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Showing metabocard for 2-Hexen-4-olide (HMDB0302935)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-23 21:54:44 UTC
Update Date2021-09-23 21:54:45 UTC
HMDB IDHMDB0302935
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Hexen-4-olide
Description2-Hexen-4-olide is a member of the class of compounds known as butenolides. Butenolides are dihydrofurans with a carbonyl group at the C2 carbon atom. 2-hexen-4-olide is soluble (in water) and a very weakly acidic compound (based on its pKa). 2-hexen-4-olide is a spice tasting compound found in red raspberry, which makes 2-hexen-4-olide a potential biomarker for the consumption of this food product.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0302935 (2-Hexen-4-olide)


  Mrv0541 02241221232D          

  8  8  0  0  0  0            999 V2000
   -1.4242    1.2767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6396    1.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0278    1.5066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6953    1.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4403    0.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3847    0.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4799    1.2766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    0.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  5  6  2  0  0  0  0
  2  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
Download

3D MOL for HMDB0302935 (2-Hexen-4-olide)

HMDB0302935
     RDKit          3D
2-Hexen-4-olide
 16 16  0  0  0  0  0  0  0  0999 V2000
   -2.0726   -0.1117    0.6485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0871    0.6488   -0.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0515   -0.1956   -0.6827 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8355   -0.8222    0.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0876   -0.4022    0.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2289    0.5474   -0.6995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2738    1.1914   -1.0512 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9942    0.6487   -1.3149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7990    0.6069    1.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6405   -0.7018    1.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6256   -0.8296   -0.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7237    1.5558    0.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6268    1.0321   -1.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2776   -0.9306   -1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4828   -1.5527    1.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8984   -0.6844    1.0413 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  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  3  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
M  END
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3D SDF for HMDB0302935 (2-Hexen-4-olide)


  Mrv0541 02241221232D          

  8  8  0  0  0  0            999 V2000
   -1.4242    1.2767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6396    1.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0278    1.5066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6953    1.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4403    0.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3847    0.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4799    1.2766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    0.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  5  6  2  0  0  0  0
  2  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302935

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1OC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O2/c1-2-5-3-4-6(7)8-5/h3-5H,2H2,1H3

> <INCHI_KEY>
GOUILHYTHSOMQJ-UHFFFAOYSA-N

> <FORMULA>
C6H8O2

> <MOLECULAR_WEIGHT>
112.1265

> <EXACT_MASS>
112.0524295

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
11.43021042841298

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-ethyl-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
1.33

> <JCHEM_LOGP>
1.4757130083333332

> <ALOGPS_LOGS>
-0.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.208791515745938

> <JCHEM_PKA_STRONGEST_BASIC>
-6.819482621115993

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
30.190199999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.48e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-ethyl-5H-furan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0302935 (2-Hexen-4-olide)

HMDB0302935
     RDKit          3D
2-Hexen-4-olide
 16 16  0  0  0  0  0  0  0  0999 V2000
   -2.0726   -0.1117    0.6485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0871    0.6488   -0.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0515   -0.1956   -0.6827 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8355   -0.8222    0.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0876   -0.4022    0.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2289    0.5474   -0.6995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2738    1.1914   -1.0512 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9942    0.6487   -1.3149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7990    0.6069    1.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6405   -0.7018    1.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6256   -0.8296   -0.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7237    1.5558    0.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6268    1.0321   -1.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2776   -0.9306   -1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4828   -1.5527    1.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8984   -0.6844    1.0413 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  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  3  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
M  END
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PDB for HMDB0302935 (2-Hexen-4-olide)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -2.659   2.383   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.194   1.907   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.052   2.812   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.298   1.907   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.822   0.443   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.718   0.443   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.762   2.383   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.907   1.352   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    2                                                       
CONECT    7    4    8                                                       
CONECT    8    7                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for HMDB0302935 (2-Hexen-4-olide)

