You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
Name(3AS,4R,9BR)-2,2-DIFLUORO-4-(4-HYDROXYPHENYL)-1,2,3,3A,4,9B-HEXAHYDROCYCLOPENTA[C]CHROMEN-8-OL
Accession NumberDB07638
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: 318.3146
Monoisotopic: 318.106750788
Chemical FormulaC18H16F2O3
InChI KeyInChIKey=QJSMFUTULGSHNQ-ZOBUZTSGSA-N
InChI
InChI=1S/C18H16F2O3/c19-18(20)8-14-13-7-12(22)5-6-16(13)23-17(15(14)9-18)10-1-3-11(21)4-2-10/h1-7,14-15,17,21-22H,8-9H2/t14-,15-,17-/m0/s1
IUPAC Name
(2R,6S,7R)-4,4-difluoro-7-(4-hydroxyphenyl)-8-oxatricyclo[7.4.0.0²,⁶]trideca-1(9),10,12-trien-12-ol
SMILES
[H][C@@]12CC(F)(F)C[C@]1([H])[C@@]([H])(OC1=C2C=C(O)C=C1)C1=CC=C(O)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 6-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-6 position of the flavonoid skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassHydroxyflavonoids
Direct Parent6-hydroxyflavonoids
Alternative Parents
Substituents
  • 6-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Flavan
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organofluoride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl fluoride
  • 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+0.9958
Blood Brain Barrier+0.9197
Caco-2 permeable+0.6088
P-glycoprotein substrateSubstrate0.5132
P-glycoprotein inhibitor INon-inhibitor0.9259
P-glycoprotein inhibitor IINon-inhibitor0.7858
Renal organic cation transporterNon-inhibitor0.8994
CYP450 2C9 substrateNon-substrate0.822
CYP450 2D6 substrateNon-substrate0.8644
CYP450 3A4 substrateNon-substrate0.6543
CYP450 1A2 substrateInhibitor0.5619
CYP450 2C9 inhibitorInhibitor0.8529
CYP450 2D6 inhibitorNon-inhibitor0.821
CYP450 2C19 inhibitorInhibitor0.6846
CYP450 3A4 inhibitorNon-inhibitor0.5901
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7213
Ames testNon AMES toxic0.7753
CarcinogenicityNon-carcinogens0.8869
BiodegradationNot ready biodegradable1.0
Rat acute toxicity3.1515 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9772
hERG inhibition (predictor II)Non-inhibitor0.6398
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 Solubility0.0532 mg/mLALOGPS
logP3.78ALOGPS
logP3.6ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)9.35ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity81.09 m3·mol-1ChemAxon
Polarizability30.4 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:
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by...
Gene Name:
ESR2
Uniprot ID:
Q92731
Molecular Weight:
59215.765 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 ]
Comments
comments powered by Disqus
Drug created on September 15, 2010 15:24 / Updated on September 16, 2013 18:07