Ganglioside GM3
PubChem CID
9812294
Structure
Molecular Formula
Synonyms
- Ganglioside GM3
- 124579-05-1
- alpha-Neu5Ac-(2->3)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1')-Cer(d18:1/18:0)
- (2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(E,2S,3R)-3-hydroxy-2-(octadecanoylamino)octadec-4-enoxy]oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
- CHEMBL5072599
Molecular Weight
1181.5 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
- Create:2006-10-25
- Modify:2024-12-07
Description
Alpha-Neu5Ac-(2->3)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1')-Cer(d18:1/18:0) is a sialotriaosylceramide consisting of beta-D-GalNAc-(1->4)-[alpha-Neu5Ac-(2->3)]-beta-D-Gal-(1->4)-beta-D-Glc attached to the primary hydroxy function of ceramide(d18:1/18:0). It has a role as a mouse metabolite. It is functionally related to an octadecanoic acid. It is a conjugate acid of an alpha-Neu5Ac-(2->3)-beta-Gal-(1->4)-beta-Glc-(1<->1')-Cer(d18:1/18:0)(1-).
A ganglioside present in abnormally large amounts in the brain and liver due to a deficient biosynthetic enzyme, G(M3):UDP-N-acetylgalactosaminyltransferase. Deficiency of this enzyme prevents the formation of G(M2) ganglioside from G(M3) ganglioside and is the cause of an anabolic sphingolipidosis.
See also: G(M3) Ganglioside (annotation moved to).
Chemical Structure Depiction
Conformer generation is disallowed since too many atoms, too flexible
(2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(E,2S,3R)-3-hydroxy-2-(octadecanoylamino)octadec-4-enoxy]oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)
InChI=1S/C59H108N2O21/c1-4-6-8-10-12-14-16-18-19-21-23-25-27-29-31-33-46(69)61-40(41(66)32-30-28-26-24-22-20-17-15-13-11-9-7-5-2)38-77-56-51(73)50(72)53(45(37-64)79-56)80-57-52(74)55(49(71)44(36-63)78-57)82-59(58(75)76)34-42(67)47(60-39(3)65)54(81-59)48(70)43(68)35-62/h30,32,40-45,47-57,62-64,66-68,70-74H,4-29,31,33-38H2,1-3H3,(H,60,65)(H,61,69)(H,75,76)/b32-30+/t40-,41+,42-,43+,44+,45+,47+,48+,49-,50+,51+,52+,53+,54+,55-,56+,57-,59-/m0/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)
UIKPUUZBQYTDRX-YRRBDHRDSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)
CCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O)O[C@@]3(C[C@@H]([C@H]([C@@H](O3)[C@@H]([C@@H](CO)O)O)NC(=O)C)O)C(=O)O)O)O)O)[C@@H](/C=C/CCCCCCCCCCCCC)O
Computed by OEChem 2.1.5 (PubChem release 2019.06.18)
C59H108N2O21
Computed by PubChem 2.1 (PubChem release 2019.06.18)
- G(M3) Ganglioside
- Ganglioside GM3
- GM3, Ganglioside
- Hematoside
- II3NeuAcLacCer
- Lactosylceramide, Sialyl
- Sialyl Lactosylceramide
- Sialyllactosylceramide
- Ganglioside GM3
- 124579-05-1
- alpha-Neu5Ac-(2->3)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1')-Cer(d18:1/18:0)
- (2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(E,2S,3R)-3-hydroxy-2-(octadecanoylamino)octadec-4-enoxy]oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
- CHEMBL5072599
- CHEBI:84675
- UIKPUUZBQYTDRX-YRRBDHRDSA-N
- GM3-d18:1/18:0
- DA-53488
- MS-32035
- 1ST183844
- HY-114456
- CS-0085856
- Q27157984
- (2S,3R,4E)-3-hydroxy-2-(octadecanoylamino)octadec-4-en-1-yl (6R)-5-(acetylamino)-3,5-dideoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]-beta-L-threo-hex-2-ulopyranonosyl-(2->3)-beta-D-galactopyranosyl-(1->4)-beta-D-glucopyranoside
- Ganglioside GM3; Ganglioside GM3;alpha-Neu5Ac-(2->3)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1')-Cer(d18:1/18:0)
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
1181.5 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
7.7
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
14
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
21
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
45
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
1180.74445846 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
1180.74445846 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
373Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
82
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
1740
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
18
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2019.01.04)
Lipids -> Sphingolipids [SP] -> Acidic glycosphingolipids [SP06] -> Gangliosides [SP0601]
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
1179.7311
Ionization
Matrix Assisted Laser Desorption Ionization (MALDI)
Ionization Mode
negative
Top 5 Peaks
393.1000 100
391.0843 79.70
392.0917 62.02
394.0862 54.19
392.0681 50.80
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Stereo Count
Same Isotope Count
Same Parent, Connectivity Count
Same Parent, Stereo Count
Same Parent, Isotope Count
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
G(M3) Ganglioside (annotation moved to)
- ChEBIAlpha-Neu5Ac-(2->3)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1')-Cer(d18:1/18:0)https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:84675
- ChEMBLLICENSEAccess to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).http://www.ebi.ac.uk/Information/termsofuse.html
- Japan Chemical Substance Dictionary (Nikkaji)
- LIPID MAPSNeuAcHex2Cer 36:1;O2https://lipidmaps.org/databases/lmsd/LMSP0601AJ02Lipid Classificationhttps://www.lipidmaps.org/
- MassBank of North America (MoNA)LICENSEThe content of the MoNA database is licensed under CC BY 4.0.https://mona.fiehnlab.ucdavis.edu/documentation/license
- Natural Product Activity and Species Source (NPASS)
- Wikidataalpha-Neu5Ac-(2->3)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1')-Cer(d18:1/18:0)https://www.wikidata.org/wiki/Q27157984
- Medical Subject Headings (MeSH)LICENSEWorks produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.https://www.nlm.nih.gov/copyright.htmlG(M3) Gangliosidehttps://www.ncbi.nlm.nih.gov/mesh/68005679
- PubChem
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
CONTENTS