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

ID: ALA1086432

PubChem CID: 44254142

Max Phase: Preclinical

Molecular Formula: C39H57N9O11

Molecular Weight: 827.94

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C39H57N9O11/c1-21(2)32(35(41)54)46-37(56)33(22(3)4)47-38(57)34(24-13-9-6-10-14-24)48-36(55)25(18-27(40)49)44-29(51)16-15-28(50)42-19-30(52)43-20-31(53)45-26(39(58)59)17-23-11-7-5-8-12-23/h5,7-8,11-12,15-16,21-22,24-26,32-34H,6,9-10,13-14,17-20H2,1-4H3,(H2,40,49)(H2,41,54)(H,42,50)(H,43,52)(H,44,51)(H,45,53)(H,46,56)(H,47,57)(H,48,55)(H,58,59)/b16-15+/t25-,26-,32-,33-,34-/m0/s1

Standard InChI Key:  XQEGTLKERLJHMK-DORITFQFSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1086432

   (2S)-2-[[2-[[2-[[(E)-4-[[(2S)-4-amino-1-[[(1S)-2-[[(2S)-1-[[(2S)-1-amino-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-cyclohexyl-2-oxoethyl]amino]-1,4-dioxobutan-2-yl]amino]-4-oxobut-2-enoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpr

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: 827.94

Molecular Weight (Monoisotopic): 827.4178

AlogP: -2.22

#Rotatable Bonds: 23

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: -2.00

CX LogD: -5.24

Aromatic Rings: 1

Heavy Atoms: 59

QED Weighted: 0.05

Np Likeness Score: -0.16

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