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Showing NP-Card for 4-hydroxy-5-methyl-2h-furan-3-one (NP0275586)

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Record Information
Version1.0
Created at2022-09-08 23:22:33 UTC
Updated at2022-09-08 23:22:34 UTC
NP-MRD IDNP0275586
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-hydroxy-5-methyl-2h-furan-3-one
DescriptionNorfuraneol, also known as 4Hm-furanone, belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group. Norfuraneol is an extremely weak basic (essentially neutral) compound (based on its pKa). Norfuraneol is a sweet, bready, and candy tasting compound. Outside of the human body, Norfuraneol has been detected, but not quantified in, a few different foods, such as blackberries, evergreen blackberries, and fruits. 4-hydroxy-5-methyl-2h-furan-3-one is found in Eurycotis floridana and Trypanosoma brucei. This could make norfuraneol a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0275586 (4-hydroxy-5-methyl-2h-furan-3-one)


  Mrv0541 05061306112D          

  8  8  0  0  0  0            999 V2000
   -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  0  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  2  0  0  0  0
  5  4  1  0  0  0  0
  6  4  2  0  0  0  0
  7  5  1  0  0  0  0
  8  2  1  0  0  0  0
  8  3  1  0  0  0  0
M  END
Download

3D MOL for NP0275586 (4-hydroxy-5-methyl-2h-furan-3-one)

     RDKit          3D

 14 14  0  0  0  0  0  0  0  0999 V2000
    1.9903   -0.5969   -0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5198   -0.4089    0.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0539    0.7820   -0.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5633    2.0124   -0.1712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4910    0.5916   -0.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4002    1.4513    0.0299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7244   -0.8653   -0.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4312   -1.3996    0.0870 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3310   -1.1827   -0.8834 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2344   -1.2213    0.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5358    0.3456    0.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4831    2.7310    0.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1433   -1.0934   -1.0942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4137   -1.1457    0.7147 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
  8  2  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  4 12  1  0
  7 13  1  0
  7 14  1  0
M  END
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3D SDF for NP0275586 (4-hydroxy-5-methyl-2h-furan-3-one)


  Mrv0541 05061306112D          

  8  8  0  0  0  0            999 V2000
   -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  0  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  2  0  0  0  0
  5  4  1  0  0  0  0
  6  4  2  0  0  0  0
  7  5  1  0  0  0  0
  8  2  1  0  0  0  0
  8  3  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0275586

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(O)C(=O)CO1

> <INCHI_IDENTIFIER>
InChI=1S/C5H6O3/c1-3-5(7)4(6)2-8-3/h7H,2H2,1H3

> <INCHI_KEY>
DLVYTANECMRFGX-UHFFFAOYSA-N

> <FORMULA>
C5H6O3

> <MOLECULAR_WEIGHT>
114.0993

> <EXACT_MASS>
114.031694058

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
10.504270220383582

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-5-methyl-2,3-dihydrofuran-3-one

> <ALOGPS_LOGP>
-0.83

> <JCHEM_LOGP>
-0.3600015483333334

> <ALOGPS_LOGS>
0.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.893366061415222

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.876746084908906

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3627795462910415

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
28.798799999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.16e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-5-methyl-2H-furan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0275586 (4-hydroxy-5-methyl-2h-furan-3-one)

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PDB for NP0275586 (4-hydroxy-5-methyl-2h-furan-3-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      -0.615  -1.536   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  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.830  -0.290   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4    8                                                       
CONECT    3    1    5    8                                                  
CONECT    4    2    5    6                                                  
CONECT    5    3    4    7                                                  
CONECT    6    4                                                            
CONECT    7    5                                                            
CONECT    8    2    3                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END

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3D PDB for NP0275586 (4-hydroxy-5-methyl-2h-furan-3-one)
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SMILES for NP0275586 (4-hydroxy-5-methyl-2h-furan-3-one)
CC1=C(O)C(=O)CO1
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INCHI for NP0275586 (4-hydroxy-5-methyl-2h-furan-3-one)
InChI=1S/C5H6O3/c1-3-5(7)4(6)2-8-3/h7H,2H2,1H3
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Synonyms
ValueSource
4-Hydroxy-5-methyl-2,3-dihydrofuran-3-oneHMDB
4-Hydroxy-5-methyl-3(2H)-furanoneHMDB
4-Hydroxy-5-methyl-3-furanoneHMDB
4-Hydroxy-5-methylfuran-3(2H)-oneHMDB
5-Methyl-4-hydroxy-3(2H)-furanoneHMDB
4Hm-FuranoneHMDB
NorfuraneolMeSH
Chemical FormulaC5H6O3
Average Mass114.0993 Da
Monoisotopic Mass114.03169 Da
IUPAC Name4-hydroxy-5-methyl-2,3-dihydrofuran-3-one
Traditional Name4-hydroxy-5-methyl-2H-furan-3-one
CAS Registry NumberNot Available
SMILES
CC1=C(O)C(=O)CO1
InChI Identifier
InChI=1S/C5H6O3/c1-3-5(7)4(6)2-8-3/h7H,2H2,1H3
InChI KeyDLVYTANECMRFGX-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Eurycotis floridanaLOTUS Database
Trypanosoma bruceiLOTUS Database
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
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.83ALOGPS
logP-0.36ChemAxon
logS0.73ALOGPS
pKa (Strongest Acidic)6.88ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity28.8 m³·mol⁻¹ChemAxon
Polarizability10.5 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031859  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008543  
KNApSAcK IDNot Available
Chemspider ID3757733  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4564493  
PDB IDNot Available
ChEBI ID74456  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]