(S)-2-((S)-6-amino-2-((S)-2-((2S,3R)-2-((S)-2-((2S,3R)-2-dodecanamido-3-hydroxybutanamido)-3-methylbutanamido)-3-hydroxybutanamido)-3-(4-hydroxyphenyl)propanamido)hexanamido)-3-phenylpropanoic acid

ID: ALA209258

PubChem CID: 44412460

Max Phase: Preclinical

Molecular Formula: C49H77N7O11

Molecular Weight: 940.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCC(=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/C49H77N7O11/c1-6-7-8-9-10-11-12-13-17-23-40(60)54-42(32(4)57)48(65)55-41(31(2)3)46(63)56-43(33(5)58)47(64)52-38(29-35-24-26-36(59)27-25-35)45(62)51-37(22-18-19-28-50)44(61)53-39(49(66)67)30-34-20-15-14-16-21-34/h14-16,20-21,24-27,31-33,37-39,41-43,57-59H,6-13,17-19,22-23,28-30,50H2,1-5H3,(H,51,62)(H,52,64)(H,53,61)(H,54,60)(H,55,65)(H,56,63)(H,66,67)/t32-,33-,37+,38+,39+,41+,42+,43+/m1/s1

Standard InChI Key:  SKPCWOADTGRUOD-QNDRFUSQSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA209258

   (S)-2-((S)-6-amino-2-((S)-2-((2S,3R)-2-((S)-2-((2S,3R)-2-dodecanamido-3-hydroxybutanamido)-3-methylbutanamido)-3-hydroxybutanamido)-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: 940.19

Molecular Weight (Monoisotopic): 939.5681

AlogP: 2.64

#Rotatable Bonds: 33

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: 1.50

CX LogD: 1.50

Aromatic Rings: 2

Heavy Atoms: 67

QED Weighted: 0.05

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