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

ID: ALA208805

Chembl Id: CHEMBL208805

PubChem CID: 44412329

Max Phase: Preclinical

Molecular Formula: C30H47N3O8

Molecular Weight: 577.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCC(=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/C30H47N3O8/c1-4-5-6-7-8-9-10-11-26(35)31-24(19-21-12-14-22(34)15-13-21)29(39)32-23(16-17-27(36)37)28(38)33-25(30(40)41)18-20(2)3/h12-15,20,23-25,34H,4-11,16-19H2,1-3H3,(H,31,35)(H,32,39)(H,33,38)(H,36,37)(H,40,41)/t23-,24-,25-/m0/s1

Standard InChI Key:  DUBNBDOVKSGEIA-SDHOMARFSA-N

Alternative Forms

1. Parent:

   

   ALA208805

   (S)-2-{(S)-4-carboxy-2-[(S)-2-decanoylamino-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: 577.72

Molecular Weight (Monoisotopic): 577.3363

AlogP: 3.53

#Rotatable Bonds: 21

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: 4.23

CX LogD: -2.23

Aromatic Rings: 1

Heavy Atoms: 41

QED Weighted: 0.12

Np Likeness Score: 0.30

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