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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7) Show 7 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2023-02-21 17:18:28 UTC

HMDB ID

HMDB0015320

Secondary Accession Numbers

HMDB15320

Metabolite Identification

Common Name

Desflurane

Description

Desflurane is a highly fluorinated methyl ethyl ether used for maintenance of general anaesthesia. Volatile agents such as desflurane may activate GABA channels and hyperpolarize cell membranes. In addition, they may inhibit certain calcium channels and therefore prevent release of neurotransmitters and inhibit glutamate channels. Volatile anesthetics easily partition into cellular membranes and could expand the volume of the cell membrane and subsequently distort channels necessary for sodium ion flux and the development of action potentials necessary for synaptic transmission. Desflurane preconditions human myocardium against ischemia through activation of mitochondrial K(ATP) channels, adenosine A1 receptor, and alpha and beta adrenoceptors.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-2-Difluoromethyl 1,2,2,2-tetrafluoroethyl ether	ChEBI
1,1,1,2-Tetrafluoro-2-(difluoromethoxy)ethane	ChEBI
Difluoromethyl 1,2,2,2-tetrafluoroethyl ether	ChEBI
Suprane	ChEBI
Baxter anaesthesia brand OF desflurane	HMDB
Baxter brand OF desflurane	HMDB
Ohmeda brand OF desflurane	HMDB
Zeneca brand OF desflurane	HMDB
1,2,2,2-Tetrafluoroethyl difluoromethyl ether	HMDB

Chemical Formula

C₃H₂F₆O

Average Molecular Weight

168.0378

Monoisotopic Molecular Weight

168.000983916

IUPAC Name

2-(difluoromethoxy)-1,1,1,2-tetrafluoroethane

Traditional Name

desflurane

CAS Registry Number

57041-67-5

SMILES

FC(F)OC(F)C(F)(F)F

InChI Identifier

InChI=1S/C3H2F6O/c4-1(3(7,8)9)10-2(5)6/h1-2H

InChI Key

DPYMFVXJLLWWEU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as organofluorides. Organofluorides are compounds containing a chemical bond between a carbon atom and a fluorine atom.

Kingdom

Organic compounds

Super Class

Organohalogen compounds

Class

Organofluorides

Sub Class

Not Available

Direct Parent

Organofluorides

Alternative Parents

Substituents

Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organofluoride
Alkyl halide
Alkyl fluoride
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organofluorine compound (CHEBI:4445 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Process

Not Available

Role

Industrial application

Inhalation anaesthetic (HMDB: HMDB0015320)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	23.5 °C	Not Available
Water Solubility	3.54 g/L	Not Available
LogP	1.9	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.54 g/L	ALOGPS
logP	2.19	ALOGPS
logP	2.4	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	18.87	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	18.12 m³·mol⁻¹	ChemAxon
Polarizability	7.89 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	133.728	30932474
DeepCCS	[M-H]-	131.451	30932474
DeepCCS	[M-2H]-	167.451	30932474
DeepCCS	[M+Na]+	142.337	30932474
AllCCS	[M+H]+	135.6	32859911
AllCCS	[M+H-H2O]+	131.6	32859911
AllCCS	[M+NH4]+	139.3	32859911
AllCCS	[M+Na]+	140.3	32859911
AllCCS	[M-H]-	120.3	32859911
AllCCS	[M+Na-2H]-	122.4	32859911
AllCCS	[M+HCOO]-	124.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Desflurane	FC(F)OC(F)C(F)(F)F	567.3	Standard polar	33892256
Desflurane	FC(F)OC(F)C(F)(F)F	355.0	Standard non polar	33892256
Desflurane	FC(F)OC(F)C(F)(F)F	357.0	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 - Desflurane GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-9400000000-9bfc58e3ef0acdde70c6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desflurane 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 - Desflurane 10V, Positive-QTOF	splash10-014i-0900000000-cb928c5773584b51d8f9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desflurane 20V, Positive-QTOF	splash10-014i-0900000000-908513735b5ab0dbea3b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desflurane 40V, Positive-QTOF	splash10-001i-9400000000-293244954cfd93a15224	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desflurane 10V, Negative-QTOF	splash10-014i-0900000000-14d2d394901471ee6fe9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desflurane 20V, Negative-QTOF	splash10-014j-0900000000-90d14c3cc1002cc1c1e1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desflurane 40V, Negative-QTOF	splash10-0f6t-4900000000-ce5b2fc5da9d94a0bb54	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desflurane 10V, Positive-QTOF	splash10-014i-0900000000-621e6be94ab63a3ea355	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desflurane 20V, Positive-QTOF	splash10-014i-0900000000-1e30f1fadbc21bfcdc25	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desflurane 40V, Positive-QTOF	splash10-00kb-4900000000-4bc2f4f843987f1be78e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desflurane 10V, Negative-QTOF	splash10-014i-0900000000-b3181a2326303b91e3bf	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desflurane 20V, Negative-QTOF	splash10-014i-1900000000-38f9e805bae921315c8d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desflurane 40V, Negative-QTOF	splash10-014i-0900000000-b3181a2326303b91e3bf	2021-10-11	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
Extracellular
Membrane

