| Record Information |
|---|
| Version | 1.0 |
|---|
| Creation Date | 2016-09-30 23:11:13 UTC |
|---|
| Update Date | 2020-05-11 20:56:29 UTC |
|---|
| BMDB ID | BMDB0004848 |
|---|
| Secondary Accession Numbers | |
|---|
| Metabolite Identification |
|---|
| Common Name | Ganglioside GM3 (d18:1/24:1(15Z)) |
|---|
| Description | Ganglioside GM3 (d18:1/24:1(15Z)), also known as ganglioside GM3 or GLAC1, 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. Ganglioside GM3 (d18:1/24:1(15Z)) is an extremely weak basic (essentially neutral) compound (based on its pKa). |
|---|
| Structure | |
|---|
| Synonyms | | Value | Source |
|---|
| (N-Acetylneuraminyl)-D-galactosyl-D-glucosylceramide | HMDB | | (N-Acetylneuraminyl)-delta-galactosyl-delta-glucosylceramide | HMDB | | alpha-N-Acetylneuraminyl-2,3-beta-D-galactosyl-1,4-beta-D-glucosylceramide | HMDB | | alpha-N-Acetylneuraminyl-2,3-beta-delta-galactosyl-1,4-beta-delta-glucosylceramide | HMDB | | Ganglioside GM3 | HMDB | | Ganglioside m3 | HMDB | | GLac1 | HMDB | | GM3 | HMDB | | Hematoside | HMDB | | N-Acetylneuraminyl-2,3-alpha-D-galactosyl-1,4-beta-D-glucosylceramide | HMDB | | N-Acetylneuraminyl-2,3-alpha-delta-galactosyl-1,4-beta-delta-glucosylceramide | HMDB | | Neu5ac-alpha2->3gal-beta1->4GLC-beta1->1'cer | HMDB | | Neu5ac-alpha2->3gal-beta1->4GLC-beta1->1'cer(D18:1/24:1 | HMDB | | Sialosyllactosylceramide | HMDB | | (2S,4S,5R,6S)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R,4Z)-3-hydroxy-2-{[(14Z)-1-hydroxytetracos-14-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-carboxylate | HMDB |
|
|---|
| Chemical Formula | C65H118N2O21 |
|---|
| Average Molecular Weight | 1263.6332 |
|---|
| Monoisotopic Molecular Weight | 1262.822708848 |
|---|
| IUPAC Name | (2S,4S,5R,6S)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R,4Z)-3-hydroxy-2-[(14Z)-tetracos-14-enamido]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-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,6S)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R,4Z)-3-hydroxy-2-[(14Z)-tetracos-14-enamido]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-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 Number | Not Available |
|---|
| SMILES | CCCCCCCCCCCCC\C=C/[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](O[C@@]3(C[C@H](O)[C@@H](NC(C)=O)[C@H](O3)[C@H](O)[C@H](O)CO)C(O)=O)[C@H]2O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCCC\C=C/CCCCCCCCC |
|---|
| 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/h19-20,36,38,46-51,53-63,68-70,72-74,76-80H,4-18,21-35,37,39-44H2,1-3H3,(H,66,71)(H,67,75)(H,81,82)/b20-19-,38-36-/t46-,47+,48-,49+,50+,51+,53+,54+,55-,56+,57+,58+,59+,60-,61-,62+,63-,65-/m0/s1 |
|---|
| InChI Key | BGMMKNTYKZAIDF-DJCHRBTISA-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. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Lipids and lipid-like molecules |
|---|
| Class | Sphingolipids |
|---|
| Sub Class | Glycosphingolipids |
|---|
| Direct Parent | Gangliosides |
|---|
| 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 Framework | Aliphatic heteromonocyclic compounds |
|---|
| External Descriptors | Not Available |
|---|
| Ontology |
|---|
| Status | Expected but not Quantified |
|---|
| Origin | |
|---|
| Biofunction | Not Available |
|---|
| Application | Not Available |
|---|
| Cellular locations | - Cell membrane
- Endosome
- Membrane
- Myelin sheath
|
|---|
| Physical Properties |
|---|
| State | Solid |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Insoluble | Not Available | | LogP | Not Available | Not Available |
|
|---|
| Predicted Properties | |
|---|
| Spectra |
|---|
| Spectra | |
|---|
