(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

Status : experimental

Chemical Classification

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.

Iridoids and derivatives

Organic compounds

Lipids and lipid-like molecules

Prenol lipids

Monoterpenoids

Calculated Property

kind Value Source
logP 5.22 ALOGPS
logS -5.7 ALOGPS
Water Solubility 1.07e-03 g/l ALOGPS
logP 4.98 ChemAxon
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 ChemAxon
Traditional 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 ChemAxon
Molecular Weight 482.4995 ChemAxon
Monoisotopic Weight 482.22556412 ChemAxon
SMILES [H][C@]1(CC[C@](C)(CCC#CC(O)(C(F)(F)F)C(F)(F)F)C1(C)C)C=CC=C1C[C@](O)([H])C[C@@](O)([H])C1 ChemAxon
Molecular Formula C24H32F6O3 ChemAxon
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 ChemAxon
InChIKey InChIKey=PCHUQQNKOFNVDU-OSXMSNBXSA-N ChemAxon
Polar Surface Area (PSA) 60.69 ChemAxon
Refractivity 115.82 ChemAxon
Polarizability 45.78 ChemAxon
Rotatable Bond Count 8 ChemAxon
H Bond Acceptor Count 3 ChemAxon
H Bond Donor Count 3 ChemAxon
pKa (strongest acidic) 6.43 ChemAxon
pKa (strongest basic) -2.7 ChemAxon
Physiological Charge -1 ChemAxon
Number of Rings 2 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five 1 ChemAxon
Ghose Filter 0 ChemAxon
MDDR-Like Rule 0 ChemAxon

Target within organism

  • Nuclear receptor coactivator 1 : in Human
  • Vitamin D3 receptor : in Human