(9BETA,11ALPHA,13ALPHA,14BETA,17ALPHA)-11-(METHOXYMETHYL)ESTRA-1(10),2,4-TRIENE-3,17-DIOL
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Identification
- Generic Name
- (9BETA,11ALPHA,13ALPHA,14BETA,17ALPHA)-11-(METHOXYMETHYL)ESTRA-1(10),2,4-TRIENE-3,17-DIOL
- DrugBank Accession Number
- DB07707
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 316.4345
Monoisotopic: 316.203844762 - Chemical Formula
- C20H28O3
- 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 estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Estrane steroids
- Direct Parent
- Estrogens and derivatives
- Alternative Parents
- 3-hydroxysteroids / 17-hydroxysteroids / Phenanthrenes and derivatives / Tetralins / 1-hydroxy-2-unsubstituted benzenoids / Secondary alcohols / Cyclic alcohols and derivatives / Dialkyl ethers / Hydrocarbon derivatives
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 17-hydroxysteroid / 3-hydroxysteroid / Alcohol / Aromatic homopolycyclic compound / Benzenoid / Cyclic alcohol / Dialkyl ether / Estrogen-skeleton / Ether
- Molecular Framework
- Aromatic homopolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- LEOPSILMAOYZBO-IUTAEKPZSA-N
- InChI
- InChI=1S/C20H28O3/c1-20-10-13(11-23-2)19-15-6-4-14(21)9-12(15)3-5-16(19)17(20)7-8-18(20)22/h4,6,9,13,16-19,21-22H,3,5,7-8,10-11H2,1-2H3/t13-,16+,17+,18+,19-,20+/m1/s1
- IUPAC Name
- (1S,3aS,3bS,9bR,10S,11aS)-10-(methoxymethyl)-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-1,7-diol
- SMILES
- [H][C@]1(O)CC[C@@]2([H])[C@]3([H])CCC4=CC(O)=CC=C4[C@@]3([H])[C@@]([H])(COC)C[C@]12C
References
- General References
- Not Available
- External Links
- PubChem Compound
- 23728517
- PubChem Substance
- 99444178
- ChemSpider
- 21169213
- ZINC
- ZINC000013610524
- PDBe Ligand
- EED
- PDB Entries
- 2qgt
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 0.00706 mg/mL ALOGPS logP 3.18 ALOGPS logP 3.32 Chemaxon logS -4.6 ALOGPS pKa (Strongest Acidic) 10.31 Chemaxon pKa (Strongest Basic) -0.89 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 49.69 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 91.06 m3·mol-1 Chemaxon Polarizability 36.6 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 No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9966 Blood Brain Barrier + 0.92 Caco-2 permeable + 0.8218 P-glycoprotein substrate Substrate 0.8322 P-glycoprotein inhibitor I Non-inhibitor 0.7205 P-glycoprotein inhibitor II Non-inhibitor 0.521 Renal organic cation transporter Non-inhibitor 0.7026 CYP450 2C9 substrate Non-substrate 0.7949 CYP450 2D6 substrate Non-substrate 0.7395 CYP450 3A4 substrate Substrate 0.7611 CYP450 1A2 substrate Inhibitor 0.7188 CYP450 2C9 inhibitor Non-inhibitor 0.7845 CYP450 2D6 inhibitor Non-inhibitor 0.9274 CYP450 2C19 inhibitor Non-inhibitor 0.767 CYP450 3A4 inhibitor Non-inhibitor 0.6627 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7979 Ames test Non AMES toxic 0.8617 Carcinogenicity Non-carcinogens 0.9188 Biodegradation Not ready biodegradable 0.982 Rat acute toxicity 2.0746 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.857 hERG inhibition (predictor II) Inhibitor 0.7341
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-0089000000-38dfb8aee6290307c044 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0029000000-759d515f9995298ac920 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0ab9-1190000000-8fc2a638898bbb8ddb5f Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0159-0094000000-da99f114c362f24c5c29 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-01b9-0091000000-22a2c341ae6e4b2033a9 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00l2-2940000000-da7ab51d268fc25d51c0 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]- 182.22342 predictedDeepCCS 1.0 (2019) [M+H]+ 184.11884 predictedDeepCCS 1.0 (2019) [M+Na]+ 189.89676 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 21:25 / Updated at June 12, 2020 16:52