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Lactupicrin (FDB014592)

Record Information
Version1.0
Creation date2010-04-08 22:11:21 UTC
Update date2019-11-26 03:10:24 UTC
Primary IDFDB014592
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLactupicrin
DescriptionLactupicrin belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. Lactupicrin has been detected, but not quantified in, several different foods, such as green vegetables, robusta coffees (Coffea canephora), endives (Cichorium endivia), coffee and coffee products, and lettuces (Lactuca sativa). This could make lactupicrin a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Lactupicrin.
CAS Number65725-11-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.088 g/LALOGPS
logP1.99ALOGPS
logP1.95ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)6.52ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area110.13 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity107.72 m³·mol⁻¹ChemAxon
Polarizability41.18 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC23H22O7
IUPAC name9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate
InChI IdentifierInChI=1S/C23H22O7/c1-11-7-17(29-18(27)8-13-3-5-15(25)6-4-13)20-12(2)23(28)30-22(20)21-14(10-24)9-16(26)19(11)21/h3-6,9,17,20-22,24-25H,2,7-8,10H2,1H3
InChI KeyUMVSOHBRAQTGQI-UHFFFAOYSA-N
Isomeric SMILESCC1=C2C(C3OC(=O)C(=C)C3C(C1)OC(=O)CC1=CC=C(O)C=C1)C(CO)=CC2=O
Average Molecular Weight410.4166
Monoisotopic Molecular Weight410.136553058
Classification
Description Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class1-hydroxy-2-unsubstituted benzenoids
Direct Parent1-hydroxy-2-unsubstituted benzenoids
Alternative Parents
Substituents
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Primary alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 67.31%; H 5.40%; O 27.29%DFC
Melting PointMp 132-178° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +73 (Py)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSLactupicrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-1902000000-447da619a6ca571ad014Spectrum
Predicted GC-MSLactupicrin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-1920210000-c224ca80e51775b73faaSpectrum
Predicted GC-MSLactupicrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSLactupicrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01p6-0449400000-0930a4dc1fe6b942c8df2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0964000000-d7776f7f46c493e2bfbb2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-2930000000-33f79bf051b7b71011fc2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0367900000-596fcf399a87d2bc872b2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a7i-0596100000-f219cb9416848503d0df2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1960000000-0202858172af131c51982015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-0591600000-872925ccdb63862452092021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0980100000-302d9ac7f387b3c8e3112021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6v-0291000000-6eb4afe572f7ac2b5c382021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-b2357ac73f1167a2b48d2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-0290000000-a2ea6f22cbd95999d34d2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-8892000000-59de1dd3685ff0a79fb22021-09-23View Spectrum
NMRNot Available
ChemSpider ID2723771
ChEMBL IDNot Available
KEGG Compound IDC09490
Pubchem Compound ID3482908
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35828
CRC / DFC (Dictionary of Food Compounds) IDJFR52-Z:JSV68-P
EAFUS IDNot Available
Dr. Duke IDLACTUPICRIN|LACTUCOPICRIN
BIGG IDNot Available
KNApSAcK IDC00003312
HET IDNot Available
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 / Bioactivities
DescriptorIDDefinitionReference
anti feedantDUKE
bitterDUKE
central nervous system depressant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
hypoglycemic35526 A drug which lowers the blood glucose level.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).