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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:11:45 UTC
Update Date2022-03-07 02:54:47 UTC
HMDB IDHMDB0036130
Secondary Accession Numbers
  • HMDB36130
Metabolite Identification
Common NameVulgarin
DescriptionVulgarin 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. Based on a literature review a significant number of articles have been published on Vulgarin.
Structure
Data?1563862825
Synonyms
ValueSource
BarrelinHMDB
JudaicinHMDB
Judaicin (eudesmane naphthofuran)HMDB
Judaicin (sesquiterpene)HMDB
TauremisinHMDB
Tauremisin aHMDB
TauremizinHMDB
TauresminHMDB
Chemical FormulaC15H20O4
Average Molecular Weight264.3169
Monoisotopic Molecular Weight264.136159128
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
Traditional Namejudaicin
CAS Registry Number3162-56-9
SMILES
CC1C2CCC3(C)C(C2OC1=O)C(C)(O)C=CC3=O
InChI Identifier
InChI=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
Chemical Taxonomy
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 Parents
Substituents
  • Eudesmanolide
  • Sesquiterpenoid
  • Naphthofuran
  • Cyclohexenone
  • Gamma butyrolactone
  • Tertiary alcohol
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • 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 Point174 - 175 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility40490 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
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]+161.58731661259
DarkChem[M-H]-157.72431661259
DeepCCS[M+H]+166.63930932474
DeepCCS[M-H]-164.28130932474
DeepCCS[M-2H]-197.16730932474
DeepCCS[M+Na]+172.73230932474
AllCCS[M+H]+160.732859911
AllCCS[M+H-H2O]+157.132859911
AllCCS[M+NH4]+164.132859911
AllCCS[M+Na]+165.032859911
AllCCS[M-H]-167.032859911
AllCCS[M+Na-2H]-167.032859911
AllCCS[M+HCOO]-167.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
VulgarinCC1C2CCC3(C)C(C2OC1=O)C(C)(O)C=CC3=O3333.6Standard polar33892256
VulgarinCC1C2CCC3(C)C(C2OC1=O)C(C)(O)C=CC3=O2108.4Standard non polar33892256
VulgarinCC1C2CCC3(C)C(C2OC1=O)C(C)(O)C=CC3=O2120.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Vulgarin,1TMS,isomer #1CC1C(=O)OC2C1CCC1(C)C(=O)C=CC(C)(O[Si](C)(C)C)C212324.5Semi standard non polar33892256
Vulgarin,1TBDMS,isomer #1CC1C(=O)OC2C1CCC1(C)C(=O)C=CC(C)(O[Si](C)(C)C(C)(C)C)C212569.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Vulgarin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ay1-7390000000-f3b7b031e2bd5ce67efb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vulgarin GC-MS (1 TMS) - 70eV, Positivesplash10-00b9-6694000000-29a96556fa9dccd120eb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vulgarin 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 - Vulgarin 10V, Positive-QTOFsplash10-00kb-0190000000-317d449691d81af7d9c02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vulgarin 20V, Positive-QTOFsplash10-00mk-0690000000-cb4df13a679d9ff6796a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vulgarin 40V, Positive-QTOFsplash10-0f6x-7920000000-c934a33edd5f8bce25212015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vulgarin 10V, Positive-QTOFsplash10-00kb-0190000000-317d449691d81af7d9c02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vulgarin 20V, Positive-QTOFsplash10-00mk-0690000000-cb4df13a679d9ff6796a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vulgarin 40V, Positive-QTOFsplash10-0f6x-7920000000-c934a33edd5f8bce25212015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vulgarin 10V, Negative-QTOFsplash10-03di-0090000000-b2d4f4080b70752b2d552015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vulgarin 20V, Negative-QTOFsplash10-03xs-0190000000-f2796cc7b5eda709c7ce2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vulgarin 40V, Negative-QTOFsplash10-0udi-9750000000-7ea279dead6bad682e4f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vulgarin 10V, Negative-QTOFsplash10-03di-0090000000-b2d4f4080b70752b2d552015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vulgarin 20V, Negative-QTOFsplash10-03xs-0190000000-f2796cc7b5eda709c7ce2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vulgarin 40V, Negative-QTOFsplash10-0udi-9750000000-7ea279dead6bad682e4f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vulgarin 10V, Negative-QTOFsplash10-03di-0090000000-3f27ef3c2ceb771717b42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vulgarin 20V, Negative-QTOFsplash10-02t9-0190000000-44d1e4851c3a25bfc4a22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vulgarin 40V, Negative-QTOFsplash10-004i-3920000000-4dbf2c15f65cf08df0212021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vulgarin 10V, Positive-QTOFsplash10-014i-0090000000-7e0609ac23949c6e91952021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vulgarin 20V, Positive-QTOFsplash10-014i-0490000000-64186fc06445ef7edc7f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vulgarin 40V, Positive-QTOFsplash10-05fu-6920000000-32d47e89a79b70f5d2f22021-09-23Wishart 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 IDFDB014979
KNApSAcK IDC00003393
Chemspider ID538241
KEGG Compound IDC09600
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound619337
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1434961
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.