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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:44:53 UTC
Update Date2022-03-07 02:53:05 UTC
HMDB IDHMDB0031694
Secondary Accession Numbers
  • HMDB31694
Metabolite Identification
Common NameButyl (S)-3-hydroxybutyrate glucoside
DescriptionButyl (S)-3-hydroxybutyrate glucoside belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. Based on a literature review a small amount of articles have been published on Butyl (S)-3-hydroxybutyrate glucoside.
Structure
Data?1563862157
Synonyms
ValueSource
Butyl (S)-3-hydroxybutyric acid glucosideGenerator
Butyl 3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanoic acidHMDB
Chemical FormulaC14H26O8
Average Molecular Weight322.3514
Monoisotopic Molecular Weight322.162767808
IUPAC Namebutyl 3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanoate
Traditional Namebutyl 3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanoate
CAS Registry NumberNot Available
SMILES
CCCCOC(=O)CC(C)OC1OC(CO)C(O)C(O)C1O
InChI Identifier
InChI=1S/C14H26O8/c1-3-4-5-20-10(16)6-8(2)21-14-13(19)12(18)11(17)9(7-15)22-14/h8-9,11-15,17-19H,3-7H2,1-2H3
InChI KeyYUPCLHHTUNDMAN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl glycosides
Direct ParentFatty acyl glycosides of mono- and disaccharides
Alternative Parents
Substituents
  • Fatty acyl glycoside of mono- or disaccharide
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty acid ester
  • Sugar acid
  • Oxane
  • Monosaccharide
  • Secondary alcohol
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Acetal
  • Primary alcohol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility33.1 g/LALOGPS
logP0.02ALOGPS
logP-0.69ChemAxon
logS-0.99ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area125.68 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity74.52 m³·mol⁻¹ChemAxon
Polarizability33.41 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+176.26231661259
DarkChem[M-H]-169.90731661259
DeepCCS[M+H]+183.60630932474
DeepCCS[M-H]-181.17230932474
DeepCCS[M-2H]-214.25930932474
DeepCCS[M+Na]+189.94930932474
AllCCS[M+H]+177.832859911
AllCCS[M+H-H2O]+175.032859911
AllCCS[M+NH4]+180.432859911
AllCCS[M+Na]+181.132859911
AllCCS[M-H]-176.532859911
AllCCS[M+Na-2H]-177.032859911
AllCCS[M+HCOO]-177.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Butyl (S)-3-hydroxybutyrate glucosideCCCCOC(=O)CC(C)OC1OC(CO)C(O)C(O)C1O3344.5Standard polar33892256
Butyl (S)-3-hydroxybutyrate glucosideCCCCOC(=O)CC(C)OC1OC(CO)C(O)C(O)C1O2354.4Standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucosideCCCCOC(=O)CC(C)OC1OC(CO)C(O)C(O)C1O2326.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Butyl (S)-3-hydroxybutyrate glucoside,1TMS,isomer #1CCCCOC(=O)CC(C)OC1OC(CO[Si](C)(C)C)C(O)C(O)C1O2441.6Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,1TMS,isomer #2CCCCOC(=O)CC(C)OC1OC(CO)C(O[Si](C)(C)C)C(O)C1O2419.5Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,1TMS,isomer #3CCCCOC(=O)CC(C)OC1OC(CO)C(O)C(O[Si](C)(C)C)C1O2403.8Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,1TMS,isomer #4CCCCOC(=O)CC(C)OC1OC(CO)C(O)C(O)C1O[Si](C)(C)C2407.3Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,2TMS,isomer #1CCCCOC(=O)CC(C)OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1O2424.7Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,2TMS,isomer #2CCCCOC(=O)CC(C)OC1OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1O2418.2Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,2TMS,isomer #3CCCCOC(=O)CC(C)OC1OC(CO[Si](C)(C)C)C(O)C(O)C1O[Si](C)(C)C2406.4Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,2TMS,isomer #4CCCCOC(=O)CC(C)OC1OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O2417.6Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,2TMS,isomer #5CCCCOC(=O)CC(C)OC1OC(CO)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C2421.1Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,2TMS,isomer #6CCCCOC(=O)CC(C)OC1OC(CO)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C2405.1Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,3TMS,isomer #1CCCCOC(=O)CC(C)OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O2410.3Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,3TMS,isomer #2CCCCOC(=O)CC(C)OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C2389.6Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,3TMS,isomer #3CCCCOC(=O)CC(C)OC1OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C2374.8Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,3TMS,isomer #4CCCCOC(=O)CC(C)OC1OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C2380.8Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,4TMS,isomer #1CCCCOC(=O)CC(C)OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C2364.3Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,1TBDMS,isomer #1CCCCOC(=O)CC(C)OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C1O2672.5Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,1TBDMS,isomer #2CCCCOC(=O)CC(C)OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C1O2660.6Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,1TBDMS,isomer #3CCCCOC(=O)CC(C)OC1OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C1O2639.1Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,1TBDMS,isomer #4CCCCOC(=O)CC(C)OC1OC(CO)C(O)C(O)C1O[Si](C)(C)C(C)(C)C2651.7Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,2TBDMS,isomer #1CCCCOC(=O)CC(C)OC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O2894.4Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,2TBDMS,isomer #2CCCCOC(=O)CC(C)OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C1O2886.9Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,2TBDMS,isomer #3CCCCOC(=O)CC(C)OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C1O[Si](C)(C)C(C)(C)C2895.0Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,2TBDMS,isomer #4CCCCOC(=O)CC(C)OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O2886.9Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,2TBDMS,isomer #5CCCCOC(=O)CC(C)OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C2899.8Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,2TBDMS,isomer #6CCCCOC(=O)CC(C)OC1OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C2891.1Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,3TBDMS,isomer #1CCCCOC(=O)CC(C)OC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O3122.7Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,3TBDMS,isomer #2CCCCOC(=O)CC(C)OC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C3126.2Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,3TBDMS,isomer #3CCCCOC(=O)CC(C)OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C3110.6Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,3TBDMS,isomer #4CCCCOC(=O)CC(C)OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C3105.4Semi standard non polar33892256
Butyl (S)-3-hydroxybutyrate glucoside,4TBDMS,isomer #1CCCCOC(=O)CC(C)OC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C3313.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Butyl (S)-3-hydroxybutyrate glucoside GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9562000000-445cf0d53157cf21d8a72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Butyl (S)-3-hydroxybutyrate glucoside GC-MS (4 TMS) - 70eV, Positivesplash10-0002-4000190000-83ca8e25590d933e8afc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Butyl (S)-3-hydroxybutyrate glucoside GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Butyl (S)-3-hydroxybutyrate glucoside 6V, Negative-QTOFsplash10-00di-0319000000-b388d8ec4bca53b44c652021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl (S)-3-hydroxybutyrate glucoside 10V, Positive-QTOFsplash10-0c03-3915000000-2e467b58ae188a0206912016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl (S)-3-hydroxybutyrate glucoside 20V, Positive-QTOFsplash10-0btc-9800000000-846c0a169c1d489ac8ba2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl (S)-3-hydroxybutyrate glucoside 40V, Positive-QTOFsplash10-052f-9700000000-23dc828d3cdf5d50e2fe2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl (S)-3-hydroxybutyrate glucoside 10V, Negative-QTOFsplash10-05fr-5946000000-e915755eb3b655aaa7532016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl (S)-3-hydroxybutyrate glucoside 20V, Negative-QTOFsplash10-0pbi-7931000000-1a41bae6e15e328ddf852016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl (S)-3-hydroxybutyrate glucoside 40V, Negative-QTOFsplash10-0a4i-9700000000-d5a9124d2019ebc483552016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl (S)-3-hydroxybutyrate glucoside 10V, Positive-QTOFsplash10-00di-5619000000-6b70848dacc410364f392021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl (S)-3-hydroxybutyrate glucoside 20V, Positive-QTOFsplash10-0a4s-8911000000-44f922f79866adec1e782021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl (S)-3-hydroxybutyrate glucoside 40V, Positive-QTOFsplash10-0a4l-9200000000-ef86482686b7e01a82572021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl (S)-3-hydroxybutyrate glucoside 10V, Negative-QTOFsplash10-00di-2109000000-4b6e064046a1b00a8c522021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl (S)-3-hydroxybutyrate glucoside 20V, Negative-QTOFsplash10-0c00-9724000000-9399f57655cf4bf3c0e32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl (S)-3-hydroxybutyrate glucoside 40V, Negative-QTOFsplash10-0a4i-9200000000-3886c9999657ba36ecc92021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
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 IDFDB008357
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound76463851
PDB IDNot Available
ChEBI ID167975
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.