Back to Compounds

Showing Compound (S)-3-Hydroxybutyric acid (FDB022048)

Record Information
Version1.0
Creation date2011-09-21 00:07:36 UTC
Update date2015-10-09 22:30:25 UTC
Primary IDFDB022048
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(S)-3-Hydroxybutyric acid
Description(S)-3-Hydroxybutyric acid is a normal human metabolite, that has been found elevated in geriatric patients remitting from depression. (PMID 17048218) 3-Hydroxybutyric acid is a ketone body. Like the other ketone bodies (acetoacetate and acetone), levels of 3-Hydroxybutyric acid are raised in ketosis. In humans, 3-Hydroxybutyric acid is synthesized in the liver from acetyl-CoA, and can be used as an energy source by the brain when blood glucose is low. [HMDB]
CAS Number6168-83-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(+)-3-Hydroxybutyric acidChEBI
(3S)-3-Hydroxybutyric acidChEBI
(S)-3-Hydroxybutanoic acidChEBI
(S)-3HbChEBI
(S)-beta-Hydroxybutyric acidChEBI
L-(+)-3-Hydroxybutyric acidChEBI
L-3-Hydroxybutyric acidChEBI
(+)-3-HydroxybutyrateGenerator
(3S)-3-HydroxybutyrateGenerator
(S)-3-HydroxybutanoateGenerator
(S)-b-HydroxybutyrateGenerator
(S)-b-Hydroxybutyric acidGenerator
(S)-beta-HydroxybutyrateGenerator
(S)-Β-hydroxybutyrateGenerator
(S)-Β-hydroxybutyric acidGenerator
L-(+)-3-HydroxybutyrateGenerator
L-3-HydroxybutyrateGenerator
(S)-3-HydroxybutyrateGenerator
(+)-3-Hydroxy-N-butyric acidHMDB
(3S)-3-Hydroxy-butanoateHMDB
(3S)-3-Hydroxy-butanoic acidHMDB
(S)-3-Hydroxy-2-methyl-propanoateHMDB
(S)-3-Hydroxy-2-methyl-propanoic acidHMDB
(S)-3-Hydroxy-butanoateHMDB
(S)-3-Hydroxy-butanoic acidHMDB
(S)-b-HydroxyisobutyrateHMDB
(S)-b-Hydroxyisobutyric acidHMDB
(S)-beta-HydroxyisobutyrateHMDB
(S)-beta-Hydroxyisobutyric acidHMDB
L-(+)-2-Methyl-hydracrylateHMDB
L-(+)-2-Methyl-hydracrylic acidHMDB
L-(+)-b-HydroxyisobutyrateHMDB
L-(+)-b-Hydroxyisobutyric acidHMDB
L-(+)-beta-HydroxyisobutyrateHMDB
L-(+)-beta-Hydroxyisobutyric acidHMDB
L-beta-HydroxybutyrateHMDB
(3S)-3-Hydroxybutanoic acidHMDB
(S)-(+)-beta-Hydroxybutyric acidHMDB
(S)-(+)-Β-hydroxybutyric acidHMDB
(S)-beta-Hydroxybutanoic acidHMDB
(S)-Β-hydroxybutanoic acidHMDB
3-Hydroxy-N-butyric acidHMDB
3-Hydroxybutanoic acidHMDB
3-Hydroxybutyric acidHMDB
L-beta-Hydroxybutyric acidHMDB
L-Β-hydroxybutyric acidHMDB
beta-Hydroxy-N-butyric acidHMDB
beta-Hydroxybutanoic acidHMDB
beta-Hydroxybutyric acidHMDB
Β-hydroxy-N-butyric acidHMDB
Β-hydroxybutanoic acidHMDB
Β-hydroxybutyric acidHMDB
(S)-3-Hydroxybutyric acidHMDB
(+)-3-Hydroxy-n-butyric acidhmdb
(3S)-3-hydroxy-Butanoatehmdb
(3S)-3-hydroxy-Butanoic acidhmdb
(S)-3-hydroxy-2-methyl-Propanoatehmdb
(S)-3-hydroxy-2-methyl-Propanoic acidhmdb
(S)-3-hydroxy-Butanoatehmdb
(S)-3-hydroxy-Butanoic acidhmdb
(S)-3-hydroxybutanoatehmdb
(S)-3HBChEBI
(S)-β-hydroxybutyrateGenerator
(S)-β-hydroxybutyric acidGenerator
L-(+)-2-methyl-Hydracrylatehmdb
L-(+)-2-methyl-Hydracrylic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility539 g/LALOGPS
logP-0.5ALOGPS
logP-0.39ChemAxon
logS0.71ALOGPS
pKa (Strongest Acidic)4.41ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.46 m³·mol⁻¹ChemAxon
Polarizability9.94 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC4H8O3
IUPAC name(3S)-3-hydroxybutanoic acid
InChI IdentifierInChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m0/s1
InChI KeyWHBMMWSBFZVSSR-VKHMYHEASA-N
Isomeric SMILESC[C@H](O)CC(O)=O
Average Molecular Weight104.1045
Monoisotopic Molecular Weight104.047344122
Classification
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
  • Short-chain hydroxy acid
  • Beta-hydroxy acid
  • Fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • 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
Disposition

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(S)-3-Hydroxybutyric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0007-9000000000-5f169537ace358b06fd0Spectrum
Predicted GC-MS(S)-3-Hydroxybutyric acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01ei-9710000000-2652bd46b41e50defdb0Spectrum
Predicted GC-MS(S)-3-Hydroxybutyric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(S)-3-Hydroxybutyric acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(S)-3-Hydroxybutyric acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(S)-3-Hydroxybutyric acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(S)-3-Hydroxybutyric acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(S)-3-Hydroxybutyric acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0a4i-9200000000-4156904e7472b5e972492012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0a4i-9300000000-505ae46abb0c49c78b1e2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0zfr-9600000000-dfed69c37c1a4d7944402012-07-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-9100000000-889e2968ad4fd52cdd922017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-9000000000-6c660170b8f4aa6bcd022017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-c39869c905b7e93b7f972017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-9800000000-532ea53160d6ca2efcaa2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pbi-9200000000-b2c59fd56b1a1d713ea92017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-29e8d104108ac71cd6402017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-de698d113a869245219a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-d964762034ff3766529f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-1c4d36fa24f00e6e9f6e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9200000000-61512767fe2a2778ee8c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-0006bf28af00ac9af39c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-58f5546067f0f7cf64bb2021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID85121
ChEMBL IDCHEMBL1162497
KEGG Compound IDC03197
Pubchem Compound ID94318
Pubchem Substance IDNot Available
ChEBI ID17290
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00442
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET ID3HL
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference