Showing metabocard for Ganglioside GD2 (d18:1/18:1(11Z)) (BMDB0011853)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:26:17 UTC
Update Date2020-04-22 15:46:56 UTC
BMDB IDBMDB0011853
Secondary Accession Numbers
  • BMDB11853
Metabolite Identification
Common NameGanglioside GD2 (d18:1/18:1(11Z))
DescriptionGanglioside GD2 (d18:1/18:1(11Z)) 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. Ganglioside GD2 (d18:1/18:1(11Z)) is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S,4S,5R)-2-{[(1S,2R)-1-[(3R,4S,6S)-6-carboxy-6-{[(2R,3S,4R,5R,6S)-3-{[(2S,3R,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(2-oxopropyl)oxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R)-3-hydroxy-2-{[(11Z)-1-hydroxyoctadec-11-en-1-ylidene]amino}octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]-1,3-dihydroxypropan-2-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylateHMDB
Chemical FormulaC79H137N3O34
Average Molecular Weight1672.9328
Monoisotopic Molecular Weight1671.908348547
IUPAC Name(2S,4S,5R)-6-[(1S,2R)-2-{[(2S,4S,5R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-1,3-dihydroxypropyl]-2-{[(2R,3S,4R,5R,6S)-3-{[(2S,3R,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(2-oxopropyl)oxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R,4E)-3-hydroxy-2-[(11Z)-octadec-11-enamido]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-4-hydroxyoxane-2-carboxylic acid
Traditional Name(2S,4S,5R)-6-[(1S,2R)-2-{[(2S,4S,5R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-1,3-dihydroxypropyl]-2-{[(2R,3S,4R,5R,6S)-3-{[(2S,3R,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(2-oxopropyl)oxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R,4E)-3-hydroxy-2-[(11Z)-octadec-11-enamido]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-4-hydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCC\C=C\[C@@H](O)[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]3CC(C)=O)[C@H](O[C@@]3(C[C@H](O)[C@@H](NC(C)=O)C(O3)[C@H](O)[C@@H](CO)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(O)=O)[C@H]2O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCC\C=C/CCCCCC
InChI Identifier
InChI=1S/C79H137N3O34/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-58(95)82-49(50(91)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2)44-107-74-66(101)65(100)68(56(42-86)109-74)111-75-67(102)72(69(57(43-87)110-75)112-73-48(36-45(3)88)61(96)63(98)54(40-84)108-73)116-79(77(105)106)38-52(93)60(81-47(5)90)71(115-79)64(99)55(41-85)113-78(76(103)104)37-51(92)59(80-46(4)89)70(114-78)62(97)53(94)39-83/h16,18,32,34,48-57,59-75,83-87,91-94,96-102H,6-15,17,19-31,33,35-44H2,1-5H3,(H,80,89)(H,81,90)(H,82,95)(H,103,104)(H,105,106)/b18-16-,34-32+/t48-,49+,50-,51+,52+,53-,54-,55-,56-,57-,59-,60-,61-,62-,63+,64-,65-,66-,67-,68-,69+,70?,71?,72-,73+,74-,75+,78-,79+/m1/s1
InChI KeyRGJYAXNXZYDRCC-BKCQNFCASA-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
  • Fatty acyl glycoside
  • C-glucuronide
  • Alkyl glycoside
  • C-glycosyl compound
  • O-glycosyl compound
  • Glycosyl compound
  • Ketal
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Fatty amide
  • Pyran
  • Oxane
  • N-acyl-amine
  • Acetamide
  • Ketone
  • Secondary alcohol
  • Carboxamide group
  • Secondary carboxylic acid amide
  • 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
logP1.69ALOGPS
logP2ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)2.46ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count34ChemAxon
Hydrogen Donor Count21ChemAxon
Polar Surface Area594.95 ŲChemAxon
Rotatable Bond Count56ChemAxon
Refractivity406.81 m³·mol⁻¹ChemAxon
Polarizability181.44 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, Positivesplash10-0uka-3014059001-95be32eec507d4c6a328View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0090023001-2ae1004f1461d3baf678View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-1890154400-9ebe5fcb0e0f27aa2798View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-4090125000-661c196f147f1fe73efcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1091002000-497fd4a937e4ec764319View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0lk9-9275041100-e807011bcdde3153ce0dView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Endosome
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0011853
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028522
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481129
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available