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

ID: ALA442473

PubChem CID: 44412334

Max Phase: Preclinical

Molecular Formula: C53H85N7O11

Molecular Weight: 996.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCC(=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/C53H85N7O11/c1-6-7-8-9-10-11-12-13-14-15-16-17-21-27-44(64)58-46(36(4)61)52(69)59-45(35(2)3)50(67)60-47(37(5)62)51(68)56-42(33-39-28-30-40(63)31-29-39)49(66)55-41(26-22-23-32-54)48(65)57-43(53(70)71)34-38-24-19-18-20-25-38/h18-20,24-25,28-31,35-37,41-43,45-47,61-63H,6-17,21-23,26-27,32-34,54H2,1-5H3,(H,55,66)(H,56,68)(H,57,65)(H,58,64)(H,59,69)(H,60,67)(H,70,71)/t36-,37-,41+,42+,43+,45+,46+,47+/m1/s1

Standard InChI Key:  ZNCWQWCMFDOVGB-SNPCEKNGSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA442473

   palmitoyl-Thr-Val-Thr-Tyr-Lys-Phe-OH

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: 996.30

Molecular Weight (Monoisotopic): 995.6307

AlogP: 4.20

#Rotatable Bonds: 37

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: 3.28

CX LogD: 3.27

Aromatic Rings: 2

Heavy Atoms: 71

QED Weighted: 0.04

Np Likeness Score: 0.22

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