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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:46:27 UTC
Update Date2022-03-07 02:55:22 UTC
HMDB IDHMDB0037523
Secondary Accession Numbers
  • HMDB37523
Metabolite Identification
Common NameGalanolactone
DescriptionGalanolactone belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Galanolactone has been detected, but not quantified in, gingers (Zingiber officinale) and herbs and spices. This could make galanolactone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Galanolactone.
Structure
Data?1563863045
SynonymsNot Available
Chemical FormulaC20H30O3
Average Molecular Weight318.4504
Monoisotopic Molecular Weight318.219494826
IUPAC Name(3Z)-3-(2-{5,5,8a-trimethyl-octahydro-1H-spiro[naphthalene-2,2'-oxirane]-1-yl}ethylidene)oxolan-2-one
Traditional Name(3Z)-3-(2-{5,5,8a-trimethyl-hexahydro-1H-spiro[naphthalene-2,2'-oxirane]-1-yl}ethylidene)oxolan-2-one
CAS Registry Number115753-79-2
SMILES
CC1(C)CCCC2(C)C(C\C=C3\CCOC3=O)C3(CO3)CCC12
InChI Identifier
InChI=1S/C20H30O3/c1-18(2)9-4-10-19(3)15(18)7-11-20(13-23-20)16(19)6-5-14-8-12-22-17(14)21/h5,15-16H,4,6-13H2,1-3H3/b14-5-
InChI KeyMBPTXJNHCBXMBP-RZNTYIFUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxirane
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point125.5 - 126 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.05 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0005 g/LALOGPS
logP3.81ALOGPS
logP4.24ChemAxon
logS-5.8ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.83 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity90.37 m³·mol⁻¹ChemAxon
Polarizability36.6 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+175.03831661259
DarkChem[M-H]-167.82231661259
DeepCCS[M-2H]-213.56230932474
DeepCCS[M+Na]+189.12830932474
AllCCS[M+H]+177.732859911
AllCCS[M+H-H2O]+174.632859911
AllCCS[M+NH4]+180.532859911
AllCCS[M+Na]+181.432859911
AllCCS[M-H]-186.632859911
AllCCS[M+Na-2H]-186.832859911
AllCCS[M+HCOO]-187.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GalanolactoneCC1(C)CCCC2(C)C(C\C=C3\CCOC3=O)C3(CO3)CCC123090.3Standard polar33892256
GalanolactoneCC1(C)CCCC2(C)C(C\C=C3\CCOC3=O)C3(CO3)CCC122507.3Standard non polar33892256
GalanolactoneCC1(C)CCCC2(C)C(C\C=C3\CCOC3=O)C3(CO3)CCC122815.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Galanolactone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f79-0691000000-76ff2be2a471bb872fd22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Galanolactone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galanolactone 10V, Positive-QTOFsplash10-014i-1079000000-1752926143446e1567712016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galanolactone 20V, Positive-QTOFsplash10-0fsj-2192000000-34665ab35024bcaec03b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galanolactone 40V, Positive-QTOFsplash10-0udi-8920000000-9070c224eeba82a073c62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galanolactone 10V, Negative-QTOFsplash10-014i-1019000000-c8e6f08fa9a4c772c41e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galanolactone 20V, Negative-QTOFsplash10-01b9-3095000000-9f4bfe9957ad918fccc72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galanolactone 40V, Negative-QTOFsplash10-0pb9-4090000000-bec7fcb4c3d0c3bfeb832016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galanolactone 10V, Positive-QTOFsplash10-014i-0009000000-f44b8f78f028f8f8f3b62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galanolactone 20V, Positive-QTOFsplash10-0g29-0913000000-29e7ab868d79d3e36a1a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galanolactone 40V, Positive-QTOFsplash10-0fi0-6923000000-8d5099da71cc9b4830522021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galanolactone 10V, Negative-QTOFsplash10-014i-0009000000-062ad2a35e11d303cf232021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galanolactone 20V, Negative-QTOFsplash10-014i-0029000000-eefd64fbf57a97fa197a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galanolactone 40V, Negative-QTOFsplash10-0a4i-2091000000-300e0967ce3af0cdcdf52021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB016604
KNApSAcK IDC00034848
Chemspider ID35014427
KEGG Compound IDC17498
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGalanolactone
METLIN IDNot Available
PubChem Compound57457805
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1861711
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.. .