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GLITAZONE
ID: ALA1061
Max Phase: Preclinical
Molecular Formula: C10H9NO3S
Molecular Weight: 223.25
Molecule Type: Small molecule
Associated Items:
Representations
Synonyms (1): Glitazone
Synonyms from Alternative Forms(1):
Canonical SMILES: O=C1NC(=O)C(Cc2ccc(O)cc2)S1
Standard InChI: InChI=1S/C10H9NO3S/c12-7-3-1-6(2-4-7)5-8-9(13)11-10(14)15-8/h1-4,8,12H,5H2,(H,11,13,14)
Standard InChI Key: NKOHRVBBQISBSB-UHFFFAOYSA-N
Associated Targets(Human)
MAOB Tclin Monoamine oxidase B (8835 Activities)
MAOA Tclin Monoamine oxidase A (11911 Activities)
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CISD1 Tchem CDGSH iron-sulfur domain-containing protein 1 (222 Activities)
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Associated Targets(non-human)
PC-12 (7051 Activities)
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Hadh Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial (1 Activities)
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Dlst Dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex, mitochondrial (1 Activities)
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Pdha1 Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial (1 Activities)
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Ldha L-lactate dehydrogenase A chain (1 Activities)
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Acads Short-chain specific acyl-CoA dehydrogenase, mitochondrial (1 Activities)
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Dld Dihydrolipoyl dehydrogenase, mitochondrial (4 Activities)
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Mdh1 Malate dehydrogenase, cytoplasmic (2 Activities)
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Acadm Medium-chain specific acyl-CoA dehydrogenase, mitochondrial (1 Activities)
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Idh2 Isocitrate dehydrogenase [NADP], mitochondrial (1 Activities)
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Acadvl Very long-chain specific acyl-CoA dehydrogenase, mitochondrial (1 Activities)
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Ogdh 2-oxoglutarate dehydrogenase, mitochondrial (2 Activities)
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Gapdh Glyceraldehyde-3-phosphate dehydrogenase (3 Activities)
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Glud1 Glutamate dehydrogenase 1, mitochondrial (1 Activities)
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Ldhb L-lactate dehydrogenase B chain (4 Activities)
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Mdh2 Malate dehydrogenase, mitochondrial (2 Activities)
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Acadl Long-chain specific acyl-CoA dehydrogenase, mitochondrial (4 Activities)
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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
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Mechanisms of Action
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Properties
| Molecular Weight: 223.25 | Molecular Weight (Monoisotopic): 223.0303 | AlogP: 1.29 | #Rotatable Bonds: 2 |
| Polar Surface Area: 66.40 | Molecular Species: NEUTRAL | HBA: 4 | HBD: 2 |
| #RO5 Violations: 0 | HBA (Lipinski): 4 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 6.61 | CX Basic pKa: | CX LogP: 1.64 | CX LogD: 0.82 |
| Aromatic Rings: 1 | Heavy Atoms: 15 | QED Weighted: 0.79 | Np Likeness Score: 0.37 |
References
| 1. Fan YH, Chen H, Natarajan A, Guo Y, Harbinski F, Iyasere J, Christ W, Aktas H, Halperin JA.. (2004) Structure-activity requirements for the antiproliferative effect of troglitazone derivatives mediated by depletion of intracellular calcium., 14 (10): [PMID:15109648] [10.1016/j.bmcl.2004.02.087] |
| 2. Carroll RT, Dluzen DE, Stinnett H, Awale PS, Funk MO, Geldenhuys WJ.. (2011) Structure-activity relationship and docking studies of thiazolidinedione-type compounds with monoamine oxidase B., 21 (16): [PMID:21742494] [10.1016/j.bmcl.2011.06.060] |
| 3. Geldenhuys WJ, Funk MO, Awale PS, Lin L, Carroll RT.. (2011) A novel binding assay identifies high affinity ligands to the rosiglitazone binding site of mitoNEET., 21 (18): [PMID:21782425] [10.1016/j.bmcl.2011.06.111] |
| 4. Hoffmann BR, El-Mansy MF, Sem DS, Greene AS.. (2012) Chemical proteomics-based analysis of off-target binding profiles for rosiglitazone and pioglitazone: clues for assessing potential for cardiotoxicity., 55 (19): [PMID:22970990] [10.1021/jm301204r] |
| 5. Geldenhuys WJ, Yonutas HM, Morris DL, Sullivan PG, Darvesh AS, Leeper TC.. (2016) Identification of small molecules that bind to the mitochondrial protein mitoNEET., 26 (21): [PMID:27687671] [10.1016/j.bmcl.2016.09.009] |
Source
Source(1):