| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 23:11:05 UTC |
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| Update Date | 2020-05-11 20:56:25 UTC |
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| BMDB ID | BMDB0004843 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Ganglioside GM3 (d18:1/9Z-18:1) |
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| Description | Ganglioside GM3 (d18:1/9Z-18:1), 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 (d18:1/9Z-18:1) is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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| Structure | |
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| Synonyms | | Value | Source |
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| (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( | 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-{[(9Z)-1-hydroxyheptadec-9-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 |
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| Chemical Formula | C58H104N2O21 |
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| Average Molecular Weight | 1165.4472 |
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| Monoisotopic Molecular Weight | 1164.7131584 |
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| IUPAC Name | (2S,4S,5R,6S)-5-acetamido-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-6-{[(2S,3R,4Z)-2-[(9Z)-heptadec-9-enamido]-3-hydroxyoctadec-4-en-1-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)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 |
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| Traditional Name | (2S,4S,5R,6S)-5-acetamido-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-6-{[(2S,3R,4Z)-2-[(9Z)-heptadec-9-enamido]-3-hydroxyoctadec-4-en-1-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)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 |
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| CAS Registry Number | Not Available |
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| 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)CCCCCCC\C=C/CCCCCCC |
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| InChI Identifier | InChI=1S/C58H104N2O21/c1-4-6-8-10-12-14-16-18-20-22-24-26-28-30-32-45(68)60-39(40(65)31-29-27-25-23-21-19-17-15-13-11-9-7-5-2)37-76-55-50(72)49(71)52(44(36-63)78-55)79-56-51(73)54(48(70)43(35-62)77-56)81-58(57(74)75)33-41(66)46(59-38(3)64)53(80-58)47(69)42(67)34-61/h16,18,29,31,39-44,46-56,61-63,65-67,69-73H,4-15,17,19-28,30,32-37H2,1-3H3,(H,59,64)(H,60,68)(H,74,75)/b18-16-,31-29-/t39-,40+,41-,42+,43+,44+,46+,47+,48-,49+,50+,51+,52+,53-,54-,55+,56-,58-/m0/s1 |
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| InChI Key | DTVMNFBOVVZUJQ-MGNOIPMISA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Sphingolipids |
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| Sub Class | Glycosphingolipids |
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| Direct Parent | Gangliosides |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aliphatic heteromonocyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Status | Expected but not Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | - Cell membrane
- Endosome
- Membrane
- Myelin sheath
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Insoluble | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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