(2S,15S,18S,21S,24S)-15-(acetamidomethyl)-2-benzyl-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: ALA1086437

PubChem CID: 44254221

Max Phase: Preclinical

Molecular Formula: C39H59N9O11

Molecular Weight: 829.95

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](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(N)=O)C(C)C

Standard InChI:  InChI=1S/C39H59N9O11/c1-21(2)15-26(36(55)46-27(16-22(3)4)37(56)48-34(23(5)6)35(40)54)47-38(57)29(18-41-24(7)49)45-31(51)14-13-30(50)42-19-32(52)43-20-33(53)44-28(39(58)59)17-25-11-9-8-10-12-25/h8-14,21-23,26-29,34H,15-20H2,1-7H3,(H2,40,54)(H,41,49)(H,42,50)(H,43,52)(H,44,53)(H,45,51)(H,46,55)(H,47,57)(H,48,56)(H,58,59)/b14-13+/t26-,27-,28-,29-,34-/m0/s1

Standard InChI Key:  OSSSLCJZHGUPON-DVFSMRMGSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1086437

   (2S)-2-[[2-[[2-[[(E)-4-[[(2S)-3-acetamido-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-oxopropan-2-yl]amino]-4-oxobut-2-enoyl]amino]acetyl]amino]acetyl]amino]-3-phen

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: 829.95

Molecular Weight (Monoisotopic): 829.4334

AlogP: -2.10

#Rotatable Bonds: 25

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: -2.02

CX LogD: -5.27

Aromatic Rings: 1

Heavy Atoms: 59

QED Weighted: 0.05

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