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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:50:15 UTC
Update Date2022-03-07 02:54:38 UTC
HMDB IDHMDB0035814
Secondary Accession Numbers
  • HMDB35814
Metabolite Identification
Common NameLactucin
DescriptionLactucin 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. Lactucin has been detected, but not quantified in, several different foods, such as herbs and spices, green vegetables, lettuces (Lactuca sativa), robusta coffees (Coffea canephora), and coffee and coffee products. This could make lactucin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Lactucin.
Structure
Data?1563862776
Synonyms
ValueSource
11beta,13-DihydrolactucinHMDB
LactucinMeSH
Chemical FormulaC15H16O5
Average Molecular Weight276.288
Monoisotopic Molecular Weight276.099773615
IUPAC Name4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione
Traditional Namelactucin
CAS Registry Number1891-29-8
SMILES
CC1=C2C(C3OC(=O)C(=C)C3C(O)C1)C(CO)=CC2=O
InChI Identifier
InChI=1S/C15H16O5/c1-6-3-9(17)12-7(2)15(19)20-14(12)13-8(5-16)4-10(18)11(6)13/h4,9,12-14,16-17H,2-3,5H2,1H3
InChI KeyVJQAFLAZRVKAKM-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 Parents
Substituents
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Ketone
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Oxacycle
  • Carbonyl group
  • Primary alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Organic oxide
  • 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 Point224 - 228 °CNot Available
Boiling Point575.60 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility71070 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.330 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.84 g/LALOGPS
logP-0.28ALOGPS
logP-0.018ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)13ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.87 m³·mol⁻¹ChemAxon
Polarizability27.92 ųChemAxon
Number of Rings3ChemAxon
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]+165.10331661259
DarkChem[M-H]-160.86831661259
DeepCCS[M+H]+163.19330932474
DeepCCS[M-H]-160.83530932474
DeepCCS[M-2H]-194.05230932474
DeepCCS[M+Na]+169.28630932474
AllCCS[M+H]+163.032859911
AllCCS[M+H-H2O]+159.432859911
AllCCS[M+NH4]+166.232859911
AllCCS[M+Na]+167.232859911
AllCCS[M-H]-165.132859911
AllCCS[M+Na-2H]-164.732859911
AllCCS[M+HCOO]-164.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LactucinCC1=C2C(C3OC(=O)C(=C)C3C(O)C1)C(CO)=CC2=O3899.4Standard polar33892256
LactucinCC1=C2C(C3OC(=O)C(=C)C3C(O)C1)C(CO)=CC2=O2437.1Standard non polar33892256
LactucinCC1=C2C(C3OC(=O)C(=C)C3C(O)C1)C(CO)=CC2=O2743.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Lactucin,1TMS,isomer #1C=C1C(=O)OC2C3C(CO)=CC(=O)C3=C(C)CC(O[Si](C)(C)C)C122583.4Semi standard non polar33892256
Lactucin,1TMS,isomer #2C=C1C(=O)OC2C3C(CO[Si](C)(C)C)=CC(=O)C3=C(C)CC(O)C122593.9Semi standard non polar33892256
Lactucin,2TMS,isomer #1C=C1C(=O)OC2C3C(CO[Si](C)(C)C)=CC(=O)C3=C(C)CC(O[Si](C)(C)C)C122620.4Semi standard non polar33892256
Lactucin,1TBDMS,isomer #1C=C1C(=O)OC2C3C(CO)=CC(=O)C3=C(C)CC(O[Si](C)(C)C(C)(C)C)C122789.7Semi standard non polar33892256
Lactucin,1TBDMS,isomer #2C=C1C(=O)OC2C3C(CO[Si](C)(C)C(C)(C)C)=CC(=O)C3=C(C)CC(O)C122809.3Semi standard non polar33892256
Lactucin,2TBDMS,isomer #1C=C1C(=O)OC2C3C(CO[Si](C)(C)C(C)(C)C)=CC(=O)C3=C(C)CC(O[Si](C)(C)C(C)(C)C)C123020.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Lactucin GC-MS (Non-derivatized) - 70eV, Positivesplash10-052b-5790000000-b95d08ba5457bf6b20692017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lactucin GC-MS (2 TMS) - 70eV, Positivesplash10-0ab9-2139000000-fe4b945f22fd4dcc89882017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lactucin 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 - Lactucin 10V, Positive-QTOFsplash10-0a6r-0090000000-adba28495fd27a8480062015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lactucin 20V, Positive-QTOFsplash10-052u-0490000000-fb65751d00ebf7cfc0482015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lactucin 40V, Positive-QTOFsplash10-0f76-5950000000-cc2ba0ae124168adaaa12015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lactucin 10V, Negative-QTOFsplash10-004i-0090000000-aa9e3a2cce7827efdc3a2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lactucin 20V, Negative-QTOFsplash10-057i-0090000000-48ae893a3deee473fadb2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lactucin 40V, Negative-QTOFsplash10-00dl-2910000000-9062473d5044314587082015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lactucin 10V, Positive-QTOFsplash10-0a4i-0090000000-5eee9e278d85992a4bc32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lactucin 20V, Positive-QTOFsplash10-0a6u-0090000000-a5e6ac486e245f455cda2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lactucin 40V, Positive-QTOFsplash10-00bd-0960000000-d62be5c7a1ff74131be22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lactucin 10V, Negative-QTOFsplash10-004i-0090000000-aa99d0f367d18fe63c0c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lactucin 20V, Negative-QTOFsplash10-0a6r-0090000000-9caf2622ff82147274962021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lactucin 40V, Negative-QTOFsplash10-004r-0290000000-3d238649ddfe7d1c32b02021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 IDFDB014575
KNApSAcK IDC00003311
Chemspider ID2985716
KEGG Compound IDC09489
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLactucin
METLIN IDNot Available
PubChem Compound3756497
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1699961
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.. .