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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:46:49 UTC
Update Date2021-09-14 15:17:01 UTC
HMDB IDHMDB0039353
Secondary Accession Numbers
  • HMDB39353
Metabolite Identification
Common Namealpha-Chaconine
Descriptionalpha-Chaconine, also known as α-chaconine, belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative. alpha-Chaconine is a very strong basic compound (based on its pKa). alpha-Chaconine is a potentially toxic compound.
Structure
Data?1563863359
Synonyms
ValueSource
a-ChaconineGenerator
Α-chaconineGenerator
ChaconineHMDB
ConineMeSH
alpha-ChaconineMeSH
Chemical FormulaC45H73NO14
Average Molecular Weight852.0594
Monoisotopic Molecular Weight851.503106049
IUPAC Name2-{[4-hydroxy-2-(hydroxymethyl)-6-({10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracos-4-en-7-yl}oxy)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol
Traditional Name2-{[4-hydroxy-2-(hydroxymethyl)-6-({10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracos-4-en-7-yl}oxy)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol
CAS Registry Number20562-03-2
SMILES
CC1C2CCC(C)CN2C2CC3C4CC=C5CC(CCC5(C)C4CCC3(C)C12)OC1OC(CO)C(OC2OC(C)C(O)C(O)C2O)C(O)C1OC1OC(C)C(O)C(O)C1O
InChI Identifier
InChI=1S/C45H73NO14/c1-19-7-10-28-20(2)31-29(46(28)17-19)16-27-25-9-8-23-15-24(11-13-44(23,5)26(25)12-14-45(27,31)6)57-43-40(60-42-37(53)35(51)33(49)22(4)56-42)38(54)39(30(18-47)58-43)59-41-36(52)34(50)32(48)21(3)55-41/h8,19-22,24-43,47-54H,7,9-18H2,1-6H3
InChI KeyTYNQWWGVEGFKRU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentSteroidal saponins
Alternative Parents
Substituents
  • Steroidal saponin
  • Diterpene glycoside
  • Solanidane skeleton
  • Oligosaccharide
  • Diterpenoid
  • Steroidal alkaloid
  • Azasteroid
  • Delta-5-steroid
  • Terpene glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Alkaloid or derivatives
  • Indolizidine
  • Piperidine
  • Oxane
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Acetal
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Polyol
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Primary alcohol
  • 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 Molecular Properties
PropertyValueReference
Melting Point243 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.29 g/LALOGPS
logP1.87ALOGPS
logP0.61ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)12.22ChemAxon
pKa (Strongest Basic)11.78ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area220.46 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity215.01 m³·mol⁻¹ChemAxon
Polarizability96.31 ųChemAxon
Number of Rings9ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0200000190-6d9e495c017061695d922021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0110000190-2e86417f4bebda88f5a72021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-1410000900-996b0c2e27f52bd986b52021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0000000090-83c168c4c7192f0110de2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0000000090-0e5b23e9074a490ffa0b2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Negativesplash10-0udi-0200000190-96329cee52f009f74c872021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0400000940-671c2cf8cc90dc83fa992021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udr-6900000000-b0ce1f718289203e6c7b2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0000000090-26d34982fdb6e82fe6802021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0000000090-6caad5aeed2685c071cd2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0w2i-5910000000-a1faf2c210f6b87206af2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-1720000920-3698201cba519e3f00cd2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0541-0009034340-178e833e323a65cd255d2015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052b-0009042100-05ed65999a0f388b6ff62015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-0209061000-1ac57f5488b5a57afce92015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udj-1219126670-bb552b307c9d7a8ded4c2015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1309022210-ade6a55d69e48c5c5e112015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ot-2509020000-6d03be521c264ab07afb2015-04-25View 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 IDFDB018909
KNApSAcK IDC00002242
Chemspider ID3328941
KEGG Compound IDC10796
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4115417
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lu MK, Chen PH, Shih YW, Chang YT, Huang ET, Liu CR, Chen PS: alpha-Chaconine inhibits angiogenesis in vitro by reducing matrix metalloproteinase-2. Biol Pharm Bull. 2010;33(4):622-30. [PubMed:20410596 ]
  2. Oda Y, Saito K, Ohara-Takada A, Mori M: Hydrolysis of the potato glycoalkaloid alpha-chaconine by filamentous fungi. J Biosci Bioeng. 2002;94(4):321-5. [PubMed:16233310 ]
  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.