Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:58:24 UTC
Update Date2022-03-07 02:54:20 UTC
HMDB IDHMDB0035034
Secondary Accession Numbers
  • HMDB35034
Metabolite Identification
Common NameHeliantriol B2
DescriptionHeliantriol B2, also known as lupene triol, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Heliantriol B2 is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862654
Synonyms
ValueSource
Lup-20(29)-ene-3,16,28-triolHMDB
Lupene triolHMDB
Heliantriol b2MeSH
Chemical FormulaC30H50O3
Average Molecular Weight458.7162
Monoisotopic Molecular Weight458.375995466
IUPAC Name5-(hydroxymethyl)-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosane-4,17-diol
Traditional Name5-(hydroxymethyl)-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosane-4,17-diol
CAS Registry Number61229-18-3
SMILES
CC(=C)C1CCC2(CO)C1C1CCC3C4(C)CCC(O)C(C)(C)C4CCC3(C)C1(C)CC2O
InChI Identifier
InChI=1S/C30H50O3/c1-18(2)19-10-15-30(17-31)24(33)16-29(7)20(25(19)30)8-9-22-27(5)13-12-23(32)26(3,4)21(27)11-14-28(22,29)6/h19-25,31-33H,1,8-17H2,2-7H3
InChI KeyTWKNDDJHVQUEJF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • 18-hydroxysteroid
  • Hydroxysteroid
  • 12-hydroxysteroid
  • Steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point300 - 301 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0015 g/LALOGPS
logP4.64ALOGPS
logP4.94ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)14.46ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity134.2 m³·mol⁻¹ChemAxon
Polarizability55.54 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+202.84931661259
DarkChem[M-H]-198.45131661259
DeepCCS[M+H]+213.86130932474
DeepCCS[M-H]-211.50330932474
DeepCCS[M-2H]-245.41930932474
DeepCCS[M+Na]+220.64630932474
AllCCS[M+H]+214.732859911
AllCCS[M+H-H2O]+213.032859911
AllCCS[M+NH4]+216.232859911
AllCCS[M+Na]+216.632859911
AllCCS[M-H]-209.832859911
AllCCS[M+Na-2H]-211.932859911
AllCCS[M+HCOO]-214.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Heliantriol B2CC(=C)C1CCC2(CO)C1C1CCC3C4(C)CCC(O)C(C)(C)C4CCC3(C)C1(C)CC2O2541.9Standard polar33892256
Heliantriol B2CC(=C)C1CCC2(CO)C1C1CCC3C4(C)CCC(O)C(C)(C)C4CCC3(C)C1(C)CC2O3438.5Standard non polar33892256
Heliantriol B2CC(=C)C1CCC2(CO)C1C1CCC3C4(C)CCC(O)C(C)(C)C4CCC3(C)C1(C)CC2O3978.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Heliantriol B2,1TMS,isomer #1C=C(C)C1CCC2(CO[Si](C)(C)C)C(O)CC3(C)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC43C)C123807.4Semi standard non polar33892256
Heliantriol B2,1TMS,isomer #2C=C(C)C1CCC2(CO)C(O)CC3(C)C(CCC4C5(C)CCC(O[Si](C)(C)C)C(C)(C)C5CCC43C)C123826.1Semi standard non polar33892256
Heliantriol B2,1TMS,isomer #3C=C(C)C1CCC2(CO)C(O[Si](C)(C)C)CC3(C)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC43C)C123833.4Semi standard non polar33892256
Heliantriol B2,2TMS,isomer #1C=C(C)C1CCC2(CO[Si](C)(C)C)C(O[Si](C)(C)C)CC3(C)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC43C)C123854.2Semi standard non polar33892256
Heliantriol B2,2TMS,isomer #2C=C(C)C1CCC2(CO[Si](C)(C)C)C(O)CC3(C)C(CCC4C5(C)CCC(O[Si](C)(C)C)C(C)(C)C5CCC43C)C123847.3Semi standard non polar33892256
Heliantriol B2,2TMS,isomer #3C=C(C)C1CCC2(CO)C(O[Si](C)(C)C)CC3(C)C(CCC4C5(C)CCC(O[Si](C)(C)C)C(C)(C)C5CCC43C)C123792.2Semi standard non polar33892256
Heliantriol B2,3TMS,isomer #1C=C(C)C1CCC2(CO[Si](C)(C)C)C(O[Si](C)(C)C)CC3(C)C(CCC4C5(C)CCC(O[Si](C)(C)C)C(C)(C)C5CCC43C)C123751.5Semi standard non polar33892256
