Back to Compounds

Showing Compound Ganglioside GT1c (d18:0/26:1(17Z)) (FDB028675)

Record Information
Version1.0
Creation date2011-09-21 01:43:09 UTC
Update date2015-07-21 06:59:30 UTC
Primary IDFDB028675
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGanglioside GT1c (d18:0/26:1(17Z))
DescriptionGanglioside GT1c (d18:0/26:1(17Z)) is a ganglioside. Ganglioside is a compound composed of a glycosphingolipid (ceramide and oligosaccharide) with one or more sialic acids (AKA n-acetylneuraminic acid, NANA) linked on the sugar chain. The 60+ known gangliosides differ mainly in the position and number of NANA residues. It is a component of the cell plasma membrane that modulates cell signal transduction events. It appears that they concentrate in lipid rafts. They have recently been found to be highly important in immunology. Natural and semisynthetic gangliosides are considered possible therapeutics for neurodegenerative disorders.[1] Gangliosides are more complex glycosphingolipids in which oligosaccharide chains containing N-acetylneuraminic acid (NeuNAc) are attached to a ceramide. NeuNAc, an acetylated derivative of the carbohydrate sialic acid, makes the head groups of Gangliosides anionic. NB: the M in GM2 stands for monosialo, i.e., one NeuNAc residue. GM2 is the second monosialo ganglioside characterized, thus the subscript 2. Their structural diversity results from variation in the composition and sequence of the sugar residues. In all Gangliosides, the ceramide is linked through its C-1 to a beta-glucosyl residue, which, in turn, is bound to a beta-galactosyl residue. [Wikipedia] Particularly, Ganglioside GT1c (d18:0/26:1(17Z)) is a GT1c ganglioside, A glycosphingolipid (ceramide and oligosaccharide) or oligoglycosylceramide with one or more sialic acids (i.e. n-acetylneuraminic acid) linked on the sugar chain. It is a component the cell plasma membrane which modulates cell signal transduction events. Gangliosides have been found to be highly important in immunology. Ganglioside GD3 carries a net-negative charge at pH 7.0 and is acidic. Gangliosides can amount to 6% of the weight of lipids from brain, but they are found at low levels in all animal tissues. Gangliosides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Gangliosides are very similar to globosides except that they also contain N-acetyl neuraminic acid (NANA) in varying amounts. The specific names for the gangliosides provide information about their structure. The letter G refers to ganglioside, and the subscripts M, D, T and Q indicate that the molecule contains mono-, di-, tri and quatra-sialic acid. The numbered subscripts 1, 2 and 3 refer to the carbohydrate sequence that is attached to the ceramide. In particular, 1 stands for GalGalNAcGalGlc-ceramide, 2 stands for GalNAcGalGlc-ceramide and 3 stands for GalGlc-ceramide. Deficiencies in lysosomal enzymes that degrade the carbohydrate portions of various gangliosides are responsible for a number of lysosomal storage diseases such as Tay-Sachs disease, Sandhoff disease, and GM1 gangliosidosis. The carbohydrate portion of the ganglioside GM1 is the site of attachment of cholera toxin, the protein secreted by Vibrio cholerae. [HMDB]
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.2 g/LALOGPS
logP1.46ALOGPS
logP1.59ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)2.26ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count47ChemAxon
Hydrogen Donor Count29ChemAxon
Polar Surface Area819.65 ŲChemAxon
Rotatable Bond Count75ChemAxon
Refractivity535.34 m³·mol⁻¹ChemAxon
Polarizability238.86 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC104H182N4O47
IUPAC name(2S,4S,5R)-2-{[(1S,2R)-1-[(3R,4S,6S)-6-carboxy-6-{[(1S,2R)-1-[(3R,4S,6S)-6-carboxy-3-acetamido-6-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-6-{[(2S,3R)-2-(hexacos-17-enamido)-3-hydroxyoctadecyl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3-hydroxy-5-{[(2S,3R,4R,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3-(2-oxopropyl)-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-hydroxyoxan-2-yl]-1,3-dihydroxypropan-2-yl]oxy}-3-acetamido-4-hydroxyoxan-2-yl]-1,3-dihydroxypropan-2-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
InChI IdentifierInChI=1S/C104H182N4O47/c1-7-9-11-13-15-17-19-21-22-23-24-25-26-27-28-29-30-32-34-36-38-40-42-44-74(125)108-62(63(120)43-41-39-37-35-33-31-20-18-16-14-12-10-8-2)56-142-96-86(134)84(132)89(72(54-114)145-96)148-98-87(135)94(90(73(55-115)146-98)149-95-61(45-57(3)116)88(80(128)69(51-111)143-95)147-97-85(133)83(131)79(127)68(50-110)144-97)155-104(101(140)141)48-66(123)77(107-60(6)119)93(154-104)82(130)71(53-113)151-103(100(138)139)47-65(122)76(106-59(5)118)92(153-103)81(129)70(52-112)150-102(99(136)137)46-64(121)75(105-58(4)117)91(152-102)78(126)67(124)49-109/h21-22,61-73,75-98,109-115,120-124,126-135H,7-20,23-56H2,1-6H3,(H,105,117)(H,106,118)(H,107,119)(H,108,125)(H,136,137)(H,138,139)(H,140,141)/t61-,62+,63-,64+,65+,66+,67-,68-,69-,70-,71-,72-,73-,75-,76-,77-,78-,79+,80+,81-,82-,83+,84?,85-,86-,87-,88-,89-,90?,91?,92?,93?,94-,95?,96-,97+,98?,102-,103-,104+/m1/s1
InChI KeyKEYCKIGVOLAROR-WYVXREEOSA-N
Isomeric SMILES[H][C@@](O)(CO)[C@@]([H])(O)C1O[C@@](C[C@]([H])(O)[C@@]1([H])NC(C)=O)(O[C@]([H])(CO)[C@@]([H])(O)C1O[C@@](C[C@]([H])(O)[C@@]1([H])NC(C)=O)(O[C@]([H])(CO)[C@@]([H])(O)C1O[C@@](C[C@]([H])(O)[C@@]1([H])NC(C)=O)(O[C@]1([H])[C@@]([H])(O)[C@]([H])(O[C@]2([H])[C@@]([H])(CO)O[C@@]([H])(OC[C@]([H])(NC(=O)CCCCCCCCCCCCCCCC=CCCCCCCCC)[C@]([H])(O)CCCCCCCCCCCCCCC)[C@]([H])(O)[C@@]2([H])O)O[C@]([H])(CO)[C@]1([H])O[C@]1([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O[C@]2([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]2([H])O)[C@@]1([H])CC(C)=O)C(O)=O)C(O)=O)C(O)=O
Average Molecular Weight2240.5565
Monoisotopic Molecular Weight2239.197439078
Classification
ClassificationNot classified
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
SpectraNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53481282
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB12006
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference