Standard InChI: InChI=1S/C25H23ClF3N3O4/c26-18-11-15-3-6-20(18)35-9-1-2-10-36-21-13-16(25(27,28)29)4-5-17(21)22(33)31-19(12-15)23(34)32-24(14-30)7-8-24/h3-6,11,13,19H,1-2,7-10,12H2,(H,31,33)(H,32,34)/t19-/m0/s1
Standard InChI Key: XAPRSGPLBWSEHV-IBGZPJMESA-N
Associated Targets(Human)
Cathepsin L 3852 Activities
Activity Type
Relation
Activity value
Units
Action Type
Journal
PubMed Id
doi
Assay Aladdin ID
Cytochrome P450 3A4 53859 Activities
Activity Type
Relation
Activity value
Units
Action Type
Journal
PubMed Id
doi
Assay Aladdin ID
Cytochrome P450 2D6 33882 Activities
Activity Type
Relation
Activity value
Units
Action Type
Journal
PubMed Id
doi
Assay Aladdin ID
Cytochrome P450 2C9 32119 Activities
Activity Type
Relation
Activity value
Units
Action Type
Journal
PubMed Id
doi
Assay Aladdin ID
Liver 3974 Activities
Activity Type
Relation
Activity value
Units
Action Type
Journal
PubMed Id
doi
Assay Aladdin ID
Cathepsin B 3822 Activities
Activity Type
Relation
Activity value
Units
Action Type
Journal
PubMed Id
doi
Assay Aladdin ID
Cathepsin K 3011 Activities
Activity Type
Relation
Activity value
Units
Action Type
Journal
PubMed Id
doi
Assay Aladdin ID
Cathepsin S 3285 Activities
Activity Type
Relation
Activity value
Units
Action Type
Journal
PubMed Id
doi
Assay Aladdin ID
Cathepsin L2 273 Activities
Activity Type
Relation
Activity value
Units
Action Type
Journal
PubMed Id
doi
Assay Aladdin ID
Associated Targets(non-human)
Rhodesain 1463 Activities
Activity Type
Relation
Activity value
Units
Action Type
Journal
PubMed Id
doi
Assay Aladdin ID
Mus musculus 284745 Activities
Activity Type
Relation
Activity value
Units
Action Type
Journal
PubMed Id
doi
Assay Aladdin ID
Trypanosoma brucei rhodesiense 7991 Activities
Activity Type
Relation
Activity value
Units
Action Type
Journal
PubMed Id
doi
Assay Aladdin ID
Plasma 10718 Activities
Activity Type
Relation
Activity value
Units
Action Type
Journal
PubMed Id
doi
Assay Aladdin ID
Brain 4256 Activities
Activity Type
Relation
Activity value
Units
Action Type
Journal
PubMed Id
doi
Assay Aladdin ID
Cerebrospinal fluid 288 Activities
Activity Type
Relation
Activity value
Units
Action Type
Journal
PubMed Id
doi
Assay Aladdin ID
Liver 4264 Activities
Activity Type
Relation
Activity value
Units
Action Type
Journal
PubMed Id
doi
Assay Aladdin ID
Blood 1764 Activities
Activity Type
Relation
Activity value
Units
Action Type
Journal
PubMed Id
doi
Assay Aladdin ID
Trypanosoma brucei brucei 13300 Activities
Activity Type
Relation
Activity value
Units
Action Type
Journal
PubMed Id
doi
Assay Aladdin ID
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
Drug Indications
MESH ID
MESH Heading
EFO IDs
EFO Terms
Max Phase for Indication
References
Mechanisms of Action
Mechanism of Action
Action Type
target ID
Target Name
Target Type
Target Organism
Binding Site Name
References
Properties
Molecular Weight: 521.92
Molecular Weight (Monoisotopic): 521.1329
AlogP: 4.42
#Rotatable Bonds: 2
Polar Surface Area: 100.45
Molecular Species: NEUTRAL
HBA: 5
HBD: 2
#RO5 Violations: 1
HBA (Lipinski): 7
HBD (Lipinski): 2
#RO5 Violations (Lipinski): 1
CX Acidic pKa: 10.56
CX Basic pKa:
CX LogP: 3.97
CX LogD: 3.97
Aromatic Rings: 2
Heavy Atoms: 36
QED Weighted: 0.61
Np Likeness Score: -0.39
References
1. (2016) Cyclic amides,
2.Giroud M, Dietzel U, Anselm L, Banner D, Kuglstatter A, Benz J, Blanc JB, Gaufreteau D, Liu H, Lin X, Stich A, Kuhn B, Schuler F, Kaiser M, Brun R, Schirmeister T, Kisker C, Diederich F, Haap W.. (2018) Repurposing a Library of Human Cathepsin L Ligands: Identification of Macrocyclic Lactams as Potent Rhodesain and Trypanosoma brucei Inhibitors., 61 (8):[PMID:29590750][10.1021/acs.jmedchem.7b01869]
3.Giroud M, Kuhn B, Saint-Auret S, Kuratli C, Martin RE, Schuler F, Diederich F, Kaiser M, Brun R, Schirmeister T, Haap W.. (2018) 2 H-1,2,3-Triazole-Based Dipeptidyl Nitriles: Potent, Selective, and Trypanocidal Rhodesain Inhibitors by Structure-Based Design., 61 (8):[PMID:29590751][10.1021/acs.jmedchem.7b01870]