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

ID: ALA209290

Chembl Id: CHEMBL209290

PubChem CID: 44412410

Max Phase: Preclinical

Molecular Formula: C26H39N3O8

Molecular Weight: 521.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCC(=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/C26H39N3O8/c1-4-5-6-7-22(31)27-20(15-17-8-10-18(30)11-9-17)25(35)28-19(12-13-23(32)33)24(34)29-21(26(36)37)14-16(2)3/h8-11,16,19-21,30H,4-7,12-15H2,1-3H3,(H,27,31)(H,28,35)(H,29,34)(H,32,33)(H,36,37)/t19-,20-,21-/m0/s1

Standard InChI Key:  QZVAWPAPHHXIMZ-ACRUOGEOSA-N

Alternative Forms

1. Parent:

   

   ALA209290

   (S)-2-{(S)-4-Carboxy-2-[(S)-2-hexanoylamino-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: 521.61

Molecular Weight (Monoisotopic): 521.2737

AlogP: 1.96

#Rotatable Bonds: 17

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: 2.46

CX LogD: -4.00

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.17

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