dimethyl (1R,4S)-5,6-bis(4-hydroxyphenyl)-7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate

Identification

Name
dimethyl (1R,4S)-5,6-bis(4-hydroxyphenyl)-7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate
Accession Number
DB07932
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: 394.3741
Monoisotopic: 394.10525293
Chemical Formula
C22H18O7
InChI Key
CRLQCBACIMUGDZ-BGYRXZFFSA-N
InChI
InChI=1S/C22H18O7/c1-27-21(25)17-18(22(26)28-2)20-16(12-5-9-14(24)10-6-12)15(19(17)29-20)11-3-7-13(23)8-4-11/h3-10,19-20,23-24H,1-2H3/t19-,20+
IUPAC Name
2,3-dimethyl (1R,4S)-5,6-bis(4-hydroxyphenyl)-7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate
SMILES
[H][[email protected]]12O[[email protected]]([H])(C(C(=O)OC)=C1C(=O)OC)C(=C2C1=CC=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
UNuclear receptor coactivator 2Not 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
11531308
PubChem Substance
99444403
ChemSpider
9706091
ChEMBL
CHEMBL1213270
HET
HZ3
PDB Entries
2qr9

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 Solubility0.00942 mg/mLALOGPS
logP2.64ALOGPS
logP3.01ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)8.91ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area102.29 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity103.3 m3·mol-1ChemAxon
Polarizability40.03 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.98
Blood Brain Barrier-0.7822
Caco-2 permeable+0.6841
P-glycoprotein substrateSubstrate0.5756
P-glycoprotein inhibitor INon-inhibitor0.5142
P-glycoprotein inhibitor IIInhibitor0.5694
Renal organic cation transporterNon-inhibitor0.857
CYP450 2C9 substrateNon-substrate0.7911
CYP450 2D6 substrateNon-substrate0.9119
CYP450 3A4 substrateNon-substrate0.5315
CYP450 1A2 substrateInhibitor0.5225
CYP450 2C9 inhibitorInhibitor0.7615
CYP450 2D6 inhibitorNon-inhibitor0.888
CYP450 2C19 inhibitorInhibitor0.6925
CYP450 3A4 inhibitorNon-inhibitor0.7185
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8398
Ames testNon AMES toxic0.8676
CarcinogenicityNon-carcinogens0.8857
BiodegradationNot ready biodegradable0.5912
Rat acute toxicity2.9210 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.93
hERG inhibition (predictor II)Non-inhibitor0.8886
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

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Stilbenes
Sub Class
Not Available
Direct Parent
Stilbenes
Alternative Parents
1-hydroxy-2-unsubstituted benzenoids / Dicarboxylic acids and derivatives / Benzene and substituted derivatives / Methyl esters / Enoate esters / Dihydrofurans / Oxacyclic compounds / Dialkyl ethers / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Stilbene / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Monocyclic benzene moiety / Dicarboxylic acid or derivatives / Benzenoid / Dihydrofuran / Alpha,beta-unsaturated carboxylic ester / Enoate ester / Methyl ester
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not 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 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transcription coactivator activity
Specific Function
Transcriptional coactivator for steroid receptors and nuclear receptors. Coactivator of the steroid binding domain (AF-2) but not of the modulating N-terminal domain (AF-1). Required with NCOA1 to ...
Gene Name
NCOA2
Uniprot ID
Q15596
Uniprot Name
Nuclear receptor coactivator 2
Molecular Weight
159155.645 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 15:27 / Updated on December 01, 2017 15:57