Showing metabocard for Ganglioside GQ1c (d18:0/22:1(13Z)) (BMDB0011940)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:28:14 UTC
Update Date2020-04-22 15:47:28 UTC
BMDB IDBMDB0011940
Secondary Accession Numbers
  • BMDB11940
Metabolite Identification
Common NameGanglioside GQ1c (d18:0/22:1(13Z))
DescriptionGanglioside GQ1c (d18:0/22:1(13Z)) belongs to the class of organic compounds known as glycosphingolipids. These are sphingolipids containing a saccharide moiety glycosidically attached to the sphingoid base. Although saccharide moieties are mostly O-glycosidically linked to the ceramide moiety, other sphingolipids with glycosidic bonds of other types (e.g. S-,C-, or N-type) has been reported. Ganglioside GQ1c (d18:0/22:1(13Z)) 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-{[(1S,2R)-1-[(3R,4S,6S)-6-carboxy-6-{[(2R,3S,4R,5R,6S)-3-{[(2S,3R,4R,5R,6R)-4-{[(2R,3R,4S,5S,6R)-4-{[(2S,4S,5R)-2-carboxy-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-3-(2-oxopropyl)oxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R)-3-hydroxy-2-{[(13Z)-1-hydroxydocos-13-en-1-ylidene]amino}octadecyl]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-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 FormulaC111H191N5O55
Average Molecular Weight2475.7047
Monoisotopic Molecular Weight2474.230255347
IUPAC Name(2S,4S,5R)-2-{[(2R,3R,4S,5S,6R)-2-{[(2S,3R,4R,5R,6R)-2-{[(2R,3S,4R,5R,6S)-4-{[(2S,4S,5R)-2-carboxy-6-[(1S,2R)-2-{[(2S,4S,5R)-2-carboxy-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]-5-acetamido-4-hydroxyoxan-2-yl]oxy}-1,3-dihydroxypropyl]-5-acetamido-4-hydroxyoxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6R)-6-{[(2S,3R)-2-[(13Z)-docos-13-enamido]-3-hydroxyoctadecyl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-3-(2-oxopropyl)oxan-4-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional Name(2S,4S,5R)-2-{[(2R,3R,4S,5S,6R)-2-{[(2S,3R,4R,5R,6R)-2-{[(2R,3S,4R,5R,6S)-4-{[(2S,4S,5R)-2-carboxy-6-[(1S,2R)-2-{[(2S,4S,5R)-2-carboxy-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]-5-acetamido-4-hydroxyoxan-2-yl]oxy}-1,3-dihydroxypropyl]-5-acetamido-4-hydroxyoxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6R)-6-{[(2S,3R)-2-[(13Z)-docos-13-enamido]-3-hydroxyoctadecyl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-3-(2-oxopropyl)oxan-4-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCC[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]4O[C@H](CO)[C@H](O)[C@H](O[C@@]5(C[C@H](O)[C@@H](NC(C)=O)C(O5)[C@H](O)[C@H](O)CO)C(O)=O)[C@H]4O)[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](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(O)=O)[C@H]2O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C111H191N5O55/c1-8-10-12-14-16-18-20-22-23-24-25-26-27-29-31-33-35-37-39-41-76(137)116-62(63(130)40-38-36-34-32-30-28-21-19-17-15-13-11-9-2)55-156-101-88(145)87(144)92(74(53-123)159-101)162-103-90(147)99(93(75(54-124)160-103)163-100-61(42-56(3)125)91(83(140)70(49-119)157-100)161-102-89(146)98(84(141)71(50-120)158-102)170-110(106(152)153)45-66(133)78(113-58(5)127)95(167-110)82(139)69(136)48-118)171-111(107(154)155)46-67(134)80(115-60(7)129)97(169-111)86(143)73(52-122)165-109(105(150)151)44-65(132)79(114-59(6)128)96(168-109)85(142)72(51-121)164-108(104(148)149)43-64(131)77(112-57(4)126)94(166-108)81(138)68(135)47-117/h22-23,61-75,77-103,117-124,130-136,138-147H,8-21,24-55H2,1-7H3,(H,112,126)(H,113,127)(H,114,128)(H,115,129)(H,116,137)(H,148,149)(H,150,151)(H,152,153)(H,154,155)/b23-22-/t61-,62+,63-,64+,65+,66+,67+,68-,69-,70-,71-,72-,73-,74-,75-,77-,78-,79-,80-,81-,82-,83+,84+,85-,86-,87-,88-,89-,90-,91-,92-,93+,94?,95?,96?,97?,98+,99-,100+,101-,102+,103+,108-,109-,110+,111+/m1/s1
InChI KeyBTZCBAWSUUCIIZ-OUXHULHTSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glycosphingolipids. These are sphingolipids containing a saccharide moiety glycosidically attached to the sphingoid base. Although saccharide moieties are mostly O-glycosidically linked to the ceramide moiety, other sphingolipids with glycosidic bonds of other types (e.g. S-,C-, or N-type) has been reported.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassGlycosphingolipids
Direct ParentGlycosphingolipids
Alternative Parents
Substituents
  • Glycosphingolipid
  • Oligosaccharide
  • N-acylneuraminic acid or derivatives
  • N-acylneuraminic acid
  • Neuraminic acid
  • Fatty acyl glycoside
  • C-glucuronide
  • Tetracarboxylic acid or derivatives
  • 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
  • Ketone
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Oxacycle
  • Organic oxide
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Primary alcohol
  • Hydrocarbon derivative
  • Organonitrogen compound
  • 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 SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.56ALOGPS
logP-2.6ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)2.16ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count55ChemAxon
Hydrogen Donor Count34ChemAxon
Polar Surface Area965.2 ŲChemAxon
Rotatable Bond Count78ChemAxon
Refractivity577.2 m³·mol⁻¹ChemAxon
Polarizability261.02 ųChemAxon
Number of Rings8ChemAxon
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, Negativesplash10-00di-5090710100-e2b11c9381a7ec37d339View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fl0-2193720110-830ffd38de356b75f9bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05gi-5368903750-679ad6e2383f6242dc1bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zi0-3302915030-ecf0d8f382a371e72902View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0391721140-52e46dfcaba683de899bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004v-0617923001-1490f0ad75b533a58823View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Endosome
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0011940
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028609
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481216
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available