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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:45 UTC
HMDB IDHMDB0014815
Secondary Accession Numbers
  • HMDB14815
Metabolite Identification
Common NameIsoflurophate
DescriptionIsoflurophate, also known as DFP or fluostigmine, belongs to the class of organic compounds known as phosphate esters. These are organic compounds containing phosphoric acid ester functional group, with the general structure R1P(=O)(R2)OR3. R1,R2 = O,N, or halogen atom; R3 = organyl group. Isoflurophate is a drug which is used for use in the eye to treat certain types of glaucoma and other eye conditions, such as accommodative esotropia. Based on a literature review very few articles have been published on Isoflurophate.
Structure
Data?1582753223
Synonyms
ValueSource
DFPChEBI
Diisopropoxyphosphoryl fluorideChEBI
Diisopropyl fluorophosphonateChEBI
Diisopropyl phosphofluoridateChEBI
Diisopropyl phosphorofluoridateChEBI
DiisopropylfluorophosphateChEBI
Diisopropylfluorophosphoric acid esterChEBI
DiisopropylphosphorofluoridateChEBI
Fluorodiisopropyl phosphateChEBI
IsofluorphateChEBI
IsoflurophosphateChEBI
Isopropyl fluophosphateChEBI
Isopropyl phosphorofluoridateChEBI
NeoglaucitChEBI
O,O'-diisopropyl phosphoryl fluorideChEBI
Diisopropyl fluorophosphateKegg
FluostigmineKegg
FloroprylKegg
Diisopropyl fluorophosphonic acidGenerator
Diisopropyl phosphofluoridic acidGenerator
Diisopropyl phosphorofluoridic acidGenerator
Diisopropylfluorophosphoric acidGenerator
Diisopropylfluorophosphate esterGenerator
Diisopropylphosphorofluoridic acidGenerator
Fluorodiisopropyl phosphoric acidGenerator
Isofluorphic acidGenerator
Isoflurophosphoric acidGenerator
Isopropyl fluophosphoric acidGenerator
Isopropyl phosphorofluoridic acidGenerator
Diisopropyl fluorophosphoric acidGenerator
Isoflurophic acidGenerator
DiflupylHMDB
DiflurophateHMDB
Di isopropylphosphorofluoridateHMDB
Merck brand OF isoflurophateHMDB
DiisopropylphosphofluoridateHMDB
FluorostigmineHMDB
Di-isopropylphosphorofluoridateHMDB
DyflosHMDB
Bis(1-methylethyl) phosphorofluoridateHMDB
IsoflurophateChEBI
Chemical FormulaC6H14FO3P
Average Molecular Weight184.1457
Monoisotopic Molecular Weight184.066459031
IUPAC Namebis(propan-2-yl) fluorophosphonate
Traditional Nameisoflurophate
CAS Registry Number55-91-4
SMILES
CC(C)OP(F)(=O)OC(C)C
InChI Identifier
InChI=1S/C6H14FO3P/c1-5(2)9-11(7,8)10-6(3)4/h5-6H,1-4H3
InChI KeyMUCZHBLJLSDCSD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phosphate esters. These are organic compounds containing phosphoric acid ester functional group, with the general structure R1P(=O)(R2)OR3. R1,R2 = O,N, or halogen atom; R3 = organyl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentPhosphate esters
Alternative Parents
Substituents
  • Phosphoric acid ester
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-82 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility6.78 g/LNot Available
LogP1.4Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.78 g/LALOGPS
logP1.1ALOGPS
logP1.76ChemAxon
logS-1.4ALOGPS
pKa (Strongest Basic)-9.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity40.89 m³·mol⁻¹ChemAxon
Polarizability16.75 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+140.15930932474
DeepCCS[M-H]-137.71830932474
DeepCCS[M-2H]-173.7430932474
DeepCCS[M+Na]+148.44430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IsoflurophateCC(C)OP(F)(=O)OC(C)C1378.5Standard polar33892256
IsoflurophateCC(C)OP(F)(=O)OC(C)C914.8Standard non polar33892256
IsoflurophateCC(C)OP(F)(=O)OC(C)C944.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isoflurophate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-5900000000-a89a631cb99168cf7ba02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoflurophate 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 - Isoflurophate 10V, Positive-QTOFsplash10-0udi-0900000000-5e57a55b5606aff19a9d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoflurophate 20V, Positive-QTOFsplash10-0udi-0900000000-f3d7a1b314068a05a4582016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoflurophate 40V, Positive-QTOFsplash10-0udi-4900000000-6b6d965cf006e47449f62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoflurophate 10V, Negative-QTOFsplash10-001i-0900000000-8dbbf0233439055f133a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoflurophate 