Record Information
Version1.0
Creation date2011-03-17 23:28:01 UTC
Update date2019-11-26 03:20:48 UTC
Primary IDFDB021725
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name11b,13-Dihydrolactucin
Description(3R,3aR,4R,9aS,9bS)-4-hydroxy-9-(hydroxymethyl)-3,6,9a-trimethyl-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione belongs to the class of organic compounds known as ambrosanolides and secoambrosanolides. These are sesquiterpene lactones from the Ambrosia family, with a backbone derivative of azuleno[6,5-b]furan-2-one (ambrosanolides) or azuleno[4,5-b]furan-2-one (secoambrosanolides). Based on a literature review very few articles have been published on (3R,3aR,4R,9aS,9bS)-4-hydroxy-9-(hydroxymethyl)-3,6,9a-trimethyl-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione.
CAS Number83117-63-9
Structure
Thumb
Synonyms
SynonymSource
11b,13-Dihydrolactucindb_source
8,15-Dihydroxy-2-oxo-1(10),3-guaiadien-12,6-olidedb_source
8,15-Dihydroxy-2-oxo-1(10),3,11(13)-guaiatrien-12,6-olide; (5a,6a,8a)-form, 11b,13-Dihydrodb_source
Predicted Properties
PropertyValueSource
Water Solubility2.69 g/LALOGPS
logP0.38ALOGPS
logP0.22ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)14.6ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity76.46 m³·mol⁻¹ChemAxon
Polarizability30.09 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H20O5
IUPAC name(3R,3aR,4R,9aS,9bS)-4-hydroxy-9-(hydroxymethyl)-3,6,9a-trimethyl-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione
InChI IdentifierInChI=1S/C16H20O5/c1-7-4-10(18)12-8(2)15(20)21-14(12)16(3)9(6-17)5-11(19)13(7)16/h5,8,10,12,14,17-18H,4,6H2,1-3H3/t8-,10-,12-,14+,16+/m1/s1
InChI KeyAVVAXORRBBPMQM-YRRGMINMSA-N
Isomeric SMILES[H][C@]12OC(=O)[C@H](C)[C@]1([H])[C@H](O)CC(C)=C1C(=O)C=C(CO)[C@]21C
Average Molecular Weight292.327
Monoisotopic Molecular Weight292.13107375
Classification
Description Belongs to the class of organic compounds known as ambrosanolides and secoambrosanolides. These are sesquiterpene lactones from the Ambrosia family, with a backbone derivative of azuleno[6,5-b]furan-2-one (ambrosanolides) or azuleno[4,5-b]furan-2-one (secoambrosanolides).
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentAmbrosanolides and secoambrosanolides
Alternative Parents
Substituents
  • Ambrosanolide
  • Pseudoguaiane sesquiterpenoid
  • Sesquiterpenoid
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Primary alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical statesolid
Physical DescriptionCryst.DFC
Mass CompositionC 64.74%; H 6.52%; O 28.74%DFC
Melting PointMp 91?DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +8.7 (c, 0.63 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0090000000-fb87a1fbe8eacf8a15502019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pdi-0190000000-1b9cc06e97b6ba5451f82019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ziu-6590000000-1f24f15ddca0bb6038772019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-bfcab6041a24ed0cbfcf2019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01vp-0090000000-a65b899ee89830e0f4ce2019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pdl-3950000000-1973c2bc8b8ec5e3eaac2019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-a24e40f173f1cf50e12f2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0490000000-38cec6861363a519750f2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0290000000-99468b12b98cf12f7f392021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-98ee3cd4933435e643192021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0090000000-6b37cba5b9c7045cbb272021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-0490000000-ae384c78950e6299a3d92021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJFR52-Z:JFR54-B
EAFUS IDNot Available
Dr. Duke ID11(S),13-DIHYDROLACTUCIN|(11S)-11,13-DIHYDROLACTUCIN
BIGG IDNot Available
KNApSAcK IDC00029376
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
bitterDUKE
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).