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

 25 28  0  0  0  0  0  0  0  0999 V2000
   -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)

PDK2 Tchem Pyruvate dehydrogenase kinase (522 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Biocomponents

Calculated Properties

Molecular Weight: 351.43Molecular Weight (Monoisotopic): 351.0929AlogP: 4.49#Rotatable Bonds: 2
Polar 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: 4.36
Aromatic 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]

Source