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Showing metabocard for 1-hydroperoxy-8-carboxyoctyl 3,4-epoxynon-(2E)-enyl ether (HMDB0062326)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-16 03:43:39 UTC
Update Date2023-02-21 17:30:48 UTC
HMDB IDHMDB0062326
Secondary Accession Numbers
  • HMDB62326
Metabolite Identification
Common Name1-hydroperoxy-8-carboxyoctyl 3,4-epoxynon-(2E)-enyl ether
Description1-hydroperoxy-8-carboxyoctyl 3,4-epoxynon-(2E)-enyl ether, also known as aether or anesthetic ether, belongs to the class of organic compounds known as dialkyl ethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are alkyl groups. This slows down the metabolism of ethanol and also inhibits the metabolism of other drugs requiring oxidative metabolism. 1-hydroperoxy-8-carboxyoctyl 3,4-epoxynon-(2E)-enyl ether is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 1-hydroperoxy-8-carboxyoctyl 3,4-epoxynon-(2E)-enyl ether has been detected, but not quantified in, tea. This could make 1-hydroperoxy-8-carboxyoctyl 3,4-epoxynon-(2E)-enyl ether a potential biomarker for the consumption of these foods. 1-hydroperoxy-8-carboxyoctyl 3,4-epoxynon-(2E)-enyl ether is a potentially toxic compound. Di1-hydroperoxy-8-carboxyoctyl 3,4-epoxynon-(2E)-enyl ether inhibits alcohol dehydrogenase. Inhalation may result in dizziness, giddiness, euphoria, drowsiness, salivation, and CNS depression. Di1-hydroperoxy-8-carboxyoctyl 3,4-epoxynon-(2E)-enyl ether can be absorbed following ingestion and inhalation, and is then rapidly distributed to the brain and fatty tissues. Di1-hydroperoxy-8-carboxyoctyl 3,4-epoxynon-(2E)-enyl ether is not metabolized in humans and is excreted mainly in expired air. Death due to respiratory depression may result from severe and prolonged exposure. Di1-hydroperoxy-8-carboxyoctyl 3,4-epoxynon-(2E)-enyl ether causes CNS depression. There is no antidote for di1-hydroperoxy-8-carboxyoctyl 3,4-epoxynon-(2E)-enyl ether poisoning, thus treatment is symptomatic and supportive. Di1-hydroperoxy-8-carboxyoctyl 3,4-epoxynon-(2E)-enyl ether is also a skin and eye irritant.
Structure
Data?1677000648
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0062326 (1-hydroperoxy-8-carboxyoctyl 3,4-epoxynon-(2E)-enyl ether)


  Mrv1652305261923512D          

  5  4  0  0  0  0            999 V2000
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
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3D MOL for HMDB0062326 (1-hydroperoxy-8-carboxyoctyl 3,4-epoxynon-(2E)-enyl ether)

HMDB0062326
     RDKit          3D
1-hydroperoxy-8-carboxyoctyl 3,4-epoxynon-(2E)-enyl ether
 15 14  0  0  0  0  0  0  0  0999 V2000
    2.2393    0.6187    0.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8451    0.0820   -0.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2741   -0.3244    0.8627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9894   -0.8384    0.7433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0036    0.0920    0.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0584    1.3793    0.8264 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7042    1.0686   -0.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8590   -0.2175    0.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0092   -0.7909   -1.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2453    0.8279   -0.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9423   -1.7649    0.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3319   -1.1440    1.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8721    0.2501    0.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6105    1.1115   -0.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4848   -0.3499   -0.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  2 10  1  0
  4 11  1  0
  4 12  1  0
  5 13  1  0
  5 14  1  0
  5 15  1  0
M  END
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3D SDF for HMDB0062326 (1-hydroperoxy-8-carboxyoctyl 3,4-epoxynon-(2E)-enyl ether)


  Mrv1652305261923512D          

  5  4  0  0  0  0            999 V2000
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0062326

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOCC

> <INCHI_IDENTIFIER>
InChI=1S/C4H10O/c1-3-5-4-2/h3-4H2,1-2H3

> <INCHI_KEY>
RTZKZFJDLAIYFH-UHFFFAOYSA-N

> <FORMULA>
C4H10O

> <MOLECULAR_WEIGHT>
74.1216

> <EXACT_MASS>
74.073164942

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
9.328323802385142

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethoxyethane

> <ALOGPS_LOGP>
1.12

> <JCHEM_LOGP>
0.8381653443333331

> <ALOGPS_LOGS>
-0.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.118795385024649

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
22.5097

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.90e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diethyl ether

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0062326 (1-hydroperoxy-8-carboxyoctyl 3,4-epoxynon-(2E)-enyl ether)

HMDB0062326
     RDKit          3D
1-hydroperoxy-8-carboxyoctyl 3,4-epoxynon-(2E)-enyl ether
 15 14  0  0  0  0  0  0  0  0999 V2000
    2.2393    0.6187    0.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8451    0.0820   -0.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2741   -0.3244    0.8627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9894   -0.8384    0.7433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0036    0.0920    0.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0584    1.3793    0.8264 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7042    1.0686   -0.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8590   -0.2175    0.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0092   -0.7909   -1.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2453    0.8279   -0.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9423   -1.7649    0.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3319   -1.1440    1.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8721    0.2501    0.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6105    1.1115   -0.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4848   -0.3499   -0.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  2 10  1  0
  4 11  1  0
  4 12  1  0
  5 13  1  0
  5 14  1  0
  5 15  1  0
M  END
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PDB for HMDB0062326 (1-hydroperoxy-8-carboxyoctyl 3,4-epoxynon-(2E)-enyl ether)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0062326 (1-hydroperoxy-8-carboxyoctyl 3,4-epoxynon-(2E)-enyl ether)

