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Cinnamoyl-KKR-H

ID: ALA494699

PubChem CID: 24971346

Max Phase: Preclinical

Molecular Formula: C27H44N8O4

Molecular Weight: 544.70

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Synonyms: Cinnamoyl-Kkr-H | Cinnamoyl-KKR-H|CHEMBL494699|BDBM24730|Capped tripeptide aldehyde inhibitor, 2|(2S)-6-amino-2-[(2S)-6-amino-2-[(2E)-3-phenylprop-2-enamido]hexanamido]-N-[(2S)-5-carbamimidamido-1-oxopentan-2-yl]hexanamide

Canonical SMILES:  N=C(N)NCCC[C@@H](C=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)/C=C/c1ccccc1

Standard InChI:  InChI=1S/C27H44N8O4/c28-16-6-4-12-22(34-24(37)15-14-20-9-2-1-3-10-20)26(39)35-23(13-5-7-17-29)25(38)33-21(19-36)11-8-18-32-27(30)31/h1-3,9-10,14-15,19,21-23H,4-8,11-13,16-18,28-29H2,(H,33,38)(H,34,37)(H,35,39)(H4,30,31,32)/b15-14+/t21-,22-,23-/m0/s1

Standard InChI Key:  KSBWCWPYOHNRDB-DFSKWLJZSA-N

Molfile:  

     RDKit          2D

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    8.5542   -1.9565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2633    3.0159    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2635   -0.2917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4063   -4.0111    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5495    2.1907    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8310    3.4338    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2667    3.4338    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4063   -0.7033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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  9 12  1  6
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 39 17  1  0
 11 39  1  0
M  END

Associated Targets(non-human)

Genome polyprotein (620 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Calculated Properties

Molecular Weight: 544.70Molecular Weight (Monoisotopic): 544.3486AlogP: -0.13#Rotatable Bonds: 20
Polar Surface Area: 218.31Molecular Species: BASEHBA: 7HBD: 8
#RO5 Violations: 2HBA (Lipinski): 12HBD (Lipinski): 11#RO5 Violations (Lipinski): 3
CX Acidic pKa: 12.40CX Basic pKa: 11.92CX LogP: -1.20CX LogD: -8.29
Aromatic Rings: 1Heavy Atoms: 39QED Weighted: 0.04Np Likeness Score: 0.48

References

1. Stoermer MJ, Chappell KJ, Liebscher S, Jensen CM, Gan CH, Gupta PK, Xu WJ, Young PR, Fairlie DP..  (2008)  Potent cationic inhibitors of West Nile virus NS2B/NS3 protease with serum stability, cell permeability and antiviral activity.,  51  (18): [PMID:18729351] [10.1021/jm800503y]

Source