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Showing metabocard for Ethyl (±)-3-hydroxybutyrate (HMDB0040409)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:56:58 UTC
Update Date2023-02-21 17:28:13 UTC
HMDB IDHMDB0040409
Secondary Accession Numbers
  • HMDB40409
Metabolite Identification
Common NameEthyl (±)-3-hydroxybutyrate
DescriptionEthyl (±)-3-hydroxybutyrate, also known as ethyl b-hydroxybutyric acid, belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Ethyl (±)-3-hydroxybutyrate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on Ethyl (±)-3-hydroxybutyrate.
Structure
Data?1677000493
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0040409 (Ethyl (±)-3-hydroxybutyrate)

  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 HMDB0040409 (Ethyl (±)-3-hydroxybutyrate)

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 HMDB0040409 (Ethyl (±)-3-hydroxybutyrate)

  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>
HMDB0040409

> <DATABASE_NAME>
hmdb

> <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 HMDB0040409 (Ethyl (±)-3-hydroxybutyrate)

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 HMDB0040409 (Ethyl (±)-3-hydroxybutyrate)

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 HMDB0040409 (Ethyl (±)-3-hydroxybutyrate)

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 HMDB0040409 (Ethyl (±)-3-hydroxybutyrate)

CCOC(=O)CC(C)O
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INCHI for HMDB0040409 (Ethyl (±)-3-hydroxybutyrate)

InChI=1S/C6H12O3/c1-3-9-6(8)4-5(2)7/h5,7H,3-4H2,1-2H3
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View in JSmolView Stereo Labels
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
Chemical FormulaC6H12O3
Average Molecular Weight132.1577
Monoisotopic Molecular Weight132.07864425
IUPAC Nameethyl 3-hydroxybutanoate
Traditional Nameethyl 3-hydroxybutanoate
CAS Registry Number35608-64-1
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
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Fatty acid ester
  • Beta-hydroxy acid
  • Fatty acyl
  • Secondary alcohol
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point170.00 to 175.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility159200 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.098 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB020141
KNApSAcK IDC00050444
Chemspider ID56334
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound62572
PDB IDNot Available
ChEBI ID87685
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1056311
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .