Showing metabocard for Monosialoganglioside GM3 (LMDB00959)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-08-04 21:13:33 UTC
Update Date2016-08-04 22:06:16 UTC
LmdbLMDB00959
Secondary Accession NumbersNone
Metabolite Identification
Common NameMonosialoganglioside GM3
Descriptionganglioside GM3, also known as GM3 or g(m3) ganglioside, belongs to the class of organic compounds known as gangliosides. These are lipid molecules composed of a glycosphingolipid (ceramide and saccharide) with one or more sialic acids linked on the sugar chain. They are usually oligoglycosylceramides derived from lactosylceramide and containing a sialic acid residue such as N-acetylneuraminic acid. Based on a literature review a significant number of articles have been published on ganglioside GM3.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
alpha-Neu5ac-(2->3)-beta-D-gal-(1->4)-beta-D-GLC-(11)-N-(15Z)-tetracos-15-enoylsphingosineChEBI
alpha-Neu5ac-(2->3)-beta-D-gal-(1->4)-beta-D-GLC-(11)-N-cis-tetracos-15-enoylsphingosineChEBI
g(m3) GangliosideChEBI
GM3ChEBI
MonosialodihexosylgangliosideChEBI
Monosialoganglioside GM3ChEBI
NANA-gal-GLC-ceramideChEBI
a-Neu5ac-(2->3)-b-D-gal-(1->4)-b-D-GLC-(11)-N-(15Z)-tetracos-15-enoylsphingosineGenerator
Α-neu5ac-(2->3)-β-D-gal-(1->4)-β-D-GLC-(11)-N-(15Z)-tetracos-15-enoylsphingosineGenerator
a-Neu5ac-(2->3)-b-D-gal-(1->4)-b-D-GLC-(11)-N-cis-tetracos-15-enoylsphingosineGenerator
Α-neu5ac-(2->3)-β-D-gal-(1->4)-β-D-GLC-(11)-N-cis-tetracos-15-enoylsphingosineGenerator
SialyllactosylceramideMeSH
HematosideMeSH
II3neuaclaccerMeSH
Sialyl lactosylceramideMeSH
GM3, GangliosideMeSH
Lactosylceramide, sialylMeSH
Ganglioside GM3MeSH
Chemical FormulaC65H118N2O21
Average Molecular Weight1263.652
Monoisotopic Molecular Weight1262.822708828
IUPAC Name(2S,4S,5R,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R,4E)-3-hydroxy-2-{[(15Z)-1-hydroxytetracos-15-en-1-ylidene]amino}octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional Name(2S,4S,5R,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R,4E)-3-hydroxy-2-{[(15Z)-1-hydroxytetracos-15-en-1-ylidene]amino}octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCCCCC)=C(/[H])CCCCCCCCCCCCCC(O)=N[C@@]([H])(CO[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O[C@]2([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O[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)[C@]([H])(O)C(\[H])=C(/[H])CCCCCCCCCCCCC
InChI Identifier
InChI=1S/C65H118N2O21/c1-4-6-8-10-12-14-16-18-19-20-21-22-23-24-25-27-29-31-33-35-37-39-52(75)67-46(47(72)38-36-34-32-30-28-26-17-15-13-11-9-7-5-2)44-83-62-57(79)56(78)59(51(43-70)85-62)86-63-58(80)61(55(77)50(42-69)84-63)88-65(64(81)82)40-48(73)53(66-45(3)71)60(87-65)54(76)49(74)41-68/h18-19,36,38,46-51,53-63,68-70,72-74,76-80H,4-17,20-35,37,39-44H2,1-3H3,(H,66,71)(H,67,75)(H,81,82)/b19-18-,38-36+/t46-,47+,48-,49+,50+,51+,53+,54+,55-,56+,57+,58+,59+,60+,61-,62+,63-,65-/m0/s1
InChI KeyPFJKOHUKELZMLE-VEUXDRLPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as gangliosides. These are lipid molecules composed of a glycosphingolipid (ceramide and saccharide) with one or more sialic acids linked on the sugar chain. They are usually oligoglycosylceramides derived from lactosylceramide and containing a sialic acid residue such as N-acetylneuraminic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassGlycosphingolipids
Direct ParentGangliosides
Alternative Parents
Substituents
  • Neuaca2-3galb1-4glcb-cer_backbone
  • Glycosyl-n-acylsphingosine
  • Oligosaccharide
  • N-acylneuraminic acid or derivatives
  • N-acylneuraminic acid
  • Neuraminic acid
  • Fatty acyl glycoside
  • C-glucuronide
  • Alkyl glycoside
  • C-glycosyl compound
  • Glycosyl compound
  • O-glycosyl compound
  • Ketal
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Oxane
  • Pyran
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organopnictogen compound
  • Alcohol
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
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
logP5.23ALOGPS
logP9.16ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)3.06ChemAxon
pKa (Strongest Basic)2.51ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count23ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area380.39 ŲChemAxon
Rotatable Bond Count50ChemAxon
Refractivity329.84 m³·mol⁻¹ChemAxon
Polarizability146.68 ųChemAxon
Number of Rings3ChemAxon
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, Positivesplash10-03dj-1290505002-488818f9f235f810e463Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0h93-1261903410-a3996cfcb5f93cd55190Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08gi-3590512000-7cdad05b00354da64968Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-08fr-4190000000-026404c7fd120463b49fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a59-2190200100-6c944d8d11e8c637a80cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9562035162-3918a8fc35c4e0c8c7d9Spectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Milk
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
MilkDetected and Quantified0.158-0.237 uMNot AvailableBovine details
DrugBank IDNot Available
HMDB IDHMDB0304771
FooDB IDFDB098136
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID34448956
ChEBI ID84118
PubChem Compound ID86583360
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available