Showing metabocard for N-Glycoloylganglioside GM1 (BMDB0000809)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:36:54 UTC
Update Date2020-04-22 15:05:25 UTC
BMDB IDBMDB0000809
Secondary Accession Numbers
  • BMDB00809
Metabolite Identification
Common NameN-Glycoloylganglioside GM1
DescriptionN-Glycoloylganglioside GM1, also known as GM1 ganglioside, 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. Based on a literature review a significant number of articles have been published on N-Glycoloylganglioside GM1.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
GM1 GangliosideHMDB
(2S,4S,5R)-2-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2R,3S,4E)-3-hydroxy-2-[(1-hydroxyicosylidene)amino]icos-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-methyloxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylateHMDB
Chemical FormulaC77H139N3O30
Average Molecular Weight1586.9297
Monoisotopic Molecular Weight1585.944340123
IUPAC Name(2S,4S,5R)-2-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2R,3S,4E)-3-hydroxy-2-icosanamidoicos-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-{[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-6-methyloxan-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-{[(2R,3S,4E)-3-hydroxy-2-icosanamidoicos-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-{[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-6-methyloxan-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](C)[C@H](O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O[C@@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)[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\CCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C77H139N3O30/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-37-39-56(90)80-49(50(87)38-36-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2)45-101-73-65(97)63(95)68(55(44-84)105-73)107-75-66(98)71(110-77(76(99)100)40-51(88)57(78-47(4)85)70(109-77)59(91)52(89)41-81)67(46(3)102-75)106-72-58(79-48(5)86)69(61(93)54(43-83)103-72)108-74-64(96)62(94)60(92)53(42-82)104-74/h36,38,46,49-55,57-75,81-84,87-89,91-98H,6-35,37,39-45H2,1-5H3,(H,78,85)(H,79,86)(H,80,90)(H,99,100)/b38-36+/t46-,49-,50+,51+,52-,53-,54-,55-,57-,58-,59-,60+,61+,62+,63-,64-,65-,66-,67+,68-,69-,70?,71-,72+,73-,74+,75+,77+/m1/s1
InChI KeyWHRNXVBQVRYAKH-MBNVEIDWSA-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
  • 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 carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Alcohol
  • Organopnictogen compound
  • 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 SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.18ALOGPS
logP4.81ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)2.83ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count30ChemAxon
Hydrogen Donor Count19ChemAxon
Polar Surface Area520.35 ŲChemAxon
Rotatable Bond Count55ChemAxon
Refractivity392.86 m³·mol⁻¹ChemAxon
Polarizability177.28 ųChemAxon
Number of Rings5ChemAxon
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, Positivesplash10-0fri-0012192110-8a7b825e58e1fdc5c105View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gi9-1373295580-ea8dd659634ffb5f063eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07br-2319370010-54276c9fd7c21e56b4f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-5040190100-e15ecb46976490aeabcbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053r-4040190620-1b160ccdde7a8ecdf9b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05r3-7231293020-2f0fa3d45b3734ff9a08View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Endosome
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000809
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022257
KNApSAcK IDNot Available
Chemspider ID17216009
KEGG Compound IDC01808
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound22833548
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceHirabayashi, Yoshio; Nakao, Toru; Matsumoto, Makoto; Obata, Kunihiko; Ando, Susumu. Improved method for large-scale purification of brain gangliosides by Q-Sepharose column chromatography. Immunochemical detection of C-series polysialogangliosides in adult bovine brains. Journal of Chromatography (1988), 445(2), 377-84.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available