You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameCompound 18
Accession NumberDB02715  (EXPT00473)
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
CategoriesNot Available
UNIINot Available
CAS number31112-66-0
WeightAverage: 463.588
Monoisotopic: 463.181729111
Chemical FormulaC27H29NO4S
InChI KeyInChIKey=UZOOIPXOYYJULJ-OALGXETFSA-N
InChI
InChI=1S/C27H29NO4S/c1-18(28-14-2-3-15-28)17-31-23-11-6-19(7-12-23)26-27(20-4-8-21(29)9-5-20)33-25-16-22(30)10-13-24(25)32-26/h4-13,16,18,26-27,29-30H,2-3,14-15,17H2,1H3/t18-,26-,27-/m0/s1
IUPAC Name
(2S,3S)-3-(4-hydroxyphenyl)-2-{4-[(2S)-2-(pyrrolidin-1-yl)propoxy]phenyl}-2,3-dihydro-1,4-benzoxathiin-6-ol
SMILES
C[C@@H](COC1=CC=C(C=C1)[C@@H]1OC2=CC=C(O)C=C2S[[email protected]]1C1=CC=C(O)C=C1)N1CCCC1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Phenol ether
  • Alkylarylthioether
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • N-alkylpyrrolidine
  • 1,4-oxathiin
  • 1,4-benzooxathiin
  • Monocyclic benzene moiety
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Thioether
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • 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+0.9957
Blood Brain Barrier+0.882
Caco-2 permeable-0.5865
P-glycoprotein substrateSubstrate0.8502
P-glycoprotein inhibitor INon-inhibitor0.6959
P-glycoprotein inhibitor IIInhibitor0.9392
Renal organic cation transporterInhibitor0.5821
CYP450 2C9 substrateNon-substrate0.6969
CYP450 2D6 substrateNon-substrate0.6207
CYP450 3A4 substrateSubstrate0.5837
CYP450 1A2 substrateNon-inhibitor0.6071
CYP450 2C9 inhibitorNon-inhibitor0.8548
CYP450 2D6 inhibitorNon-inhibitor0.5281
CYP450 2C19 inhibitorInhibitor0.6305
CYP450 3A4 inhibitorInhibitor0.6303
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7851
Ames testNon AMES toxic0.7302
CarcinogenicityNon-carcinogens0.9427
BiodegradationNot ready biodegradable0.9922
Rat acute toxicity2.5633 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7587
hERG inhibition (predictor II)Inhibitor0.5387
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 Solubility0.00178 mg/mLALOGPS
logP5.69ALOGPS
logP5.03ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)9.55ChemAxon
pKa (Strongest Basic)9ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area62.16 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity132.46 m3·mol-1ChemAxon
Polarizability51.15 Å3ChemAxon
Number of Rings5ChemAxon
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 Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription fact...
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:18