Heliantriol B2,1TBDMS,isomer #1C=C(C)C1CCC2(CO[Si](C)(C)C(C)(C)C)C(O)CC3(C)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC43C)C124041.0Semi standard non polar33892256
Heliantriol B2,1TBDMS,isomer #2C=C(C)C1CCC2(CO)C(O)CC3(C)C(CCC4C5(C)CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C124042.6Semi standard non polar33892256
Heliantriol B2,1TBDMS,isomer #3C=C(C)C1CCC2(CO)C(O[Si](C)(C)C(C)(C)C)CC3(C)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC43C)C124048.8Semi standard non polar33892256
Heliantriol B2,2TBDMS,isomer #1C=C(C)C1CCC2(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)CC3(C)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC43C)C124314.9Semi standard non polar33892256
Heliantriol B2,2TBDMS,isomer #2C=C(C)C1CCC2(CO[Si](C)(C)C(C)(C)C)C(O)CC3(C)C(CCC4C5(C)CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C124305.3Semi standard non polar33892256
Heliantriol B2,2TBDMS,isomer #3C=C(C)C1CCC2(CO)C(O[Si](C)(C)C(C)(C)C)CC3(C)C(CCC4C5(C)CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C124260.1Semi standard non polar33892256
Heliantriol B2,3TBDMS,isomer #1C=C(C)C1CCC2(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)CC3(C)C(CCC4C5(C)CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C124432.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Heliantriol B2 GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ou-0303900000-d19106a2ebcb1e6862112017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heliantriol B2 GC-MS (3 TMS) - 70eV, Positivesplash10-0bt9-1010129000-929402b5a65988c488d92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heliantriol B2 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heliantriol B2 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 - Heliantriol B2 10V, Positive-QTOFsplash10-006x-0000900000-e79b4a9e48c41466e9442016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heliantriol B2 20V, Positive-QTOFsplash10-00dl-0002900000-bc515c3b0133b5c43aee2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heliantriol B2 40V, Positive-QTOFsplash10-00yr-3095600000-86c12c2d64c9a69d9c862016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heliantriol B2 10V, Negative-QTOFsplash10-0a4i-0000900000-0cb83f01092b866f89612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heliantriol B2 20V, Negative-QTOFsplash10-0a4r-0000900000-446dc98d66088c140d862016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heliantriol B2 40V, Negative-QTOFsplash10-0bvi-0001900000-bf048c42f768c20dacae2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heliantriol B2 10V, Positive-QTOFsplash10-0a4i-0101900000-c623423f83594884ffdd2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heliantriol B2 20V, Positive-QTOFsplash10-0abl-0931100000-2369060ae72a87a3c4b72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heliantriol B2 40V, Positive-QTOFsplash10-007c-2921000000-6d816d7a7d38773c1e352021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heliantriol B2 10V, Negative-QTOFsplash10-0a4i-0000900000-2e8eabc98b7e3f409adf2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heliantriol B2 20V, Negative-QTOFsplash10-0a4i-0000900000-d3c5f3ca2f88169aece92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heliantriol B2 40V, Negative-QTOFsplash10-056r-0000900000-f463274cd9850ca0285d2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB013640
KNApSAcK IDNot Available
Chemspider ID288421
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound325735
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.