Showing Compound Ganglioside GM1 (d18:0/12:0) (FDB028544)

Record Information

Version

1.0

Creation date

2011-09-21 01:41:23 UTC

Update date

2015-07-21 06:59:27 UTC

Primary ID

FDB028544

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Ganglioside GM1 (d18:0/12:0)

Description

Ganglioside GM1 (d18:0/12:0) 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 GM1 (d18:0/12:0) is a GM1 Ganglioside. GM1 (monosialotetrahexosylganglioside), the prototype ganglioside, is a member of the ganglio series of gangliosides which contain one sialic acid residue. GM1 has important physiological properties and impacts neuronal plasticity and repair mechanisms, and the release of neurotrophins in the brain. Besides its function in the physiology of the brain, GM1 acts as the site of binding for both Cholera toxin and E. coli heat-labile enterotoxin (Traveller's diarrhea).[1][2] Antibodies to GM1 are increased in Guillain-Barre syndrome, dementia and lupus but their function is not clear.[3] There is some evidence to suggest these antibodies are associated with diarrhea in Guillain-Barre syndrome.[4] 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 Number

Not Available

Structure

MOL SDF PDB SMILES InChI

Synonyms

Show entries

Search:

Synonym

Source

(2S,4S,5R)-2-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R)-3-hydroxy-2-[(1-hydroxydodecylidene)amino]octadecyl]oxy}-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-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

Generator, HMDB

Showing 1 to 1 of 1 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.66 g/L	ALOGPS
logP	1.23	ALOGPS
logP	0.54	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	2.82	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	31	ChemAxon
Hydrogen Donor Count	19	ChemAxon
Polar Surface Area	528.55 Å²	ChemAxon
Rotatable Bond Count	48	ChemAxon
Refractivity	349.26 m³·mol⁻¹	ChemAxon
Polarizability	158.17 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C68H122N2O31

IUPAC name

(2S,4S,5R)-2-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-6-{[(2S,3R)-2-dodecanamido-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}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

InChI Identifier

InChI=1S/C68H122N2O31/c1-5-7-9-11-13-15-16-17-18-20-21-23-25-27-41(78)40(70-48(81)28-26-24-22-19-14-12-10-8-6-2)36-92-64-56(88)54(86)59(46(34-74)95-64)98-66-57(89)62(101-68(67(90)91)30-42(79)49(69-38(4)77)61(100-68)50(82)43(80)31-71)60(47(35-75)96-66)99-63-39(29-37(3)76)58(52(84)45(33-73)93-63)97-65-55(87)53(85)51(83)44(32-72)94-65/h39-47,49-66,71-75,78-80,82-89H,5-36H2,1-4H3,(H,69,77)(H,70,81)(H,90,91)/t39-,40+,41-,42+,43-,44-,45-,46-,47-,49-,50-,51+,52+,53+,54-,55-,56-,57-,58-,59-,60+,61?,62-,63+,64-,65+,66+,68+/m1/s1

InChI Key

QENJYHSDDMJVTR-UEGOYZRMSA-N

Isomeric 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@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](O)CO)C(O)=O)[C@H]2O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCC

Average Molecular Weight

1463.6911

Monoisotopic Molecular Weight

1462.803155196

Classification

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Glycosphingolipids

Direct Parent

Glycosphingolipids

Alternative Parents

Substituents

Glycosphingolipid
Oligosaccharide
N-acylneuraminic acid
N-acylneuraminic acid or derivatives
Neuraminic acid
Fatty acyl glycoside
C-glucuronide
Alkyl glycoside
Glycosyl compound
C-glycosyl compound
O-glycosyl compound
Ketal
Fatty amide
Fatty acyl
Pyran
N-acyl-amine
Oxane
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Ketone
Acetal
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Polyol
Hydrocarbon derivative
Alcohol
Organic oxide
Organic nitrogen compound
Organic oxygen compound
Primary alcohol
Organopnictogen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect:

Touch:

Smooth

Disposition

Route of exposure:

Enteral:

Ingestion

Animal

Process

Naturally occurring process:

Biological process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Biochemical process:

Cellular process:

Cell signaling

Role

Industrial application:

Food and nutrition:

Biological role:

Molecular messenger:

Signaling molecule

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Show entries

Search:

Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00l2-0221901000-e11244d6d47d2e2913c4	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0h9s-0192604020-a8864407f201d2547a0d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01pt-9732601000-702f1c898bf5875dd8ec	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-6052900000-62f46fd6eae53204f5bb	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06si-5064901110-d3f2e8753b5c08cb1f4d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-007o-9364611102-9b59a3fb63402e01b4d9	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

53481151

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB11875

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Show entries

Search:

Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Show entries

Search:

Name	Gene Name	UniProt ID
Alpha-N-acetylneuraminide alpha-2,8-sialyltransferase	ST8SIA1	Q92185
Antigen-presenting glycoprotein CD1d	CD1D	P15813
Beta-1,3-galactosyltransferase 4	B3GALT4	O96024
Beta-1,3-galactosyltransferase 5	B3GALT5	Q9Y2C3
Epididymal secretory protein E1	NPC2	P61916
Ganglioside GM2 activator	GM2A	P17900
GPI ethanolamine phosphate transferase 1	PIGN	O95427
GPI ethanolamine phosphate transferase 2	PIGG	Q5H8A4
GPI ethanolamine phosphate transferase 3	PIGO	Q8TEQ8
GPI mannosyltransferase 1	PIGM	Q9H3S5