(2R,4R,5S,6S)-2-({[(2R,3S,4S,5R,6S)-2-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-{[(2R,3S)-3-hydroxy-2-octadecanamidooctadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-{[(2R,3S,4S,5S,6S)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}methyl)-5-acetamido-4-hydroxy-6-[(1S,2S)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

• ChemBase ID: 127599
• Molecular Formular: C68H123N3O26
• Molecular Mass: 1398.70872
• Monoisotopic Mass: 1397.83948107
• SMILES: CCCCCCCCCCCCCCCCCC(=O)N[C@H](CO[C@H]1[C@H]([C@@H]([C@H]([C@@H](O1)CO)O[C@@H]1[C@H]([C@@H]([C@@H]([C@@H](O1)CO)O[C@@H]1[C@H]([C@@H]([C@@H]([C@@H](O1)CO)O)O)NC(=O)C)OC[C@]1(C[C@H]([C@@H]([C@H](O1)[C@H]([C@H](CO)O)O)NC(=O)C)O)C(=O)O)O)O)O)[C@H](/C=C/CCCCCCCCCCCCC)O
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@@H]([C@H](NC(=O)CCCCCCCCCCCCCCCCC)CO[C@@H]1O[C@@H](CO)[C@@H]([C@H]([C@@H]1O)O)O[C@H]1O[C@@H](CO)[C@H]([C@H]([C@@H]1O)OC[C@]1(C[C@@H](O)[C@@H]([C@H](O1)[C@H]([C@H](CO)O)O)NC(=O)C)C(=O)O)O[C@H]1O[C@@H](CO)[C@H]([C@H]([C@@H]1NC(=O)C)O)O)O
• 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)/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
• InChIKey: USMMPBVNWHAJBE-DVECSUJISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R,5S,6S)-2-({[(2R,3S,4S,5R,6S)-2-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-{[(2R,3S)-3-hydroxy-2-octadecanamidooctadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-{[(2R,3S,4S,5S,6S)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}methyl)-5-acetamido-4-hydroxy-6-[(1S,2S)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• IUPAC Traditional name: (2R,4R,5S,6S)-2-({[(2R,3S,4S,5R,6S)-2-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-{[(2R,3S)-3-hydroxy-2-octadecanamidooctadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-{[(2R,3S,4S,5S,6S)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}methyl)-5-acetamido-4-hydroxy-6-[(1S,2S)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• Synonyms: Ganglioside GM2; Tay-Sachs ganglioside; β-D-GalNAc-(1→4)-[α-Neu5Ac-(2→3)]-β-D-Gal-(1→4)-β-D-Glc-(1?1)-N-octadecanoylsphingosine; GM2 (ganglioside)

Database IDs

• CAS Number: 19600-01-2
• PubChem SID: 162221918
• PubChem CID: 71308211
• CHEBI ID: 60327
• Chemspider ID: 26286730
• Wikipedia Title: GM2_(ganglioside)

CALCULATED PROPERTIES

• Acid pKa: 3.269635
• H Acceptors: 26
• H Donor: 17
• LogD (pH = 5.5): 0.7530921
• LogD (pH = 7.4): -0.46765527
• Log P: 2.9647238
• Molar Refractivity: 348.7184 cm^3
• Polarizability: 140.975 Å^3
• Polar Surface Area: 461.43 Å^2
• Rotatable Bonds: 50
• Lipinski's Rule of Five: false