Showing metabocard for Disialoganglioside Ib (BMDB0062120)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-06-25 21:52:10 UTC
Update Date2020-06-04 18:59:40 UTC
MCDB ID BMDB0062120
Secondary Accession Numbers
  • BMDB62120
Metabolite Identification
Common NameDisialoganglioside Ib
DescriptionDisialoganglioside ib 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. Disialoganglioside ib is possibly soluble (in water) and 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
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Not Available
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.001 - 1 uM details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound92132037
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]