Ixocarpalactone A (CHEM028444)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:27:51 UTC
Update Date2016-11-09 01:18:41 UTC
Accession NumberCHEM028444
Identification
Common NameIxocarpalactone A
ClassSmall Molecule
DescriptionConstituent of Physalis ixocarpa (tomatillo). Ixocarpalactone A is found in fruits.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5,6-Epoxy-4,16,20,22,23-pentahydroxy-1-oxoergost-2-en-26-Oic acid, g-lactoneHMDB
5,6-Epoxy-4,16,20,22-tetrahydroxy-1-oxoergost-2-eno-26,23-lactoneHMDB
IxoA CPDHMDB
Chemical FormulaC28H40O8
Average Molecular Mass504.612 g/mol
Monoisotopic Mass504.272 g/mol
CAS Registry Number71801-45-1
IUPAC Name15-[1-(3,4-dimethyl-5-oxooxolan-2-yl)-1,2-dihydroxypropan-2-yl]-6,14-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one
Traditional Name15-[1-(3,4-dimethyl-5-oxooxolan-2-yl)-1,2-dihydroxypropan-2-yl]-6,14-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one
SMILESCC1C(C)C(=O)OC1C(O)C(C)(O)C1C(O)CC2C3CC4OC44C(O)C=CC(=O)C4(C)C3CCC12C
InChI IdentifierInChI=1S/C28H40O8/c1-12-13(2)24(33)35-21(12)23(32)27(5,34)22-17(29)11-16-14-10-20-28(36-20)19(31)7-6-18(30)26(28,4)15(14)8-9-25(16,22)3/h6-7,12-17,19-23,29,31-32,34H,8-11H2,1-5H3
InChI KeyPHBPDHFIJFLEGD-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentWithanolides and derivatives
Alternative Parents
Substituents
  • Withanolide-skeleton
  • Prostaglandin skeleton
  • Bile acid, alcohol, or derivatives
  • Eicosanoid
  • 5,6-epoxysteroid
  • Cyclohexenone
  • Oxepane
  • Fatty acyl
  • Gamma butyrolactone
  • Cyclic alcohol
  • Tetrahydrofuran
  • Tertiary alcohol
  • Carboxylic acid ester
  • Secondary alcohol
  • Ketone
  • Lactone
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxacycle
  • Oxirane
  • Ether
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.26 g/LALOGPS
logP0.91ALOGPS
logP1.4ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)12.82ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area136.82 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity129.12 m³·mol⁻¹ChemAxon
Polarizability53.76 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-9136400000-ee788418b853d49d8525Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-053r-9041216000-ceeec2c3924125875e0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06rl-1109730000-cd9cfd6988219eb97b80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9637800000-0e9b105292e3dace8cd8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k96-9237000000-522b51015f19dd0c7e37Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0403690000-e2b8c30c798ad015f250Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kp-1946100000-08da103d7ed6e74b4546Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-9118000000-be43fc1509ae094a91beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0001290000-dbfcb55f41b99ce1d024Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0w2c-1309440000-2ba4f6510a9fc307735bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kb-4397000000-b79c5ff396a2cfbae7a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0601890000-6634aec8a8a4d4fe42ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01u0-2426910000-bfa8c918744c3034cd3bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ldj-8915100000-507f3271917c8f66f267Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0034393
FooDB IDFDB012779
Phenol Explorer IDNot Available
KNApSAcK IDC00031918
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID289842
ChEBI IDNot Available
PubChem Compound ID327287
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM