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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:16:32 UTC
Update Date2022-03-07 02:57:05 UTC
HMDB IDHMDB0041582
Secondary Accession Numbers
  • HMDB41582
Metabolite Identification
Common NameSapidolide A
DescriptionSapidolide A 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. Sapidolide A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, sapidolide a has been detected, but not quantified in, fruits. This could make sapidolide a a potential biomarker for the consumption of these foods.
Structure
Data?1563863679
SynonymsNot Available
Chemical FormulaC14H18O5
Average Molecular Weight266.2897
Monoisotopic Molecular Weight266.115423686
IUPAC Name13-ethenyl-1,7-dihydroxy-12-methyl-2,10-dioxatetracyclo[5.4.1.1⁸,¹¹.0⁴,¹²]tridecan-9-one
Traditional Name13-ethenyl-1,7-dihydroxy-12-methyl-2,10-dioxatetracyclo[5.4.1.1⁸,¹¹.0⁴,¹²]tridecan-9-one
CAS Registry Number182191-87-3
SMILES
CC12C3CCC1(O)C1C(C=C)C(OC1=O)C2(O)OC3
InChI Identifier
InChI=1S/C14H18O5/c1-3-8-9-11(15)19-10(8)14(17)12(2)7(6-18-14)4-5-13(9,12)16/h3,7-10,16-17H,1,4-6H2,2H3
InChI KeyOZRZMHKATMSFPV-UHFFFAOYSA-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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point147 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility18 g/LALOGPS
logP0.1ALOGPS
logP0.51ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)10.66ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity64.45 m³·mol⁻¹ChemAxon
Polarizability26.11 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+160.47131661259
DarkChem[M-H]-158.02931661259
DeepCCS[M-2H]-196.28430932474
DeepCCS[M+Na]+171.74130932474
AllCCS[M+H]+160.132859911
AllCCS[M+H-H2O]+156.532859911
AllCCS[M+NH4]+163.532859911
AllCCS[M+Na]+164.432859911
AllCCS[M-H]-165.032859911
AllCCS[M+Na-2H]-164.632859911
AllCCS[M+HCOO]-164.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Sapidolide ACC12C3CCC1(O)C1C(C=C)C(OC1=O)C2(O)OC33251.0Standard polar33892256
Sapidolide ACC12C3CCC1(O)C1C(C=C)C(OC1=O)C2(O)OC32110.3Standard non polar33892256
Sapidolide ACC12C3CCC1(O)C1C(C=C)C(OC1=O)C2(O)OC32287.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Sapidolide A,1TMS,isomer #1C=CC1C2OC(=O)C1C1(O[Si](C)(C)C)CCC3COC2(O)C31C2065.2Semi standard non polar33892256
Sapidolide A,1TMS,isomer #2C=CC1C2C(=O)OC1C1(O[Si](C)(C)C)OCC3CCC2(O)C31C2057.0Semi standard non polar33892256
Sapidolide A,2TMS,isomer #1C=CC1C2C(=O)OC1C1(O[Si](C)(C)C)OCC3CCC2(O[Si](C)(C)C)C31C2161.2Semi standard non polar33892256
Sapidolide A,1TBDMS,isomer #1C=CC1C2OC(=O)C1C1(O[Si](C)(C)C(C)(C)C)CCC3COC2(O)C31C2296.6Semi standard non polar33892256
Sapidolide A,1TBDMS,isomer #2C=CC1C2C(=O)OC1C1(O[Si](C)(C)C(C)(C)C)OCC3CCC2(O)C31C2302.9Semi standard non polar33892256
Sapidolide A,2TBDMS,isomer #1C=CC1C2C(=O)OC1C1(O[Si](C)(C)C(C)(C)C)OCC3CCC2(O[Si](C)(C)C(C)(C)C)C31C2609.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sapidolide A GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pb9-2960000000-78130230edff068879d42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sapidolide A GC-MS (2 TMS) - 70eV, Positivesplash10-000i-9004000000-3210efd61cf0b2e8b6972017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sapidolide A 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 - Sapidolide A 10V, Positive-QTOFsplash10-00kb-0090000000-ff1d4db8330473d160b52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sapidolide A 20V, Positive-QTOFsplash10-00kb-0090000000-34c3c8424b7f50c569f32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sapidolide A 40V, Positive-QTOFsplash10-001i-4390000000-ae036373a32a43ee7e862017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sapidolide A 10V, Negative-QTOFsplash10-014i-0090000000-8c403c84986dffbe43d12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sapidolide A 20V, Negative-QTOFsplash10-01ba-0090000000-59e7bd50b8f5ab99d9cb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sapidolide A 40V, Negative-QTOFsplash10-014l-4970000000-9208d06fbf2390a231092017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sapidolide A 10V, Positive-QTOFsplash10-014i-0090000000-217dac9cdc002dbfa8f22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sapidolide A 20V, Positive-QTOFsplash10-066r-0390000000-e12cf184973fbefdda192021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sapidolide A 40V, Positive-QTOFsplash10-014i-3190000000-9c9cfcde25c25350f2f42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sapidolide A 10V, Negative-QTOFsplash10-014i-0090000000-569df53f621f3bfc4e5e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sapidolide A 20V, Negative-QTOFsplash10-014i-0090000000-4f658ff6c2210f38e4002021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sapidolide A 40V, Negative-QTOFsplash10-014j-0290000000-50c923d1d12e357e08272021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart 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 IDFDB021574
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound85214158
PDB IDNot Available
ChEBI IDNot Available
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .