Showing metabocard for Monosialoganglioside GM1 (BMDB0062121)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-06-25 21:52:14 UTC
Update Date2020-06-04 19:29:25 UTC
MCDB ID BMDB0062121
Secondary Accession Numbers
  • BMDB62121
Metabolite Identification
Common NameMonosialoganglioside GM1
DescriptionMonosialoganglioside GM1, also known as g(m1) 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. Monosialoganglioside GM1 is possibly soluble (in water) and a moderately basic compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S,4S,5R,6S)-2-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(4E)-3-hydroxy-2-[(1-hydroxyoctadecylidene)amino]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-3-hydroxy-5-{[(2S,3R,4R,5R,6R)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylateGenerator
Ceramide, monosialosyl tetraglycosylMeSH
g(m1) GangliosideMeSH
GM1a MonosialogangliosideMeSH
Monosialoganglioside, GM1aMeSH
Monosialosyl tetraglycosyl ceramideMeSH
Tetraglycosyl ceramide, monosialosylMeSH
Chemical FormulaC73H131N3O31
Average Molecular Weight1546.841
Monoisotopic Molecular Weight1545.87665445
IUPAC Name(2S,4S,5R,6S)-2-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(4E)-3-hydroxy-2-[(1-hydroxyoctadecylidene)amino]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-3-hydroxy-5-{[(2S,3R,4R,5R,6R)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
Traditional Name(2S,4S,5R,6S)-2-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(4E)-3-hydroxy-2-[(1-hydroxyoctadecylidene)amino]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-3-hydroxy-5-{[(2S,3R,4R,5R,6R)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
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@]4([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]4([H])O)[C@@]3([H])N=C(C)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)N=C(O)CCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C73H131N3O31/c1-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-52(87)76-44(45(84)33-31-29-27-25-23-21-18-16-14-12-10-8-6-2)41-98-69-61(94)59(92)63(50(39-80)101-69)103-71-62(95)67(107-73(72(96)97)35-46(85)53(74-42(3)82)66(106-73)55(88)47(86)36-77)64(51(40-81)102-71)104-68-54(75-43(4)83)65(57(90)49(38-79)99-68)105-70-60(93)58(91)56(89)48(37-78)100-70/h31,33,44-51,53-71,77-81,84-86,88-95H,5-30,32,34-41H2,1-4H3,(H,74,82)(H,75,83)(H,76,87)(H,96,97)/b33-31+/t44?,45?,46-,47?,48+,49+,50+,51+,53+,54+,55?,56-,57-,58-,59+,60+,61+,62+,63+,64-,65+,66-,67+,68-,69+,70-,71-,73-/m0/s1
InChI KeyQPJBWNIQKHGLAU-BVLUPYCXSA-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
  • N-acylneuraminic acid or derivatives
  • Neuraminic acid
  • N-acyl-alpha-hexosamine
  • Fatty acyl glycoside
  • C-glucuronide
  • Alkyl glycoside
  • C-glycosyl compound
  • Glycosyl compound
  • O-glycosyl compound
  • Ketal
  • Fatty acyl
  • Pyran
  • N-acyl-amine
  • Oxane
  • Fatty amide
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Primary alcohol
  • Organopnictogen compound
  • Carbonyl group
  • 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
logP2.67ALOGPS
logP3.84ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)2.98ChemAxon
pKa (Strongest Basic)2.37ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count34ChemAxon
Hydrogen Donor Count20ChemAxon
Polar Surface Area551.05 ŲChemAxon
Rotatable Bond Count52ChemAxon
Refractivity377.57 m³·mol⁻¹ChemAxon
Polarizability170.44 ųChemAxon
Number of Rings5ChemAxon
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, Positivesplash10-00mk-1043190010-81e5733b5d10d3ea13122021-10-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00n1-2135391270-b478f9702288a0a60e4c2021-10-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01q0-1931430000-e6969f7a25e2892329ad2021-10-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-5050190000-82a079a2747f40cc6a3f2021-10-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001l-5090680310-698d005898df2d2e5a942021-10-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kbo-9020460101-1f862c3a93813ed417432021-10-22View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.5 uM details
HMDB IDHMDB0304760
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB097529
KNApSAcK IDNot Available
Chemspider ID4593688
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5497107
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 ]