Showing metabocard for Sotolon (MMDBc0033547)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:53:05 UTC
Update Date2022-08-31 22:36:41 UTC
Metabolite IDMMDBc0033547
Metabolite Identification
Common NameSotolon
DescriptionSotolon, also known as 3-hydroxy-4,5-dimethyl-2(5H)-furanone or sotolone, is key flavoring compound found in raw cane sugar, aged sake, coffee, fenugreek, lovage and wines. Sotolon (also known as sotolone) is a lactone and an extremely powerful aroma compound, with the typical smell of fenugreek or curry at high concentrations and maple syrup, caramel, or burnt sugar at lower concentrations. In 1999 it was shown that sotolon is the cause of the odor found in patients with maple syrup urine disease (MSUD) - PMID 10234605 . This compound was found in the urine of 7 MSUD patients but was undetectable in normal individuals. Sotolon belongs to the family of Butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x0000560be1d62660>


  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 #<Metabolite:0x0000560be1d62660>

HMDB0031306
     RDKit          3D
3-Hydroxy-4,5-dimethyl-2(5H)-furanone
 17 17  0  0  0  0  0  0  0  0999 V2000
   -0.0966   -1.8186   -0.4006 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2302   -0.3967   -0.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3423    0.0701    0.3181 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4207   -0.6782    0.8057 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2959    1.5076    0.3303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2234    2.2654    0.7828 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0927    1.8908   -0.2243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190    0.7359   -0.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9579    0.7215    0.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9287   -2.1659    0.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3226   -1.9594   -1.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7595   -2.4941   -0.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2879   -0.7595    0.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7914    0.8077   -1.6857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4303   -0.2606    0.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6108    1.4536   -0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8952    1.0807    1.1673 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  9  1  0
  8  2  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  4 13  1  0
  8 14  1  0
  9 15  1  0
  9 16  1  0
  9 17  1  0
M  END
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3D SDF for #<Metabolite:0x0000560be1d62660>


  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>
MMDBc0033547

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x0000560be1d62660>

HMDB0031306
     RDKit          3D
3-Hydroxy-4,5-dimethyl-2(5H)-furanone
 17 17  0  0  0  0  0  0  0  0999 V2000
   -0.0966   -1.8186   -0.4006 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2302   -0.3967   -0.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3423    0.0701    0.3181 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4207   -0.6782    0.8057 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2959    1.5076    0.3303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2234    2.2654    0.7828 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0927    1.8908   -0.2243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190    0.7359   -0.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9579    0.7215    0.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9287   -2.1659    0.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3226   -1.9594   -1.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7595   -2.4941   -0.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2879   -0.7595    0.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7914    0.8077   -1.6857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4303   -0.2606    0.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6108    1.4536   -0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8952    1.0807    1.1673 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  9  1  0
  8  2  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  4 13  1  0
  8 14  1  0
  9 15  1  0
  9 16  1  0
  9 17  1  0
M  END
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PDB for #<Metabolite:0x0000560be1d62660>

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 #<Metabolite:0x0000560be1d62660>

COMPND    HMDB0031306
HETATM    1  C1  UNL     1      -0.097  -1.819  -0.401  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.230  -0.397  -0.214  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.342   0.070   0.318  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.421  -0.678   0.806  1.00  0.00           O  
HETATM    5  C4  UNL     1       1.296   1.508   0.330  1.00  0.00           C  
HETATM    6  O2  UNL     1       2.223   2.265   0.783  1.00  0.00           O  
HETATM    7  O3  UNL     1       0.093   1.891  -0.224  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.619   0.736  -0.585  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.958   0.722   0.125  1.00  0.00           C  
HETATM   10  H1  UNL     1      -0.929  -2.166   0.244  1.00  0.00           H  
HETATM   11  H2  UNL     1      -0.323  -1.959  -1.491  1.00  0.00           H  
HETATM   12  H3  UNL     1       0.760  -2.494  -0.185  1.00  0.00           H  
HETATM   13  H4  UNL     1       3.288  -0.760   0.260  1.00  0.00           H  
HETATM   14  H5  UNL     1      -0.791   0.808  -1.686  1.00  0.00           H  
HETATM   15  H6  UNL     1      -2.430  -0.261   0.015  1.00  0.00           H  
HETATM   16  H7  UNL     1      -2.611   1.454  -0.414  1.00  0.00           H  
HETATM   17  H8  UNL     1      -1.895   1.081   1.167  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    3    8
CONECT    3    4    5
CONECT    4   13
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   14
CONECT    9   15   16   17
END
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SMILES for #<Metabolite:0x0000560be1d62660>

CC1OC(=O)C(O)=C1C
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INCHI for #<Metabolite:0x0000560be1d62660>

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, MeSH
4,5-Dimethyl-3-hydroxy-2,5-dihydro-2-furanoneHMDB
4,5-Dimethyl-3-hydroxy-2,5-dihydrofuran-2-oneHMDB
SautaloneHMDB
SotolonHMDB
SotoloneHMDB, MeSH
Molecular FormulaC6H8O3
Average Mass128.1259
Monoisotopic Mass128.047344122
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