Hmdb loader
Survey

Showing metabocard for 4-Hydroxy-2-butenoic acid gamma-lactone (HMDB0032330)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:49:13 UTC
Update Date2023-02-21 17:21:54 UTC
HMDB IDHMDB0032330
Secondary Accession Numbers
  • HMDB32330
Metabolite Identification
Common Name4-Hydroxy-2-butenoic acid gamma-lactone
Description4-Hydroxy-2-butenoic acid gamma-lactone, also known as butenolide or g-hydroxycrotonic acid lactone, belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. Based on a literature review a significant number of articles have been published on 4-Hydroxy-2-butenoic acid gamma-lactone.
Structure
Data?1677000114
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0032330 (4-Hydroxy-2-butenoic acid gamma-lactone)


  Mrv0541 05061306282D          

  6  6  0  0  0  0            999 V2000
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  3  1  0  0  0  0
  6  4  1  0  0  0  0
M  END
Download

3D MOL for HMDB0032330 (4-Hydroxy-2-butenoic acid gamma-lactone)

HMDB0032330
     RDKit          3D
4-Hydroxy-2-butenoic acid gamma-lactone
 10 10  0  0  0  0  0  0  0  0999 V2000
    2.4894   -0.8189   -0.2050 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2610   -0.5197   -0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7289    0.8286   -0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5797    0.7887    0.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9873   -0.6243    0.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1832   -1.3581   -0.0545 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2982    1.7754   -0.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2183    1.6768    0.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7262   -0.8476   -0.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4492   -0.9010    1.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  2  1  0
  3  7  1  0
  4  8  1  0
  5  9  1  0
  5 10  1  0
M  END
Download

3D SDF for HMDB0032330 (4-Hydroxy-2-butenoic acid gamma-lactone)


  Mrv0541 05061306282D          

  6  6  0  0  0  0            999 V2000
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  3  1  0  0  0  0
  6  4  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032330

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1OCC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2

> <INCHI_KEY>
VIHAEDVKXSOUAT-UHFFFAOYSA-N

> <FORMULA>
C4H4O2

> <MOLECULAR_WEIGHT>
84.0734

> <EXACT_MASS>
84.021129372

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
7.476396106679556

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.12

> <JCHEM_LOGP>
0.5366155886666665

> <ALOGPS_LOGS>
0.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.366791671417149

> <JCHEM_PKA_STRONGEST_BASIC>
-6.810635355667466

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
21.247400000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.87e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(5H)-furanone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0032330 (4-Hydroxy-2-butenoic acid gamma-lactone)

HMDB0032330
     RDKit          3D
4-Hydroxy-2-butenoic acid gamma-lactone
 10 10  0  0  0  0  0  0  0  0999 V2000
    2.4894   -0.8189   -0.2050 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2610   -0.5197   -0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7289    0.8286   -0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5797    0.7887    0.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9873   -0.6243    0.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1832   -1.3581   -0.0545 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2982    1.7754   -0.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2183    1.6768    0.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7262   -0.8476   -0.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4492   -0.9010    1.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  2  1  0
  3  7  1  0
  4  8  1  0
  5  9  1  0
  5 10  1  0
M  END
Download

PDB for HMDB0032330 (4-Hydroxy-2-butenoic acid gamma-lactone)

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    6                                                       
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    3    4                                                       
MASTER        0    0    0    0    0    0    0    0    6    0   12    0
END
Download

3D PDB for HMDB0032330 (4-Hydroxy-2-butenoic acid gamma-lactone)

COMPND    HMDB0032330
HETATM    1  O1  UNL     1       2.489  -0.819  -0.205  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.261  -0.520  -0.112  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.729   0.829  -0.046  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.580   0.789   0.045  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.987  -0.624   0.043  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.183  -1.358  -0.054  1.00  0.00           O  
HETATM    7  H1  UNL     1       1.298   1.775  -0.066  1.00  0.00           H  
HETATM    8  H2  UNL     1      -1.218   1.677   0.109  1.00  0.00           H  
HETATM    9  H3  UNL     1      -1.726  -0.848  -0.763  1.00  0.00           H  
HETATM   10  H4  UNL     1      -1.449  -0.901   1.050  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    6
CONECT    3    4    4    7
CONECT    4    5    8
CONECT    5    6    9   10
END
Download

SMILES for HMDB0032330 (4-Hydroxy-2-butenoic acid gamma-lactone)

O=C1OCC=C1
Download

INCHI for HMDB0032330 (4-Hydroxy-2-butenoic acid gamma-lactone)

