(2S,15S,18S,21S,24S)-15-(acetamidomethyl)-2-benzyl-24-carbamoyl-18-cyclohexyl-21,25-dimethyl-4,7,10,13,16,19,22-heptaoxo-3,6,9,14,17,20,23-heptaazahexacos-11-en-1-oic acid

ID: ALA1086434

Chembl Id: CHEMBL1086434

PubChem CID: 44254314

Max Phase: Preclinical

Molecular Formula: C38H55N9O11

Molecular Weight: 813.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)NC[C@H](NC(=O)/C=C/C(=O)NCC(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)O)C(=O)N[C@H](C(=O)N[C@@H](C)C(=O)N[C@H](C(N)=O)C(C)C)C1CCCCC1

Standard InChI:  InChI=1S/C38H55N9O11/c1-21(2)32(34(39)53)46-35(54)22(3)43-37(56)33(25-13-9-6-10-14-25)47-36(55)27(18-40-23(4)48)45-29(50)16-15-28(49)41-19-30(51)42-20-31(52)44-26(38(57)58)17-24-11-7-5-8-12-24/h5,7-8,11-12,15-16,21-22,25-27,32-33H,6,9-10,13-14,17-20H2,1-4H3,(H2,39,53)(H,40,48)(H,41,49)(H,42,51)(H,43,56)(H,44,52)(H,45,50)(H,46,54)(H,47,55)(H,57,58)/b16-15+/t22-,26-,27-,32-,33-/m0/s1

Standard InChI Key:  VWDPXMPUFFUQLR-OMOXUGFUSA-N

Alternative Forms

1. Parent:

   

   ALA1086434

   (2S)-2-[[2-[[2-[[(E)-4-[[(2S)-3-acetamido-1-[[(1S)-2-[[(2S)-1-[[(2S)-1-amino-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-cyclohexyl-2-oxoethyl]amino]-1-oxopropan-2-yl]amino]-4-oxobut-2-enoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoic

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: 813.91

Molecular Weight (Monoisotopic): 813.4021

AlogP: -2.60

#Rotatable Bonds: 22

Polar Surface Area: 313.19

Molecular Species: ACID

HBA: 10

HBD: 10

#RO5 Violations: 2

HBA (Lipinski): 20

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.84

CX Basic pKa:

CX LogP: -2.77

CX LogD: -6.02

Aromatic Rings: 1

Heavy Atoms: 58

QED Weighted: 0.05

Np Likeness Score: -0.23

References

1. Machon U, Büchold C, Stempka M, Schirmeister T, Gelhaus C, Leippe M, Gut J, Rosenthal PJ, Kisker C, Leyh M, Schmuck C..  (2009)  On-bead screening of a combinatorial fumaric acid derived peptide library yields antiplasmodial cysteine protease inhibitors with unusual peptide sequences.,  52  (18): [PMID:19715342] [10.1021/jm900629w]

Source

Source(1):

• Scientific Literature