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Identification
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
Accession NumberDB08607
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIINot Available
CAS numberNot Available
WeightAverage: 441.54
Monoisotopic: 441.160993669
Chemical FormulaC24H27NO5S
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct Parent1-benzopyrans
Alternative Parents
Substituents
  • 1-benzopyran
  • Phenol ether
  • Thiazolidinedione
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Thiazolidine
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Thioether
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.868
Blood Brain Barrier+0.8183
Caco-2 permeable-0.6915
P-glycoprotein substrateSubstrate0.7514
P-glycoprotein inhibitor INon-inhibitor0.7854
P-glycoprotein inhibitor IINon-inhibitor0.7015
Renal organic cation transporterNon-inhibitor0.861
CYP450 2C9 substrateNon-substrate0.8329
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateSubstrate0.7408
CYP450 1A2 substrateNon-inhibitor0.5726
CYP450 2C9 inhibitorNon-inhibitor0.6843
CYP450 2D6 inhibitorNon-inhibitor0.9266
CYP450 2C19 inhibitorNon-inhibitor0.6359
CYP450 3A4 inhibitorNon-inhibitor0.5517
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5121
Ames testNon AMES toxic0.584
CarcinogenicityNon-carcinogens0.9211
BiodegradationNot ready biodegradable0.9881
Rat acute toxicity1.9768 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9911
hERG inhibition (predictor II)Non-inhibitor0.6643
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00121 mg/mLALOGPS
logP4.16ALOGPS
logP5.5ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)6.61ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area84.86 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity120.99 m3·mol-1ChemAxon
Polarizability47.21 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 Da
References
  1. 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. [PubMed:10592235 ]

Carriers

Kind
Protein
Organism
Human
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
Molecular Weight:
14718.815 Da
References
  1. 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. [PubMed:10592235 ]
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Drug created on September 15, 2010 15:33 / Updated on September 16, 2013 18:10