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Showing metabocard for furaneol (keto form) (HMDB0304357)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-24 09:10:07 UTC
Update Date2021-09-24 09:10:07 UTC
HMDB IDHMDB0304357
Secondary Accession NumbersNone
Metabolite Identification
Common Namefuraneol (keto form)
DescriptionFuraneol (keto form), also known as 2,5-dimethyl-4-hydroxy-3(2h)-furanone or hdmf, is a member of the class of compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group. Furaneol (keto form) is soluble (in water) and a very weakly acidic compound (based on its pKa). Furaneol (keto form) can be found in a number of food items such as globe artichoke, nuts, quinoa, and purslane, which makes furaneol (keto form) a potential biomarker for the consumption of these food products.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0304357 (furaneol (keto form))


  Mrv1533007131517142D          

  9  9  0  0  0  0            999 V2000
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    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
   -0.0997    0.6294    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
   -0.8843    0.8843    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  6  5  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  3  1  0  0  0  0
  9  4  1  0  0  0  0
M  CHG  1   8  -1
M  END
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3D MOL for HMDB0304357 (furaneol (keto form))

HMDB0304357
     RDKit          3D
furaneol (keto form)
 16 16  0  0  0  0  0  0  0  0999 V2000
    2.5201   -0.2041   -0.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1175   -0.1292   -0.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8196   -0.0813    1.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6878   -0.0896    2.2594 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.6509   -0.0147    1.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3349   -0.2953    2.2532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0561    0.4374   -0.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4175   -0.0472   -0.5152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0232   -0.1006   -0.9157 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5774   -0.6536   -1.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9605    0.8143   -0.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1211   -0.8175    0.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0224    1.5313   -0.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6632    0.4523   -1.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4936   -1.1273   -0.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1422    0.3250    0.2295 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9  2  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  7 13  1  0
  8 14  1  0
  8 15  1  0
  8 16  1  0
M  CHG  1   4  -1
M  END
Download

3D SDF for HMDB0304357 (furaneol (keto form))


  Mrv1533007131517142D          

  9  9  0  0  0  0            999 V2000
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    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
   -0.0997    0.6294    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
   -0.8843    0.8843    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  6  5  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  3  1  0  0  0  0
  9  4  1  0  0  0  0
M  CHG  1   8  -1
M  END
> <DATABASE_ID>
HMDB0304357

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1OC(C)=C([O-])C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O3/c1-3-5(7)6(8)4(2)9-3/h3,8H,1-2H3/p-1

> <INCHI_KEY>
INAXVXBDKKUCGI-UHFFFAOYSA-M

> <FORMULA>
C6H7O3

> <MOLECULAR_WEIGHT>
127.12

> <EXACT_MASS>
127.040067665

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
12.111279114116224

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,5-dimethyl-4-oxo-4,5-dihydrofuran-3-olate

> <ALOGPS_LOGP>
0.08

> <JCHEM_LOGP>
0.20876269400000025

> <ALOGPS_LOGS>
0.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.354201377373752

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.76173119540573

> <JCHEM_PKA_STRONGEST_BASIC>
-4.325980311633708

> <JCHEM_POLAR_SURFACE_AREA>
49.36

> <JCHEM_REFRACTIVITY>
43.843

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.56e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,5-dimethyl-4-oxo-5H-furan-3-olate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0304357 (furaneol (keto form))

HMDB0304357
     RDKit          3D
furaneol (keto form)
 16 16  0  0  0  0  0  0  0  0999 V2000
    2.5201   -0.2041   -0.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1175   -0.1292   -0.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8196   -0.0813    1.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6878   -0.0896    2.2594 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.6509   -0.0147    1.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3349   -0.2953    2.2532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0561    0.4374   -0.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4175   -0.0472   -0.5152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0232   -0.1006   -0.9157 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5774   -0.6536   -1.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9605    0.8143   -0.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1211   -0.8175    0.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0224    1.5313   -0.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6632    0.4523   -1.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4936   -1.1273   -0.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1422    0.3250    0.2295 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9  2  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  7 13  1  0
  8 14  1  0
  8 15  1  0
  8 16  1  0
M  CHG  1   4  -1
M  END
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PDB for HMDB0304357 (furaneol (keto form))

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0       3.770   1.651   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O-1
HETATM    9  O   UNK     0       1.830  -0.290   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5    9                                                  
CONECT    4    2    6    9                                                  
CONECT    5    3    6    7                                                  
CONECT    6    4    5    8                                                  
CONECT    7    5                                                            
CONECT    8    6                                                            
CONECT    9    3    4                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for HMDB0304357 (furaneol (keto form))

