Record Information
Version1.0
Creation date2010-04-08 22:11:35 UTC
Update date2018-05-29 01:16:13 UTC
Primary IDFDB014979
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameVulgarin
DescriptionConstituent of Artemisia vulgaris (mugwort). Vulgarin is found in mugwort.
CAS Number3162-56-9
Structure
Thumb
Synonyms
SynonymSource
BarrelinHMDB
JudaicinHMDB
Judaicin (eudesmane naphthofuran)HMDB
Judaicin (sesquiterpene)HMDB
TauremisinHMDB
Tauremisin aHMDB
TauremizinHMDB
TauresminHMDB
Tauremisin Adb_source
Vulgarindb_source
Predicted Properties
PropertyValueSource
Water Solubility1.32 g/LALOGPS
logP0.75ALOGPS
logP1.78ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)14.25ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity69.83 m³·mol⁻¹ChemAxon
Polarizability27.77 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H20O4
IUPAC name9-hydroxy-3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,6H,9H,9aH,9bH-naphtho[1,2-b]furan-2,6-dione
InChI IdentifierInChI=1S/C15H20O4/c1-8-9-4-6-14(2)10(16)5-7-15(3,18)12(14)11(9)19-13(8)17/h5,7-9,11-12,18H,4,6H2,1-3H3
InChI KeyNGPDZEACIWDCKX-UHFFFAOYSA-N
Isomeric SMILESCC1C2CCC3(C)C(C2OC1=O)C(C)(O)C=CC3=O
Average Molecular Weight264.3169
Monoisotopic Molecular Weight264.136159128
Classification
Description belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentEudesmanolides, secoeudesmanolides, and derivatives
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 68.16%; H 7.63%; O 24.21%DFC
Melting PointMp 174-175°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]27Hg +48.7 (c, 3.86 in CHCl3)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, Positivesplash10-0ay1-7390000000-f3b7b031e2bd5ce67efbView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00b9-6694000000-29a96556fa9dccd120ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0190000000-317d449691d81af7d9c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00mk-0690000000-cb4df13a679d9ff6796aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-7920000000-c934a33edd5f8bce2521View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0190000000-317d449691d81af7d9c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00mk-0690000000-cb4df13a679d9ff6796aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-7920000000-c934a33edd5f8bce2521View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-b2d4f4080b70752b2d55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xs-0190000000-f2796cc7b5eda709c7ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-9750000000-7ea279dead6bad682e4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-b2d4f4080b70752b2d55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xs-0190000000-f2796cc7b5eda709c7ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-9750000000-7ea279dead6bad682e4fView in MoNA
ChemSpider ID538241
ChEMBL IDNot Available
KEGG Compound IDC09600
Pubchem Compound ID619337
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36130
CRC / DFC (Dictionary of Food Compounds) IDJXR35-S:JXR36-T
EAFUS IDNot Available
Dr. Duke IDVULGARIN|TAUREMISIN
BIGG IDNot Available
KNApSAcK IDC00003393
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
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cardiotonic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
parasympathomimeticDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.