alpha-Chaconine (T3D4050)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2014-08-29 04:58:10 UTC
Update Date2014-12-24 20:26:36 UTC
Accession NumberT3D4050
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).
Compound Type
  • Amine
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
a-Chaconine
Chaconine
α-Chaconine
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=1/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 KeyInChIKey=TYNQWWGVEGFKRU-UHFFFAOYNA-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
LogPNot 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ufr-0700001290-87a24f415f3c7015b02a2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0npj-2904051330-7e14c020906c0c7534302021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056v-9611001100-3589c97eb528ae916b492021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000190-b28d66a21f14994129142021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udm-5711001690-664c5f1412d02fdab0e02021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-6400094100-d862c762a4da4f346c722021-09-24View Spectrum
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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB39353
PubChem Compound ID4115417
ChEMBL IDNot Available
ChemSpider ID3328941
KEGG IDC10796
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D4050.pdf
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. [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. [16233310 ]
  3. Shih YW, Chen PS, Wu CH, Jeng YF, Wang CJ: Alpha-chaconine-reduced metastasis involves a PI3K/Akt signaling pathway with downregulation of NF-kappaB in human lung adenocarcinoma A549 cells. J Agric Food Chem. 2007 Dec 26;55(26):11035-43. Epub 2007 Nov 29. [18044836 ]
  4. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available