4-[(1S,2R,5S)-4,4,8-TRIMETHYL-3-OXABICYCLO[3.3.1]NON-7-EN-2-YL]PHENOL
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Identification
- Generic Name
- 4-[(1S,2R,5S)-4,4,8-TRIMETHYL-3-OXABICYCLO[3.3.1]NON-7-EN-2-YL]PHENOL
- DrugBank Accession Number
- DB08595
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 258.3554
Monoisotopic: 258.161979948 - Chemical Formula
- C17H22O2
- 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 / Hydrocarbon derivatives
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / Aromatic heteropolycyclic compound / Dialkyl ether / Ether / Hydrocarbon derivative / Monocyclic benzene moiety / Organic oxygen compound / Organoheterocyclic compound / Organooxygen compound / Oxacycle
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- BBZPJHFECDCNGT-BPUTZDHNSA-N
- InChI
- InChI=1S/C17H22O2/c1-11-4-7-13-10-15(11)16(19-17(13,2)3)12-5-8-14(18)9-6-12/h4-6,8-9,13,15-16,18H,7,10H2,1-3H3/t13-,15-,16-/m0/s1
- IUPAC Name
- 4-[(1S,2R,5S)-4,4,8-trimethyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]phenol
- SMILES
- [H][C@]12CC=C(C)[C@]([H])(C1)[C@@]([H])(OC2(C)C)C1=CC=C(O)C=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 15942662
- PubChem Substance
- 99445066
- ChemSpider
- 13085331
- ZINC
- ZINC000002496982
- PDBe Ligand
- T3O
- PDB Entries
- 2g44
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 0.0355 mg/mL ALOGPS logP 4.76 ALOGPS logP 3.74 Chemaxon logS -3.9 ALOGPS pKa (Strongest Acidic) 9.47 Chemaxon pKa (Strongest Basic) -4.2 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 29.46 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 77.62 m3·mol-1 Chemaxon Polarizability 29.42 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.7116 Caco-2 permeable + 0.7888 P-glycoprotein substrate Substrate 0.6607 P-glycoprotein inhibitor I Inhibitor 0.6115 P-glycoprotein inhibitor II Inhibitor 0.6831 Renal organic cation transporter Non-inhibitor 0.8592 CYP450 2C9 substrate Non-substrate 0.7646 CYP450 2D6 substrate Non-substrate 0.8516 CYP450 3A4 substrate Substrate 0.6231 CYP450 1A2 substrate Non-inhibitor 0.6928 CYP450 2C9 inhibitor Inhibitor 0.5557 CYP450 2D6 inhibitor Non-inhibitor 0.8955 CYP450 2C19 inhibitor Inhibitor 0.7617 CYP450 3A4 inhibitor Non-inhibitor 0.6401 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6991 Ames test Non AMES toxic 0.808 Carcinogenicity Non-carcinogens 0.8703 Biodegradation Not ready biodegradable 0.9882 Rat acute toxicity 2.5436 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8987 hERG inhibition (predictor II) Non-inhibitor 0.8696
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0006-9850000000-2a09fad5d4c8ee1b6961 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-0490000000-b403896890256ab21987 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0090000000-ef45a69fa30bb69a87ec Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-7940000000-84433ab5e8c208c5e155 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4r-0790000000-b6b1f2536c1a517db95a Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-002r-3290000000-0f41abdf560da95dba85 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0k96-8940000000-7cddb98d80dc63c5485e 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]- 169.71483 predictedDeepCCS 1.0 (2019) [M+H]+ 172.1104 predictedDeepCCS 1.0 (2019) [M+Na]+ 178.02292 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 21:33 / Updated at June 12, 2020 16:52