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 DB01189	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01189	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01189

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

38403

KEGG Compound ID

C07519

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Desflurane

METLIN ID

Not Available

PubChem Compound

42113

PDB ID

Not Available

ChEBI ID

4445

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. NADH-ubiquinone oxidoreductase chain 1

General function:: Involved in oxidation reduction
Specific function:: Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:: MT-ND1
Uniprot ID:: P03886
Molecular weight:: 35660.055

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

2. ATP synthase subunit delta, mitochondrial

General function:: Involved in hydrogen ion transporting ATP synthase activity, rotational mechanism
Specific function:: Mitochondrial membrane ATP synthase (F(1)F(0) ATP synthase or Complex V) produces ATP from ADP in the presence of a proton gradient across the membrane which is generated by electron transport complexes of the respiratory chain. F-type ATPases consist of two structural domains, F(1) - containing the extramembraneous catalytic core, and F(0) - containing the membrane proton channel, linked together by a central stalk and a peripheral stalk. During catalysis, ATP turnover in the catalytic domain of F(1) is coupled via a rotary mechanism of the central stalk subunits to proton translocation. Part of the complex F(1) domain and of the central stalk which is part of the complex rotary element. Rotation of the central stalk against the surrounding alpha(3)beta(3) subunits leads to hydrolysis of ATP in three separate catalytic sites on the beta subunits
Gene Name:: ATP5D
Uniprot ID:: P30049
Molecular weight:: 17489.8

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kosk-Kosicka D, Roszczynska G: Inhibition of plasma membrane Ca(2+)-ATPase activity by volatile anesthetics. Anesthesiology. 1993 Oct;79(4):774-80. [PubMed:8214757 ]

Enzyme Details

3. Calcium-transporting ATPase type 2C member 1

General function:: Involved in ATP binding
Specific function:: This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of the calcium.
Gene Name:: ATP2C1
Uniprot ID:: P98194
Molecular weight:: 96959.125

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

4. Glutamate receptor 1

General function:: Involved in ionotropic glutamate receptor activity
Specific function:: Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L- glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist
Gene Name:: GRIA1
Uniprot ID:: P42261
Molecular weight:: 101505.2

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Dildy-Mayfield JE, Eger EI 2nd, Harris RA: Anesthetics produce subunit-selective actions on glutamate receptors. J Pharmacol Exp Ther. 1996 Mar;276(3):1058-65. [PubMed:8786535 ]

Enzyme Details

5. Gamma-aminobutyric acid receptor subunit alpha-1

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA1
Uniprot ID:: P14867
Molecular weight:: 51801.4

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Seo K, Seino H, Yoshikawa H, Petrenko AB, Baba H, Fujiwara N, Someya G, Kawano Y, Maeda T, Matsuda M, Kanematsu T, Hirata M: Genetic reduction of GABA(A) receptor gamma2 subunit expression potentiates the immobilizing action of isoflurane. Neurosci Lett. 2010 Mar 12;472(1):1-4. doi: 10.1016/j.neulet.2010.01.031. Epub 2010 Jan 25. [PubMed:20097266 ]

Enzyme Details

6. Glycine receptor subunit alpha-1

General function:: Involved in ion transport
Specific function:: The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing)
Gene Name:: GLRA1
Uniprot ID:: P23415
Molecular weight:: 52623.4

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Grasshoff C, Antkowiak B: Effects of isoflurane and enflurane on GABAA and glycine receptors contribute equally to depressant actions on spinal ventral horn neurones in rats. Br J Anaesth. 2006 Nov;97(5):687-94. Epub 2006 Sep 13. [PubMed:16973644 ]

Enzyme Details

7. Potassium voltage-gated channel subfamily A member 1

General function:: Involved in protein binding
Specific function:: Mediates the voltage-dependent potassium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a potassium-selective channel through which potassium ions may pass in accordance with their electrochemical gradient
Gene Name:: KCNA1
Uniprot ID:: Q09470
Molecular weight:: 56465.0

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Matchett GA, Allard MW, Martin RD, Zhang JH: Neuroprotective effect of volatile anesthetic agents: molecular mechanisms. Neurol Res. 2009 Mar;31(2):128-34. doi: 10.1179/174313209X393546. [PubMed:19298752 ]

Showing metabocard for Desflurane (HMDB0015320)

MOL for HMDB0015320 (Desflurane)

3D MOL for HMDB0015320 (Desflurane)

3D SDF for HMDB0015320 (Desflurane)

3D-SDF for HMDB0015320 (Desflurane)

PDB for HMDB0015320 (Desflurane)

3D PDB for HMDB0015320 (Desflurane)

SMILES for HMDB0015320 (Desflurane)

INCHI for HMDB0015320 (Desflurane)

Structure for HMDB0015320 (Desflurane)

3D Structure for HMDB0015320 (Desflurane)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Enzymes

References

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