Showing metabocard for Ganglioside GM2 (d18:1/20:0) (BMDB0004940)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:13:23 UTC
Update Date2020-05-11 20:32:11 UTC
BMDB IDBMDB0004940
Secondary Accession Numbers
  • BMDB04940
Metabolite Identification
Common NameGanglioside GM2 (d18:1/20:0)
DescriptionGanglioside GM2 (d18:1/20:0), 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 (d18:1/20:0) 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-hydroxyicosylidene)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
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 FormulaC69H125N3O26
Average Molecular Weight1412.7353
Monoisotopic Molecular Weight1411.855131187
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-icosanamidooctadec-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-icosanamidooctadec-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
CCCCCCCCCCCCCCCCCCCC(=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/C69H125N3O26/c1-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-52(82)72-45(46(79)35-33-31-29-27-25-23-18-16-14-12-10-8-6-2)42-91-66-59(87)58(86)61(50(40-75)93-66)95-67-60(88)64(62(51(41-76)94-67)96-65-54(71-44(4)78)57(85)56(84)49(39-74)92-65)98-69(68(89)90)37-47(80)53(70-43(3)77)63(97-69)55(83)48(81)38-73/h33,35,45-51,53-67,73-76,79-81,83-88H,5-32,34,36-42H2,1-4H3,(H,70,77)(H,71,78)(H,72,82)(H,89,90)/b35-33+/t45-,46+,47-,48+,49+,50+,51+,53+,54+,55+,56-,57+,58+,59+,60+,61+,62-,63?,64+,65-,66+,67-,69-/m0/s1
InChI KeyOBOZLYBYENZWAE-PWUMRELJSA-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
logP3.24ALOGPS
logP4.64ChemAxon
logS-4.5ALOGPS
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 Count51ChemAxon
Refractivity352.79 m³·mol⁻¹ChemAxon
Polarizability158.92 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, Positivesplash10-0nou-2368792100-f88c9dd3af8025041093View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fi3-1293236200-ef51d576a3faca159889View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0nnj-1191320000-b1f9486c2cc1bbc366b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-8096800000-fce0c93a063fb42b5ba7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0nn9-3296302100-29e8ec72a7bead0d83d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-3193020200-6d4680770b24a52e69ecView 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 IDHMDB0004940
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023528
KNApSAcK IDNot Available
Chemspider ID16744926
KEGG Compound IDC01808
BioCyc IDCPD-1100
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7193
PubChem Compound20057336
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available