alpha-Chaconine (CHEM003010)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-08-29 04:58:10 UTC
Update Date2026-04-06 01:49:50 UTC
Accession NumberCHEM003010
Identification
Common Namealpha-Chaconine
ClassSmall Molecule
Descriptionalpha-Chaconine is found in potato. alpha-Chaconine is an alkaloid from Solanum chacoense and very many other Solanum species (Solanaceae). Alpha-chaconine has been shown to exhibit anti-angiogenic and anti-fungal functions (1, 2).
Contaminant Sources
  • FooDB Chemicals
  • T3DB toxins
Contaminant Type
  • Amine
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
a-ChaconineGenerator
Α-chaconineGenerator
ConineMeSH
ChaconineHMDB
alpha-ChaconineMeSH
Chemical FormulaC45H73NO14
Average Molecular Mass852.059 g/mol
Monoisotopic Mass851.503 g/mol
CAS Registry Number20562-03-2
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
SMILESCC1C2CCC(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 IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point243°C
Boiling PointNot Available
SolubilityNot Available
Predicted 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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0200000190-6d9e495c017061695d92Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0110000190-2e86417f4bebda88f5a7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-1410000900-996b0c2e27f52bd986b5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0000000090-83c168c4c7192f0110deSpectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0000000090-0e5b23e9074a490ffa0bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Negativesplash10-0udi-0200000190-96329cee52f009f74c87Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0400000940-671c2cf8cc90dc83fa99Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udr-6900000000-b0ce1f718289203e6c7bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0000000090-26d34982fdb6e82fe680Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0000000090-6caad5aeed2685c071cdSpectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0w2i-5910000000-a1faf2c210f6b87206afSpectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-1720000920-3698201cba519e3f00cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0541-0009034340-178e833e323a65cd255dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052b-0009042100-05ed65999a0f388b6ff6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-0209061000-1ac57f5488b5a57afce9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udj-1219126670-bb552b307c9d7a8ded4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1309022210-ade6a55d69e48c5c5e11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ot-2509020000-6d03be521c264ab07afbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ufr-0700001290-87a24f415f3c7015b02aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0npj-2904051330-7e14c020906c0c753430Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056v-9611001100-3589c97eb528ae916b49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000190-b28d66a21f1499412914Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udm-5711001690-664c5f1412d02fdab0e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-6400094100-d862c762a4da4f346c72Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityAlpha-Chaconine has inhibitory effect on lung adenocarcinoma cell metastasis in vitro. Alpha-chaconine could inhibit phosphorylation of c-Jun N-terminal kinase (JNK) and Akt, whereas it did not affected phosphorylation of extracellular signal regulating kinase (ERK) and p38. In addition, alpha-chaconine significantly decreased the nuclear level of nuclear factor kappa B (NF-_B) and the binding ability of NF-_B. Therefore, alpha-chaconine inhibited A549 cell metastasis by a reduction of matrix metalloproteinase-2 (MMP-2) and matrix metalloproteinase-9 (MMP-9) activities involving suppression of phosphoinositide 3-kinase/Akt/NF-_B (PI3K/Akt/NF-_B) signaling pathway. Alpha-chaconine has exhibited its antiproliferative and apoptotic effects on the growth of cancer cells originating from human skin, liver, prostate, breast, and colon. In addition to the cytotoxicity in various cancer cells, R-chaconine induces significant cytotoxicity in Chang, normal human liver cells. (3)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/Sourcesalpha-Chaconine is found in potato.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0039353
FooDB IDFDB018909
Phenol Explorer IDNot Available
KNApSAcK IDC00002242
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID3328941
ChEBI IDNot Available
PubChem Compound ID4115417
Kegg Compound IDC10796
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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.
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.
3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
7. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
8. The lipid handbook with CD-ROM