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Showing NP-Card for ethyl 3-hydroxybutyrate (NP0316757)

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Record Information
Version1.0
Created at2022-09-11 16:09:52 UTC
Updated at2022-09-11 16:09:52 UTC
NP-MRD IDNP0316757
Secondary Accession NumbersNone
Natural Product Identification
Common Nameethyl 3-hydroxybutyrate
DescriptionEthyl (±)-3-hydroxybutyrate, also known as ethyl b-hydroxybutyric acid or fema 3428, 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 an extremely weak basic (essentially neutral) compound (based on its pKa). ethyl 3-hydroxybutyrate is found in Camellia sinensis, Dactylanthus taylorii and Opuntia ficus-indica. It was first documented in 2014 (PMID: 24830411). The fatty acid ethyl ester of 3-hydroxybutyric acid (PMID: 26098542).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0316757 (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
Download

3D MOL for NP0316757 (ethyl 3-hydroxybutyrate)

     RDKit          3D

 21 20  0  0  0  0  0  0  0  0999 V2000
    3.2754   -0.0429   -0.7572 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7998    0.0021    0.6589 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4771    0.5462    0.7619 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3929   -0.0289    0.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5972   -1.0681   -0.5435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9863    0.5200    0.2311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9710   -0.3153   -0.5542 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3376    0.3024   -0.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6038   -0.4319   -1.8905 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7688   -1.0327   -0.9247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0486    0.7440   -0.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4439    0.1429   -1.4527 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4507    0.7239    1.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8731   -0.9763    1.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0705    1.5514   -0.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3130    0.4593    1.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9303   -1.3446   -0.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2127    1.4094   -0.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6742    0.1589    0.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0692   -0.0915   -1.1223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9588   -1.2283   -2.3225 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  1
  8 18  1  0
  8 19  1  0
  8 20  1  0
  9 21  1  0
M  END
Download

3D SDF for NP0316757 (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>
NP0316757

> <DATABASE_NAME>
NP-MRD

> <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 NP0316757 (ethyl 3-hydroxybutyrate)

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PDB for NP0316757 (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 NP0316757 (ethyl 3-hydroxybutyrate)
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SMILES for NP0316757 (ethyl 3-hydroxybutyrate)
CCOC(=O)CC(C)O
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INCHI for NP0316757 (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 JSmol
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
(S)-Ethyl 3-hydroxybutyrateMeSH
(R)-Ethyl 3-hydroxybutyrateMeSH
Ethyl 3-hydroxybutyric acidGenerator
Chemical FormulaC6H12O3
Average Mass132.1577 Da
Monoisotopic Mass132.07864 Da
IUPAC Nameethyl 3-hydroxybutanoate
Traditional Nameethyl 3-hydroxybutanoate
CAS Registry NumberNot Available
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
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
Camellia sinensisLOTUS Database
Dactylanthus tayloriiLOTUS Database
Opuntia ficus-indicaLOTUS Database
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
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
logP0.39ALOGPS
logP0.12ChemAxon
logS0.35ALOGPS
pKa (Strongest Acidic)15.41ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity32.98 m³·mol⁻¹ChemAxon
Polarizability14.02 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0040409  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB020141  
KNApSAcK IDNot Available
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  
Good Scents IDNot Available
References
General References
  1. Perestrelo R, Silva C, Camara JS: A useful approach for the differentiation of wines according to geographical origin based on global volatile patterns. J Sep Sci. 2014 Aug;37(15):1974-81. doi: 10.1002/jssc.201400374. Epub 2014 Jun  20. [PubMed:24830411  ] 
  2. Krause Pham C, Ray A: Conservation of Olfactory Avoidance in Drosophila Species and Identification of Repellents for Drosophila suzukii. Sci Rep. 2015 Jun 22;5:11527. doi: 10.1038/srep11527. [PubMed:26098542  ] 
  3. LOTUS database [Link]