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4-[2-(thiophen-2-yl)-1,2,3,4-tetrahydroquinoline-1-carbonyl]benzene-1,3-diol ID: ALA3717054
PubChem CID: 117968087
Max Phase: Preclinical
Molecular Formula: C20H17NO3S
Molecular Weight: 351.43
Molecule Type: Small molecule
This compound is available for customization.
Associated Items:
Names and Identifiers Canonical SMILES: O=C(c1ccc(O)cc1O)N1c2ccccc2CCC1c1cccs1
Standard InChI: InChI=1S/C20H17NO3S/c22-14-8-9-15(18(23)12-14)20(24)21-16-5-2-1-4-13(16)7-10-17(21)19-6-3-11-25-19/h1-6,8-9,11-12,17,22-23H,7,10H2
Standard InChI Key: XOEWAGGFKMWDPJ-UHFFFAOYSA-N
Molfile:
RDKit 2D
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-2.5954 -5.2538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.2959 -6.0029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.0027 -5.2521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.0018 -3.7520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.2978 -3.0029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.5964 -3.7538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.0423 -5.8514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-3.6342 -5.8545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
1.2995 -2.9981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.3402 -3.5957 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-1.2964 1.4973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.6111 0.7486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.6111 -0.7486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.2964 -1.4973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.0000 0.7486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.0000 -0.7486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.2964 -1.4973 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.5929 -0.7486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.5929 0.7486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.2964 1.4973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.8926 -1.4990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.2449 -0.8800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.2469 -1.9962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.4950 -3.2941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.0282 -2.9800 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0
1 2 2 0
2 3 1 0
3 4 2 0
4 5 1 0
5 6 2 0
6 1 1 0
3 7 1 0
1 8 1 0
4 9 1 0
9 17 1 0
9 10 2 0
15 11 1 0
11 12 2 0
12 13 1 0
13 14 2 0
14 16 1 0
15 16 2 0
15 20 1 0
16 17 1 0
17 18 1 0
18 19 1 0
19 20 1 0
18 21 1 0
21 22 2 0
22 23 1 0
23 24 2 0
24 25 1 0
25 21 1 0
M END Associated Targets(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: 351.43Molecular Weight (Monoisotopic): 351.0929AlogP: 4.49#Rotatable Bonds: 2Polar Surface Area: 60.77Molecular Species: NEUTRALHBA: 4HBD: 2#RO5 Violations: ┄HBA (Lipinski): 4HBD (Lipinski): 2#RO5 Violations (Lipinski): ┄CX Acidic pKa: 7.82CX Basic pKa: ┄CX LogP: 4.50CX LogD: 4.36Aromatic Rings: 3Heavy Atoms: 25QED Weighted: 0.71Np Likeness Score: -0.75
References 1. (2015) Tetrahydroisoquinoline compounds and their use as pyruvate dehydrogenase kinase inhibitors, 2. Morrell, J A JA and 5 more authors. 2003-12 AZD7545 is a selective inhibitor of pyruvate dehydrogenase kinase 2. [PMID:14641019 ] 3. Moore, Jonathan D and 12 more authors. 2014-12-30 VER-246608, a novel pan-isoform ATP competitive inhibitor of pyruvate dehydrogenase kinase, disrupts Warburg metabolism and induces context-dependent cytostasis in cancer cells. [PMID:25404640 ] 4. Tso, Shih-Chia and 9 more authors. 2017-02-09 Development of Dihydroxyphenyl Sulfonylisoindoline Derivatives as Liver-Targeting Pyruvate Dehydrogenase Kinase Inhibitors. [PMID:28085286 ]