(S)-2-{(S)-4-carboxy-2-[(S)-2-dodecanoylamino-3-(4-hydroxy-phenyl)-propionylamino]-butyrylamino}-4-methyl-pentanoic acid

ID: ALA377773

Chembl Id: CHEMBL377773

PubChem CID: 44412153

Max Phase: Preclinical

Molecular Formula: C32H51N3O8

Molecular Weight: 605.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC(C)C)C(=O)O

Standard InChI:  InChI=1S/C32H51N3O8/c1-4-5-6-7-8-9-10-11-12-13-28(37)33-26(21-23-14-16-24(36)17-15-23)31(41)34-25(18-19-29(38)39)30(40)35-27(32(42)43)20-22(2)3/h14-17,22,25-27,36H,4-13,18-21H2,1-3H3,(H,33,37)(H,34,41)(H,35,40)(H,38,39)(H,42,43)/t25-,26-,27-/m0/s1

Standard InChI Key:  ZGNLQBIHPRRCNP-QKDODKLFSA-N

Alternative Forms

1. Parent:

   

   ALA377773

   (S)-2-{(S)-4-carboxy-2-[(S)-2-dodecanoylamino-3-(4-hydroxy-phenyl)-propionylamino]-butyrylamino}-4-methyl-pentanoic 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: 605.77

Molecular Weight (Monoisotopic): 605.3676

AlogP: 4.31

#Rotatable Bonds: 23

Polar Surface Area: 182.13

Molecular Species: ACID

HBA: 6

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.52

CX Basic pKa: ┄

CX LogP: 5.12

CX LogD: -1.34

Aromatic Rings: 1

Heavy Atoms: 43

QED Weighted: 0.10

Np Likeness Score: 0.29

References

1. Basse N, Papapostolou D, Pagano M, Reboud-Ravaux M, Bernard E, Felten AS, Vanderesse R..  (2006)  Development of lipopeptides for inhibiting 20S proteasomes.,  16  (12): [PMID:16630721] [10.1016/j.bmcl.2006.03.033]

Source

Source(1):

• Scientific Literature