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

ID: ALA1086429

PubChem CID: 44254499

Max Phase: Preclinical

Molecular Formula: C43H60N8O10

Molecular Weight: 849.00

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C43H60N8O10/c1-25(2)19-30(40(57)50-31(20-26(3)4)42(59)51-38(27(5)6)39(44)56)49-41(58)32(21-28-13-9-7-10-14-28)47-35(53)18-17-34(52)45-23-36(54)46-24-37(55)48-33(43(60)61)22-29-15-11-8-12-16-29/h7-18,25-27,30-33,38H,19-24H2,1-6H3,(H2,44,56)(H,45,52)(H,46,54)(H,47,53)(H,48,55)(H,49,58)(H,50,57)(H,51,59)(H,60,61)/b18-17+/t30-,31-,32-,33-,38-/m0/s1

Standard InChI Key:  FBWRCRYYBACCOH-KCCKNQBXSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1086429

   (2S)-2-[[2-[[2-[[(E)-4-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-3-methyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobut-2-enoyl]amino]acetyl]amino]acetyl]amino]-3-phenylp

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: 849.00

Molecular Weight (Monoisotopic): 848.4432

AlogP: 0.00

#Rotatable Bonds: 25

Polar Surface Area: 284.09

Molecular Species: ACID

HBA: 9

HBD: 9

#RO5 Violations: 2

HBA (Lipinski): 18

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.84

CX Basic pKa: ┄

CX LogP: 0.97

CX LogD: -2.28

Aromatic Rings: 2

Heavy Atoms: 61

QED Weighted: 0.06

Np Likeness Score: -0.18

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