(S)-2-((S)-6-amino-2-((S)-2-((2S,3R)-3-hydroxy-2-((S)-2-((2S,3R)-3-hydroxy-2-tetradecanamidobutanamido)-3-methylbutanamido)butanamido)-3-(4-hydroxyphenyl)propanamido)hexanamido)-3-phenylpropanoic acid

ID: ALA209275

Chembl Id: CHEMBL209275

PubChem CID: 44412461

Max Phase: Preclinical

Molecular Formula: C51H81N7O11

Molecular Weight: 968.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](Cc1ccccc1)C(=O)O)[C@@H](C)O)C(C)C)[C@@H](C)O

Standard InChI:  InChI=1S/C51H81N7O11/c1-6-7-8-9-10-11-12-13-14-15-19-25-42(62)56-44(34(4)59)50(67)57-43(33(2)3)48(65)58-45(35(5)60)49(66)54-40(31-37-26-28-38(61)29-27-37)47(64)53-39(24-20-21-30-52)46(63)55-41(51(68)69)32-36-22-17-16-18-23-36/h16-18,22-23,26-29,33-35,39-41,43-45,59-61H,6-15,19-21,24-25,30-32,52H2,1-5H3,(H,53,64)(H,54,66)(H,55,63)(H,56,62)(H,57,67)(H,58,65)(H,68,69)/t34-,35-,39+,40+,41+,43+,44+,45+/m1/s1

Standard InChI Key:  FRXCNTKLYDTMQD-FUFDYEGGSA-N

Alternative Forms

1. Parent:

   

   ALA209275

   (S)-2-((S)-6-amino-2-((S)-2-((2S,3R)-3-hydroxy-2-((S)-2-((2S,3R)-3-hydroxy-2-tetradecanamidobutanamido)-3-methylbutanamido)butanamido)-3-(4-hydroxyphenyl)propanamido)hexanamido)-3-phenylpropanoic 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: 968.25

Molecular Weight (Monoisotopic): 967.5994

AlogP: 3.42

#Rotatable Bonds: 35

Polar Surface Area: 298.61

Molecular Species: ZWITTERION

HBA: 11

HBD: 11

#RO5 Violations: 3

HBA (Lipinski): 18

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.70

CX Basic pKa: 17.64

CX LogP: 2.39

CX LogD: 2.39

Aromatic Rings: 2

Heavy Atoms: 69

QED Weighted: 0.04

Np Likeness Score: 0.23

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