Showing metabocard for Ganglioside GM2 (d18:1/18:0) (BMDB0004939)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:13:21 UTC
Update Date2020-05-11 20:32:10 UTC
BMDB IDBMDB0004939
Secondary Accession Numbers
  • BMDB04939
Metabolite Identification
Common NameGanglioside GM2 (d18:1/18:0)
DescriptionGanglioside GM2 (d18:1/18:0), also known as ganglioside GM2 or ii3neuacggose3cer, belongs to the class of organic compounds known as galnacb1-4galb1-4glc- (ganglio series). These are neutral glycosphingolipids in which the root sequence is GalNAcb1-4Galb1-4Glc. Ganglioside GM2 (d18:1/18:0) is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S,4S,5R)-2-{[(2R,3S,4R,5R,6S)-3-{[(2S,3R,4R,5R,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R,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}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylateHMDB
GalNAc-beta1->4(neu5ac-alpha2->3)gal-beta1->4GLC-beta1->1'cerHMDB
Ganglioside GM2HMDB
GM2HMDB
II3neuacggose3cerHMDB
N-Acetyl-D-galactosaminyl-(N-acetylneuraminyl)-D-galactosyl-1,4-beta-D-glucosyl-N-acylsphingosineHMDB
N-Acetyl-D-galactosaminyl-(N-acetylneuraminyl)-D-galactosyl-D-glucosylceramideHMDB
N-Acetyl-delta-galactosaminyl-(N-acetylneuraminyl)-delta-galactosyl-1,4-beta-delta-glucosyl-N-acylsphingosineHMDB
N-Acetyl-delta-galactosaminyl-(N-acetylneuraminyl)-delta-galactosyl-delta-glucosylceramideHMDB
N-Acetyl-ganglioside GM2HMDB
N-Acetylganglioside GM2HMDB
NeuAc-GM2HMDB
Tay-sachs gangliosideHMDB
Chemical FormulaC67H121N3O26
Average Molecular Weight1384.6821
Monoisotopic Molecular Weight1383.823831059
IUPAC Name(2S,4S,5R)-2-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R,4E)-3-hydroxy-2-octadecanamidooctadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-{[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional Name(2S,4S,5R)-2-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R,4E)-3-hydroxy-2-octadecanamidooctadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-{[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3NC(C)=O)[C@H](O[C@@]3(C[C@H](O)[C@@H](NC(C)=O)C(O3)[C@H](O)[C@H](O)CO)C(O)=O)[C@H]2O)[C@H](O)[C@H]1O)[C@H](O)\C=C\CCCCCCCCCCCCC
InChI Identifier
InChI=1S/C67H121N3O26/c1-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-50(80)70-43(44(77)33-31-29-27-25-23-21-18-16-14-12-10-8-6-2)40-89-64-57(85)56(84)59(48(38-73)91-64)93-65-58(86)62(60(49(39-74)92-65)94-63-52(69-42(4)76)55(83)54(82)47(37-72)90-63)96-67(66(87)88)35-45(78)51(68-41(3)75)61(95-67)53(81)46(79)36-71/h31,33,43-49,51-65,71-74,77-79,81-86H,5-30,32,34-40H2,1-4H3,(H,68,75)(H,69,76)(H,70,80)(H,87,88)/b33-31+/t43-,44+,45-,46+,47+,48+,49+,51+,52+,53+,54-,55+,56+,57+,58+,59+,60-,61?,62+,63-,64+,65-,67-/m0/s1
InChI KeyGIVLTTJNORAZON-RLADFVFXSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as galnacb1-4galb1-4glc- (ganglio series). These are neutral glycosphingolipids in which the root sequence is GalNAcb1-4Galb1-4Glc.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassGlycosphingolipids
Direct ParentGalNAcb1-4Galb1-4Glc- (Ganglio series)
Alternative Parents
Substituents
  • Galnacb1-4galb1-4glcb-cer_backbone
  • Neuaca2-3galb1-4glcb-cer_backbone
  • Glycosyl-n-acylsphingosine
  • Oligosaccharide
  • N-acylneuraminic acid or derivatives
  • N-acylneuraminic acid
  • Neuraminic acid
  • Fatty acyl glycoside
  • N-acyl-alpha-hexosamine
  • C-glucuronide
  • Alkyl glycoside
  • C-glycosyl compound
  • Glycosyl compound
  • O-glycosyl compound
  • Ketal
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Oxane
  • Pyran
  • Acetamide
  • Secondary alcohol
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organic oxide
  • Primary alcohol
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organopnictogen compound
  • Alcohol
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Endosome
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityInsolubleNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.89ALOGPS
logP3.75ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)2.8ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count26ChemAxon
Hydrogen Donor Count17ChemAxon
Polar Surface Area461.43 ŲChemAxon
Rotatable Bond Count49ChemAxon
Refractivity343.59 m³·mol⁻¹ChemAxon
Polarizability154.68 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fsj-2139051000-0b6d143c2f34dac2a7ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kpi-2295036200-5cdd7e0da796173689b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kai-1191120000-8c4b09e7a63b541e2d59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-6098000000-a24540f07a263a2b0effView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3096002100-f00d98c23e796592011fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ec-3193020200-290065f8ef80affc4d0dView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Endosome
  • Membrane
Biospecimen Locations
  • Brain
  • Neuron
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0004939
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023527
KNApSAcK IDNot Available
Chemspider ID16744925
KEGG Compound IDC04884
BioCyc IDCPD-1100
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7192
PubChem Compound20057335
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available