dimethyl (1R,4S)-5,6-bis(4-hydroxyphenyl)-7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate
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Identification
- Generic Name
- dimethyl (1R,4S)-5,6-bis(4-hydroxyphenyl)-7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate
- DrugBank Accession Number
- DB07932
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 394.3741
Monoisotopic: 394.10525293 - Chemical Formula
- C22H18O7
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UEstrogen receptor Not Available Humans UNuclear receptor coactivator 2 Not Available Humans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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 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
- 1-hydroxy-2-unsubstituted benzenoid / Alpha,beta-unsaturated carboxylic ester / Aromatic heteropolycyclic compound / Benzenoid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Dialkyl ether / Dicarboxylic acid or derivatives / Dihydrofuran show 12 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- 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][C@]12O[C@]([H])(C(C(=O)OC)=C1C(=O)OC)C(=C2C1=CC=C(O)C=C1)C1=CC=C(O)C=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 11531308
- PubChem Substance
- 99444403
- ChemSpider
- 9706091
- ChEMBL
- CHEMBL1213270
- ZINC
- ZINC000016052474
- PDBe Ligand
- HZ3
- PDB Entries
- 2qr9
Clinical Trials
- Clinical Trials
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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
Property Value Source Water Solubility 0.00942 mg/mL ALOGPS logP 2.64 ALOGPS logP 3.01 Chemaxon logS -4.6 ALOGPS pKa (Strongest Acidic) 5.87 Chemaxon pKa (Strongest Basic) -4.3 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 102.29 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 103.3 m3·mol-1 Chemaxon Polarizability 39.94 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.98 Blood Brain Barrier - 0.7822 Caco-2 permeable + 0.6841 P-glycoprotein substrate Substrate 0.5756 P-glycoprotein inhibitor I Non-inhibitor 0.5142 P-glycoprotein inhibitor II Inhibitor 0.5694 Renal organic cation transporter Non-inhibitor 0.857 CYP450 2C9 substrate Non-substrate 0.7911 CYP450 2D6 substrate Non-substrate 0.9119 CYP450 3A4 substrate Non-substrate 0.5315 CYP450 1A2 substrate Inhibitor 0.5225 CYP450 2C9 inhibitor Inhibitor 0.7615 CYP450 2D6 inhibitor Non-inhibitor 0.888 CYP450 2C19 inhibitor Inhibitor 0.6925 CYP450 3A4 inhibitor Non-inhibitor 0.7185 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8398 Ames test Non AMES toxic 0.8676 Carcinogenicity Non-carcinogens 0.8857 Biodegradation Not ready biodegradable 0.5912 Rat acute toxicity 2.9210 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.93 hERG inhibition (predictor II) Non-inhibitor 0.8886
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0009000000-092b047c2da18204a579 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0009000000-a4a576509c12d1b6dd20 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0009000000-9f83aecd426258344770 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0019000000-0907cba85a9969b9a744 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-0559000000-43f8408c39a0424569a0 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0fb9-2098000000-87bc72a19b2e0cb2da0a Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 181.07387 predictedDeepCCS 1.0 (2019) [M+H]+ 183.46944 predictedDeepCCS 1.0 (2019) [M+Na]+ 189.38197 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsEstrogen receptor
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General 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 factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3 (PubMed:17922032). Maintains neuronal survival in response to ischemic reperfusion injury when in the presence of circulating estradiol (17-beta-estradiol/E2) (By similarity)
- Specific Function
- 14-3-3 protein binding
- Gene Name
- ESR1
- Uniprot ID
- P03372
- Uniprot Name
- Estrogen receptor
- Molecular Weight
- 66215.45 Da
References
- 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]
2. DetailsNuclear receptor coactivator 2
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transcriptional coactivator for steroid receptors and nuclear receptors (PubMed:23508108, PubMed:8670870, PubMed:9430642). Coactivator of the steroid binding domain (AF-2) but not of the modulating N-terminal domain (AF-1) (PubMed:23508108, PubMed:8670870, PubMed:9430642). Required with NCOA1 to control energy balance between white and brown adipose tissues (PubMed:23508108, PubMed:8670870, PubMed:9430642). Critical regulator of glucose metabolism regulation, acts as a RORA coactivator to specifically modulate G6PC1 expression (PubMed:23508108, PubMed:8670870, PubMed:9430642). Involved in the positive regulation of the transcriptional activity of the glucocorticoid receptor NR3C1 by sumoylation enhancer RWDD3 (PubMed:23508108). Positively regulates the circadian clock by acting as a transcriptional coactivator for the CLOCK-BMAL1 heterodimer (By similarity)
- Specific Function
- aryl hydrocarbon receptor binding
- Gene Name
- NCOA2
- Uniprot ID
- Q15596
- Uniprot Name
- Nuclear receptor coactivator 2
- Molecular Weight
- 159155.645 Da
References
- 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 21:27 / Updated at June 12, 2020 16:52