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Identification
Name(2R,3R,4S)-3-(4-HYDROXYPHENYL)-4-METHYL-2-[4-(2-PYRROLIDIN-1-YLETHOXY)PHENYL]CHROMAN-6-OL
Accession NumberDB07567
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 numberNot Available
WeightAverage: 445.55
Monoisotopic: 445.225308485
Chemical FormulaC28H31NO4
InChI KeyInChIKey=XPVKGTWRXBSJKO-LHXLBICKSA-N
InChI
InChI=1S/C28H31NO4/c1-19-25-18-23(31)10-13-26(25)33-28(27(19)20-4-8-22(30)9-5-20)21-6-11-24(12-7-21)32-17-16-29-14-2-3-15-29/h4-13,18-19,27-28,30-31H,2-3,14-17H2,1H3/t19-,27-,28+/m1/s1
IUPAC Name
(2R,3R,4S)-3-(4-hydroxyphenyl)-4-methyl-2-{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}-3,4-dihydro-2H-1-benzopyran-6-ol
SMILES
[H][C@@]1(C)C2=CC(O)=CC=C2O[C@@]([H])(C2=CC=C(OCCN3CCCC3)C=C2)[C@@]1([H])C1=CC=C(O)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as isoflavanols. These are polycyclic compounds containing a hydroxylated isoflavan skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflavans
Direct ParentIsoflavanols
Alternative Parents
Substituents
  • Hydroxyisoflavonoid
  • Isoflavanol
  • Hydroxyflavonoid
  • 6-hydroxyflavonoid
  • Flavan
  • Stilbene
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Phenol ether
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • N-alkylpyrrolidine
  • Monocyclic benzene moiety
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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+0.987
Blood Brain Barrier+0.9174
Caco-2 permeable-0.6159
P-glycoprotein substrateSubstrate0.7921
P-glycoprotein inhibitor INon-inhibitor0.5487
P-glycoprotein inhibitor IIInhibitor0.9063
Renal organic cation transporterInhibitor0.6239
CYP450 2C9 substrateNon-substrate0.8086
CYP450 2D6 substrateNon-substrate0.6137
CYP450 3A4 substrateSubstrate0.6106
CYP450 1A2 substrateNon-inhibitor0.6012
CYP450 2C9 inhibitorNon-inhibitor0.878
CYP450 2D6 inhibitorInhibitor0.6771
CYP450 2C19 inhibitorInhibitor0.5072
CYP450 3A4 inhibitorInhibitor0.625
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7728
Ames testNon AMES toxic0.8502
CarcinogenicityNon-carcinogens0.946
BiodegradationNot ready biodegradable0.9799
Rat acute toxicity2.4754 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.8024
hERG inhibition (predictor II)Inhibitor0.5801
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 Solubility0.00444 mg/mLALOGPS
logP5.26ALOGPS
logP5.17ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)9.78ChemAxon
pKa (Strongest Basic)8.9ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area62.16 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity129.81 m3·mol-1ChemAxon
Polarizability50.08 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 EntriesNot Available
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. 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 15:23 / Updated on September 16, 2013 18:07