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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:01:37 UTC
Update Date2017-10-23 19:06:15 UTC
HMDB IDHMDB0014256
Secondary Accession Numbers
  • HMDB14256
Metabolite Identification
Common NameTafluprost free acid
DescriptionTafluprost free acid is only found in individuals that have used or taken Tafluprost. Tafluprost free acid is a metabolite of Tafluprost. Tafluprost free acid belongs to the family of Halogenated Fatty Acids. These are fatty acids contaning an halogen atom (Cl,F,I,Br).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC22H28F2O5
Average Molecular Weight410.4515
Monoisotopic Molecular Weight410.190480416
IUPAC Name(5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoic acid
Traditional Name(5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoic acid
CAS Registry NumberNot Available
SMILES
OC1CC(O)C(\C=C\C(F)(F)COC2=CC=CC=C2)C1C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C22H28F2O5/c23-22(24,15-29-16-8-4-3-5-9-16)13-12-18-17(19(25)14-20(18)26)10-6-1-2-7-11-21(27)28/h1,3-6,8-9,12-13,17-20,25-26H,2,7,10-11,14-15H2,(H,27,28)/b6-1-,13-12+
InChI KeyKIQXRQVVYTYYAZ-MTNCBHNASA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentProstaglandins and related compounds
Alternative Parents
Substituents
  • Prostaglandin skeleton
  • Long-chain fatty acid
  • 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
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organohalogen compound
  • Organofluoride
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Alkyl halide
  • Alkyl fluoride
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Route of exposure:

  Enteral:

Role

Biological role:

  Modulator:

Industrial application:

  Pharmaceutical industry:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

    Multicellular process:

    Cellular process:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.034 g/LALOGPS
logP3.42ALOGPS
logP3.37ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity106.65 m³·mol⁻¹ChemAxon
Polarizability42 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014r-1219000000-8e1ec65ae01361e172d1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03di-5500489000-95bafbabe02fb2fdaf57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002g-1029100000-204ed18144108c4fbbb2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002e-1229000000-25077f9e4ce508bf95e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000b-9260000000-076c2111abf02e5ae67bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9002200000-c00792117fdb4db5e3efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9001000000-08fd3ce154d6769f5222View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9110000000-0e95f48713dae3d60241View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00481
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID21467507
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for prostaglandin F2-alpha (PGF2-alpha). The activity of this receptor is mediated by G proteins which activate a phosphatidylinositol-calcium second messenger system. Initiates luteolysis in the corpus luteum
Gene Name:
PTGFR
Uniprot ID:
P43088
Molecular weight:
40054.1
References
  1. 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 ]