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

ID: ALA379316

Chembl Id: CHEMBL379316

PubChem CID: 44412423

Max Phase: Preclinical

Molecular Formula: C28H43N3O8

Molecular Weight: 549.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCC(=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/C28H43N3O8/c1-4-5-6-7-8-9-24(33)29-22(17-19-10-12-20(32)13-11-19)27(37)30-21(14-15-25(34)35)26(36)31-23(28(38)39)16-18(2)3/h10-13,18,21-23,32H,4-9,14-17H2,1-3H3,(H,29,33)(H,30,37)(H,31,36)(H,34,35)(H,38,39)/t21-,22-,23-/m0/s1

Standard InChI Key:  ARVTVHARLYVZJW-VABKMULXSA-N

Alternative Forms

1. Parent:

   

   ALA379316

   (S)-2-{(S)-4-Carboxy-2-[(S)-3-(4-hydroxy-phenyl)-2-octanoylamino-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: 549.67

Molecular Weight (Monoisotopic): 549.3050

AlogP: 2.75

#Rotatable Bonds: 19

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: 3.34

CX LogD: -3.12

Aromatic Rings: 1

Heavy Atoms: 39

QED Weighted: 0.14

Np Likeness Score: 0.31

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