4-[(1S,2S,5S,9R)-5-(HYDROXYMETHYL)-8,9-DIMETHYL-3-OXABICYCLO[3.3.1]NON-7-EN-2-YL]PHENOL
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Identification
- Generic Name
- 4-[(1S,2S,5S,9R)-5-(HYDROXYMETHYL)-8,9-DIMETHYL-3-OXABICYCLO[3.3.1]NON-7-EN-2-YL]PHENOL
- DrugBank Accession Number
- DB07087
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 276.3707
Monoisotopic: 276.172544634 - Chemical Formula
- C17H24O3
- 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 1-hydroxy-2-unsubstituted benzenoids. These are phenols that a unsubstituted at the 2-position.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Phenols
- Sub Class
- 1-hydroxy-2-unsubstituted benzenoids
- Direct Parent
- 1-hydroxy-2-unsubstituted benzenoids
- Alternative Parents
- Oxanes / Benzene and substituted derivatives / Oxacyclic compounds / Dialkyl ethers / Primary alcohols / Hydrocarbon derivatives
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / Alcohol / Aromatic heteropolycyclic compound / Dialkyl ether / Ether / Hydrocarbon derivative / Monocyclic benzene moiety / Organic oxygen compound / Organoheterocyclic compound / Organooxygen compound
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- YMSZEVAWRFDVQX-GHVWTTSJSA-N
- InChI
- InChI=1S/C17H24O3/c1-11-7-8-17(9-18)10-20-16(15(11)12(17)2)13-3-5-14(19)6-4-13/h3-6,11-12,15-16,18-19H,7-10H2,1-2H3/t11-,12+,15+,16+,17-/m0/s1
- IUPAC Name
- 4-[(1R,2S,5S,8S,9R)-5-(hydroxymethyl)-8,9-dimethyl-3-oxabicyclo[3.3.1]nonan-2-yl]phenol
- SMILES
- [H][C@]1(C)CC[C@]2(CO)CO[C@]([H])(C3=CC=C(O)C=C3)[C@@]1([H])[C@@]2([H])C
References
- General References
- Not Available
- External Links
- PubChem Compound
- 46937048
- PubChem Substance
- 99443558
- ChemSpider
- 25057735
- ZINC
- ZINC000036773869
- PDBe Ligand
- 459
- PDB Entries
- 2fai
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 0.0558 mg/mL ALOGPS logP 2.4 ALOGPS logP 2.84 Chemaxon logS -3.7 ALOGPS pKa (Strongest Acidic) 9.47 Chemaxon pKa (Strongest Basic) -2.8 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 78.43 m3·mol-1 Chemaxon Polarizability 31.24 Å3 Chemaxon Number of Rings 3 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 + 0.9958 Blood Brain Barrier + 0.8781 Caco-2 permeable + 0.5974 P-glycoprotein substrate Substrate 0.801 P-glycoprotein inhibitor I Non-inhibitor 0.8511 P-glycoprotein inhibitor II Inhibitor 0.7195 Renal organic cation transporter Non-inhibitor 0.7495 CYP450 2C9 substrate Non-substrate 0.7771 CYP450 2D6 substrate Non-substrate 0.7788 CYP450 3A4 substrate Substrate 0.5594 CYP450 1A2 substrate Inhibitor 0.5466 CYP450 2C9 inhibitor Non-inhibitor 0.6317 CYP450 2D6 inhibitor Non-inhibitor 0.909 CYP450 2C19 inhibitor Non-inhibitor 0.5204 CYP450 3A4 inhibitor Non-inhibitor 0.5654 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5541 Ames test Non AMES toxic 0.7404 Carcinogenicity Non-carcinogens 0.8776 Biodegradation Not ready biodegradable 0.9961 Rat acute toxicity 2.8065 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8758 hERG inhibition (predictor II) Non-inhibitor 0.5591
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0090000000-875e0ab252962f0b94e0 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-0090000000-2d059633c7f781e99d55 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-1390000000-55430c6835bee140f931 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-0090000000-2eab6669f2413ac81e1b Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-016s-0950000000-081d5f9ac6a9bdc0d5f0 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0adj-3960000000-f4240386712e7a416089 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]- 164.4642 predictedDeepCCS 1.0 (2019) [M+H]+ 166.8322 predictedDeepCCS 1.0 (2019) [M+Na]+ 173.73286 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 21:18 / Updated at June 12, 2020 16:52