1,3-CYCLOHEXANEDIOL, 4-METHYLENE-5-[(2E)-[(1S,3AS,7AS)-OCTAHYDRO-1-(5-HYDROXY-5-METHYL-1,3-HEXADIYNYL)-7A-METHYL-4H-INDEN-4-YLIDENE]ETHYLIDENE]-, (1R,3S,5Z)
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Identification
- Generic Name
- 1,3-CYCLOHEXANEDIOL, 4-METHYLENE-5-[(2E)-[(1S,3AS,7AS)-OCTAHYDRO-1-(5-HYDROXY-5-METHYL-1,3-HEXADIYNYL)-7A-METHYL-4H-INDEN-4-YLIDENE]ETHYLIDENE]-, (1R,3S,5Z)
- DrugBank Accession Number
- DB08742
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 394.5464
Monoisotopic: 394.250794954 - Chemical Formula
- C26H34O3
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UNuclear receptor coactivator 1 Not Available Humans UVitamin D3 receptor 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 steroids and steroid derivatives. These are compounds based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated; there are usually methyl groups at C-10 and C-13, and often an alkyl group at C-17. By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Not Available
- Direct Parent
- Steroids and steroid derivatives
- Alternative Parents
- Ynones / Tertiary alcohols / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
- Substituents
- Alcohol / Aliphatic homopolycyclic compound / Cyclic alcohol / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Secondary alcohol / Steroid / Tertiary alcohol / Ynone
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- CEEUUHVULXTFGS-BQXVGYHGSA-N
- InChI
- InChI=1S/C26H34O3/c1-18-20(16-22(27)17-24(18)28)11-10-19-8-7-15-26(4)21(12-13-23(19)26)9-5-6-14-25(2,3)29/h10-11,21-24,27-29H,1,7-8,12-13,15-17H2,2-4H3/b19-10+,20-11-/t21-,22+,23-,24-,26+/m0/s1
- IUPAC Name
- (1R,3S,5Z)-5-{2-[(1S,3aS,4E,7aS)-1-(5-hydroxy-5-methylhexa-1,3-diyn-1-yl)-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
- SMILES
- C=C1\C(=C/C=C2\CCC[C@]3(C)[C@]([H])(CC[C@@]23[H])C#CC#CC(C)(O)C)C[C@](O)([H])C[C@@]1(O)[H]
References
- General References
- Not Available
- External Links
- PubChem Compound
- 11269429
- PubChem Substance
- 99445213
- ChemSpider
- 9444440
- ZINC
- ZINC000058660808
- PDBe Ligand
- XE4
- PDB Entries
- 2hbh
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
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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 0.00898 mg/mL ALOGPS logP 4.52 ALOGPS logP 3.39 Chemaxon logS -4.6 ALOGPS pKa (Strongest Acidic) 14.06 Chemaxon pKa (Strongest Basic) -2.8 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 60.69 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 120.55 m3·mol-1 Chemaxon Polarizability 46.99 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 + 0.9812 Blood Brain Barrier + 0.7486 Caco-2 permeable + 0.7708 P-glycoprotein substrate Substrate 0.7566 P-glycoprotein inhibitor I Non-inhibitor 0.6002 P-glycoprotein inhibitor II Non-inhibitor 0.8568 Renal organic cation transporter Non-inhibitor 0.857 CYP450 2C9 substrate Non-substrate 0.8186 CYP450 2D6 substrate Non-substrate 0.9026 CYP450 3A4 substrate Substrate 0.7574 CYP450 1A2 substrate Non-inhibitor 0.7994 CYP450 2C9 inhibitor Non-inhibitor 0.7723 CYP450 2D6 inhibitor Non-inhibitor 0.9341 CYP450 2C19 inhibitor Non-inhibitor 0.6107 CYP450 3A4 inhibitor Non-inhibitor 0.6819 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.591 Ames test Non AMES toxic 0.9325 Carcinogenicity Non-carcinogens 0.8856 Biodegradation Not ready biodegradable 0.9962 Rat acute toxicity 4.6385 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9182 hERG inhibition (predictor II) Non-inhibitor 0.8643
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-05r0-0039000000-d3017b4314857a452d15 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-052f-0009000000-abdcdda61413e09801df Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-0192000000-90792ba3d22173295b83 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00tf-1009000000-b61b806d9e431e09cfe2 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0ap1-7965000000-12b9c6dca0785c559a97 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0avi-1419000000-a491a5067fa41b6a6392 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]- 182.13663 predictedDeepCCS 1.0 (2019) [M+H]+ 183.96152 predictedDeepCCS 1.0 (2019) [M+Na]+ 189.69453 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsNuclear receptor coactivator 1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Nuclear receptor coactivator that directly binds nuclear receptors and stimulates the transcriptional activities in a hormone-dependent fashion. Involved in the coactivation of different nuclear receptors, such as for steroids (PGR, GR and ER), retinoids (RXRs), thyroid hormone (TRs) and prostanoids (PPARs). Also involved in coactivation mediated by STAT3, STAT5A, STAT5B and STAT6 transcription factors. Displays histone acetyltransferase activity toward H3 and H4; the relevance of such activity remains however unclear. Plays a central role in creating multisubunit coactivator complexes that act via remodeling of chromatin, and possibly acts by participating in both chromatin remodeling and recruitment of general transcription factors. Required with NCOA2 to control energy balance between white and brown adipose tissues. Required for mediating steroid hormone response. Isoform 2 has a higher thyroid hormone-dependent transactivation activity than isoform 1 and isoform 3
- Specific Function
- chromatin binding
- Gene Name
- NCOA1
- Uniprot ID
- Q15788
- Uniprot Name
- Nuclear receptor coactivator 1
- Molecular Weight
- 156755.44 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. DetailsVitamin D3 receptor
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Nuclear receptor for calcitriol, the active form of vitamin D3 which mediates the action of this vitamin on cells (PubMed:10678179, PubMed:15728261, PubMed:16913708, PubMed:28698609, PubMed:37478846). Enters the nucleus upon vitamin D3 binding where it forms heterodimers with the retinoid X receptor/RXR (PubMed:28698609). The VDR-RXR heterodimers bind to specific response elements on DNA and activate the transcription of vitamin D3-responsive target genes (PubMed:28698609). Plays a central role in calcium homeostasis (By similarity). Also functions as a receptor for the secondary bile acid lithocholic acid (LCA) and its metabolites (PubMed:12016314, PubMed:32354638)
- Specific Function
- bile acid nuclear receptor activity
- Gene Name
- VDR
- Uniprot ID
- P11473
- Uniprot Name
- Vitamin D3 receptor
- Molecular Weight
- 48288.64 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 21:34 / Updated at June 12, 2020 16:52