COMPND    HMDB0304357
HETATM    1  C1  UNL     1       2.520  -0.204  -0.631  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.117  -0.129  -0.129  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.820  -0.081   1.160  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.688  -0.090   2.259  1.00  0.00           O1-
HETATM    5  C4  UNL     1      -0.651  -0.015   1.236  1.00  0.00           C  
HETATM    6  O2  UNL     1      -1.335  -0.295   2.253  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.056   0.437  -0.111  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.417  -0.047  -0.515  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.023  -0.101  -0.916  1.00  0.00           O  
HETATM   10  H1  UNL     1       2.577  -0.654  -1.627  1.00  0.00           H  
HETATM   11  H2  UNL     1       2.961   0.814  -0.608  1.00  0.00           H  
HETATM   12  H3  UNL     1       3.121  -0.817   0.077  1.00  0.00           H  
HETATM   13  H4  UNL     1      -1.022   1.531  -0.207  1.00  0.00           H  
HETATM   14  H5  UNL     1      -2.663   0.452  -1.477  1.00  0.00           H  
HETATM   15  H6  UNL     1      -2.494  -1.127  -0.647  1.00  0.00           H  
HETATM   16  H7  UNL     1      -3.142   0.325   0.230  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    3    9
CONECT    3    4    5
CONECT    5    6    6    7
CONECT    7    8    9   13
CONECT    8   14   15   16
END
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SMILES for HMDB0304357 (furaneol (keto form))

CC1OC(C)=C([O-])C1=O
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INCHI for HMDB0304357 (furaneol (keto form))

InChI=1S/C6H8O3/c1-3-5(7)6(8)4(2)9-3/h3,8H,1-2H3/p-1
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2,5-Dimethyl-4-oxofuran-3-olic acidGenerator
Furaneol (keto form)MetaCyc
HDMFMetaCyc
Chemical FormulaC6H7O3
Average Molecular Weight127.12
Monoisotopic Molecular Weight127.040067665
IUPAC Name2,5-dimethyl-4-oxo-4,5-dihydrofuran-3-olate
Traditional Name2,5-dimethyl-4-oxo-5H-furan-3-olate
CAS Registry NumberNot Available
SMILES
CC1OC(C)=C([O-])C1=O
InChI Identifier
InChI=1S/C6H8O3/c1-3-5(7)6(8)4(2)9-3/h3,8H,1-2H3/p-1
InChI KeyINAXVXBDKKUCGI-UHFFFAOYSA-M
Chemical Taxonomy
Description Belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydrofurans
Sub ClassFuranones
Direct ParentFuranones
Alternative Parents
Substituents
  • 3-furanone
  • Vinylogous ester
  • Cyclic ketone
  • Ketone
  • Oxacycle
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Organic anion
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
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
logP0.08ALOGPS
logP0.21ChemAxon
logS0.5ALOGPS
pKa (Strongest Acidic)7.76ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area49.36 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.84 m³·mol⁻¹ChemAxon
Polarizability12.11 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
AllCCS[M+H]+126.99632859911
AllCCS[M+H-H2O]+122.22232859911
AllCCS[M+Na]+132.73932859911
AllCCS[M+NH4]+131.45332859911
AllCCS[M-H]-119.99932859911
AllCCS[M+Na-2H]-122.0232859911
AllCCS[M+HCOO]-124.28432859911
DeepCCS[M+H]+127.3230932474
DeepCCS[M-H]-123.530932474
DeepCCS[M-2H]-161.22630932474
DeepCCS[M+Na]+136.39930932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
furaneol (keto form),1TMS,isomer #1CC1=C([O-])C(O[Si](C)(C)C)=C(C)O11224.4Semi standard non polar33892256
furaneol (keto form),1TMS,isomer #1CC1=C([O-])C(O[Si](C)(C)C)=C(C)O11196.5Standard non polar33892256
furaneol (keto form),1TMS,isomer #1CC1=C([O-])C(O[Si](C)(C)C)=C(C)O11342.8Standard polar33892256
furaneol (keto form),1TBDMS,isomer #1CC1=C([O-])C(O[Si](C)(C)C(C)(C)C)=C(C)O11483.1Semi standard non polar33892256
furaneol (keto form),1TBDMS,isomer #1CC1=C([O-])C(O[Si](C)(C)C(C)(C)C)=C(C)O11399.1Standard non polar33892256
furaneol (keto form),1TBDMS,isomer #1CC1=C([O-])C(O[Si](C)(C)C(C)(C)C)=C(C)O11537.1Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - furaneol (keto form) 10V, Negative-QTOFsplash10-004i-2900000000-0eea56cdcc238a46b5df2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - furaneol (keto form) 20V, Negative-QTOFsplash10-004i-0900000000-523716ac3545ef2838022019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - furaneol (keto form) 40V, Negative-QTOFsplash10-0a4l-9000000000-7a9f8f19c1a30dfa4d112019-02-23Wishart 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 IDFDB030866
KNApSAcK IDNot Available
Chemspider ID24785033
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25200937
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