Showing metabocard for Disialoganglioside Ib (LMDB00956)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-08-04 21:13:15 UTC
Update Date2016-08-04 22:06:15 UTC
LmdbLMDB00956
Secondary Accession NumbersNone
Metabolite Identification
Common NameDisialoganglioside Ib
DescriptionGD1b-Ganglioside 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. GD1b-Ganglioside is a moderately basic compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC84H148N4O40
Average Molecular Weight1854.096
Monoisotopic Molecular Weight1852.966985582
IUPAC Name(2S,4S,5R,6R)-2-{[(1S,2R)-1-[(2R,3R,4S,6S)-6-carboxy-6-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-({3-hydroxy-2-[(1-hydroxyoctadecylidene)amino]octadec-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-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]-1,3-dihydroxypropan-2-yl]oxy}-5-[(1,2-dihydroxyethylidene)amino]-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional Name(2S,4S,5R,6R)-2-{[(1S,2R)-1-[(2R,3R,4S,6S)-6-carboxy-6-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-({3-hydroxy-2-[(1-hydroxyoctadecylidene)amino]octadec-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-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]-1,3-dihydroxypropan-2-yl]oxy}-5-[(1,2-dihydroxyethylidene)amino]-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
[H]C(CCCCCCCCCCCCC)=C([H])C([H])(O)C([H])(CO[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O[C@]2([H])O[C@]([H])(CO)[C@]([H])(O[C@]3([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O[C@]4([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]4([H])O)[C@@]3([H])N=C(C)O)[C@]([H])(O[C@@]3(C[C@]([H])(O)[C@@]([H])(N=C(C)O)[C@@]([H])(O3)[C@]([H])(O)[C@@]([H])(CO)O[C@@]3(C[C@]([H])(O)[C@@]([H])(N=C(O)CO)[C@@]([H])(O3)[C@]([H])(O)[C@]([H])(O)CO)C(O)=O)C(O)=O)[C@@]2([H])O)[C@]([H])(O)[C@@]1([H])O)N=C(O)CCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C84H148N4O40/c1-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-57(102)87-47(48(98)33-31-29-27-25-23-21-18-16-14-12-10-8-6-2)44-117-78-69(111)67(109)71(55(41-93)120-78)122-80-70(112)76(72(56(42-94)121-80)123-77-61(86-46(4)97)73(64(106)53(39-91)118-77)124-79-68(110)66(108)63(105)52(38-90)119-79)128-84(82(115)116)36-49(99)59(85-45(3)96)75(127-84)65(107)54(40-92)125-83(81(113)114)35-50(100)60(88-58(103)43-95)74(126-83)62(104)51(101)37-89/h31,33,47-56,59-80,89-95,98-101,104-112H,5-30,32,34-44H2,1-4H3,(H,85,96)(H,86,97)(H,87,102)(H,88,103)(H,113,114)(H,115,116)/b33-31+/t47?,48?,49-,50-,51+,52+,53+,54+,55+,56+,59+,60+,61+,62+,63-,64-,65+,66-,67+,68+,69+,70+,71+,72-,73+,74+,75+,76+,77-,78+,79-,80-,83+,84-/m0/s1
InChI KeyVPUOVUBYFYUBRY-INNWTUFDSA-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
  • N-acyl-alpha-hexosamine
  • C-glucuronide
  • Alkyl glycoside
  • C-glycosyl compound
  • Glycosyl compound
  • O-glycosyl compound
  • Ketal
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • N-acyl-amine
  • Oxane
  • Pyran
  • Fatty amide
  • Acetamide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Secondary alcohol
  • 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
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.56ALOGPS
logP1.17ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)2.64ChemAxon
pKa (Strongest Basic)2.16ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count44ChemAxon
Hydrogen Donor Count26ChemAxon
Polar Surface Area720.32 ŲChemAxon
Rotatable Bond Count60ChemAxon
Refractivity440.06 m³·mol⁻¹ChemAxon
Polarizability198.29 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Milk
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
MilkDetected and Quantified0.378 uMNot AvailableBovine details
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID92132037
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available