ID: ALA8758
Chembl Id: CHEMBL8758
Cas Number: 345953-08-4
PubChem CID: 9848618
Max Phase: Preclinical
Molecular Formula: C22H18BrF2O4P
Molecular Weight: 495.26
Molecule Type: Small molecule
Associated Items:
Canonical SMILES: O=C(c1ccccc1)C(Cc1ccc(C(F)(F)P(=O)(O)O)c(Br)c1)c1ccccc1
Standard InChI: InChI=1S/C22H18BrF2O4P/c23-20-14-15(11-12-19(20)22(24,25)30(27,28)29)13-18(16-7-3-1-4-8-16)21(26)17-9-5-2-6-10-17/h1-12,14,18H,13H2,(H2,27,28,29)
Standard InChI Key: WDTMVBQZDFMOIK-UHFFFAOYSA-N
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| 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 |
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
|---|
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
|---|
| Molecular Weight: 495.26 | Molecular Weight (Monoisotopic): 494.0094 | AlogP: 5.89 | #Rotatable Bonds: 7 |
| Polar Surface Area: 74.60 | Molecular Species: ACID | HBA: 2 | HBD: 2 |
| #RO5 Violations: 1 | HBA (Lipinski): 4 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): 1 |
| CX Acidic pKa: 0.49 | CX Basic pKa: ┄ | CX LogP: 5.46 | CX LogD: 2.71 |
| Aromatic Rings: 3 | Heavy Atoms: 30 | QED Weighted: 0.32 | Np Likeness Score: -0.16 |
| 1. Dufresne C, Roy P, Wang Z, Asante-Appiah E, Cromlish W, Boie Y, Forghani F, Desmarais S, Wang Q, Skorey K, Waddleton D, Ramachandran C, Kennedy BP, Xu L, Gordon R, Chan CC, Leblanc Y.. (2004) The development of potent non-peptidic PTP-1B inhibitors., 14 (4): [PMID:15013019] [10.1016/j.bmcl.2003.11.048] |
| 2. Han Y, Belley M, Bayly CI, Colucci J, Dufresne C, Giroux A, Lau CK, Leblanc Y, McKay D, Therien M, Wilson MC, Skorey K, Chan CC, Scapin G, Kennedy BP.. (2008) Discovery of [(3-bromo-7-cyano-2-naphthyl)(difluoro)methyl]phosphonic acid, a potent and orally active small molecule PTP1B inhibitor., 18 (11): [PMID:18477508] [10.1016/j.bmcl.2008.04.064] |
| 3. Combs AP.. (2010) Recent advances in the discovery of competitive protein tyrosine phosphatase 1B inhibitors for the treatment of diabetes, obesity, and cancer., 53 (6): [PMID:20000419] [10.1021/jm901090b] |
| 4. Basu S, Prasad UV, Barawkar DA, De S, Palle VP, Menon S, Patel M, Thorat S, Singh UP, Das Sarma K, Waman Y, Niranjan S, Pathade V, Gaur A, Reddy S, Ansari S.. (2012) Discovery of novel and potent heterocyclic carboxylic acid derivatives as protein tyrosine phosphatase 1B inhibitors., 22 (8): [PMID:22424978] [10.1016/j.bmcl.2012.02.070] |
| 5. Zhang R, Yu R, Xu Q, Li X, Luo J, Jiang B, Wang L, Guo S, Wu N, Shi D.. (2017) Discovery and evaluation of the hybrid of bromophenol and saccharide as potent and selective protein tyrosine phosphatase 1B inhibitors., 134 [PMID:28395151] [10.1016/j.ejmech.2017.04.004] |
| 6. Meanwell NA.. (2018) Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design., 61 (14): [PMID:29400967] [10.1021/acs.jmedchem.7b01788] |
| 7. Kousaxidis A, Petrou A, Lavrentaki V, Fesatidou M, Nicolaou I, Geronikaki A.. (2020) Aldose reductase and protein tyrosine phosphatase 1B inhibitors as a promising therapeutic approach for diabetes mellitus., 207 [PMID:32871344] [10.1016/j.ejmech.2020.112742] |
Source(1):