20V, Negative-QTOFsplash10-0759-1900000000-7937b3536f2dc54c0c292016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoflurophate 40V, Negative-QTOFsplash10-000t-9200000000-1d33f0f21ddbdd2b7c0f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoflurophate 10V, Positive-QTOFsplash10-0006-4900000000-ede71f832a76c9c97c9f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoflurophate 20V, Positive-QTOFsplash10-0udl-6900000000-7cf48245983466f2c5892021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoflurophate 40V, Positive-QTOFsplash10-0006-9000000000-592d7b59484aa24b43c92021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoflurophate 10V, Negative-QTOFsplash10-001i-0900000000-a2542f139983a30b47182021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoflurophate 20V, Negative-QTOFsplash10-00dl-0900000000-da1ecfccef442de7cb492021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoflurophate 40V, Negative-QTOFsplash10-00di-0900000000-59f087ea748c7270dfbb2021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00677 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00677 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00677
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5723
KEGG Compound IDC00202
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsoflurophate
METLIN IDNot Available
PubChem Compound5936
PDB IDNot Available
ChEBI ID17941
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in carboxylesterase activity
Specific function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular weight:
67795.525
References
  1. Malatova Z, Gottlieb M, Marsala J: Depression of acetylcholinesterase synthesis following transient cerebral ischemia in rat: pharmacohistochemical and biochemical investigation. Gen Physiol Biophys. 1999 Mar;18(1):57-71. [PubMed:10378121 ]
  2. Quistad GB, Zhang N, Sparks SE, Casida JE: Phosphoacetylcholinesterase: toxicity of phosphorus oxychloride to mammals and insects that can be attributed to selective phosphorylation of acetylcholinesterase by phosphorodichloridic acid. Chem Res Toxicol. 2000 Jul;13(7):652-7. [PubMed:10898598 ]
  3. da Costa VL Jr, Lapa AJ, Godinho RO: Short- and long-term influences of calcitonin gene-related peptide on the synthesis of acetylcholinesterase in mammalian myotubes. Br J Pharmacol. 2001 May;133(2):229-36. [PubMed:11350858 ]
  4. Pang YP, Kollmeyer TM, Hong F, Lee JC, Hammond PI, Haugabouk SP, Brimijoin S: Rational design of alkylene-linked bis-pyridiniumaldoximes as improved acetylcholinesterase reactivators. Chem Biol. 2003 Jun;10(6):491-502. [PubMed:12837382 ]
  5. Ashani Y, Gentry MK, Doctor BP: Differences in conformational stability between native and phosphorylated acetylcholinesterase as evidenced by a monoclonal antibody. Biochemistry. 1990 Mar 13;29(10):2456-63. [PubMed:1692236 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in carboxylesterase activity
Specific function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular weight:
68417.575
References
  1. Kamata R, Saito S, Suzuki T, Takewaki T, Kobayashi H: Correlation of binding sites for diisopropyl phosphorofluoridate with cholinesterase and neuropathy target esterase in membrane and cytosol preparations from hen. Neurotoxicology. 2001 Apr;22(2):203-14. [PubMed:11405252 ]
  2. Acey RA, Bailey S, Healy P, Jo C, Unger TF, Hudson RA: A butyrylcholinesterase in the early development of the brine shrimp (Artemia salina) larvae: a target for phthalate ester embryotoxicity? Biochem Biophys Res Commun. 2002 Dec 13;299(4):659-62. [PubMed:12459190 ]
  3. Pittel Z, Cohen S, Fisher A, Heldman E: Differential long-term effect of AF64A on [3H]ACh synthesis and release in rat hippocampal synaptosomes. Brain Res. 1992 Jul 17;586(1):148-51. [PubMed:1511344 ]
  4. Miller RB, Blank CL: Determination of serum cholinesterase activity by liquid chromatography with electrochemical detection. Anal Biochem. 1991 Aug 1;196(2):377-84. [PubMed:1776688 ]
  5. Kelly SS, Ferry CB, Bamforth JP: The effects of anticholinesterases on the latencies of action potentials in mouse skeletal muscles. Br J Pharmacol. 1990 Apr;99(4):721-6. [PubMed:2361169 ]
  6. Masson P, Fortier PL, Albaret C, Froment MT, Bartels CF, Lockridge O: Aging of di-isopropyl-phosphorylated human butyrylcholinesterase. Biochem J. 1997 Oct 15;327 ( Pt 2):601-7. [PubMed:9359435 ]