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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:21:10 UTC
Update Date2022-03-07 02:56:43 UTC
HMDB IDHMDB0040770
Secondary Accession Numbers
  • HMDB40770
Metabolite Identification
Common Name3beta-3-Lupanol
Description4-O-alpha-D-Galactopyranosylcalystegine B2 belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. 4-O-alpha-D-Galactopyranosylcalystegine B2 is a very strong basic compound (based on its pKa). Outside of the human body, 4-O-alpha-D-Galactopyranosylcalystegine B2 has been detected, but not quantified in, fruits. This could make 4-O-alpha-D-galactopyranosylcalystegine B2 a potential biomarker for the consumption of these foods.
Structure
Data?1563863586
Synonyms
ValueSource
4-O-a-D-Galactopyranosylcalystegine b2Generator
4-O-Α-D-galactopyranosylcalystegine b2Generator
3b-3-LupanolGenerator
3Β-3-lupanolGenerator
Chemical FormulaC30H52O
Average Molecular Weight428.7333
Monoisotopic Molecular Weight428.401816286
IUPAC Name1,2,5,14,18,18-hexamethyl-8-(propan-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-ol
Traditional Name8-isopropyl-1,2,5,14,18,18-hexamethylpentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-ol
CAS Registry Number3186-86-5
SMILES
CC(C)C1CCC2(C)CCC3(C)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C12
InChI Identifier
InChI=1S/C30H52O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h19-25,31H,9-18H2,1-8H3
InChI KeyUBLNLUPLUKPSPP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glycosyl compounds
Alternative Parents
Substituents
  • Hexose monosaccharide
  • O-glycosyl compound
  • Tropane alkaloid
  • Monosaccharide
  • Oxane
  • Piperidine
  • Pyrrolidine
  • Cyclic alcohol
  • Secondary alcohol
  • Hemiaminal
  • Oxacycle
  • Secondary amine
  • Azacycle
  • Polyol
  • Organoheterocyclic compound
  • Alkanolamine
  • Secondary aliphatic amine
  • Acetal
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Primary alcohol
  • 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 Point201 - 202 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.8e-05 g/LALOGPS
logP6.08ALOGPS
logP7.8ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)19.49ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity131.13 m³·mol⁻¹ChemAxon
Polarizability54.72 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+199.43631661259
DarkChem[M-H]-195.83231661259
DeepCCS[M-2H]-248.01730932474
DeepCCS[M+Na]+223.24530932474
AllCCS[M+H]+214.432859911
AllCCS[M+H-H2O]+212.632859911
AllCCS[M+NH4]+216.032859911
AllCCS[M+Na]+216.432859911
AllCCS[M-H]-207.932859911
AllCCS[M+Na-2H]-209.932859911
AllCCS[M+HCOO]-212.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3beta-3-LupanolCC(C)C1CCC2(C)CCC3(C)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C122686.5Standard polar33892256
3beta-3-LupanolCC(C)C1CCC2(C)CCC3(C)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C123312.5Standard non polar33892256
3beta-3-LupanolCC(C)C1CCC2(C)CCC3(C)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C123403.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3beta-3-Lupanol,1TMS,isomer #1CC(C)C1CCC2(C)CCC3(C)C(CCC4C5(C)CCC(O[Si](C)(C)C)C(C)(C)C5CCC43C)C123454.4Semi standard non polar33892256
3beta-3-Lupanol,1TBDMS,isomer #1CC(C)C1CCC2(C)CCC3(C)C(CCC4C5(C)CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C123672.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3beta-3-Lupanol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dj-0118900000-534845b709be17d40da72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3beta-3-Lupanol GC-MS (1 TMS) - 70eV, Positivesplash10-0079-1011900000-b51dc4b4f239a33462812017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3beta-3-Lupanol 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 - 3beta-3-Lupanol 10V, Positive-QTOFsplash10-03fr-0001900000-b4de3c6d070909ade2222015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta-3-Lupanol 20V, Positive-QTOFsplash10-08i0-0559800000-b22c3bafe82f090a1fda2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta-3-Lupanol 40V, Positive-QTOFsplash10-0a6u-1569100000-c04c05ba228204529d762015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta-3-Lupanol 10V, Negative-QTOFsplash10-004i-0000900000-500075665ab4759f6ea42015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta-3-Lupanol 20V, Negative-QTOFsplash10-004i-0000900000-7dd8b7ad2d89731a820f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta-3-Lupanol 40V, Negative-QTOFsplash10-01ot-1009500000-f5b86e6794b487a0acac2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta-3-Lupanol 10V, Positive-QTOFsplash10-004i-0005900000-d36f67cb6ac9463de8422021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta-3-Lupanol 20V, Positive-QTOFsplash10-002r-7691400000-f5c56e6091b3d8d9c95f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta-3-Lupanol 40V, Positive-QTOFsplash10-0r10-4950000000-6ab0415285f9dea0b5db2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta-3-Lupanol 10V, Negative-QTOFsplash10-004i-0000900000-ed006f256d0151ef06142021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta-3-Lupanol 20V, Negative-QTOFsplash10-004i-0000900000-ed006f256d0151ef06142021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta-3-Lupanol 40V, Negative-QTOFsplash10-004i-0000900000-9b0b398f5fb1880472382021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB017473
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound75092867
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.