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

• ChemBase ID: 127598
• Molecular Formular: C77H139N3O31
• Molecular Mass: 1602.92906
• Monoisotopic Mass: 1601.93925468
• SMILES: O[C@H]1[C@H](O[C@@H]2O[C@H](CO)[C@H](O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O[C@@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)[C@H]3NC(=O)C)[C@H](O[C@@]3(C(=O)O)O[C@@H]([C@H](O)[C@H](O)CO)[C@H](NC(=O)C)[C@@H](O)C3)[C@H]2O)[C@@H](CO)O[C@@H](OC[C@@H]([C@@H](O)/C=C/CCCCCCCCCCCCCCC)NC(=O)CCCCCCCCCCCCCCCCCCC)[C@@H]1O
• Canonical SMILES: CCCCCCCCCCCCCCC/C=C/[C@@H]([C@@H](NC(=O)CCCCCCCCCCCCCCCCCCC)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)O[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[C@@H]1O[C@H](CO)[C@@H]([C@@H]([C@H]1O)O)O)O)O
• InChI: InChI=1S/C77H139N3O31/c1-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-38-56(91)80-48(49(88)37-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-2)45-102-73-65(98)63(96)67(54(43-84)105-73)107-75-66(99)71(111-77(76(100)101)39-50(89)57(78-46(3)86)70(110-77)59(92)51(90)40-81)68(55(44-85)106-75)108-72-58(79-47(4)87)69(61(94)53(42-83)103-72)109-74-64(97)62(95)60(93)52(41-82)104-74/h35,37,48-55,57-75,81-85,88-90,92-99H,5-34,36,38-45H2,1-4H3,(H,78,86)(H,79,87)(H,80,91)(H,100,101)/t48-,49-,50-,51+,52+,53+,54+,55+,57+,58+,59+,60-,61-,62-,63+,64+,65+,66+,67+,68-,69+,70+,71+,72-,73+,74-,75-,77-/m0/s1
• InChIKey: GTTLZSUWCRJZRC-CAVGVHMXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5R,6R)-2-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3S)-3-hydroxy-2-icosanamidoicos-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-{[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,4S,5R,6R)-2-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3S)-3-hydroxy-2-icosanamidoicos-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-{[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• Synonyms: Monosialotetrahexosylganglioside; GM1

Database IDs

• CAS Number: 37758-47-7
• PubChem SID: 162221917
• PubChem CID: 5497107; 57449167
• Chemspider ID: 4593688
• MeSH Name: G(M1)+Ganglioside
• Wikipedia Title: GM1

CALCULATED PROPERTIES

• Acid pKa: 2.8020196
• H Acceptors: 31
• H Donor: 20
• LogD (pH = 5.5): 1.1200218
• LogD (pH = 7.4): 0.26524156
• Log P: 3.7591555
• Molar Refractivity: 394.4075 cm^3
• Polarizability: 160.19633 Å^3
• Polar Surface Area: 540.58 Å^2
• Rotatable Bonds: 56
• Lipinski's Rule of Five: false