Fluprostenol (CHEM018753)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:30:21 UTC
Update Date2016-11-09 01:15:52 UTC
Accession NumberCHEM018753
Identification
Common NameFluprostenol
ClassSmall Molecule
DescriptionAn organofluorine compound that is racemic prostaglandin F2alpha in which the pentyl group is replaced by a 3-(trifluoromethyl)phenoxymethyl group. A synthetic analogue of prostaglandin F2alpha, ophthalmic solutions of its isopropyl ester prodrug, travoprost, are used as a topical medication for controlling the progression of open-angle glaucoma and ocular hypertension, by reducing intraocular pressure. The isopropyl ester group of travoprost is hydrolysed to the biologically active free acid by esterases in the cornea.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
EINECS 255-029-3ChEBI
FluprostenolumChEBI
ICI 81,008ChEBI
Travoprost acidChEBI
Travoprost free acidChEBI
Fluprostenol, ((1alpha(Z),2beta(1E,3R*),3alpha,5alpha)-(+-))-isomerMeSH
Fluprostenol monosodium saltMeSH
Fluprostenol, ((1R-(1alpha(Z),2beta(1E,3R*),3alpha,5alpha))-(+-))-isomerMeSH
(Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(e,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-enyl]cyclopentyl]hept-5-enoateGenerator
FluprostenolMeSH
Chemical FormulaC23H29F3O6
Average Molecular Mass458.474 g/mol
Monoisotopic Mass458.192 g/mol
CAS Registry Number40666-16-8
IUPAC Name(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-en-1-yl]cyclopentyl]hept-5-enoic acid
Traditional Name(+)-fluprostenol
SMILES[H]\C(CCCC(O)=O)=C(/[H])C[C@@]1([H])[C@@]([H])(O)C[C@@]([H])(O)[C@]1([H])C(\[H])=C(/[H])[C@@]([H])(O)COC1=CC=CC(=C1)C(F)(F)F
InChI IdentifierInChI=1S/C23H29F3O6/c24-23(25,26)15-6-5-7-17(12-15)32-14-16(27)10-11-19-18(20(28)13-21(19)29)8-3-1-2-4-9-22(30)31/h1,3,5-7,10-12,16,18-21,27-29H,2,4,8-9,13-14H2,(H,30,31)/b3-1-,11-10+/t16-,18-,19-,20+,21-/m1/s1
InChI KeyWWSWYXNVCBLWNZ-QIZQQNKQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative Parents
Substituents
  • Prostaglandin skeleton
  • Long-chain fatty acid
  • Trifluoromethylbenzene
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Halogenated fatty acid
  • Hydroxy fatty acid
  • Monocyclic benzene moiety
  • Fatty acid
  • Benzenoid
  • Unsaturated fatty acid
  • Cyclopentanol
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Alkyl fluoride
  • Organofluoride
  • Organohalogen compound
  • Alkyl halide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.016 g/LALOGPS
logP3.39ALOGPS
logP2.92ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity113.92 m³·mol⁻¹ChemAxon
Polarizability44.7 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0010900000-4684394dbc817873f84fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0229-0388900000-929860f48d5c3fda197eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-3931000000-3379e32347ab999d00a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-0410900000-2a880966f74d70adc4ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0910100000-c6fd6708023d45985baaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0900000000-93aa104ef86f4c51afccSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB11519
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID60782
PubChem Compound ID5311100
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11832489
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11929662
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=550147
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=6090118
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=6911921
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=6916556
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=941381
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=951924