(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

Identification

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
Accession Number
DB07530
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 482.4995
Monoisotopic: 482.22556412
Chemical Formula
C24H32F6O3
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][[email protected]]1(CC[[email protected]](C)(CCC#CC(O)(C(F)(F)F)C(F)(F)F)C1(C)C)\C=C\C=C1C[[email protected]](O)([H])C[[email protected]@](O)([H])C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UNuclear receptor coactivator 1Not AvailableHuman
UVitamin D3 receptorNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
10457944
PubChem Substance
99444001
ChemSpider
8633358
HET
C5D
PDB Entries
3dr1

Clinical Trials

Clinical Trials
Not Available

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
PropertyValueSource
Water Solubility0.00107 mg/mLALOGPS
logP5.22ALOGPS
logP4.98ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)6.43ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity115.82 m3·mol-1ChemAxon
Polarizability45.78 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9949
Blood Brain Barrier+0.9087
Caco-2 permeable+0.6534
P-glycoprotein substrateSubstrate0.6085
P-glycoprotein inhibitor INon-inhibitor0.7684
P-glycoprotein inhibitor IINon-inhibitor0.7345
Renal organic cation transporterNon-inhibitor0.9038
CYP450 2C9 substrateNon-substrate0.8331
CYP450 2D6 substrateNon-substrate0.861
CYP450 3A4 substrateSubstrate0.6768
CYP450 1A2 substrateNon-inhibitor0.8298
CYP450 2C9 inhibitorNon-inhibitor0.6685
CYP450 2D6 inhibitorNon-inhibitor0.9054
CYP450 2C19 inhibitorNon-inhibitor0.6469
CYP450 3A4 inhibitorNon-inhibitor0.6447
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5091
Ames testNon AMES toxic0.6651
CarcinogenicityNon-carcinogens0.82
BiodegradationNot ready biodegradable0.9973
Rat acute toxicity3.8675 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8714
hERG inhibition (predictor II)Non-inhibitor0.8407
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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 / Monocyclic monoterpenoid / Ynone / Cyclic alcohol / Tertiary alcohol / Halohydrin / Fluorohydrin / Secondary alcohol / Organooxygen compound / Organofluoride
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transcription coactivator activity
Specific 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 re...
Gene Name
NCOA1
Uniprot ID
Q15788
Uniprot Name
Nuclear receptor coactivator 1
Molecular Weight
156755.44 Da
References
  1. 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. Transcription factor that mediates the action of vitamin D3 by controlling the expression of hormone sensitive genes. Recruited to promoters via its interaction with BAZ1B...
Gene Name
VDR
Uniprot ID
P11473
Uniprot Name
Vitamin D3 receptor
Molecular Weight
48288.64 Da
References
  1. 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. [PubMed:10592235]

Drug created on September 15, 2010 15:23 / Updated on December 01, 2017 15:52