Showing metabocard for Monosialoganglioside GM3 (BMDB0062123)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-06-25 21:52:24 UTC
Update Date2020-06-04 19:19:17 UTC
MCDB ID BMDB0062123
Secondary Accession Numbers
  • BMDB62123
Metabolite Identification
Common NameMonosialoganglioside GM3
DescriptionMonosialoganglioside GM3, also known as GM3 or sialyl lactosylceramide, 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. Monosialoganglioside GM3 is possibly soluble (in water) and a moderately basic compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
alpha-Neu5ac-(2->3)-beta-D-gal-(1->4)-beta-D-GLC-(11)-N-(15Z)-tetracos-15-enoylsphingosineChEBI
alpha-Neu5ac-(2->3)-beta-D-gal-(1->4)-beta-D-GLC-(11)-N-cis-tetracos-15-enoylsphingosineChEBI
g(m3) GangliosideChEBI
GM3ChEBI
MonosialodihexosylgangliosideChEBI
Monosialoganglioside GM3ChEBI
NANA-gal-GLC-ceramideChEBI
a-Neu5ac-(2->3)-b-D-gal-(1->4)-b-D-GLC-(11)-N-(15Z)-tetracos-15-enoylsphingosineGenerator
Α-neu5ac-(2->3)-β-D-gal-(1->4)-β-D-GLC-(11)-N-(15Z)-tetracos-15-enoylsphingosineGenerator
a-Neu5ac-(2->3)-b-D-gal-(1->4)-b-D-GLC-(11)-N-cis-tetracos-15-enoylsphingosineGenerator
Α-neu5ac-(2->3)-β-D-gal-(1->4)-β-D-GLC-(11)-N-cis-tetracos-15-enoylsphingosineGenerator
SialyllactosylceramideMeSH
HematosideMeSH
II3neuaclaccerMeSH
Sialyl lactosylceramideMeSH
GM3, GangliosideMeSH
Lactosylceramide, sialylMeSH
Ganglioside GM3MeSH
Chemical FormulaC65H118N2O21
Average Molecular Weight1263.652
Monoisotopic Molecular Weight1262.822708828
IUPAC Name(2S,4S,5R,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R,4E)-3-hydroxy-2-{[(15Z)-1-hydroxytetracos-15-en-1-ylidene]amino}octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-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-carboxylic acid
Traditional Name(2S,4S,5R,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R,4E)-3-hydroxy-2-{[(15Z)-1-hydroxytetracos-15-en-1-ylidene]amino}octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-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-carboxylic acid
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCCCCC)=C(/[H])CCCCCCCCCCCCCC(O)=N[C@@]([H])(CO[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O[C@]2([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O[C@@]3(C[C@]([H])(O)[C@@]([H])(N=C(C)O)[C@@]([H])(O3)[C@]([H])(O)[C@]([H])(O)CO)C(O)=O)[C@@]2([H])O)[C@]([H])(O)[C@@]1([H])O)[C@]([H])(O)C(\[H])=C(/[H])CCCCCCCCCCCCC
InChI Identifier
InChI=1S/C65H118N2O21/c1-4-6-8-10-12-14-16-18-19-20-21-22-23-24-25-27-29-31-33-35-37-39-52(75)67-46(47(72)38-36-34-32-30-28-26-17-15-13-11-9-7-5-2)44-83-62-57(79)56(78)59(51(43-70)85-62)86-63-58(80)61(55(77)50(42-69)84-63)88-65(64(81)82)40-48(73)53(66-45(3)71)60(87-65)54(76)49(74)41-68/h18-19,36,38,46-51,53-63,68-70,72-74,76-80H,4-17,20-35,37,39-44H2,1-3H3,(H,66,71)(H,67,75)(H,81,82)/b19-18-,38-36+/t46-,47+,48-,49+,50+,51+,53+,54+,55-,56+,57+,58+,59+,60+,61-,62+,63-,65-/m0/s1
InChI KeyPFJKOHUKELZMLE-VEUXDRLPSA-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 or derivatives
  • N-acylneuraminic acid
  • Neuraminic acid
  • Fatty acyl glycoside
  • C-glucuronide
  • Alkyl glycoside
  • C-glycosyl compound
  • Glycosyl compound
  • O-glycosyl compound
  • Ketal
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Oxane
  • Pyran
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organopnictogen compound
  • Alcohol
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
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
logP5.23ALOGPS
logP9.16ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)3.06ChemAxon
pKa (Strongest Basic)2.51ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count23ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area380.39 ŲChemAxon
Rotatable Bond Count50ChemAxon
Refractivity329.84 m³·mol⁻¹ChemAxon
Polarizability146.68 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-1290505002-488818f9f235f810e4632021-10-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0h93-1261903410-a3996cfcb5f93cd551902021-10-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08gi-3590512000-7cdad05b00354da649682021-10-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-08fr-4190000000-026404c7fd120463b49f2021-10-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a59-2190200100-6c944d8d11e8c637a80c2021-10-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9562035162-3918a8fc35c4e0c8c7d92021-10-22View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
Detected and Quantified uM details
HMDB IDHMDB0304771
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB098136
KNApSAcK IDNot Available
Chemspider ID34448956
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound86583360
PDB IDNot Available
ChEBI ID84118
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. [PubMed:1779072 ]