(5S,8S,11S,14S)-5-((1H-indol-3-yl)methyl)-8-(3-amino-3-oxopropyl)-11-sec-butyl-14-(2-(methylsulfonyl)vinyl)-3,6,9,12-tetraoxo-1-phenyl-2-oxa-4,7,10,13-tetraazahexadecan-16-oic acid

ID: ALA2324340

Chembl Id: CHEMBL2324340

PubChem CID: 71718085

Max Phase: Preclinical

Molecular Formula: C36H46N6O10S

Molecular Weight: 754.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)OCc1ccccc1)C(=O)N[C@H](/C=C/S(C)(=O)=O)CC(=O)O

Standard InChI:  InChI=1S/C36H46N6O10S/c1-4-22(2)32(35(48)39-25(19-31(44)45)16-17-53(3,50)51)42-33(46)28(14-15-30(37)43)40-34(47)29(18-24-20-38-27-13-9-8-12-26(24)27)41-36(49)52-21-23-10-6-5-7-11-23/h5-13,16-17,20,22,25,28-29,32,38H,4,14-15,18-19,21H2,1-3H3,(H2,37,43)(H,39,48)(H,40,47)(H,41,49)(H,42,46)(H,44,45)/b17-16+/t22-,25+,28-,29-,32-/m0/s1

Standard InChI Key:  NFNHDUDACIDJAE-GQNWZVDISA-N

Alternative Forms

1. Parent:

   

   ALA2324340

   (E,3S)-3-[[(2S,3S)-2-[[(2S)-5-amino-2-[[(2S)-3-(1H-indol-3-yl)-2-(phenylmethoxycarbonylamino)propanoyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]amino]-5-methylsulfonylpent-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: 754.86

Molecular Weight (Monoisotopic): 754.2996

AlogP: 1.80

#Rotatable Bonds: 20

Polar Surface Area: 255.95

Molecular Species: ACID

HBA: 9

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.97

CX Basic pKa: ┄

CX LogP: 0.69

CX LogD: -2.49

Aromatic Rings: 3

Heavy Atoms: 53

QED Weighted: 0.09

Np Likeness Score: 0.13

References

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

Source

Source(1):

• Scientific Literature