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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

enzymes (2) Show 2 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2023-02-21 17:18:17 UTC

HMDB ID

HMDB0014815

Secondary Accession Numbers

HMDB14815

Metabolite Identification

Common Name

Isoflurophate

Description

Isoflurophate, 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
DFP	ChEBI
Diisopropoxyphosphoryl fluoride	ChEBI
Diisopropyl fluorophosphonate	ChEBI
Diisopropyl phosphofluoridate	ChEBI
Diisopropyl phosphorofluoridate	ChEBI
Diisopropylfluorophosphate	ChEBI
Diisopropylfluorophosphoric acid ester	ChEBI
Diisopropylphosphorofluoridate	ChEBI
Fluorodiisopropyl phosphate	ChEBI
Isofluorphate	ChEBI
Isoflurophosphate	ChEBI
Isopropyl fluophosphate	ChEBI
Isopropyl phosphorofluoridate	ChEBI
Neoglaucit	ChEBI
O,O'-diisopropyl phosphoryl fluoride	ChEBI
Diisopropyl fluorophosphate	Kegg
Fluostigmine	Kegg
Floropryl	Kegg
Diisopropyl fluorophosphonic acid	Generator
Diisopropyl phosphofluoridic acid	Generator
Diisopropyl phosphorofluoridic acid	Generator
Diisopropylfluorophosphoric acid	Generator
Diisopropylfluorophosphate ester	Generator
Diisopropylphosphorofluoridic acid	Generator
Fluorodiisopropyl phosphoric acid	Generator
Isofluorphic acid	Generator
Isoflurophosphoric acid	Generator
Isopropyl fluophosphoric acid	Generator
Isopropyl phosphorofluoridic acid	Generator
Diisopropyl fluorophosphoric acid	Generator
Isoflurophic acid	Generator
Diflupyl	HMDB
Diflurophate	HMDB
Di isopropylphosphorofluoridate	HMDB
Merck brand OF isoflurophate	HMDB
Diisopropylphosphofluoridate	HMDB
Fluorostigmine	HMDB
Di-isopropylphosphorofluoridate	HMDB
Dyflos	HMDB
Bis(1-methylethyl) phosphorofluoridate	HMDB
Isoflurophate	ChEBI

Chemical Formula

C₆H₁₄FO₃P

Average Molecular Weight

184.1457

Monoisotopic Molecular Weight

184.066459031

IUPAC Name

bis(propan-2-yl) fluorophosphonate

Traditional Name

isoflurophate

CAS Registry Number

55-91-4

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 Key

MUCZHBLJLSDCSD-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Phosphate esters

Alternative Parents

Substituents

Phosphoric acid ester
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dialkyl phosphate (CHEBI:17941 )
a small molecule (DIISOPROPYL-FLUOROPHOSPHATE )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0014815)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-82 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	6.78 g/L	Not Available
LogP	1.4	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.78 g/L	ALOGPS
logP	1.1	ALOGPS
logP	1.76	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Basic)	-9.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	40.89 m³·mol⁻¹	ChemAxon
Polarizability	16.75 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	140.159	30932474
DeepCCS	[M-H]-	137.718	30932474
DeepCCS	[M-2H]-	173.74	30932474
DeepCCS	[M+Na]+	148.444	30932474
AllCCS	[M+H]+	142.1	32859911
AllCCS	[M+H-H2O]+	138.5	32859911
AllCCS	[M+NH4]+	145.5	32859911
AllCCS	[M+Na]+	146.5	32859911
AllCCS	[M-H]-	138.8	32859911
AllCCS	[M+Na-2H]-	141.1	32859911
AllCCS	[M+HCOO]-	143.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isoflurophate	CC(C)OP(F)(=O)OC(C)C	1378.5	Standard polar	33892256
Isoflurophate	CC(C)OP(F)(=O)OC(C)C	914.8	Standard non polar	33892256
Isoflurophate	CC(C)OP(F)(=O)OC(C)C	944.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isoflurophate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-5900000000-a89a631cb99168cf7ba0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoflurophate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoflurophate 10V, Positive-QTOF	splash10-0udi-0900000000-5e57a55b5606aff19a9d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoflurophate 20V, Positive-QTOF	splash10-0udi-0900000000-f3d7a1b314068a05a458	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoflurophate 40V, Positive-QTOF	splash10-0udi-4900000000-6b6d965cf006e47449f6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoflurophate 10V, Negative-QTOF	splash10-001i-0900000000-8dbbf0233439055f133a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoflurophate 20V, Negative-QTOF	splash10-0759-1900000000-7937b3536f2dc54c0c29	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoflurophate 40V, Negative-QTOF	splash10-000t-9200000000-1d33f0f21ddbdd2b7c0f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoflurophate 10V, Positive-QTOF	splash10-0006-4900000000-ede71f832a76c9c97c9f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoflurophate 20V, Positive-QTOF	splash10-0udl-6900000000-7cf48245983466f2c589	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoflurophate 40V, Positive-QTOF	splash10-0006-9000000000-592d7b59484aa24b43c9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoflurophate 10V, Negative-QTOF	splash10-001i-0900000000-a2542f139983a30b4718	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoflurophate 20V, Negative-QTOF	splash10-00dl-0900000000-da1ecfccef442de7cb49	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoflurophate 40V, Negative-QTOF	splash10-00di-0900000000-59f087ea748c7270dfbb	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00677	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00677	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00677

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5723

KEGG Compound ID

C00202

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Isoflurophate

METLIN ID

Not Available

PubChem Compound

5936

PDB ID

Not Available

ChEBI ID

17941

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Acetylcholinesterase

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

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 ]
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 ]
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 ]
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 ]
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 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. Cholinesterase

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

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]

Showing metabocard for Isoflurophate (HMDB0014815)

MOL for HMDB0014815 (Isoflurophate)

3D MOL for HMDB0014815 (Isoflurophate)

3D SDF for HMDB0014815 (Isoflurophate)

3D-SDF for HMDB0014815 (Isoflurophate)

PDB for HMDB0014815 (Isoflurophate)

3D PDB for HMDB0014815 (Isoflurophate)

SMILES for HMDB0014815 (Isoflurophate)

INCHI for HMDB0014815 (Isoflurophate)

Structure for HMDB0014815 (Isoflurophate)

3D Structure for HMDB0014815 (Isoflurophate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

References

References