COMPND    HMDB0302935
HETATM    1  C1  UNL     1      -2.073  -0.112   0.649  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.087   0.649  -0.166  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.052  -0.196  -0.683  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.835  -0.822   0.380  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.088  -0.402   0.379  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.229   0.547  -0.699  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.274   1.191  -1.051  1.00  0.00           O  
HETATM    8  O2  UNL     1       0.994   0.649  -1.315  1.00  0.00           O  
HETATM    9  H1  UNL     1      -2.799   0.607   1.072  1.00  0.00           H  
HETATM   10  H2  UNL     1      -1.640  -0.702   1.463  1.00  0.00           H  
HETATM   11  H3  UNL     1      -2.626  -0.830  -0.022  1.00  0.00           H  
HETATM   12  H4  UNL     1      -0.724   1.556   0.357  1.00  0.00           H  
HETATM   13  H5  UNL     1      -1.627   1.032  -1.076  1.00  0.00           H  
HETATM   14  H6  UNL     1      -0.278  -0.931  -1.441  1.00  0.00           H  
HETATM   15  H7  UNL     1       0.483  -1.553   1.112  1.00  0.00           H  
HETATM   16  H8  UNL     1       2.898  -0.684   1.041  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3   12   13
CONECT    3    4    8   14
CONECT    4    5    5   15
CONECT    5    6   16
CONECT    6    7    7    8
END
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SMILES for HMDB0302935 (2-Hexen-4-olide)

CCC1OC(=O)C=C1
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INCHI for HMDB0302935 (2-Hexen-4-olide)

InChI=1S/C6H8O2/c1-2-5-3-4-6(7)8-5/h3-5H,2H2,1H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
5-Ethyl-2(5H)-furanoneMeSH
Chemical FormulaC6H8O2
Average Molecular Weight112.1265
Monoisotopic Molecular Weight112.0524295
IUPAC Name5-ethyl-2,5-dihydrofuran-2-one
Traditional Name5-ethyl-5H-furan-2-one
CAS Registry NumberNot Available
SMILES
CCC1OC(=O)C=C1
InChI Identifier
InChI=1S/C6H8O2/c1-2-5-3-4-6(7)8-5/h3-5H,2H2,1H3
InChI KeyGOUILHYTHSOMQJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydrofurans
Sub ClassFuranones
Direct ParentButenolides
Alternative Parents
Substituents
  • 2-furanone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Organoleptic effect
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP1.33ALOGPS
logP1.48ChemAxon
logS-0.66ALOGPS
pKa (Strongest Acidic)8.21ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity30.19 m³·mol⁻¹ChemAxon
Polarizability11.43 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+123.21532859911
AllCCS[M+H-H2O]+118.27932859911
AllCCS[M+Na]+129.15732859911
AllCCS[M+NH4]+127.82532859911
AllCCS[M-H]-123.2832859911
AllCCS[M+Na-2H]-125.78932859911
AllCCS[M+HCOO]-128.58632859911
DeepCCS[M+H]+124.45830932474
DeepCCS[M-H]-121.35930932474
DeepCCS[M-2H]-158.24430932474
DeepCCS[M+Na]+133.14130932474

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Predicted by Siyang on May 30, 202212.4976 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.5 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1479.4 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid403.5 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid143.7 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid280.8 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid117.6 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid415.2 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 Acid523.4 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)140.9 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid898.1 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid326.9 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1144.1 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid296.2 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid331.4 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate606.4 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA390.2 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water127.4 seconds40023050

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexen-4-olide 10V, Positive-QTOFsplash10-0w29-9400000000-7e329021523c20fe27482016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexen-4-olide 20V, Positive-QTOFsplash10-0udi-9100000000-2d1347ed24f35ede2bfd2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexen-4-olide 40V, Positive-QTOFsplash10-0udi-9000000000-8d4d3bf8509949086c762016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexen-4-olide 10V, Negative-QTOFsplash10-03di-3900000000-0ae2a580ce4b44b9a9f82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexen-4-olide 20V, Negative-QTOFsplash10-03xr-9600000000-8b364948dd82301e35672016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexen-4-olide 40V, Negative-QTOFsplash10-014i-9000000000-44254bfba591b42f577c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexen-4-olide 10V, Positive-QTOFsplash10-03di-6900000000-fc015fe59739d56d75f12021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexen-4-olide 20V, Positive-QTOFsplash10-00kr-9000000000-626f391725971ea0d0022021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexen-4-olide 40V, Positive-QTOFsplash10-0006-9000000000-e675e34009a2e70293cf2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexen-4-olide 10V, Negative-QTOFsplash10-03di-3900000000-b2f31fb9893ed7f6c17a2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexen-4-olide 20V, Negative-QTOFsplash10-00lr-9000000000-ea3dcf2621ba65e366302021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexen-4-olide 40V, Negative-QTOFsplash10-014r-9000000000-d0686e09a8819e9f0c4a2021-10-21Wishart LabView Spectrum
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB006953
KNApSAcK IDNot Available
Chemspider ID16103
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16997
PDB IDNot Available
ChEBI IDNot Available
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