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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:14:17 UTC
Update Date2019-07-23 06:18:14 UTC
HMDB IDHMDB0035282
Secondary Accession Numbers
  • HMDB35282
Metabolite Identification
Common NameSolasodine
DescriptionSolasodine, also known as purapuridine or salasdine, belongs to the class of organic compounds known as spirosolanes and derivatives. These are steroidal alkaloids with a structure containing a spirosolane skeleton. Siporosolane is a polycyclic compound that is characterized by a 1-oxa-6-azaspiro[4.5]decane moiety where the oxolane ring is fused to a docosahydronaphth[2,1:4',5']indene ring system. Spirosolane arises from the conversion of a cholestane side-chain into a bicyclic system containing a piperidine and a tetrahydrofuran ring. Solasodine is a very strong basic compound (based on its pKa).
Structure
Data?1563862694
Synonyms
ValueSource
PurapuridineHMDB
SalasdineHMDB
SalasodineHMDB
SolancarpidineHMDB
SolancarpineHMDB
Solanidine SHMDB
Solanidine-SHMDB
Solasod-5-en-3 beta-olHMDB
Solasod-5-en-3beta -olHMDB
SolasodinHMDB
Solasodine hydrochloride baseHMDB
SosasodineHMDB
Spirosol-5-en-3-olHMDB
TomatidenolHMDB
SolasodineMeSH
Solasodine, (3beta,22beta,25S)-isomerMeSH
Solasodine citrate, (3alpha,22alpha,25R)-isomerMeSH
Chemical FormulaC27H43NO2
Average Molecular Weight413.6358
Monoisotopic Molecular Weight413.329379625
IUPAC Name5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-16-ol
Traditional Namesolassodine
CAS Registry Number126-17-0
SMILES
CC1C2C(CC3C4CC=C5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)CN1
InChI Identifier
InChI=1S/C27H43NO2/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28-29H,6-15H2,1-4H3
InChI KeyKWVISVAMQJWJSZ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as spirosolanes and derivatives. These are steroidal alkaloids with a structure containing a spirosolane skeleton. Siporosolane is a polycyclic compound that is characterized by a 1-oxa-6-azaspiro[4.5]decane moiety where the oxolane ring is fused to a docosahydronaphth[2,1:4',5']indene ring system. Spirosolane arises from the conversion of a cholestane side-chain into a bicyclic system containing a piperidine and a tetrahydrofuran ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal alkaloids
Direct ParentSpirosolanes and derivatives
Alternative Parents
Substituents
  • Spirosolane skeleton
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • Azasteroid
  • Delta-5-steroid
  • Azaspirodecane
  • Alkaloid or derivatives
  • Piperidine
  • Cyclic alcohol
  • Tetrahydrofuran
  • Hemiaminal
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Secondary aliphatic amine
  • Organoheterocyclic compound
  • Secondary amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Alcohol
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point200 - 201 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00084 g/LALOGPS
logP4.45ALOGPS
logP4.61ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area41.49 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity121.95 m³·mol⁻¹ChemAxon
Polarizability50.31 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000w-0129000000-c0f006faa45f6504b94aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-2116900000-ffdb43be61543b5cdf31Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0000900000-e0308c250bfeb4a8e3f0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0100900000-885f5ba1460df2a81f9dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4j-0910000000-83c702d144b914031b01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0009500000-894bee60ed0946470ec4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w91-0198200000-bd353c3bcebbb6b18195Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0mpp-4298000000-ff41d9eaa787776766c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-556f3f408a422b05cd8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-0009600000-00a27d38d42e4d209801Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-3119000000-6c61de8babead29f83fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0009500000-894bee60ed0946470ec4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w91-0198200000-bd353c3bcebbb6b18195Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0mpp-4298000000-ff41d9eaa787776766c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-556f3f408a422b05cd8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-0009600000-00a27d38d42e4d209801Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-3119000000-6c61de8babead29f83fbSpectrum
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 IDFDB013944
KNApSAcK IDC00002264
Chemspider ID5060
KEGG Compound IDC10822
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSolasodine
METLIN IDNot Available
PubChem Compound5250
PDB IDNot Available
ChEBI ID565242
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pandurangan A, Khosa RL, Hemalatha S: Antinociceptive activity of steroid alkaloids isolated from Solanum trilobatum Linn. J Asian Nat Prod Res. 2010 Aug;12(8):691-5. doi: 10.1080/10286020.2010.497997. [PubMed:20706906 ]
  2. Pandurangan A, Khosa RL, Hemalatha S: Anti-inflammatory activity of an alkaloid from Solanum trilobatum on acute and chronic inflammation models. Nat Prod Res. 2011 Jul;25(12):1132-41. doi: 10.1080/14786410903370783. [PubMed:21391109 ]
  3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  8. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.