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Showing metabocard for 3-Hydroxy-2H-pyran-2-one (HMDB0032994)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:53:08 UTC
Update Date2023-02-21 17:22:57 UTC
HMDB IDHMDB0032994
Secondary Accession Numbers
  • HMDB32994
Metabolite Identification
Common Name3-Hydroxy-2H-pyran-2-one
Description3-Hydroxy-2H-pyran-2-one belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. 3-Hydroxy-2H-pyran-2-one has been detected, but not quantified in, alcoholic beverages. This could make 3-hydroxy-2H-pyran-2-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Hydroxy-2H-pyran-2-one.
Structure
Data?1677000177
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0032994 (3-Hydroxy-2H-pyran-2-one)


  Mrv0541 05061306512D          

  8  8  0  0  0  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  3  1  0  0  0  0
  8  5  1  0  0  0  0
M  END
Download

3D MOL for HMDB0032994 (3-Hydroxy-2H-pyran-2-one)

HMDB0032994
     RDKit          3D
3-Hydroxy-2H-pyran-2-one
 12 12  0  0  0  0  0  0  0  0999 V2000
    1.0606   -2.3897    0.1132 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3461   -1.3463    0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9582   -1.4392   -0.1367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7521   -0.3991   -0.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1760    0.8533   -0.1427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1971    0.9949    0.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9880   -0.1284    0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.0790    0.3026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8251   -0.5167   -0.3674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8056    1.7289   -0.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6704    1.9652    0.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8904    0.7562    0.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  2  1  0
  4  9  1  0
  5 10  1  0
  6 11  1  0
  8 12  1  0
M  END
Download

3D SDF for HMDB0032994 (3-Hydroxy-2H-pyran-2-one)


  Mrv0541 05061306512D          

  8  8  0  0  0  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  3  1  0  0  0  0
  8  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032994

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=COC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H4O3/c6-4-2-1-3-8-5(4)7/h1-3,6H

> <INCHI_KEY>
LIPRKYKMVQPYPG-UHFFFAOYSA-N

> <FORMULA>
C5H4O3

> <MOLECULAR_WEIGHT>
112.0835

> <EXACT_MASS>
112.016043994

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
9.528927479639272

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxy-2H-pyran-2-one

> <ALOGPS_LOGP>
0.12

> <JCHEM_LOGP>
0.4991981573333333

> <ALOGPS_LOGS>
0.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.361928674402355

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5770923978164095

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
28.062900000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.53e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2H-pyran-2-one, 3-hydroxy-

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0032994 (3-Hydroxy-2H-pyran-2-one)

HMDB0032994
     RDKit          3D
3-Hydroxy-2H-pyran-2-one
 12 12  0  0  0  0  0  0  0  0999 V2000
    1.0606   -2.3897    0.1132 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3461   -1.3463    0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9582   -1.4392   -0.1367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7521   -0.3991   -0.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1760    0.8533   -0.1427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1971    0.9949    0.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9880   -0.1284    0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.0790    0.3026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8251   -0.5167   -0.3674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8056    1.7289   -0.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6704    1.9652    0.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8904    0.7562    0.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  2  1  0
  4  9  1  0
  5 10  1  0
  6 11  1  0
  8 12  1  0
M  END
Download

PDB for HMDB0032994 (3-Hydroxy-2H-pyran-2-one)

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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    8                                                       
CONECT    4    2    5    6                                                  
CONECT    5    4    7    8                                                  
CONECT    6    4                                                            
CONECT    7    5                                                            
CONECT    8    3    5                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
Download

3D PDB for HMDB0032994 (3-Hydroxy-2H-pyran-2-one)

COMPND    HMDB0032994
HETATM    1  O1  UNL     1       1.061  -2.390   0.113  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.346  -1.346   0.032  1.00  0.00           C  
HETATM    3  O2  UNL     1      -0.958  -1.439  -0.137  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.752  -0.399  -0.229  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.176   0.853  -0.143  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.197   0.995   0.035  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.988  -0.128   0.126  1.00  0.00           C  
HETATM    8  O3  UNL     1       2.365  -0.079   0.303  1.00  0.00           O  
HETATM    9  H1  UNL     1      -2.825  -0.517  -0.367  1.00  0.00           H  
HETATM   10  H2  UNL     1      -1.806   1.729  -0.215  1.00  0.00           H  
HETATM   11  H3  UNL     1       0.670   1.965   0.105  1.00  0.00           H  
HETATM   12  H4  UNL     1       2.890   0.756   0.378  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    7
CONECT    3    4
CONECT    4    5    5    9
CONECT    5    6   10
CONECT    6    7    7   11
CONECT    7    8
CONECT    8   12
END
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SMILES for HMDB0032994 (3-Hydroxy-2H-pyran-2-one)

