Showing metabocard for Ganglioside GM1 (d18:0/20:0) (BMDB0011881)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:26:55 UTC
Update Date2020-04-22 15:47:06 UTC
BMDB IDBMDB0011881
Secondary Accession Numbers
  • BMDB11881
Metabolite Identification
Common NameGanglioside GM1 (d18:0/20:0)
DescriptionGanglioside GM1 (d18:0/20:0) belongs to the class of organic compounds known as glycosphingolipids. These are sphingolipids containing a saccharide moiety glycosidically attached to the sphingoid base. Although saccharide moieties are mostly O-glycosidically linked to the ceramide moiety, other sphingolipids with glycosidic bonds of other types (e.g. S-,C-, or N-type) has been reported. Ganglioside GM1 (d18:0/20:0) is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S,4S,5R)-2-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R)-3-hydroxy-2-[(1-hydroxyicosylidene)amino]octadecyl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-3-hydroxy-5-{[(2S,3R,4R,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3-(2-oxopropyl)-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-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylateHMDB
Chemical FormulaC76H138N2O31
Average Molecular Weight1575.9037
Monoisotopic Molecular Weight1574.928355708
IUPAC Name(2S,4S,5R)-2-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R)-3-hydroxy-2-icosanamidooctadecyl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-3-hydroxy-5-{[(2S,3R,4R,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3-(2-oxopropyl)-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}-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)-3-hydroxy-2-icosanamidooctadecyl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-3-hydroxy-5-{[(2S,3R,4R,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3-(2-oxopropyl)-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}-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]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)[C@H]3CC(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)CCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C76H138N2O31/c1-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-56(89)78-48(49(86)35-33-31-29-27-25-23-18-16-14-12-10-8-6-2)44-100-72-64(96)62(94)67(54(42-82)103-72)106-74-65(97)70(109-76(75(98)99)38-50(87)57(77-46(4)85)69(108-76)58(90)51(88)39-79)68(55(43-83)104-74)107-71-47(37-45(3)84)66(60(92)53(41-81)101-71)105-73-63(95)61(93)59(91)52(40-80)102-73/h47-55,57-74,79-83,86-88,90-97H,5-44H2,1-4H3,(H,77,85)(H,78,89)(H,98,99)/t47-,48+,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+,76+/m1/s1
InChI KeyVEJUBWNJMJQFNN-KFTCUWJOSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glycosphingolipids. These are sphingolipids containing a saccharide moiety glycosidically attached to the sphingoid base. Although saccharide moieties are mostly O-glycosidically linked to the ceramide moiety, other sphingolipids with glycosidic bonds of other types (e.g. S-,C-, or N-type) has been reported.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassGlycosphingolipids
Direct ParentGlycosphingolipids
Alternative Parents
Substituents
  • Glycosphingolipid
  • Oligosaccharide
  • N-acylneuraminic acid
  • N-acylneuraminic acid or derivatives
  • Neuraminic acid
  • Fatty acyl glycoside
  • C-glucuronide
  • Alkyl glycoside
  • Glycosyl compound
  • C-glycosyl compound
  • O-glycosyl compound
  • Ketal
  • Fatty amide
  • Fatty acyl
  • Pyran
  • N-acyl-amine
  • Oxane
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Ketone
  • 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
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
logP2.55ALOGPS
logP4.09ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)2.82ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count31ChemAxon
Hydrogen Donor Count19ChemAxon
Polar Surface Area528.55 ŲChemAxon
Rotatable Bond Count56ChemAxon
Refractivity386.07 m³·mol⁻¹ChemAxon
Polarizability175.4 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, Positivesplash10-06vj-1002190000-0ba4a539839c08011982View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fi0-2295085130-31276a4a563af2a3e7c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01pk-9551352000-67104b62c92a8e87c51aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-6050290000-854c713c6d01d1ab17efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05gi-4070290300-fddb44ec2829d95e00e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007o-8046290201-9a927b32b33747147a61View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Endosome
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0011881
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028550
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481157
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available