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

ID: ALA1086435

PubChem CID: 44254143

Max Phase: Preclinical

Molecular Formula: C37H56N8O10

Molecular Weight: 772.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(=O)[C@H](C)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/C37H56N8O10/c1-20(2)15-25(35(52)44-26(16-21(3)4)36(53)45-32(22(5)6)33(38)50)43-34(51)23(7)41-29(47)14-13-28(46)39-18-30(48)40-19-31(49)42-27(37(54)55)17-24-11-9-8-10-12-24/h8-14,20-23,25-27,32H,15-19H2,1-7H3,(H2,38,50)(H,39,46)(H,40,48)(H,41,47)(H,42,49)(H,43,51)(H,44,52)(H,45,53)(H,54,55)/b14-13+/t23-,25-,26-,27-,32-/m0/s1

Standard InChI Key:  PBNMBULNRARQKS-ACHRGXQGSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1086435

   (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-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: 772.90

Molecular Weight (Monoisotopic): 772.4119

AlogP: -1.22

#Rotatable Bonds: 23

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: -0.69

CX LogD: -3.93

Aromatic Rings: 1

Heavy Atoms: 55

QED Weighted: 0.06

Np Likeness Score: -0.26

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