Showing NP-Card for Methyl-beta-hydroxybutyrate (NP0046260)

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Record Information
Version2.0
Created at2022-03-17 19:55:10 UTC
Updated at2022-03-17 19:55:10 UTC
NP-MRD IDNP0046260
Secondary Accession NumbersNone
Natural Product Identification
Common NameMethyl-beta-hydroxybutyrate
DescriptionMethyl-beta-hydroxybutyrate, also known as methyl-β-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. Methyl-beta-hydroxybutyrate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Thus, methyl 3-hydroxybutyrate is considered to be a fatty ester lipid molecule. Outside of the human body, Methyl-beta-hydroxybutyrate is found, on average, in the highest concentration within pineapples. This could make methyl-beta-hydroxybutyrate a potential biomarker for the consumption of these foods. Methyl 3-hydroxybutyrate belongs to beta hydroxy acids and derivatives class of compounds. Those are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Methyl 3-hydroxybutyrate is soluble (in water) and an extremely weak acidic compound (based on its pKa). Methyl 3-hydroxybutyrate has a mild and apple taste.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0046260 (Methyl-beta-hydroxybutyrate)

  Mrv1652307201900092D          

  8  7  0  0  0  0            999 V2000
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  2  1  0  0  0  0
  8  5  1  0  0  0  0
M  END
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3D MOL for NP0046260 (Methyl-beta-hydroxybutyrate)

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3D SDF for NP0046260 (Methyl-beta-hydroxybutyrate)
  Mrv1652307201900092D          

  8  7  0  0  0  0            999 V2000
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  2  1  0  0  0  0
  8  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046260

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H10O3/c1-4(6)3-5(7)8-2/h4,6H,3H2,1-2H3

> <INCHI_KEY>
LDLDJEAVRNAEBW-UHFFFAOYSA-N

> <FORMULA>
C5H10O3

> <MOLECULAR_WEIGHT>
118.132

> <EXACT_MASS>
118.062994182

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
12.066054360244188

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 3-hydroxybutanoate

> <ALOGPS_LOGP>
-0.08

> <JCHEM_LOGP>
-0.24111194333333352

> <ALOGPS_LOGS>
0.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.407247721653402

> <JCHEM_PKA_STRONGEST_BASIC>
-2.620669846548802

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
28.2332

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.00e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3-hydroxybutyrate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0046260 (Methyl-beta-hydroxybutyrate)
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PDB for NP0046260 (Methyl-beta-hydroxybutyrate)
HEADER    PROTEIN                                 20-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUL-19         0                                  
HETATM    1  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.311   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.976   3.644   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.644   3.644   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.977   1.334   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    8                                                            
CONECT    3    4    5                                                       
CONECT    4    1    3    6                                                  
CONECT    5    3    7    8                                                  
CONECT    6    4                                                            
CONECT    7    5                                                            
CONECT    8    2    5                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

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3D PDB for NP0046260 (Methyl-beta-hydroxybutyrate)
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SMILES for NP0046260 (Methyl-beta-hydroxybutyrate)
COC(=O)CC(C)O
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INCHI for NP0046260 (Methyl-beta-hydroxybutyrate)
InChI=1S/C5H10O3/c1-4(6)3-5(7)8-2/h4,6H,3H2,1-2H3
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Synonyms
ValueSource
Methyl-b-hydroxybutyrateGenerator
Methyl-b-hydroxybutyric acidGenerator
Methyl-beta-hydroxybutyric acidGenerator
Methyl-β-hydroxybutyrateGenerator
Methyl-β-hydroxybutyric acidGenerator
Methyl 3-hydroxybutyric acidGenerator
Chemical FormulaC5H10O3
Average Mass118.1320 Da
Monoisotopic Mass118.06299 Da
IUPAC Namemethyl 3-hydroxybutanoate
Traditional Namemethyl 3-hydroxybutyrate
CAS Registry Number1487-49-6
SMILES
COC(=O)CC(C)O
InChI Identifier
InChI=1S/C5H10O3/c1-4(6)3-5(7)8-2/h4,6H,3H2,1-2H3
InChI KeyLDLDJEAVRNAEBW-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Ananas comosusFooDB
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
  • Beta-hydroxy acid
    • 

  • Fatty acid ester
    • 

  • Fatty acid methyl ester
    • 

  • Fatty acyl
    • 

  • Methyl ester
    • 

  • Carboxylic acid ester
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid derivative
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Alcohol
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • 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
logP-0.08ALOGPS
logP-0.24ChemAxon
logS0.63ALOGPS
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 Count3ChemAxon
Refractivity28.23 m³·mol⁻¹ChemAxon
Polarizability12.07 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0041603  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003804  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15146  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available