Showing metabocard for Ganglioside GD1a (d18:0/18:0) (BMDB0011780)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:24:32 UTC
Update Date2020-04-22 15:46:28 UTC
BMDB IDBMDB0011780
Secondary Accession Numbers
  • BMDB11780
Metabolite Identification
Common NameGanglioside GD1a (d18:0/18:0)
DescriptionGanglioside GD1a (d18:0/18:0) 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. Based on a literature review a significant number of articles have been published on Ganglioside GD1a (d18:0/18:0).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S,4S,5R)-2-{[(2R,3R,4S,5S,6R)-2-{[(2S,3R,4R,5R,6R)-2-{[(2R,3S,4R,5R,6S)-4-{[(2S,4S,5R)-2-carboxy-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R)-3-hydroxy-2-[(1-hydroxyoctadecylidene)amino]octadecyl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-3-(2-oxopropyl)oxan-4-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylateGenerator, HMDB
Chemical FormulaC85H151N3O39
Average Molecular Weight1839.1051
Monoisotopic Molecular Weight1837.992472105
IUPAC Name(2S,4S,5R)-2-{[(2R,3R,4S,5S,6R)-2-{[(2S,3R,4R,5R,6R)-2-{[(2R,3S,4R,5R,6S)-4-{[(2S,4S,5R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R)-3-hydroxy-2-octadecanamidooctadecyl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-3-(2-oxopropyl)oxan-4-yl]oxy}-3,5-dihydroxy-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-{[(2R,3R,4S,5S,6R)-2-{[(2S,3R,4R,5R,6R)-2-{[(2R,3S,4R,5R,6S)-4-{[(2S,4S,5R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R)-3-hydroxy-2-octadecanamidooctadecyl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-3-(2-oxopropyl)oxan-4-yl]oxy}-3,5-dihydroxy-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
CCCCCCCCCCCCCCCCCC(=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@@]5(C[C@H](O)[C@@H](NC(C)=O)C(O5)[C@H](O)[C@H](O)CO)C(O)=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/C85H151N3O39/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-60(103)88-50(51(98)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2)45-116-79-68(109)67(108)72(58(43-93)119-79)122-81-70(111)77(127-85(83(114)115)38-53(100)62(87-48(5)97)75(125-85)64(105)55(102)40-90)73(59(44-94)120-81)123-78-49(36-46(3)95)71(65(106)56(41-91)117-78)121-80-69(110)76(66(107)57(42-92)118-80)126-84(82(112)113)37-52(99)61(86-47(4)96)74(124-84)63(104)54(101)39-89/h49-59,61-81,89-94,98-102,104-111H,6-45H2,1-5H3,(H,86,96)(H,87,97)(H,88,103)(H,112,113)(H,114,115)/t49-,50+,51-,52+,53+,54-,55-,56-,57-,58-,59-,61-,62-,63-,64-,65+,66+,67-,68-,69-,70-,71-,72-,73+,74?,75?,76+,77-,78+,79-,80+,81+,84+,85+/m1/s1
InChI KeyWPIVTGKDYBIKRA-XCSDPKIZSA-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
  • O-glycosyl compound
  • C-glycosyl compound
  • Glycosyl compound
  • Ketal
  • Fatty acyl
  • Fatty amide
  • Dicarboxylic acid or derivatives
  • Pyran
  • N-acyl-amine
  • Oxane
  • Acetamide
  • Ketone
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxygen compound
  • Primary alcohol
  • Organopnictogen compound
  • 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
logP1.28ALOGPS
logP0.8ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)2.54ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count39ChemAxon
Hydrogen Donor Count24ChemAxon
Polar Surface Area674.1 ŲChemAxon
Rotatable Bond Count61ChemAxon
Refractivity437.14 m³·mol⁻¹ChemAxon
Polarizability198.84 ųChemAxon
Number of Rings6ChemAxon
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, Negativesplash10-000i-7090001260-940692fccce81b7a4c08View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00m0-4090101740-5102d1d3b066be13b0abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f8l-7261372950-e0f13e6320d30ea39b85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fy9-1104061190-b2a5caeaf278f24bddd1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05g0-3682049580-fdaabc608e9d6623820fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05a9-1180759440-7dcc02bcb4e631cf3808View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Endosome
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0011780
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028449
KNApSAcK IDNot Available
Chemspider ID35032095
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481056
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available