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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
39 39 0 0 0 0 0 0 0 0999 V2000
12.1178 -0.7118 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
12.8335 -0.2953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
13.5535 -1.5367 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
13.5535 -0.7118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
12.8335 0.5296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
13.5535 0.9462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
13.5535 1.7710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.2691 2.1877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.9766 -0.7067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
15.6922 0.5347 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
15.6922 -0.2901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.9766 -1.5315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
15.6922 -1.9481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
15.6922 -2.7730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
16.4122 -3.1896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
18.5441 3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
17.1194 -0.2883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
17.8351 -1.5297 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
17.8351 -0.7048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
17.1194 0.5366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
17.8351 0.9532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
17.8351 1.7780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
11.4019 -0.3019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
10.6891 -0.7168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
11.3990 0.5230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
9.9741 -0.3048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
9.2641 -1.5448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
9.2652 -0.7196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
8.5523 -0.3079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.8377 -0.7202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.8407 -1.5486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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
14 15 1 0
17 19 1 0
19 18 2 0
17 20 1 1
20 21 1 0
21 22 1 0
1 23 1 0
23 24 1 0
23 25 2 0
1 2 1 0
24 26 2 0
26 28 1 0
2 4 1 0
4 3 2 0
27 28 1 0
2 5 1 1
28 29 2 0
5 6 1 0
29 30 1 0
6 7 1 0
30 31 2 0
7 8 1 0
31 32 1 0
32 27 2 0
9 11 1 0
11 10 2 0
9 12 1 6
12 13 1 0
13 14 1 0
36 16 1 0
22 36 1 0
4 34 1 0
34 9 1 0
16 37 1 0
8 33 1 0
16 38 2 0
15 35 1 0
39 17 1 0
11 39 1 0
M END Associated Targets(non-human) Molecule Features Natural Product: NoOral: NoChemical Probe: NoParenteral: NoMolecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: NoChirality: NoAvailability: NoProdrug: No
Calculated Properties Molecular Weight: 544.70Molecular Weight (Monoisotopic): 544.3486AlogP: -0.13#Rotatable Bonds: 20Polar Surface Area: 218.31Molecular Species: BASEHBA: 7HBD: 8#RO5 Violations: 2HBA (Lipinski): 12HBD (Lipinski): 11#RO5 Violations (Lipinski): 3CX Acidic pKa: 12.40CX Basic pKa: 11.92CX LogP: -1.20CX LogD: -8.29Aromatic 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 ]