Showing metabocard for Monosialoganglioside GM2 (LMDB00958)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-08-04 21:13:27 UTC
Update Date2016-08-04 22:06:16 UTC
LmdbLMDB00958
Secondary Accession NumbersNone
Metabolite Identification
Common NameMonosialoganglioside GM2
Description(2R,4R,5S,6S)-2-({[(2S,3R,4S,5S,6R)-3-{[(2R,3S,4S,5S,6S)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-{[(2R,3S,4E)-3-hydroxy-2-[(1-hydroxyoctadecylidene)amino]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}methyl)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1S,2S)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid belongs to the class of organic compounds known as glycosyl-n-acylsphingosines. Glycosyl-N-acylsphingosines are compounds containing a sphingosine linked to a simple glucosyl moiety. Based on a literature review very few articles have been published on (2R,4R,5S,6S)-2-({[(2S,3R,4S,5S,6R)-3-{[(2R,3S,4S,5S,6S)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-{[(2R,3S,4E)-3-hydroxy-2-[(1-hydroxyoctadecylidene)amino]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}methyl)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1S,2S)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R,4R,5S,6S)-2-({[(2S,3R,4S,5S,6R)-3-{[(2R,3S,4S,5S,6S)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-{[(2R,3S,4E)-3-hydroxy-2-[(1-hydroxyoctadecylidene)amino]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}methyl)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1S,2S)-1,2,3-trihydroxypropyl]oxane-2-carboxylateGenerator
GM2, GangliosideMeSH
Tay sachs disease gangliosideMeSH
Ganglioside, tay-sachs diseaseMeSH
Tay-sachs disease gangliosideMeSH
g(m2) GangliosideMeSH
Ganglioside GM2MeSH
Chemical FormulaC68H123N3O26
Average Molecular Weight1398.727
Monoisotopic Molecular Weight1397.839481093
IUPAC Name(2R,4R,5S,6S)-2-({[(2S,3R,4S,5S,6R)-3-{[(2R,3S,4S,5S,6S)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-{[(2R,3S,4E)-3-hydroxy-2-[(1-hydroxyoctadecylidene)amino]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}methyl)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1S,2S)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional NameGM2 (ganglioside)
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCCCCCCCCCC)=C(\[H])[C@]([H])(O)[C@@]([H])(CO[C@]1([H])O[C@@]([H])(CO)[C@]([H])(O[C@@]2([H])O[C@@]([H])(CO)[C@@]([H])(O[C@@]3([H])O[C@@]([H])(CO)[C@@]([H])(O)[C@@]([H])(O)[C@]3([H])N=C(C)O)[C@@]([H])(OC[C@]3(C[C@@]([H])(O)[C@]([H])(N=C(C)O)[C@]([H])(O3)[C@@]([H])(O)[C@@]([H])(O)CO)C(O)=O)[C@]2([H])O)[C@@]([H])(O)[C@]1([H])O)N=C(O)CCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C68H123N3O26/c1-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-51(81)71-44(45(78)33-31-29-27-25-23-21-18-16-14-12-10-8-6-2)40-90-65-58(86)57(85)60(49(38-74)93-65)95-66-59(87)63(61(50(39-75)94-66)96-64-53(70-43(4)77)56(84)55(83)48(37-73)92-64)91-41-68(67(88)89)35-46(79)52(69-42(3)76)62(97-68)54(82)47(80)36-72/h31,33,44-50,52-66,72-75,78-80,82-87H,5-30,32,34-41H2,1-4H3,(H,69,76)(H,70,77)(H,71,81)(H,88,89)/b33-31+/t44-,45+,46-,47+,48+,49+,50+,52+,53+,54+,55-,56+,57+,58+,59+,60+,61-,62+,63+,64-,65-,66-,68-/m1/s1
InChI KeyUSMMPBVNWHAJBE-YMEOXFOQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glycosyl-n-acylsphingosines. Glycosyl-N-acylsphingosines are compounds containing a sphingosine linked to a simple glucosyl moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassGlycosphingolipids
Direct ParentGlycosyl-N-acylsphingosines
Alternative Parents
Substituents
  • Glycosyl-n-acylsphingosine
  • Oligosaccharide
  • Fatty acyl glycoside
  • N-acyl-alpha-hexosamine
  • C-glucuronide
  • Alkyl glycoside
  • C-glycosyl compound
  • O-glycosyl compound
  • Glycosyl compound
  • Fatty amide
  • Oxane
  • N-acyl-amine
  • Pyran
  • Fatty acyl
  • Acetamide
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Polyol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxide
  • Primary alcohol
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.36ALOGPS
logP5.02ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)3.34ChemAxon
pKa (Strongest Basic)2.61ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count29ChemAxon
Hydrogen Donor Count17ChemAxon
Polar Surface Area471.9 ŲChemAxon
Rotatable Bond Count50ChemAxon
Refractivity350.28 m³·mol⁻¹ChemAxon
Polarizability155.08 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f7k-1359021000-766a422017398cb952edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007a-2198017100-23398b2d5a3a30b3dea3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udj-1592210000-1cbe9dc85117408fd9acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-5019000000-623d76b7e04365b07fa2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pvj-3039002100-06584fda1a8fdbf58924Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0096-6396023300-7f485a84c7d05ef41c0cSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Milk
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
MilkDetected and Quantified0.500-0 uMNot AvailableBovine details
DrugBank IDNot Available
HMDB IDHMDB0304654
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID26286730
ChEBI IDNot Available
PubChem Compound ID71308211
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available