Record Information
Version1.0
Creation date2010-04-08 22:11:21 UTC
Update date2018-05-29 01:13:14 UTC
Primary IDFDB014592
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLactupicrin
DescriptionConstituent of Lactuca sativa (lettuce), Cichorium intybus (chicory) and Cichorium endivia (endive). Lactupicrin is found in many foods, some of which are endive, romaine lettuce, chicory, and lettuce.
CAS Number65725-11-3
Structure
Thumb
Synonyms
SynonymSource
IntybinHMDB
LactucopicrinHMDB
9-(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)acetic acidGenerator
Lactucopicrin3,3a,4,5,9a,9b-hexahydro-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methyleneazuleno(4,5-b)furan-2,7-dione p-hydroxyphenylacetate hydrateMeSH
Lactupicrindb_source
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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 guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentGuaianolides and derivatives
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1902000000-447da619a6ca571ad014View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-1920210000-c224ca80e51775b73faaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01p6-0449400000-0930a4dc1fe6b942c8dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0964000000-d7776f7f46c493e2bfbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-2930000000-33f79bf051b7b71011fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0367900000-596fcf399a87d2bc872bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a7i-0596100000-f219cb9416848503d0dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1960000000-0202858172af131c5198View in MoNA
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
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).