(3aS,4R,9bR)-2,2-difluoro-4-(4-hydroxyphenyl)-6-(methoxymethyl)-1,2,3,3a,4,9b-hexahydrocyclopenta[c]chromen-8-ol

Identification

Generic Name
(3aS,4R,9bR)-2,2-difluoro-4-(4-hydroxyphenyl)-6-(methoxymethyl)-1,2,3,3a,4,9b-hexahydrocyclopenta[c]chromen-8-ol
DrugBank Accession Number
DB07036
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 362.3672
Monoisotopic: 362.132965538
Chemical Formula
C20H20F2O4
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UEstrogen receptor betaNot AvailableHumans
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
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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 6-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-6 position of the flavonoid skeleton.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Flavonoids
Sub Class
Hydroxyflavonoids
Direct Parent
6-hydroxyflavonoids
Alternative Parents
4'-hydroxyflavonoids / Flavans / 1-benzopyrans / Alkyl aryl ethers / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Oxacyclic compounds / Dialkyl ethers / Organofluorides / Hydrocarbon derivatives
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Substituents
1-benzopyran / 1-hydroxy-2-unsubstituted benzenoid / 4'-hydroxyflavonoid / 6-hydroxyflavonoid / Alkyl aryl ether / Alkyl fluoride / Alkyl halide / Aromatic heteropolycyclic compound / Benzenoid / Benzopyran
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Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
GPFRMIHXGMVMGF-BZSNNMDCSA-N
InChI
InChI=1S/C20H20F2O4/c1-25-10-12-6-14(24)7-15-16-8-20(21,22)9-17(16)18(26-19(12)15)11-2-4-13(23)5-3-11/h2-7,16-18,23-24H,8-10H2,1H3/t16-,17-,18-/m0/s1
IUPAC Name
(2R,6S,7R)-4,4-difluoro-7-(4-hydroxyphenyl)-10-(methoxymethyl)-8-oxatricyclo[7.4.0.0^{2,6}]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=C1COC)C1=CC=C(O)C=C1

References

General References
Not Available
PubChem Compound
16758226
PubChem Substance
99443507
ChemSpider
24682221
BindingDB
19990
ChEMBL
CHEMBL236720
ZINC
ZINC000014972457
PDBe Ligand
3AS
PDB Entries
2qtu

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
PropertyValueSource
Water Solubility0.0413 mg/mLALOGPS
logP3.6ALOGPS
logP3.47Chemaxon
logS-3.9ALOGPS
pKa (Strongest Acidic)9.31Chemaxon
pKa (Strongest Basic)-4.1Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area58.92 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity92.66 m3·mol-1Chemaxon
Polarizability35.7 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9838
Blood Brain Barrier+0.939
Caco-2 permeable+0.63
P-glycoprotein substrateSubstrate0.7764
P-glycoprotein inhibitor INon-inhibitor0.8564
P-glycoprotein inhibitor IIInhibitor0.754
Renal organic cation transporterNon-inhibitor0.8132
CYP450 2C9 substrateNon-substrate0.7841
CYP450 2D6 substrateNon-substrate0.7841
CYP450 3A4 substrateSubstrate0.51
CYP450 1A2 substrateNon-inhibitor0.5598
CYP450 2C9 inhibitorInhibitor0.7134
CYP450 2D6 inhibitorNon-inhibitor0.6952
CYP450 2C19 inhibitorInhibitor0.7904
CYP450 3A4 inhibitorInhibitor0.7274
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8398
Ames testNon AMES toxic0.6111
CarcinogenicityNon-carcinogens0.9071
BiodegradationNot ready biodegradable1.0
Rat acute toxicity3.2353 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.955
hERG inhibition (predictor II)Non-inhibitor0.6227
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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Details
1. Estrogen receptor beta
Kind
Protein
Organism
Humans
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 m...
Gene Name
ESR2
Uniprot ID
Q92731
Uniprot Name
Estrogen receptor beta
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. [Article]

Drug created at September 15, 2010 21:18 / Updated at June 12, 2020 16:52