1.0 2018-06-25 21:52:19 UTC 2020-06-04 19:19:13 UTC BMDB0062122 BMDB62122 Monosialoganglioside GM2 Monosialoganglioside GM2, also known as GM2, ganglioside or ganglioside GM2, belongs to the class of organic compounds known as glycosyl-n-acylsphingosines. Glycosyl-N-acylsphingosines are compounds containing a sphingosine linked to a simple glucosyl moiety. Monosialoganglioside GM2 is possibly soluble (in water) and a moderately basic compound (based on its pKa). (2R,4R,5S,6S)-2-({[(2S,3R,4S,5S,6R)-3-{[(2R,3S,4S,5S,6S)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-{[(2R,3S,4E)-3-hydroxy-2-[(1-hydroxyoctadecylidene)amino]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}methyl)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1S,2S)-1,2,3-trihydroxypropyl]oxane-2-carboxylate GM2, Ganglioside Tay sachs disease ganglioside Ganglioside, tay-sachs disease Tay-sachs disease ganglioside g(m2) Ganglioside Ganglioside GM2 C68H123N3O26 1398.727 1397.839481093 (2R,4R,5S,6S)-2-({[(2S,3R,4S,5S,6R)-3-{[(2R,3S,4S,5S,6S)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-{[(2R,3S,4E)-3-hydroxy-2-[(1-hydroxyoctadecylidene)amino]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}methyl)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1S,2S)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid GM2 (ganglioside) [H]\C(CCCCCCCCCCCCC)=C(\[H])[C@]([H])(O)[C@@]([H])(CO[C@]1([H])O[C@@]([H])(CO)[C@]([H])(O[C@@]2([H])O[C@@]([H])(CO)[C@@]([H])(O[C@@]3([H])O[C@@]([H])(CO)[C@@]([H])(O)[C@@]([H])(O)[C@]3([H])N=C(C)O)[C@@]([H])(OC[C@]3(C[C@@]([H])(O)[C@]([H])(N=C(C)O)[C@]([H])(O3)[C@@]([H])(O)[C@@]([H])(O)CO)C(O)=O)[C@]2([H])O)[C@@]([H])(O)[C@]1([H])O)N=C(O)CCCCCCCCCCCCCCCCC InChI=1S/C68H123N3O26/c1-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-51(81)71-44(45(78)33-31-29-27-25-23-21-18-16-14-12-10-8-6-2)40-90-65-58(86)57(85)60(49(38-74)93-65)95-66-59(87)63(61(50(39-75)94-66)96-64-53(70-43(4)77)56(84)55(83)48(37-73)92-64)91-41-68(67(88)89)35-46(79)52(69-42(3)76)62(97-68)54(82)47(80)36-72/h31,33,44-50,52-66,72-75,78-80,82-87H,5-30,32,34-41H2,1-4H3,(H,69,76)(H,70,77)(H,71,81)(H,88,89)/b33-31+/t44-,45+,46-,47+,48+,49+,50+,52+,53+,54+,55-,56+,57+,58+,59+,60+,61-,62+,63+,64-,65-,66-,68-/m1/s1 USMMPBVNWHAJBE-YMEOXFOQSA-N belongs to the class of organic compounds known as glycosyl-n-acylsphingosines. Glycosyl-N-acylsphingosines are compounds containing a sphingosine linked to a simple glucosyl moiety. Organic compounds Lipids and lipid-like molecules Sphingolipids Glycosphingolipids Glycosyl-N-acylsphingosines Acetals Acetamides Alkyl glycosides C-glucuronides C-glycosyl compounds Carbonyl compounds Carboxylic acids Dialkyl ethers Hydrocarbon derivatives Monocarboxylic acids and derivatives N-acyl amines N-acyl-alpha-hexosamines O-glycosyl compounds Oligosaccharides Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Polyols Primary alcohols Pyrans Secondary alcohols Secondary carboxylic acid amides Acetal Acetamide Alcohol Aliphatic heteromonocyclic compound Alkyl glycoside C-glucuronide C-glycosyl compound Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid derivative Dialkyl ether Ether Fatty acyl Fatty acyl glycoside Fatty amide Glycosyl compound Glycosyl-n-acylsphingosine Hydrocarbon derivative Monocarboxylic acid or derivatives N-acyl-alpha-hexosamine N-acyl-amine O-glycosyl compound Oligosaccharide Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Oxane Polyol Primary alcohol Pyran Secondary alcohol Secondary carboxylic acid amide Aliphatic heteromonocyclic compounds logp 3.36 ALOGPS logs -4.66 ALOGPS logp 5.02 ChemAxon pka_strongest_acidic 3.34 ChemAxon pka_strongest_basic 2.61 ChemAxon iupac (2R,4R,5S,6S)-2-({[(2S,3R,4S,5S,6R)-3-{[(2R,3S,4S,5S,6S)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-{[(2R,3S,4E)-3-hydroxy-2-[(1-hydroxyoctadecylidene)amino]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}methyl)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1S,2S)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid ChemAxon average_mass 1398.727 ChemAxon mono_mass 1397.839481093 ChemAxon smiles [H]\C(CCCCCCCCCCCCC)=C(\[H])[C@]([H])(O)[C@@]([H])(CO[C@]1([H])O[C@@]([H])(CO)[C@]([H])(O[C@@]2([H])O[C@@]([H])(CO)[C@@]([H])(O[C@@]3([H])O[C@@]([H])(CO)[C@@]([H])(O)[C@@]([H])(O)[C@]3([H])N=C(C)O)[C@@]([H])(OC[C@]3(C[C@@]([H])(O)[C@]([H])(N=C(C)O)[C@]([H])(O3)[C@@]([H])(O)[C@@]([H])(O)CO)C(O)=O)[C@]2([H])O)[C@@]([H])(O)[C@]1([H])O)N=C(O)CCCCCCCCCCCCCCCCC ChemAxon formula C68H123N3O26 ChemAxon inchi InChI=1S/C68H123N3O26/c1-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-51(81)71-44(45(78)33-31-29-27-25-23-21-18-16-14-12-10-8-6-2)40-90-65-58(86)57(85)60(49(38-74)93-65)95-66-59(87)63(61(50(39-75)94-66)96-64-53(70-43(4)77)56(84)55(83)48(37-73)92-64)91-41-68(67(88)89)35-46(79)52(69-42(3)76)62(97-68)54(82)47(80)36-72/h31,33,44-50,52-66,72-75,78-80,82-87H,5-30,32,34-41H2,1-4H3,(H,69,76)(H,70,77)(H,71,81)(H,88,89)/b33-31+/t44-,45+,46-,47+,48+,49+,50+,52+,53+,54+,55-,56+,57+,58+,59+,60+,61-,62+,63+,64-,65-,66-,68-/m1/s1 ChemAxon inchikey USMMPBVNWHAJBE-YMEOXFOQSA-N ChemAxon polar_surface_area 471.9 ChemAxon refractivity 350.28 ChemAxon polarizability 155.08 ChemAxon rotatable_bond_count 50 ChemAxon acceptor_count 29 ChemAxon donor_count 17 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::MsMs 3609667 Specdb::MsMs 3609668 Specdb::MsMs 3609669 Specdb::MsMs 3609670 Specdb::MsMs 3609671 Specdb::MsMs 3609672 Milk 0.158 - 0.237 uM Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. 11913692 26286730 71308211 Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. 11913692