Isofucosterol 3-O-[6-O-(9-Octadecenoyl)-b-D-glucopyranoside] (CHEM027134)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 23:31:11 UTC
Update Date2016-11-09 01:18:24 UTC
Accession NumberCHEM027134
Identification
Common NameIsofucosterol 3-O-[6-O-(9-Octadecenoyl)-b-D-glucopyranoside]
ClassSmall Molecule
DescriptionConstituent of Lycopersicon esculentum (tomato). Isofucosterol 3-O-[6-O-(9-Octadecenoyl)-b-D-glucopyranoside] is found in garden tomato.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
[6-({2,15-dimethyl-14-[(5E)-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl (9E)-octadec-9-enoic acidGenerator
Chemical FormulaC53H90O7
Average Molecular Mass839.278 g/mol
Monoisotopic Mass838.669 g/mol
CAS Registry Number209903-45-7
IUPAC Name[6-({2,15-dimethyl-14-[(5E)-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl (9E)-octadec-9-enoate
Traditional Name[3,4,5-trihydroxy-6-({14-[(5E)-5-isopropylhept-5-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl}oxy)oxan-2-yl]methyl (9E)-octadec-9-enoate
SMILESCCCCCCCC\C=C\CCCCCCCC(=O)OCC1OC(OC2CCC3(C)C4CCC5(C)C(CCC5C4CC=C3C2)C(C)CC\C(=C/C)C(C)C)C(O)C(O)C1O
InChI IdentifierInChI=1S/C53H90O7/c1-8-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-47(54)58-36-46-48(55)49(56)50(57)51(60-46)59-41-31-33-52(6)40(35-41)27-28-42-44-30-29-43(53(44,7)34-32-45(42)52)38(5)25-26-39(9-2)37(3)4/h9,16-17,27,37-38,41-46,48-51,55-57H,8,10-15,18-26,28-36H2,1-7H3/b17-16+,39-9+
InChI KeyYEAUSGDLYXRRSE-LMNLQXKHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassStigmastanes and derivatives
Direct ParentStigmastanes and derivatives
Alternative ParentsNot Available
SubstituentsNot Available
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 Solubility0.00012 g/LALOGPS
logP9.86ALOGPS
logP13.12ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.45 ŲChemAxon
Rotatable Bond Count25ChemAxon
Refractivity246.94 m³·mol⁻¹ChemAxon
Polarizability104.92 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-1058930170-f545cbf4691c46dcc354Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-4278900000-b9ecb6003c417f3080d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02tj-6598300100-cc8253c678e6e18c95fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03e9-0092410040-2ed34685ba0fd5011e78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03e9-0092600000-7095ff50c1fc9842292bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-4086900000-bda3470934efa25469ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000310090-a35a4cf8fc4785a1f961Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01p9-1021630090-70dbe8fbe4cf1d9553aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fs-4054901000-cbd86011f4d95af7e4adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0111200190-ae6e85d87245365ed1ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ot-9046120020-273943f5a25a18af89f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5c-9110000000-4a7023c0c17ac743786dSpectrum
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 IDHMDB0032813
FooDB IDFDB010787
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID131751319
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