Showing metabocard for ethyl 3-hydroxybutanoate (MMDBc0033458)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:49:29 UTC
Update Date2024-04-30 20:09:44 UTC
Metabolite IDMMDBc0033458
Metabolite Identification
Common Nameethyl 3-hydroxybutanoate
DescriptionEthyl-3-hydroxybutyrate is a volatile ethyl ester found in wine and produced during fermentation by yeast. Ethyl esters are formed by the reaction of ethanol with a fatty acid. Ethyl-3-hydroxybutyrate is responsible for marshmallow-like aromas. The concentrations of ethyl ester decrease over time as a wine ages due to spontaneous hydrolysis.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fa4ecf51840>


  Mrv0541 05061311492D          

  9  8  0  0  0  0            999 V2000
   -1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1599   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  3  1  0  0  0  0
  9  6  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fa4ecf51840>

HMDB0040409
     RDKit          3D
Ethyl (±)-3-hydroxybutyrate
 21 20  0  0  0  0  0  0  0  0999 V2000
    3.2433    0.5767   -0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7902   -0.8732   -0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5043   -0.9879    0.4003 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3996   -0.3612   -0.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6128    0.3188   -1.1941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8955   -0.5399    0.4827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0232    0.1889   -0.2169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3309   -0.0454    0.5095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7393    1.5663   -0.0787 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7838    1.1584   -0.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3465    0.5346   -0.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1774    1.0529    0.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5111   -1.4048    0.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8606   -1.2488   -1.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1611   -1.6178    0.4982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8091   -0.2231    1.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0912   -0.0471   -1.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1783    0.2653    1.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0937    0.6647    0.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6960   -1.0740    0.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2113    2.0967   -0.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  6 15  1  0
  6 16  1  0
  7 17  1  0
  8 18  1  0
  8 19  1  0
  8 20  1  0
  9 21  1  0
M  END
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3D SDF for #<Metabolite:0x00007fa4ecf51840>


  Mrv0541 05061311492D          

  9  8  0  0  0  0            999 V2000
   -1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1599   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  3  1  0  0  0  0
  9  6  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033458

> <DATABASE_NAME>
MIME

> <SMILES>
CCOC(=O)CC(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O3/c1-3-9-6(8)4-5(2)7/h5,7H,3-4H2,1-2H3

> <INCHI_KEY>
OMSUIQOIVADKIM-UHFFFAOYSA-N

> <FORMULA>
C6H12O3

> <MOLECULAR_WEIGHT>
132.1577

> <EXACT_MASS>
132.07864425

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
14.017304871558679

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl 3-hydroxybutanoate

> <ALOGPS_LOGP>
0.39

> <JCHEM_LOGP>
0.11569601133333332

> <ALOGPS_LOGS>
0.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.407232472549236

> <JCHEM_PKA_STRONGEST_BASIC>
-2.620676516506963

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
32.9818

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.99e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl 3-hydroxybutanoate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007fa4ecf51840>

HMDB0040409
     RDKit          3D
Ethyl (±)-3-hydroxybutyrate
 21 20  0  0  0  0  0  0  0  0999 V2000
    3.2433    0.5767   -0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7902   -0.8732   -0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5043   -0.9879    0.4003 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3996   -0.3612   -0.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6128    0.3188   -1.1941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8955   -0.5399    0.4827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0232    0.1889   -0.2169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3309   -0.0454    0.5095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7393    1.5663   -0.0787 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7838    1.1584   -0.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3465    0.5346   -0.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1774    1.0529    0.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5111   -1.4048    0.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8606   -1.2488   -1.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1611   -1.6178    0.4982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8091   -0.2231    1.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0912   -0.0471   -1.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1783    0.2653    1.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0937    0.6647    0.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6960   -1.0740    0.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2113    2.0967   -0.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  6 15  1  0
  6 16  1  0
  7 17  1  0
  8 18  1  0
  8 19  1  0
  8 20  1  0
  9 21  1  0
M  END
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PDB for #<Metabolite:0x00007fa4ecf51840>

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      -2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.898  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.231  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.565  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.897  -1.334   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.565  -2.874   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.897  -2.874   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.564  -0.564   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    5                                                            
CONECT    3    1    9                                                       
CONECT    4    5    6                                                       
CONECT    5    2    4    7                                                  
CONECT    6    4    8    9                                                  
CONECT    7    5                                                            
CONECT    8    6                                                            
CONECT    9    3    6                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for #<Metabolite:0x00007fa4ecf51840>

COMPND    HMDB0040409
HETATM    1  C1  UNL     1       3.243   0.577  -0.183  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.790  -0.873  -0.149  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.504  -0.988   0.400  1.00  0.00           O  
HETATM    4  C3  UNL     1       0.400  -0.361  -0.161  1.00  0.00           C  
HETATM    5  O2  UNL     1       0.613   0.319  -1.194  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.896  -0.540   0.483  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.023   0.189  -0.217  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.331  -0.045   0.509  1.00  0.00           C  
HETATM    9  O3  UNL     1      -1.739   1.566  -0.079  1.00  0.00           O  
HETATM   10  H1  UNL     1       2.784   1.158  -0.981  1.00  0.00           H  
HETATM   11  H2  UNL     1       4.347   0.535  -0.420  1.00  0.00           H  
HETATM   12  H3  UNL     1       3.177   1.053   0.816  1.00  0.00           H  
HETATM   13  H4  UNL     1       3.511  -1.405   0.498  1.00  0.00           H  
HETATM   14  H5  UNL     1       2.861  -1.249  -1.185  1.00  0.00           H  
HETATM   15  H6  UNL     1      -1.161  -1.618   0.498  1.00  0.00           H  
HETATM   16  H7  UNL     1      -0.809  -0.223   1.538  1.00  0.00           H  
HETATM   17  H8  UNL     1      -2.091  -0.047  -1.279  1.00  0.00           H  
HETATM   18  H9  UNL     1      -3.178   0.265   1.576  1.00  0.00           H  
HETATM   19  H10 UNL     1      -4.094   0.665   0.099  1.00  0.00           H  
HETATM   20  H11 UNL     1      -3.696  -1.074   0.425  1.00  0.00           H  
HETATM   21  H12 UNL     1      -2.211   2.097  -0.759  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3   13   14
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   15   16
CONECT    7    8    9   17
CONECT    8   18   19   20
CONECT    9   21
END
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SMILES for #<Metabolite:0x00007fa4ecf51840>

CCOC(=O)CC(C)O
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INCHI for #<Metabolite:0x00007fa4ecf51840>

InChI=1S/C6H12O3/c1-3-9-6(8)4-5(2)7/h5,7H,3-4H2,1-2H3
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Synonyms
ValueSource
Ethyl beta-hydroxybutyrateChEBI
Ethyl b-hydroxybutyrateGenerator
Ethyl b-hydroxybutyric acidGenerator
Ethyl beta-hydroxybutyric acidGenerator
Ethyl β-hydroxybutyrateGenerator
Ethyl β-hydroxybutyric acidGenerator
Ethyl (±)-3-hydroxybutyric acidGenerator
Ethyl 3-hydroxybutyrateHMDB
FEMA 3428HMDB
Ethyl 3-hydroxybutyric acidGenerator
(S)-Ethyl 3-hydroxybutyrateMeSH
(R)-Ethyl 3-hydroxybutyrateMeSH
Molecular FormulaC6H12O3
Average Mass132.1577
Monoisotopic Mass132.07864425
IUPAC Nameethyl 3-hydroxybutanoate
Traditional Nameethyl 3-hydroxybutanoate
CAS Registry Number5405-41-4
SMILES
CCOC(=O)CC(C)O
InChI Identifier
InChI=1S/C6H12O3/c1-3-9-6(8)4-5(2)7/h5,7H,3-4H2,1-2H3
InChI KeyOMSUIQOIVADKIM-UHFFFAOYSA-N