Showing metabocard for Monosialoganglioside GM2 (BMDB0062122)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-06-25 21:52:19 UTC
Update Date2020-06-04 19:19:13 UTC
MCDB ID BMDB0062122
Secondary Accession Numbers
  • BMDB62122
Metabolite Identification
Common NameMonosialoganglioside GM2
DescriptionMonosialoganglioside GM2, also known as GM2, ganglioside or ganglioside GM2, 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. Monosialoganglioside GM2 is possibly soluble (in water) and a moderately basic compound (based on its pKa).
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
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f7k-1359021000-766a422017398cb952ed2021-10-21View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007a-2198017100-23398b2d5a3a30b3dea32021-10-21View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udj-1592210000-1cbe9dc85117408fd9ac2021-10-21View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-5019000000-623d76b7e04365b07fa22021-10-21View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pvj-3039002100-06584fda1a8fdbf589242021-10-21View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0096-6396023300-7f485a84c7d05ef41c0c2021-10-21View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.158 - 0.237 uM details
HMDB IDHMDB0304654
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID26286730
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound71308211
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]