(1R,3R)-5-[(2E)-3-{(1S,3R)-2,2,3-trimethyl-3-[6,6,6-trifluoro-5-hydroxy-5-(trifluoromethyl)hex-3-yn-1-yl]cyclopentyl}prop-2-en-1-ylidene]cyclohexane-1,3-diol
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Identification
- Generic Name
- (1R,3R)-5-[(2E)-3-{(1S,3R)-2,2,3-trimethyl-3-[6,6,6-trifluoro-5-hydroxy-5-(trifluoromethyl)hex-3-yn-1-yl]cyclopentyl}prop-2-en-1-ylidene]cyclohexane-1,3-diol
- DrugBank Accession Number
- DB07530
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 482.4995
Monoisotopic: 482.22556412 - Chemical Formula
- C24H32F6O3
- 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 iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Prenol lipids
- Sub Class
- Monoterpenoids
- Direct Parent
- Iridoids and derivatives
- Alternative Parents
- Monocyclic monoterpenoids / Ynones / Tertiary alcohols / Secondary alcohols / Fluorohydrins / Cyclic alcohols and derivatives / Organofluorides / Hydrocarbon derivatives / Alkyl fluorides
- Substituents
- 11-noriridane monoterpenoid / Alcohol / Aliphatic homomonocyclic compound / Alkyl fluoride / Alkyl halide / Cyclic alcohol / Fluorohydrin / Halohydrin / Hydrocarbon derivative / Monocyclic monoterpenoid
- Molecular Framework
- Aliphatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- PCHUQQNKOFNVDU-OSXMSNBXSA-N
- InChI
- InChI=1S/C24H32F6O3/c1-20(2)17(8-6-7-16-13-18(31)15-19(32)14-16)9-12-21(20,3)10-4-5-11-22(33,23(25,26)27)24(28,29)30/h6-8,17-19,31-33H,4,9-10,12-15H2,1-3H3/b8-6+/t17-,18-,19-,21+/m1/s1
- IUPAC Name
- (1R,3R)-5-[(2E)-3-[(1S,3R)-2,2,3-trimethyl-3-[6,6,6-trifluoro-5-hydroxy-5-(trifluoromethyl)hex-3-yn-1-yl]cyclopentyl]prop-2-en-1-ylidene]cyclohexane-1,3-diol
- SMILES
- [H][C@]1(CC[C@](C)(CCC#CC(O)(C(F)(F)F)C(F)(F)F)C1(C)C)\C=C\C=C1C[C@](O)([H])C[C@@](O)([H])C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 10457944
- PubChem Substance
- 99444001
- ChemSpider
- 8633358
- ZINC
- ZINC000038911928
- PDBe Ligand
- C5D
- PDB Entries
- 3dr1
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 0.00107 mg/mL ALOGPS logP 5.22 ALOGPS logP 4.98 Chemaxon logS -5.6 ALOGPS pKa (Strongest Acidic) 6.43 Chemaxon pKa (Strongest Basic) -2.7 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 60.69 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 115.82 m3·mol-1 Chemaxon Polarizability 45.59 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9949 Blood Brain Barrier + 0.9087 Caco-2 permeable + 0.6534 P-glycoprotein substrate Substrate 0.6085 P-glycoprotein inhibitor I Non-inhibitor 0.7684 P-glycoprotein inhibitor II Non-inhibitor 0.7345 Renal organic cation transporter Non-inhibitor 0.9038 CYP450 2C9 substrate Non-substrate 0.8331 CYP450 2D6 substrate Non-substrate 0.861 CYP450 3A4 substrate Substrate 0.6768 CYP450 1A2 substrate Non-inhibitor 0.8298 CYP450 2C9 inhibitor Non-inhibitor 0.6685 CYP450 2D6 inhibitor Non-inhibitor 0.9054 CYP450 2C19 inhibitor Non-inhibitor 0.6469 CYP450 3A4 inhibitor Non-inhibitor 0.6447 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5091 Ames test Non AMES toxic 0.6651 Carcinogenicity Non-carcinogens 0.82 Biodegradation Not ready biodegradable 0.9973 Rat acute toxicity 3.8675 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8714 hERG inhibition (predictor II) Non-inhibitor 0.8407
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-053u-0125900000-44952b7fadc85433d1c5 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0000900000-a311db3937d74fbd7888 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-01q9-2001900000-19774495fb619249a50d Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4l-0361900000-ed698dc446582a2435fa Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0f7w-2612900000-19a3f4c000ea142c092a Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-0910000000-657dc2cb70b828d01b62 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]- 194.75471 predictedDeepCCS 1.0 (2019) [M+H]+ 197.15028 predictedDeepCCS 1.0 (2019) [M+Na]+ 203.04256 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 21:23 / Updated at June 12, 2020 16:52