: 18

Polar Surface Area: 226.53

Molecular Species: ACID

HBA: 9

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.78

CX Basic pKa: ┄

CX LogP: 2.21

CX LogD: -3.99

Aromatic Rings: 2

Heavy Atoms: 48

QED Weighted: 0.10

Np Likeness Score: 0.04

References

1. Rosse G..  (2013)  Irreversible inhibitors of cysteine proteases.,  4  (2): [PMID:24900651] [10.1021/ml400021b]

Source

Source(1):

• Scientific Literature