(2S,15S,18S,21S,24S)-15-(2-amino-2-oxoethyl)-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: ALA1086431

Chembl Id: CHEMBL1086431

PubChem CID: 44254582

Max Phase: Preclinical

Molecular Formula: C37H53N9O11

Molecular Weight: 799.88

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C37H53N9O11/c1-20(2)31(33(39)52)45-34(53)21(3)42-36(55)32(23-12-8-5-9-13-23)46-35(54)24(17-26(38)47)43-28(49)15-14-27(48)40-18-29(50)41-19-30(51)44-25(37(56)57)16-22-10-6-4-7-11-22/h4,6-7,10-11,14-15,20-21,23-25,31-32H,5,8-9,12-13,16-19H2,1-3H3,(H2,38,47)(H2,39,52)(H,40,48)(H,41,50)(H,42,55)(H,43,49)(H,44,51)(H,45,53)(H,46,54)(H,56,57)/b15-14+/t21-,24-,25-,31-,32-/m0/s1

Standard InChI Key:  WIPHQXXPMAFGBP-KAYIZFEWSA-N

Alternative Forms

1. Parent:

   

   ALA1086431

   (2S)-2-[[2-[[2-[[(E)-4-[[(2S)-4-amino-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]-1,4-dioxobutan-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: 799.88

Molecular Weight (Monoisotopic): 799.3865

AlogP: -2.86

#Rotatable Bonds: 22

Polar Surface Area: 327.18

Molecular Species: ACID

HBA: 10

HBD: 10

#RO5 Violations: 2

HBA (Lipinski): 20

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.84

CX Basic pKa:

CX LogP: -2.89

CX LogD: -6.13

Aromatic Rings: 1

Heavy Atoms: 57

QED Weighted: 0.05

Np Likeness Score: -0.19

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