| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
ID: ALA1956290
Max Phase: Preclinical
Molecular Formula: C14H9F6N5
Molecular Weight: 361.25
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: Cc1cc(Nc2ccc(C(F)(F)F)cc2)n2nc(C(F)(F)F)nc2n1
Standard InChI: InChI=1S/C14H9F6N5/c1-7-6-10(22-9-4-2-8(3-5-9)13(15,16)17)25-12(21-7)23-11(24-25)14(18,19)20/h2-6,22H,1H3
Standard InChI Key: OFUZRRSLIRZBNG-UHFFFAOYSA-N
Associated Targets(Human)
Liver microsomes (16955 Activities)
Plasma (7708 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
DHODH Tclin Dihydroorotate dehydrogenase (2737 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Associated Targets(non-human)
Liver (8163 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Plasmodium falciparum (966862 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
dhod Dihydroorotate dehydrogenase (710 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Dhodh Dihydroorotate dehydrogenase (165 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Dhodh Dihydroorotate dehydrogenase (104 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Dihydroorotate dehydrogenase (quinone), mitochondrial (90 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: 361.25 | Molecular Weight (Monoisotopic): 361.0762 | AlogP: 4.21 | #Rotatable Bonds: 2 |
| Polar Surface Area: 55.11 | Molecular Species: NEUTRAL | HBA: 5 | HBD: 1 |
| #RO5 Violations: 0 | HBA (Lipinski): 5 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: | CX Basic pKa: | CX LogP: 4.32 | CX LogD: 4.32 |
| Aromatic Rings: 3 | Heavy Atoms: 25 | QED Weighted: 0.69 | Np Likeness Score: -2.08 |
References
| 1. Coteron JM, Marco M, Esquivias J, Deng X, White KL, White J, Koltun M, El Mazouni F, Kokkonda S, Katneni K, Bhamidipati R, Shackleford DM, Angulo-Barturen I, Ferrer SB, Jiménez-Díaz MB, Gamo FJ, Goldsmith EJ, Charman WN, Bathurst I, Floyd D, Matthews D, Burrows JN, Rathod PK, Charman SA, Phillips MA.. (2011) Structure-guided lead optimization of triazolopyrimidine-ring substituents identifies potent Plasmodium falciparum dihydroorotate dehydrogenase inhibitors with clinical candidate potential., 54 (15): [PMID:21696174] [10.1021/jm200592f] |
| 2. Deng X, Kokkonda S, El Mazouni F, White J, Burrows JN, Kaminsky W, Charman SA, Matthews D, Rathod PK, Phillips MA.. (2014) Fluorine modulates species selectivity in the triazolopyrimidine class of Plasmodium falciparum dihydroorotate dehydrogenase inhibitors., 57 (12): [PMID:24801997] [10.1021/jm500481t] |
| 3. (2016) Antimalarial agents that are inhibitors of dihydroorotate dehydrogenase, |
| 4. Singh A, Maqbool M, Mobashir M, Hoda N.. (2017) Dihydroorotate dehydrogenase: A drug target for the development of antimalarials., 125 [PMID:27721149] [10.1016/j.ejmech.2016.09.085] |
| 5. Aggarwal R, Sumran G.. (2020) An insight on medicinal attributes of 1,2,4-triazoles., 205 [PMID:32771798] [10.1016/j.ejmech.2020.112652] |
Source
Source(2):