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5-Chloro-1-[5-chloro-2-(methylsulfonyl)benzyl]-2-imino-1,2-dihydropyridine-3-carboxamide ID: ALA3799553
Cas Number: 1192348-73-4
PubChem CID: 44247584
Max Phase: Preclinical
Molecular Formula: C14H13Cl2N3O3S
Molecular Weight: 374.25
Molecule Type: Small molecule
Associated Items:
Names and Identifiers Canonical SMILES: CS(=O)(=O)c1ccc(Cl)cc1Cn1cc(Cl)cc(C(N)=O)c1=N
Standard InChI: InChI=1S/C14H13Cl2N3O3S/c1-23(21,22)12-3-2-9(15)4-8(12)6-19-7-10(16)5-11(13(19)17)14(18)20/h2-5,7,17H,6H2,1H3,(H2,18,20)
Standard InChI Key: CVBJUEIAUOTXLV-UHFFFAOYSA-N
Molfile:
RDKit 2D
23 24 0 0 0 0 0 0 0 0999 V2000
2.3383 -1.3500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
1.2990 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.2990 0.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.5972 1.5031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.5951 3.0039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.8915 3.7585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.1939 3.0127 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0
3.8863 5.2585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.5847 6.0040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.2883 5.2495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.2470 5.8459 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
1.2934 3.7495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.0000 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.3383 1.3500 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
-1.2990 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.0000 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.0031 -3.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.0351 -3.6026 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-1.0432 -3.5994 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
6.2308 3.6166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.1988 1.8127 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
6.2355 2.4168 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
1 2 2 0
2 3 1 0
3 4 1 0
4 5 1 0
5 6 2 0
6 7 1 0
6 8 1 0
8 9 2 0
9 10 1 0
10 11 1 0
10 12 2 0
5 12 1 0
3 13 1 0
13 14 2 0
14 15 1 0
14 16 1 0
16 17 2 0
2 17 1 0
17 18 1 0
18 19 1 0
18 20 2 0
7 21 1 0
7 22 2 0
7 23 2 0
M END Associated Targets(Human) 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
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
Calculated Properties Molecular Weight: 374.25Molecular Weight (Monoisotopic): 373.0055AlogP: 1.83#Rotatable Bonds: 4Polar Surface Area: 106.01Molecular Species: BASEHBA: 5HBD: 2#RO5 Violations: ┄HBA (Lipinski): 6HBD (Lipinski): 3#RO5 Violations (Lipinski): ┄CX Acidic pKa: ┄CX Basic pKa: 8.66CX LogP: 0.86CX LogD: -0.39Aromatic Rings: 2Heavy Atoms: 23QED Weighted: 0.85Np Likeness Score: -1.43
References 1. Sakauchi N, Kohara Y, Sato A, Suzaki T, Imai Y, Okabe Y, Imai S, Saikawa R, Nagabukuro H, Kuno H, Fujita H, Kamo I, Yoshida M.. (2016) Discovery of 5-Chloro-1-(5-chloro-2-(methylsulfonyl)benzyl)-2-imino-1,2-dihydropyridine-3-carboxamide (TAK-259) as a Novel, Selective, and Orally Active α1D Adrenoceptor Antagonist with Antiurinary Frequency Effects: Reducing Human Ether-a-go-go-Related Gene (hERG) Liabilities., 59 (7): [PMID:26954848 ] [10.1021/acs.jmedchem.5b01528 ]