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Showing metabocard for Desflurane (HMDB0015320)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2023-02-21 17:18:28 UTC
HMDB IDHMDB0015320
Secondary Accession Numbers
  • HMDB15320
Metabolite Identification
Common NameDesflurane
DescriptionDesflurane 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0015320 (Desflurane)

1189
  Mrv0541 02231215182D          

 10  9  0  0  1  0            999 V2000
    3.0791    0.9760    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.6740    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.4529    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.9760    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.2615    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.9760    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.2615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  2  9  1  0  0  0  0
  3  9  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
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3D MOL for HMDB0015320 (Desflurane)

HMDB0015320
     RDKit          3D
Desflurane
 12 11  0  0  0  0  0  0  0  0999 V2000
   -1.4535    0.9845   -0.4282 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6359   -0.6411   -0.7406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8666   -0.8140    0.8711 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3681   -0.8620   -0.6708 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2961   -0.2372    0.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7931   -1.2560    1.1813 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.5066    0.5387   -0.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1771    1.5200   -1.0237 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.4414   -0.2951   -0.6607 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.0717    1.1576    0.9888 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6098   -0.4713   -0.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3522    0.3760    1.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
  2 11  1  0
  5 12  1  0
M  END
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3D SDF for HMDB0015320 (Desflurane)

1189
  Mrv0541 02231215182D          

 10  9  0  0  1  0            999 V2000
    3.0791    0.9760    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.6740    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.4529    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.9760    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.2615    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.9760    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.2615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  2  9  1  0  0  0  0
  3  9  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015320

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C3H2F6O

> <MOLECULAR_WEIGHT>
168.0378

> <EXACT_MASS>
168.000983916

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
7.894929046218448

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(difluoromethoxy)-1,1,1,2-tetrafluoroethane

> <ALOGPS_LOGP>
2.19

> <JCHEM_LOGP>
2.4025108229999996

> <ALOGPS_LOGS>
-1.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.870108514803245

> <JCHEM_PKA_STRONGEST_BASIC>
-4.810489555332021

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
18.1205

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.54e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
desflurane

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0015320 (Desflurane)

HMDB0015320
     RDKit          3D
Desflurane
 12 11  0  0  0  0  0  0  0  0999 V2000
   -1.4535    0.9845   -0.4282 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6359   -0.6411   -0.7406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8666   -0.8140    0.8711 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3681   -0.8620   -0.6708 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2961   -0.2372    0.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7931   -1.2560    1.1813 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.5066    0.5387   -0.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1771    1.5200   -1.0237 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.4414   -0.2951   -0.6607 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.0717    1.1576    0.9888 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6098   -0.4713   -0.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3522    0.3760    1.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
  2 11  1  0
  5 12  1  0
M  END
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PDB for HMDB0015320 (Desflurane)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1189                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  F   UNK     0       5.748   1.822   0.000  0.00  0.00           F+0
HETATM    2  F   UNK     0       3.080  -1.258   0.000  0.00  0.00           F+0
HETATM    3  F   UNK     0       3.644   0.845   0.000  0.00  0.00           F+0
HETATM    4  F   UNK     0       5.184  -1.822   0.000  0.00  0.00           F+0
HETATM    5  F   UNK     0       9.748  -0.488   0.000  0.00  0.00           F+0
HETATM    6  F   UNK     0       8.415   1.822   0.000  0.00  0.00           F+0
HETATM    7  O   UNK     0       7.081  -0.488   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.748   0.282   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -0.488   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415   0.282   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3    9                                                            
CONECT    4    9                                                            
CONECT    5   10                                                            
CONECT    6   10                                                            
CONECT    7    8   10                                                       
CONECT    8    1    7    9                                                  
CONECT    9    2    3    4    8                                             
CONECT   10    5    6    7                                                  
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for HMDB0015320 (Desflurane)

COMPND    HMDB0015320
HETATM    1  F1  UNL     1      -1.453   0.984  -0.428  1.00  0.00           F  
HETATM    2  C1  UNL     1      -1.636  -0.641  -0.741  1.00  0.00           C  
HETATM    3  F2  UNL     1      -1.867  -0.814   0.871  1.00  0.00           F  
HETATM    4  O1  UNL     1      -0.368  -0.862  -0.671  1.00  0.00           O  
HETATM    5  C2  UNL     1       0.296  -0.237   0.371  1.00  0.00           C  
HETATM    6  F3  UNL     1       0.793  -1.256   1.181  1.00  0.00           F  
HETATM    7  C3  UNL     1       1.507   0.539  -0.120  1.00  0.00           C  
HETATM    8  F4  UNL     1       1.177   1.520  -1.024  1.00  0.00           F  
HETATM    9  F5  UNL     1       2.441  -0.295  -0.661  1.00  0.00           F  
HETATM   10  F6  UNL     1       2.072   1.158   0.989  1.00  0.00           F  
HETATM   11  H1  UNL     1      -2.610  -0.471  -0.794  1.00  0.00           H  
HETATM   12  H2  UNL     1      -0.352   0.376   1.026  1.00  0.00           H  
CONECT    1    2
CONECT    2    3    4   11
CONECT    4    5
CONECT    5    6    7   12
CONECT    7    8    9   10
END
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SMILES for HMDB0015320 (Desflurane)

FC(F)OC(F)C(F)(F)F
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INCHI for HMDB0015320 (Desflurane)

InChI=1S/C3H2F6O/c4-1(3(7,8)9)10-2(5)6/h1-2H
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View in JSmolView Stereo Labels
Synonyms
ValueSource
(+-)-2-Difluoromethyl 1,2,2,2-tetrafluoroethyl etherChEBI
1,1,1,2-Tetrafluoro-2-(difluoromethoxy)ethaneChEBI
Difluoromethyl 1,2,2,2-tetrafluoroethyl etherChEBI
SupraneChEBI
Baxter anaesthesia brand OF desfluraneHMDB
Baxter brand OF desfluraneHMDB
Ohmeda brand OF desfluraneHMDB
Zeneca brand OF desfluraneHMDB
1,2,2,2-Tetrafluoroethyl difluoromethyl etherHMDB
Chemical FormulaC3H2F6O
Average Molecular Weight168.0378
Monoisotopic Molecular Weight168.000983916
IUPAC Name2-(difluoromethoxy)-1,1,1,2-tetrafluoroethane
Traditional Namedesflurane
CAS Registry Number57041-67-5
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 KeyDPYMFVXJLLWWEU-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.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassOrganofluorides
Sub ClassNot Available
Direct ParentOrganofluorides
Alternative Parents
Substituents
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organofluoride
  • Alkyl halide
  • Alkyl fluoride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point23.5 °CNot Available
Water Solubility3.54 g/LNot Available
LogP1.9Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01189 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01189 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01189
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID38403
KEGG Compound IDC07519
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDesflurane
METLIN IDNot Available
PubChem Compound42113
PDB IDNot Available
ChEBI ID4445
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

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
  1. 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 ]
  2. 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
  1. 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 ]
  2. 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 ]
  3. 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
  1. 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 ]
  2. 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
  1. 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 ]
  2. 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 ]
  3. 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
  1. 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 ]
  2. 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 ]
  3. 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
  1. 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 ]
  2. 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 ]
  3. 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
  1. 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 ]
  2. 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 ]
  3. 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 ]