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Showing NP-Card for 3-Hydroxy-4,5-dimethyl-2(5H)-furanone (NP0046141)

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Record Information
Version2.0
Created at2022-03-17 19:49:09 UTC
Updated at2022-03-17 19:49:09 UTC
NP-MRD IDNP0046141
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Hydroxy-4,5-dimethyl-2(5H)-furanone
Description3-Hydroxy-4,5-dimethyl-2(5H)-furanone, also known as sotolon or 2-hydroxy-3,4-dimethyl-2-buten-1,4-olide, belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. 3-Hydroxy-4,5-dimethyl-2(5H)-furanone is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Hydroxy-4,5-dimethyl-2(5H)-furanone is a strong, extremely sweet, and burnt tasting compound. Outside of the human body, 3-Hydroxy-4,5-dimethyl-2(5H)-furanone has been detected, but not quantified in, several different foods, such as coffee and coffee products, herbs and spices, fenugreeks, alcoholic beverages, and blackberries. This could make 3-hydroxy-4,5-dimethyl-2(5H)-furanone a potential biomarker for the consumption of these foods. 3-Hydroxy-4,5-dimethyl-2(5H)-furanone is found in Mallotus peltatus. 3-Hydroxy-4,5-dimethyl-2(5H)-furanone was first documented in 1999 (PMID: 10234605). 3-Hydroxy-4,5-dimethyl-2(5H)-furanone, with regard to humans, has been linked to the inborn metabolic disorder maple syrup urine disease.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0046141 (3-Hydroxy-4,5-dimethyl-2(5H)-furanone)


  Mrv0541 02241218472D          

  9  9  0  0  0  0            999 V2000
   -0.7603   -0.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9975    0.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2792    1.0168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3846    0.5269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1003   -0.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5745   -0.9666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2501   -0.9113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7719    0.8271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1748    0.7640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  2  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2  8  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  2  0  0  0  0
  5  6  1  0  0  0  0
M  END
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3D MOL for NP0046141 (3-Hydroxy-4,5-dimethyl-2(5H)-furanone)

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3D SDF for NP0046141 (3-Hydroxy-4,5-dimethyl-2(5H)-furanone)

  Mrv0541 02241218472D          

  9  9  0  0  0  0            999 V2000
   -0.7603   -0.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9975    0.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2792    1.0168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3846    0.5269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1003   -0.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5745   -0.9666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2501   -0.9113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7719    0.8271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1748    0.7640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  2  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2  8  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  2  0  0  0  0
  5  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046141

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(=O)C(O)=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O3/c1-3-4(2)9-6(8)5(3)7/h4,7H,1-2H3

> <INCHI_KEY>
UNYNVICDCJHOPO-UHFFFAOYSA-N

> <FORMULA>
C6H8O3

> <MOLECULAR_WEIGHT>
128.1259

> <EXACT_MASS>
128.047344122

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
12.348203095543226

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.14

> <JCHEM_LOGP>
0.6778942036666665

> <ALOGPS_LOGS>
0.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.255657026428107

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.276714669633304

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0517646399019753

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
31.915599999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.18e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sotolon

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0046141 (3-Hydroxy-4,5-dimethyl-2(5H)-furanone)
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PDB for NP0046141 (3-Hydroxy-4,5-dimethyl-2(5H)-furanone)
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  C   UNK     0      -1.419  -0.462   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.862   1.013   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.521   1.898   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.718   0.984   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.187  -0.462   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.072  -1.804   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.334  -1.701   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.308   1.544   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.193   1.426   0.000  0.00  0.00           O+0
CONECT    1    2    5    7                                                  
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    1    4    6                                                  
CONECT    6    5                                                            
CONECT    7    1                                                            
CONECT    8    2                                                            
CONECT    9    4                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END

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3D PDB for NP0046141 (3-Hydroxy-4,5-dimethyl-2(5H)-furanone)
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SMILES for NP0046141 (3-Hydroxy-4,5-dimethyl-2(5H)-furanone)
CC1OC(=O)C(O)=C1C
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INCHI for NP0046141 (3-Hydroxy-4,5-dimethyl-2(5H)-furanone)
InChI=1S/C6H8O3/c1-3-4(2)9-6(8)5(3)7/h4,7H,1-2H3
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Synonyms
ValueSource
2,3-Dimethyl-4-hydroxy-2,5-dihydrofuran-5-oneHMDB
2-Hydroxy-3,4-dimethyl-2-buten-1,4-olideHMDB
2-Hydroxy-3-methyl-2-penten-4-olideHMDB
3,4-Dimethyl-2-hydroxy-2-butan-1,4-olideHMDB
3-Hydroxy-4,5(R)-dimethyl-2(5H)-furanoneHMDB
3-Hydroxy-4,5-dimethyl-5H-furan-2-oneHMDB
3-Hydroxy-4,5-dimethyl-furan-2(5H)-oneHMDB
3-Hydroxy-4,5-dimethylfuran-2(5H)-oneHMDB
4,5-Dimethyl-3-hydroxy-2(5H)-furanoneHMDB
4,5-Dimethyl-3-hydroxy-2,5-dihydro-2-furanoneHMDB
4,5-Dimethyl-3-hydroxy-2,5-dihydrofuran-2-oneHMDB
SautaloneHMDB
SotolonHMDB
SotoloneHMDB
Chemical FormulaC6H8O3
Average Mass128.1259 Da
Monoisotopic Mass128.04734 Da
IUPAC Name3-hydroxy-4,5-dimethyl-2,5-dihydrofuran-2-one
Traditional Namesotolon
CAS Registry Number28664-35-9
SMILES
CC1OC(=O)C(O)=C1C
InChI Identifier
InChI=1S/C6H8O3/c1-3-4(2)9-6(8)5(3)7/h4,7H,1-2H3
InChI KeyUNYNVICDCJHOPO-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Coffea arabica L.FooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephoraFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Mallotus peltatusLOTUS Database
Trigonella foenum-graecumFooDB
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
    • 

  • Enol
    • 

  • Carboxylic acid derivative
    • 

  • 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-0.14ALOGPS
logP0.68ChemAxon
logS0.23ALOGPS
pKa (Strongest Acidic)9.28ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity31.92 m³·mol⁻¹ChemAxon
Polarizability12.35 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031306  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003360  
KNApSAcK IDNot Available
Chemspider ID56569  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound62835  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Podebrad F, Heil M, Reichert S, Mosandl A, Sewell AC, Bohles H: 4,5-dimethyl-3-hydroxy-2[5H]-furanone (sotolone)--the odour of maple syrup urine disease. J Inherit Metab Dis. 1999 Apr;22(2):107-14. doi: 10.1023/a:1005433516026. [PubMed:10234605  ]