(3AS,4R,9BR)-2,2-DIFLUORO-4-(4-HYDROXYPHENYL)-1,2,3,3A,4,9B-HEXAHYDROCYCLOPENTA[C]CHROMEN-8-OL

Identification

Name
(3AS,4R,9BR)-2,2-DIFLUORO-4-(4-HYDROXYPHENYL)-1,2,3,3A,4,9B-HEXAHYDROCYCLOPENTA[C]CHROMEN-8-OL
Accession Number
DB07638
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 318.3146
Monoisotopic: 318.106750788
Chemical Formula
C18H16F2O3
InChI Key
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][[email protected]@]12CC(F)(F)C[[email protected]]1([H])[[email protected]@]([H])(OC1=C2C=C(O)C=C1)C1=CC=C(O)C=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UEstrogen receptor alphaNot AvailableHuman
UEstrogen receptor betaNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
11197931
PubChem Substance
99444109
ChemSpider
9373000
BindingDB
19982
ChEMBL
CHEMBL236718
HET
DC8
PDB Entries
2q70 / 2z4b

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.0532 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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

Taxonomy

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 / Organofluorides / Hydrocarbon derivatives / Alkyl fluorides
Substituents
4'-hydroxyflavonoid / 6-hydroxyflavonoid / Flavan / 1-benzopyran / Chromane / Benzopyran / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Alkyl aryl ether / Benzenoid
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Details
1. Estrogen receptor alpha
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 tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
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]
Details
2. Estrogen receptor beta
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 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. [PubMed:10592235]

Drug created on September 15, 2010 15:24 / Updated on December 01, 2017 15:53