(5R)-5-(4-{[(2R)-6-HYDROXY-2,5,7,8-TETRAMETHYL-3,4-DIHYDRO-2H-CHROMEN-2-YL]METHOXY}BENZYL)-1,3-THIAZOLIDINE-2,4-DIONE
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Identification
- Generic Name
- (5R)-5-(4-{[(2R)-6-HYDROXY-2,5,7,8-TETRAMETHYL-3,4-DIHYDRO-2H-CHROMEN-2-YL]METHOXY}BENZYL)-1,3-THIAZOLIDINE-2,4-DIONE
- DrugBank Accession Number
- DB08607
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 441.54
Monoisotopic: 441.160993669 - Chemical Formula
- C24H27NO5S
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UCytochrome P450 2C8 Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzopyrans
- Sub Class
- 1-benzopyrans
- Direct Parent
- 1-benzopyrans
- Alternative Parents
- Phenoxy compounds / Phenol ethers / Thiazolidinediones / Alkyl aryl ethers / Dicarboximides / Thiocarbamic acid derivatives / Organic carbonic acids and derivatives / Oxacyclic compounds / Azacyclic compounds / Organopnictogen compounds show 4 more
- Substituents
- 1-benzopyran / Alkyl aryl ether / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonic acid derivative / Carbonyl group / Carboxylic acid derivative / Dicarboximide / Ether show 14 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 1A70L3TM4P
- CAS number
- Not Available
- InChI Key
- GXPHKUHSUJUWKP-NTKDMRAZSA-N
- InChI
- InChI=1S/C24H27NO5S/c1-13-14(2)21-18(15(3)20(13)26)9-10-24(4,30-21)12-29-17-7-5-16(6-8-17)11-19-22(27)25-23(28)31-19/h5-8,19,26H,9-12H2,1-4H3,(H,25,27,28)/t19-,24-/m1/s1
- IUPAC Name
- (5R)-5-[(4-{[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]methoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione
- SMILES
- [H][C@]1(CC2=CC=C(OC[C@@]3(C)CCC4=C(C)C(O)=C(C)C(C)=C4O3)C=C2)SC(=O)NC1=O
References
- General References
- Not Available
- External Links
- PubChem Compound
- 9824580
- PubChem Substance
- 99445078
- ChemSpider
- 8000327
- ZINC
- ZINC000000968278
- PDBe Ligand
- TDZ
- PDB Entries
- 2qm9 / 2vn0 / 6hn8 / 7m23
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00121 mg/mL ALOGPS logP 4.16 ALOGPS logP 5.5 Chemaxon logS -5.6 ALOGPS pKa (Strongest Acidic) 6.61 Chemaxon pKa (Strongest Basic) -4.6 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 84.86 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 120.99 m3·mol-1 Chemaxon Polarizability 47.21 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.868 Blood Brain Barrier + 0.8183 Caco-2 permeable - 0.6915 P-glycoprotein substrate Substrate 0.7514 P-glycoprotein inhibitor I Non-inhibitor 0.7854 P-glycoprotein inhibitor II Non-inhibitor 0.7015 Renal organic cation transporter Non-inhibitor 0.861 CYP450 2C9 substrate Non-substrate 0.8329 CYP450 2D6 substrate Substrate 0.8919 CYP450 3A4 substrate Substrate 0.7408 CYP450 1A2 substrate Non-inhibitor 0.5726 CYP450 2C9 inhibitor Non-inhibitor 0.6843 CYP450 2D6 inhibitor Non-inhibitor 0.9266 CYP450 2C19 inhibitor Non-inhibitor 0.6359 CYP450 3A4 inhibitor Non-inhibitor 0.5517 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5121 Ames test Non AMES toxic 0.584 Carcinogenicity Non-carcinogens 0.9211 Biodegradation Not ready biodegradable 0.9881 Rat acute toxicity 1.9768 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9911 hERG inhibition (predictor II) Non-inhibitor 0.6643
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0030900000-fdd75d7e6404f192d09f Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0070900000-060bbd2c79b0f09312c0 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0076-0456900000-a342f584359e970180ad Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9224600000-07dbc891f26c5f46d1e9 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-05fu-0791200000-c7c08dfdb95225c51cd3 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0f6x-4911100000-7ab3094b0cb821251309 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 233.1116792 predictedDarkChem Lite v0.1.0 [M-H]- 205.57256 predictedDeepCCS 1.0 (2019) [M+H]+ 234.9546792 predictedDarkChem Lite v0.1.0 [M+H]+ 207.96814 predictedDeepCCS 1.0 (2019) [M+Na]+ 233.9056792 predictedDarkChem Lite v0.1.0 [M+Na]+ 213.88066 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsCytochrome P450 2C8
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Carriers
1. DetailsFatty acid-binding protein, adipocyte
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transporter activity
- Specific Function
- Lipid transport protein in adipocytes. Binds both long chain fatty acids and retinoic acid. Delivers long-chain fatty acids and retinoic acid to their cognate receptors in the nucleus (By similarity).
- Gene Name
- FABP4
- Uniprot ID
- P15090
- Uniprot Name
- Fatty acid-binding protein, adipocyte
- Molecular Weight
- 14718.815 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Drug created at September 15, 2010 21:33 / Updated at June 12, 2020 16:52