Showing metabocard for Ganglioside GD2 (d18:1/24:1(15Z)) (BMDB0004929)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:13:09 UTC
Update Date2020-05-11 20:32:03 UTC
BMDB IDBMDB0004929
Secondary Accession Numbers
  • BMDB04929
Metabolite Identification
Common NameGanglioside GD2 (d18:1/24:1(15Z))
DescriptionGanglioside GD2 (d18:1/24:1(15Z)), also known as GD2 ganglioside, belongs to the class of organic compounds known as galnacb1-4galb1-4glc- (ganglio series). These are neutral glycosphingolipids in which the root sequence is GalNAcb1-4Galb1-4Glc. Ganglioside GD2 (d18:1/24:1(15Z)) 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-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R)-3-hydroxy-2-{[(15Z)-1-hydroxytetracos-15-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
GalNAc-beta1->4(neuac-alpha2->8neuac2->3)gal-beta1->4GLC-beta1->1'cerHMDB
GalNAc-beta1->4(neuac-alpha2->8neuac2->3)gal-beta1->4GLC-beta1->1'cer(D18:1/24:1HMDB
GalNAc-beta1->4(neuac-alpha2->8neuac2->3)laccerHMDB
GD2 GangliosideHMDB
Chemical FormulaC84H148N4O34
Average Molecular Weight1758.0803
Monoisotopic Molecular Weight1756.997497904
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-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R,4E)-3-hydroxy-2-[(15Z)-tetracos-15-enamido]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-{[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxy-6-(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-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R,4E)-3-hydroxy-2-[(15Z)-tetracos-15-enamido]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-{[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxy-6-(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]3NC(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)CCCCCCCCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C84H148N4O34/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-26-27-29-31-33-35-37-39-41-62(101)88-53(54(97)40-38-36-34-32-30-28-19-17-15-13-11-9-7-2)49-113-79-71(107)70(106)73(60(47-92)115-79)117-80-72(108)77(74(61(48-93)116-80)118-78-65(87-52(5)96)69(105)67(103)58(45-90)114-78)122-84(82(111)112)43-56(99)64(86-51(4)95)76(121-84)68(104)59(46-91)119-83(81(109)110)42-55(98)63(85-50(3)94)75(120-83)66(102)57(100)44-89/h20-21,38,40,53-61,63-80,89-93,97-100,102-108H,6-19,22-37,39,41-49H2,1-5H3,(H,85,94)(H,86,95)(H,87,96)(H,88,101)(H,109,110)(H,111,112)/b21-20-,40-38+/t53-,54+,55-,56-,57+,58+,59+,60+,61+,63+,64+,65+,66+,67-,68+,69+,70+,71+,72+,73+,74-,75?,76?,77+,78-,79+,80-,83+,84-/m0/s1
InChI KeyNWBZYNQCPKLRGN-VYQGQGJDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as galnacb1-4galb1-4glc- (ganglio series). These are neutral glycosphingolipids in which the root sequence is GalNAcb1-4Galb1-4Glc.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassGlycosphingolipids
Direct ParentGalNAcb1-4Galb1-4Glc- (Ganglio series)
Alternative Parents
Substituents
  • Galnacb1-4galb1-4glcb-cer_backbone
  • Neuaca2-3galb1-4glcb-cer_backbone
  • 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
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Oxane
  • Pyran
  • Acetamide
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Organoheterocyclic compound
  • Polyol
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Organonitrogen compound
  • Organic oxide
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary alcohol
  • Organopnictogen 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 SolubilityInsolubleNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.47ALOGPS
logP3.65ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)2.45ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count34ChemAxon
Hydrogen Donor Count22ChemAxon
Polar Surface Area606.98 ŲChemAxon
Rotatable Bond Count61ChemAxon
Refractivity432.58 m³·mol⁻¹ChemAxon
Polarizability193.37 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, Negativesplash10-0a5i-5090110700-dc6a51d67f8db6d5fe3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kai-1090101200-8fa90becb3991faf5743View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-6394323110-fba42e77d00ba5c0d0b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ka9-1132306900-f936b129fca7f068a20fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0q3d-1190017703-e01c163b8f2fb7860686View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kbf-0753009401-8ab551f15bf75024a97fView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Endosome
  • Membrane
Biospecimen Locations
  • Brain
  • Neuron
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0004929
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023519
KNApSAcK IDNot Available
Chemspider ID17216308
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound22833641
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available