InChI=1S/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2
Download
View in JSmolView Stereo Labels
Synonyms
ValueSource
2(5H)-FuranoneChEBI
2-Buten-4-olideChEBI
2-ButenolideChEBI
2-oxo-2,5-DihydrofuranChEBI
4-Hydroxy-2-butenoic acid lactoneChEBI
alpha,beta-CrotonolactoneChEBI
ButenolideChEBI
gamma-CrotonolactoneChEBI
gamma-Hydroxycrotonic acid lactoneChEBI
4-Hydroxy-2-butenoate lactoneGenerator
a,b-CrotonolactoneGenerator
Α,β-crotonolactoneGenerator
g-CrotonolactoneGenerator
Γ-crotonolactoneGenerator
g-Hydroxycrotonate lactoneGenerator
g-Hydroxycrotonic acid lactoneGenerator
gamma-Hydroxycrotonate lactoneGenerator
Γ-hydroxycrotonate lactoneGenerator
Γ-hydroxycrotonic acid lactoneGenerator
4-Hydroxy-2-butenoate g-lactoneGenerator
4-Hydroxy-2-butenoate gamma-lactoneGenerator
4-Hydroxy-2-butenoate γ-lactoneGenerator
4-Hydroxy-2-butenoic acid g-lactoneGenerator
4-Hydroxy-2-butenoic acid γ-lactoneGenerator
2(5H)-Furanone (laquo gammaraquo -crotonolactone)HMDB
2-(5H)-FuranoneHMDB
2-Buten-1,4-olideHMDB
2-Butenoic acid gamma-lactoneHMDB
2-Butenoic acid, 4-hydroxy-, gamma-lactoneHMDB
2-Butenoic acid, 4-hydroxy-, laquo gammaraquo -lactoneHMDB
2-Butenoic acid-gamma-lactoneHMDB
2-Butenoic acid-laquo gammaraquo -lactoneHMDB
2-oxo-2,5-Dihydrofuran(2-[5H]-furanone)HMDB
4-Hydroxy-2-butenoic acid laquo gammaraquo -lactoneHMDB
4-Hydroxycrotonic acid gamma-lactoneHMDB
5 H-Furan-2-oneHMDB
5H-Furan-2-oneHMDB
alpha,alpha,beta-ButolideHMDB
Crotonic acid, 4-hydroxy-, gamma-lactone (6ci,7ci)HMDB
Crotonic acid, 4-hydroxy-, laquo gammaraquo -lactoneHMDB
CrotonolactoneHMDB
delta,alpha,beta-ButenolideHMDB
Furan-2(5H)-oneHMDB
gamma-CrotolactoneHMDB
IsocrotonolactoneHMDB
Laquo deltaraquo ,alpha,beta-butenolideHMDB
Laquo gammaraquo -crotolactoneHMDB
Laquo gammaraquo -crotonolactoneHMDB
Laquo gammaraquo -hydroxycrotonic acid lactoneHMDB
2-b4OHMDB
2-FuranoneHMDB
Chemical FormulaC4H4O2
Average Molecular Weight84.0734
Monoisotopic Molecular Weight84.021129372
IUPAC Name2,5-dihydrofuran-2-one
Traditional Name2-(5H)-furanone
CAS Registry Number497-23-4
SMILES
O=C1OCC=C1
InChI Identifier
InChI=1S/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2
InChI KeyVIHAEDVKXSOUAT-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 Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point4.5 °CNot Available
Boiling Point86.00 to 87.00 °C. @ 12.00 mm HgThe Good Scents Company Information System
Water Solubility417800 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.60Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility187 g/LALOGPS
logP0.12ALOGPS
logP0.54ChemAxon
logS0.35ALOGPS
pKa (Strongest Acidic)7.37ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity21.25 m³·mol⁻¹ChemAxon
Polarizability7.48 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
DarkChem[M+H]+114.23331661259
DarkChem[M-H]-107.03731661259
DeepCCS[M+H]+119.93230932474
DeepCCS[M-H]-117.73430932474
DeepCCS[M-2H]-153.55930932474
DeepCCS[M+Na]+128.15730932474
AllCCS[M+H]+116.532859911
AllCCS[M+H-H2O]+111.332859911
AllCCS[M+NH4]+121.532859911
AllCCS[M+Na]+122.932859911
AllCCS[M-H]-115.832859911
AllCCS[M+Na-2H]-119.532859911
AllCCS[M+HCOO]-123.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Hydroxy-2-butenoic acid gamma-lactoneO=C1OCC=C11717.8Standard polar33892256
4-Hydroxy-2-butenoic acid gamma-lactoneO=C1OCC=C1815.8Standard non polar33892256
4-Hydroxy-2-butenoic acid gamma-lactoneO=C1OCC=C1929.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-2-butenoic acid gamma-lactone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fal-9000000000-b30235e27faf90d4b6c32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-2-butenoic acid gamma-lactone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-2-butenoic acid gamma-lactone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2-butenoic acid gamma-lactone 10V, Positive-QTOFsplash10-000i-9000000000-968628430901cf9ae0522016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2-butenoic acid gamma-lactone 20V, Positive-QTOFsplash10-000i-9000000000-a4a4a638305768fbd07f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2-butenoic acid gamma-lactone 40V, Positive-QTOFsplash10-0006-9000000000-57b64ec26d3e4a9cfe052016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2-butenoic acid gamma-lactone 10V, Negative-QTOFsplash10-001i-9000000000-72a8324c2fdf8f1f21aa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2-butenoic acid gamma-lactone 20V, Negative-QTOFsplash10-001r-9000000000-3914beef718329100f702016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2-butenoic acid gamma-lactone 40V, Negative-QTOFsplash10-000i-9000000000-8af264d6baab1a9e126f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2-butenoic acid gamma-lactone 10V, Positive-QTOFsplash10-000i-9000000000-676e1fabc8739718707a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2-butenoic acid gamma-lactone 20V, Positive-QTOFsplash10-000l-9000000000-a7ef3976cebeb90004122021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2-butenoic acid gamma-lactone 40V, Positive-QTOFsplash10-000i-9000000000-462396c2282621c47aa42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2-butenoic acid gamma-lactone 10V, Negative-QTOFsplash10-001i-9000000000-3219da110319872c09ba2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2-butenoic acid gamma-lactone 20V, Negative-QTOFsplash10-001i-9000000000-f2a483017b4b14a273e32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2-butenoic acid gamma-lactone 40V, Negative-QTOFsplash10-0670-9000000000-a93906c52803dc560c842021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB009600
KNApSAcK IDC00052584
Chemspider ID9917
KEGG Compound IDC17601
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10341
PDB IDNot Available
ChEBI ID38118
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1158161
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). EAFUS: Everything Added to Food in the United States.. .