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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:05 UTC
HMDB IDHMDB0015704
Secondary Accession Numbers
  • HMDB15704
Metabolite Identification
Common NameTafluprost
DescriptionTafluprost is only found in individuals that have used or taken this drug. It is a prostaglandin analogue used topically (as eye drops) to control the progression of glaucoma and in the management of ocular hypertension. Tafluprost was approved for use in the U.S. on February 10, 2012.Tafluprost is a prostaglandin F2a analogue. Specifically, Tafluprost is a prostanoid selective FP receptor agonist that is believed to reduce the intraocular pressure (IOP) by increasing the outflow of aqueous humor. Studies in animals and man suggest that the main mechanism of action is increased uveoscleral outflow.
Structure
Data?1582753325
Synonyms
ValueSource
ZioptanChEBI
AFP-168HMDB
SaflutanHMDB
1-Methylethyl (5Z)-7-((1R,2R, 3R,5S)-2-((1E)-3,3-difluoro-4-phenoxy -1-butenyl)-3,5-dihydroxycyclopentyl)-5-heptenoateHMDB
Chemical FormulaC25H34F2O5
Average Molecular Weight452.5313
Monoisotopic Molecular Weight452.237430608
IUPAC Namepropan-2-yl (5Z)-7-[(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl]hept-5-enoate
Traditional Nametafluprost
CAS Registry Number209860-87-7
SMILES
CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\C(F)(F)COC1=CC=CC=C1
InChI Identifier
InChI=1S/C25H34F2O5/c1-18(2)32-24(30)13-9-4-3-8-12-20-21(23(29)16-22(20)28)14-15-25(26,27)17-31-19-10-6-5-7-11-19/h3,5-8,10-11,14-15,18,20-23,28-29H,4,9,12-13,16-17H2,1-2H3/b8-3-,15-14+/t20-,21-,22+,23-/m1/s1
InChI KeyWSNODXPBBALQOF-VEJSHDCNSA-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
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Fatty acid ester
  • Benzenoid
  • Monocyclic benzene moiety
  • Cyclopentanol
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Organooxygen compound
  • Alkyl fluoride
  • Alcohol
  • Organohalogen compound
  • Organofluoride
  • Carbonyl group
  • Hydrocarbon derivative
  • Alkyl halide
  • Organic oxygen compound
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0053 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0053 g/LALOGPS
logP4.46ALOGPS
logP4.29ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)14.51ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity120.59 m³·mol⁻¹ChemAxon
Polarizability48.65 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+213.34730932474
DeepCCS[M-H]-211.06830932474
DeepCCS[M-2H]-244.30830932474
DeepCCS[M+Na]+219.25930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TafluprostCC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\C(F)(F)COC1=CC=CC=C13913.9Standard polar33892256
TafluprostCC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\C(F)(F)COC1=CC=CC=C12953.1Standard non polar33892256
TafluprostCC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\C(F)(F)COC1=CC=CC=C13034.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tafluprost,1TMS,isomer #1CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C)C[C@@H](O)[C@@H]1/C=C/C(F)(F)COC1=CC=CC=C12891.4Semi standard non polar33892256
Tafluprost,1TMS,isomer #2CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O[Si](C)(C)C)[C@@H]1/C=C/C(F)(F)COC1=CC=CC=C12901.4Semi standard non polar33892256
Tafluprost,2TMS,isomer #1CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@H]1/C=C/C(F)(F)COC1=CC=CC=C12877.4Semi standard non polar33892256
Tafluprost,1TBDMS,isomer #1CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H]1/C=C/C(F)(F)COC1=CC=CC=C13098.7Semi standard non polar33892256
Tafluprost,1TBDMS,isomer #2CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1/C=C/C(F)(F)COC1=CC=CC=C13111.0Semi standard non polar33892256
Tafluprost,2TBDMS,isomer #1CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1/C=C/C(F)(F)COC1=CC=CC=C13277.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tafluprost GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-4439700000-5f902e96f572f76cc5932017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tafluprost GC-MS (2 TMS) - 70eV, Positivesplash10-001l-7200690000-8373b0788e1ed396a7fa2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tafluprost GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tafluprost 10V, Positive-QTOFsplash10-00kv-3015900000-c886925c3b2c359329fb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tafluprost 20V, Positive-QTOFsplash10-03dj-6119200000-4d3efe181e45c7a457c42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tafluprost 40V, Positive-QTOFsplash10-03dj-9011000000-010b663ce499bf30d9482016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tafluprost 10V, Negative-QTOFsplash10-0006-9000200000-0e451520fe294c5b8f6b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tafluprost 20V, Negative-QTOFsplash10-0006-9000000000-36b6f74a5c34571e3a782016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tafluprost 40V, Negative-QTOFsplash10-0a4l-9000000000-921114351b038266dd2e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tafluprost 10V, Positive-QTOFsplash10-0py3-0019500000-5b4599f3f7676f5d531e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tafluprost 20V, Positive-QTOFsplash10-00mo-2119200000-d5684e822eb13b29e9b92021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tafluprost 40V, Positive-QTOFsplash10-0561-9610000000-eb4fe1a3cbe0fdfe9daa2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tafluprost 10V, Negative-QTOFsplash10-0006-9000400000-706df0cdfeceb3c1bf1a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tafluprost 20V, Negative-QTOFsplash10-0006-9000000000-f096008f6b882e68cef42021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tafluprost 40V, Negative-QTOFsplash10-0006-9000000000-08485aaf085c13d5129a2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB08819 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB08819 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08819
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8044182
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTafluprost
METLIN IDNot Available
PubChem Compound9868491
PDB IDNot Available
ChEBI ID66899
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1799771
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Takagi Y, Nakajima T, Shimazaki A, Kageyama M, Matsugi T, Matsumura Y, Gabelt BT, Kaufman PL, Hara H: Pharmacological characteristics of AFP-168 (tafluprost), a new prostanoid FP receptor agonist, as an ocular hypotensive drug. Exp Eye Res. 2004 Apr;78(4):767-76. [PubMed:15037111 ]
  2. Pantcheva MB, Seibold LK, Awadallah NS, Kahook MY: Tafluprost: a novel prostaglandin analog for treatment of glaucoma. Adv Ther. 2011 Sep;28(9):707-15. doi: 10.1007/s12325-011-0055-8. Epub 2011 Aug 18. [PubMed:21858491 ]
  3. Fukano Y, Kawazu K: Disposition and metabolism of a novel prostanoid antiglaucoma medication, tafluprost, following ocular administration to rats. Drug Metab Dispos. 2009 Aug;37(8):1622-34. doi: 10.1124/dmd.108.024885. Epub 2009 May 28. [PubMed:19477946 ]
  4. Papadia M, Bagnis A, Scotto R, Traverso CE: Tafluprost for glaucoma. Expert Opin Pharmacother. 2011 Oct;12(15):2393-401. doi: 10.1517/14656566.2011.606810. [PubMed:21916788 ]
  5. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  6. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  7. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  8. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  9. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.