COMPND    HMDB0062326
HETATM    1  C1  UNL     1       2.239   0.619   0.027  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.845   0.082  -0.322  1.00  0.00           C  
HETATM    3  O1  UNL     1       0.274  -0.324   0.863  1.00  0.00           O  
HETATM    4  C3  UNL     1      -0.989  -0.838   0.743  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.004   0.092   0.173  1.00  0.00           C  
HETATM    6  H1  UNL     1       2.058   1.379   0.826  1.00  0.00           H  
HETATM    7  H2  UNL     1       2.704   1.069  -0.868  1.00  0.00           H  
HETATM    8  H3  UNL     1       2.859  -0.217   0.395  1.00  0.00           H  
HETATM    9  H4  UNL     1       1.009  -0.791  -1.018  1.00  0.00           H  
HETATM   10  H5  UNL     1       0.245   0.828  -0.843  1.00  0.00           H  
HETATM   11  H6  UNL     1      -0.942  -1.765   0.108  1.00  0.00           H  
HETATM   12  H7  UNL     1      -1.332  -1.144   1.752  1.00  0.00           H  
HETATM   13  H8  UNL     1      -2.872   0.250   0.876  1.00  0.00           H  
HETATM   14  H9  UNL     1      -1.610   1.112  -0.044  1.00  0.00           H  
HETATM   15  H10 UNL     1      -2.485  -0.350  -0.746  1.00  0.00           H  
CONECT    1    2    6    7    8
CONECT    2    3    9   10
CONECT    3    4
CONECT    4    5   11   12
CONECT    5   13   14   15
END
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SMILES for HMDB0062326 (1-hydroperoxy-8-carboxyoctyl 3,4-epoxynon-(2E)-enyl ether)

CCOCC
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INCHI for HMDB0062326 (1-hydroperoxy-8-carboxyoctyl 3,4-epoxynon-(2E)-enyl ether)

InChI=1S/C4H10O/c1-3-5-4-2/h3-4H2,1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1,1'-OxybisethaneChEBI
3-OxapentaneChEBI
AetherChEBI
Aether pro narcosiChEBI
Anesthetic etherChEBI
Diethyl oxideChEBI
DiethylaetherChEBI
EtherChEBI
EthoxyethaneChEBI
Ethyl etherChEBI
Ethyl oxideChEBI
PronarcolChEBI
R-610ChEBI
Diethyl etherKegg
Ether, diethylHMDB
Ether, ethylHMDB
Chemical FormulaC4H10O
Average Molecular Weight74.1216
Monoisotopic Molecular Weight74.073164942
IUPAC Nameethoxyethane
Traditional Namediethyl ether
CAS Registry Number60-29-7
SMILES
CCOCC
InChI Identifier
InChI=1S/C4H10O/c1-3-5-4-2/h3-4H2,1-2H3
InChI KeyRTZKZFJDLAIYFH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dialkyl ethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are alkyl groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassEthers
Direct ParentDialkyl ethers
Alternative Parents
Substituents
  • Dialkyl ether
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility39 g/lALOGPS
LogP1.12ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP1.12ALOGPS
logP0.84ChemAxon
logS-0.28ALOGPS
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.51 m³·mol⁻¹ChemAxon
Polarizability9.33 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+122.40230932474
DeepCCS[M-H]-120.51230932474
DeepCCS[M-2H]-155.88830932474
DeepCCS[M+Na]+129.9330932474
AllCCS[M+H]+120.832859911
AllCCS[M+H-H2O]+116.332859911
AllCCS[M+NH4]+125.032859911
AllCCS[M+Na]+126.232859911
AllCCS[M-H]-134.832859911
AllCCS[M+Na-2H]-140.532859911
AllCCS[M+HCOO]-146.832859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter)). Predicted by Afia on May 17, 2022.2.57 minutes32390414
Predicted by Siyang on May 30, 202212.9651 minutes33406817
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1520.2 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid506.6 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid189.8 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid345.8 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid125.8 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid467.2 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid526.9 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)204.5 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid989.0 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid336.5 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1128.3 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid387.5 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid303.1 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate515.3 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA501.9 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water96.8 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-hydroperoxy-8-carboxyoctyl 3,4-epoxynon-(2E)-enyl etherCCOCC600.5Standard polar33892256
1-hydroperoxy-8-carboxyoctyl 3,4-epoxynon-(2E)-enyl etherCCOCC485.1Standard non polar33892256
1-hydroperoxy-8-carboxyoctyl 3,4-epoxynon-(2E)-enyl etherCCOCC469.4Semi standard non polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB13598
Phenol Explorer Compound IDNot Available
FooDB IDFDB004482
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC13240
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDiethyl_ether
METLIN IDNot Available
PubChem Compound3283
PDB IDNot Available
ChEBI ID35702
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