OC1=CC=COC1=O
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INCHI for HMDB0032994 (3-Hydroxy-2H-pyran-2-one)

InChI=1S/C5H4O3/c6-4-2-1-3-8-5(4)7/h1-3,6H
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View in JSmolView Stereo Labels
Synonyms
ValueSource
3-Hydroxy-2-pyranoneHMDB
3-Hydroxy-2-pyroneHMDB
3-Hydroxy-2H-pyran-4-oneHMDB
3-Hydroxy-a-pyroneHMDB
3-HydroxypyroneHMDB
HydroxycoumalinHMDB
Isopyromucic acidHMDB
Chemical FormulaC5H4O3
Average Molecular Weight112.0835
Monoisotopic Molecular Weight112.016043994
IUPAC Name3-hydroxy-2H-pyran-2-one
Traditional Name2H-pyran-2-one, 3-hydroxy-
CAS Registry Number496-64-0
SMILES
OC1=CC=COC1=O
InChI Identifier
InChI=1S/C5H4O3/c6-4-2-1-3-8-5(4)7/h1-3,6H
InChI KeyLIPRKYKMVQPYPG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrans
Sub ClassPyranones and derivatives
Direct ParentPyranones and derivatives
Alternative Parents
Substituents
  • Pyranone
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point92 °CNot Available
Boiling Point285.00 to 286.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility988200 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.763 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility153 g/LALOGPS
logP0.12ALOGPS
logP0.5ChemAxon
logS0.14ALOGPS
pKa (Strongest Acidic)10.36ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity28.06 m³·mol⁻¹ChemAxon
Polarizability9.53 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+119.86531661259
DarkChem[M-H]-116.38231661259
DeepCCS[M+H]+127.35430932474
DeepCCS[M-H]-124.57730932474
DeepCCS[M-2H]-160.89530932474
DeepCCS[M+Na]+135.80630932474
AllCCS[M+H]+122.032859911
AllCCS[M+H-H2O]+117.032859911
AllCCS[M+NH4]+126.832859911
AllCCS[M+Na]+128.132859911
AllCCS[M-H]-116.432859911
AllCCS[M+Na-2H]-118.832859911
AllCCS[M+HCOO]-121.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Hydroxy-2H-pyran-2-oneOC1=CC=COC1=O1880.5Standard polar33892256
3-Hydroxy-2H-pyran-2-oneOC1=CC=COC1=O1011.5Standard non polar33892256
3-Hydroxy-2H-pyran-2-oneOC1=CC=COC1=O986.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Hydroxy-2H-pyran-2-one,1TMS,isomer #1C[Si](C)(C)OC1=CC=COC1=O1246.7Semi standard non polar33892256
3-Hydroxy-2H-pyran-2-one,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=COC1=O1496.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxy-2H-pyran-2-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-03e9-9200000000-fd9ba258a526aac216eb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxy-2H-pyran-2-one GC-MS (1 TMS) - 70eV, Positivesplash10-00di-7900000000-486b332aacec86d1d67c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxy-2H-pyran-2-one 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 - 3-Hydroxy-2H-pyran-2-one 10V, Positive-QTOFsplash10-03di-0900000000-1686a0593413d635eb072016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2H-pyran-2-one 20V, Positive-QTOFsplash10-03di-6900000000-6cd451c9786a8590441b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2H-pyran-2-one 40V, Positive-QTOFsplash10-014i-9000000000-8e7721cb55fe783eba822016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2H-pyran-2-one 10V, Negative-QTOFsplash10-03di-1900000000-163c68faf2609d9a531b2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2H-pyran-2-one 20V, Negative-QTOFsplash10-03di-3900000000-ac4814c1b3f744ef90772016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2H-pyran-2-one 40V, Negative-QTOFsplash10-0uxr-9000000000-7f5edd2de0d2e58d45492016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2H-pyran-2-one 10V, Positive-QTOFsplash10-03di-6900000000-0f912d6f407d4b7d8ad22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2H-pyran-2-one 20V, Positive-QTOFsplash10-029i-9300000000-bc7b4b9431b9193408a42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2H-pyran-2-one 40V, Positive-QTOFsplash10-0f79-9000000000-a003bff52f175560936a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2H-pyran-2-one 10V, Negative-QTOFsplash10-03di-2900000000-c7ba4b5b67825bb825db2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2H-pyran-2-one 20V, Negative-QTOFsplash10-08fr-9400000000-07eb7a9cda13d228f0412021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2H-pyran-2-one 40V, Negative-QTOFsplash10-00kf-9000000000-5cda0a325045b80110cb2021-09-23Wishart 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+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 IDFDB010983
KNApSAcK IDNot Available
Chemspider ID61438
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound68130
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1637111
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .