NP-MRD: Showing NP-Card for Monosialoganglioside GM1 (NP0340052)

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Record Information

Version

2.0

Created at

2024-09-12 01:11:54 UTC

Updated at

2024-09-12 01:11:54 UTC

NP-MRD ID

NP0340052

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Monosialoganglioside GM1

Description

(2S,4S,5R,6S)-2-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(4E)-3-hydroxy-2-[(1-hydroxyoctadecylidene)amino]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-3-hydroxy-5-{[(2S,3R,4R,5R,6R)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid 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 (2S,4S,5R,6S)-2-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(4E)-3-hydroxy-2-[(1-hydroxyoctadecylidene)amino]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-3-hydroxy-5-{[(2S,3R,4R,5R,6R)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid is a moderately basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304032008102D          

136140  0  0  1  0            999 V2000
    7.1447    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4354   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3483    8.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   15.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7210   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7210   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0065   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0065    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2920    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2920    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5775    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5775    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8631    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8631    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4770   11.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9732    8.5923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197   15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907   12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328    7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618   11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6305    9.0810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1948   10.6315    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.7857    8.7355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052   15.6750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.5762   13.2000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.1473    8.2500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.1473   11.5500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.2907    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7251    9.9995    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.1473   14.0250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.0679    9.5108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052   16.5000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.5762   14.0250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.2907   16.9125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.8618    9.4875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.5762   16.5000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.5762    9.0750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.7184   10.7250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.1473    9.0750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.4328   11.9625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.8618   14.4375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.5376   10.1428    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.7184   11.5500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.1473   13.2000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.5762    8.2500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.5762   15.6750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.4328   10.3125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.0073   12.3252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   11.5500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.4429    9.2243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   14.4375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052    5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6911    7.8170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341   15.6750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052   13.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762   11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1002    9.7130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473   15.6750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197    7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3823   10.4882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3160    8.1035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8803    9.6540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197   16.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907   14.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907   17.7375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618   10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618   16.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907    9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5376   12.9572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1948   12.4685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907    7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618   12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907   15.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618    7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473   10.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328    9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618   15.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8197   10.9180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   11.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197    5.3625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486    7.0125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052    7.4250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197    6.1875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9126    9.8562    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.2554    9.3675    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197   16.0875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907   13.6125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328    8.6625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473   12.3750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.0073   10.7748    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473   14.8500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.5982    8.8788    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052   17.3250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762   14.8500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907   16.0875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473    9.9000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762   17.3250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762    9.9000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   11.1375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618    8.6625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   12.3750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618   13.6125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3344    9.9292    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   11.1375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   13.6125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   15.6204   10.1692    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
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 68133  1  6  0  0  0
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 70135  1  6  0  0  0
 71136  1  6  0  0  0
M  END


  Mrv1652304032008102D          

136140  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0340052

> <DATABASE_NAME>
NP-MRD

> <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@]4([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]4([H])O)[C@@]3([H])N=C(C)O)[C@]([H])(O[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_IDENTIFIER>
InChI=1S/C73H131N3O31/c1-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-52(87)76-44(45(84)33-31-29-27-25-23-21-18-16-14-12-10-8-6-2)41-98-69-61(94)59(92)63(50(39-80)101-69)103-71-62(95)67(107-73(72(96)97)35-46(85)53(74-42(3)82)66(106-73)55(88)47(86)36-77)64(51(40-81)102-71)104-68-54(75-43(4)83)65(57(90)49(38-79)99-68)105-70-60(93)58(91)56(89)48(37-78)100-70/h31,33,44-51,53-71,77-81,84-86,88-95H,5-30,32,34-41H2,1-4H3,(H,74,82)(H,75,83)(H,76,87)(H,96,97)/b33-31+/t44?,45?,46-,47?,48+,49+,50+,51+,53+,54+,55?,56-,57-,58-,59+,60+,61+,62+,63+,64-,65+,66-,67+,68-,69+,70-,71-,73-/m0/s1

> <INCHI_KEY>
QPJBWNIQKHGLAU-BVLUPYCXSA-N

> <FORMULA>
C73H131N3O31

> <MOLECULAR_WEIGHT>
1546.841

> <EXACT_MASS>
1545.87665445

> <JCHEM_ACCEPTOR_COUNT>
34

> <JCHEM_ATOM_COUNT>
238

> <JCHEM_AVERAGE_POLARIZABILITY>
170.4405954580253

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
20

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4S,5R,6S)-2-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(4E)-3-hydroxy-2-[(1-hydroxyoctadecylidene)amino]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-3-hydroxy-5-{[(2S,3R,4R,5R,6R)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid

> <ALOGPS_LOGP>
2.67

> <JCHEM_LOGP>
3.8411654960684314

> <ALOGPS_LOGS>
-4.39

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
5.094930441248309

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.98089859967372

> <JCHEM_PKA_STRONGEST_BASIC>
2.3674625567751324

> <JCHEM_POLAR_SURFACE_AREA>
551.0500000000003

> <JCHEM_REFRACTIVITY>
377.5685999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
52

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4S,5R,6S)-2-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(4E)-3-hydroxy-2-[(1-hydroxyoctadecylidene)amino]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-3-hydroxy-5-{[(2S,3R,4R,5R,6R)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-APR-20         0                                  
HETATM    1  C   UNK     0      13.337  10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      49.346  -3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.050  15.504   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      29.341  29.260   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.671  10.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      48.013  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.004  10.780   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      48.013  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.338  10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      46.679  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.672  10.780   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      46.679   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.005  10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      45.345   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.339  10.780   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      45.345   3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.673  10.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      44.011   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      24.006  10.780   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      25.340  10.010   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      44.011   5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.674  10.780   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      42.678   6.160   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      28.007  10.010   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      42.678   7.700   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      29.341  10.780   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      41.344   8.470   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      30.675  10.010   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      41.344  10.010   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      32.008  10.780   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      40.010  10.780   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      33.342  10.010   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      40.010  12.320   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      34.676  10.780   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      25.157  21.293   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      26.083  16.039   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      38.677  28.490   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      36.009  23.870   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      30.675  14.630   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      33.342  22.330   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      36.009  13.090   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      23.577  16.951   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      30.675  28.490   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      37.343  12.320   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      38.677  13.090   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      24.630  19.845   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      27.600  16.306   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      37.343  29.260   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      34.676  24.640   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      32.008  15.400   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      32.008  21.560   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      36.009  10.010   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      25.620  18.666   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      32.008  26.180   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      28.127  17.753   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      37.343  30.800   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      34.676  26.180   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      36.009  31.570   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      33.342  17.710   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      34.676  30.800   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      34.676  16.940   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      29.341  20.020   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      32.008  16.940   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      30.675  22.330   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      33.342  26.950   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      27.137  18.933   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      29.341  21.560   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      32.008  24.640   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      34.676  15.400   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      34.676  29.260   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      30.675  19.250   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      26.147  23.007   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      26.674  21.560   0.000  0.00  0.00           C+0
HETATM   74  N   UNK     0      25.093  17.219   0.000  0.00  0.00           N+0
HETATM   75  N   UNK     0      30.675  26.950   0.000  0.00  0.00           N+0
HETATM   76  N   UNK     0      37.343  10.780   0.000  0.00  0.00           N+0
HETATM   77  O   UNK     0      25.557  14.592   0.000  0.00  0.00           O+0
HETATM   78  O   UNK     0      40.010  29.260   0.000  0.00  0.00           O+0
HETATM   79  O   UNK     0      37.343  24.640   0.000  0.00  0.00           O+0
HETATM   80  O   UNK     0      30.675  13.090   0.000  0.00  0.00           O+0
HETATM   81  O   UNK     0      34.676  21.560   0.000  0.00  0.00           O+0
HETATM   82  O   UNK     0      22.587  18.131   0.000  0.00  0.00           O+0
HETATM   83  O   UNK     0      32.008  29.260   0.000  0.00  0.00           O+0
HETATM   84  O   UNK     0      38.677  14.630   0.000  0.00  0.00           O+0
HETATM   85  O   UNK     0      23.114  19.578   0.000  0.00  0.00           O+0
HETATM   86  O   UNK     0      28.590  15.127   0.000  0.00  0.00           O+0
HETATM   87  O   UNK     0      36.009   8.470   0.000  0.00  0.00           O+0
HETATM   88  O   UNK     0      29.643  18.021   0.000  0.00  0.00           O+0
HETATM   89  O   UNK     0      38.677  31.570   0.000  0.00  0.00           O+0
HETATM   90  O   UNK     0      36.009  26.950   0.000  0.00  0.00           O+0
HETATM   91  O   UNK     0      36.009  33.110   0.000  0.00  0.00           O+0
HETATM   92  O   UNK     0      33.342  19.250   0.000  0.00  0.00           O+0
HETATM   93  O   UNK     0      33.342  31.570   0.000  0.00  0.00           O+0
HETATM   94  O   UNK     0      36.009  17.710   0.000  0.00  0.00           O+0
HETATM   95  O   UNK     0      28.007  19.250   0.000  0.00  0.00           O+0
HETATM   96  O   UNK     0      27.137  24.187   0.000  0.00  0.00           O+0
HETATM   97  O   UNK     0      24.630  23.275   0.000  0.00  0.00           O+0
HETATM   98  O   UNK     0      36.009  14.630   0.000  0.00  0.00           O+0
HETATM   99  O   UNK     0      33.342  23.870   0.000  0.00  0.00           O+0
HETATM  100  O   UNK     0      36.009  28.490   0.000  0.00  0.00           O+0
HETATM  101  O   UNK     0      33.342  14.630   0.000  0.00  0.00           O+0
HETATM  102  O   UNK     0      32.008  20.020   0.000  0.00  0.00           O+0
HETATM  103  O   UNK     0      30.675  17.710   0.000  0.00  0.00           O+0
HETATM  104  O   UNK     0      30.675  23.870   0.000  0.00  0.00           O+0
HETATM  105  O   UNK     0      33.342  28.490   0.000  0.00  0.00           O+0
HETATM  106  O   UNK     0      27.663  20.380   0.000  0.00  0.00           O+0
HETATM  107  O   UNK     0      28.007  22.330   0.000  0.00  0.00           O+0
HETATM  108  H   UNK     0      38.677  10.010   0.000  0.00  0.00           H+0
HETATM  109  H   UNK     0      41.344  13.090   0.000  0.00  0.00           H+0
HETATM  110  H   UNK     0      37.343  13.860   0.000  0.00  0.00           H+0
HETATM  111  H   UNK     0      38.677  11.550   0.000  0.00  0.00           H+0
HETATM  112  H   UNK     0      24.104  18.398   0.000  0.00  0.00           H+0
HETATM  113  H   UNK     0      26.610  17.486   0.000  0.00  0.00           H+0
HETATM  114  H   UNK     0      38.677  30.030   0.000  0.00  0.00           H+0
HETATM  115  H   UNK     0      36.009  25.410   0.000  0.00  0.00           H+0
HETATM  116  H   UNK     0      30.675  16.170   0.000  0.00  0.00           H+0
HETATM  117  H   UNK     0      32.008  23.100   0.000  0.00  0.00           H+0
HETATM  118  H   UNK     0      26.147  20.113   0.000  0.00  0.00           H+0
HETATM  119  H   UNK     0      32.008  27.720   0.000  0.00  0.00           H+0
HETATM  120  H   UNK     0      29.117  16.574   0.000  0.00  0.00           H+0
HETATM  121  H   UNK     0      37.343  32.340   0.000  0.00  0.00           H+0
HETATM  122  H   UNK     0      34.676  27.720   0.000  0.00  0.00           H+0
HETATM  123  H   UNK     0      36.009  30.030   0.000  0.00  0.00           H+0
HETATM  124  H   UNK     0      32.008  18.480   0.000  0.00  0.00           H+0
HETATM  125  H   UNK     0      34.676  32.340   0.000  0.00  0.00           H+0
HETATM  126  H   UNK     0      34.676  18.480   0.000  0.00  0.00           H+0
HETATM  127  H   UNK     0      30.675  20.790   0.000  0.00  0.00           H+0
HETATM  128  H   UNK     0      33.342  16.170   0.000  0.00  0.00           H+0
HETATM  129  H   UNK     0      29.341  23.100   0.000  0.00  0.00           H+0
HETATM  130  H   UNK     0      33.342  25.410   0.000  0.00  0.00           H+0
HETATM  131  H   UNK     0      28.624  18.535   0.000  0.00  0.00           H+0
HETATM  132  H   UNK     0      28.007  20.790   0.000  0.00  0.00           H+0
HETATM  133  H   UNK     0      30.675  25.410   0.000  0.00  0.00           H+0
HETATM  134  H   UNK     0      36.009  16.170   0.000  0.00  0.00           H+0
HETATM  135  H   UNK     0      33.342  30.030   0.000  0.00  0.00           H+0
HETATM  136  H   UNK     0      29.158  18.983   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2    6                                                            
CONECT    3   42                                                            
CONECT    4   43                                                            
CONECT    5    1    7                                                       
CONECT    6    2    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   18                                                       
CONECT   17   15   19                                                       
CONECT   18   16   21                                                       
CONECT   19   17   20                                                       
CONECT   20   19   22                                                       
CONECT   21   18   23                                                       
CONECT   22   20   24                                                       
CONECT   23   21   25                                                       
CONECT   24   22   26                                                       
CONECT   25   23   27                                                       
CONECT   26   24   28                                                       
CONECT   27   25   29                                                       
CONECT   28   26   30                                                       
CONECT   29   27   31                                                       
CONECT   30   28   32                                                       
CONECT   31   29   33  108                                                  
CONECT   32   30   34                                                       
CONECT   33   31   45  109                                                  
CONECT   34   32   52                                                       
CONECT   35   46   73                                                       
CONECT   36   47   77                                                       
CONECT   37   48   78                                                       
CONECT   38   49   79                                                       
CONECT   39   50   80                                                       
CONECT   40   51   81                                                       
CONECT   41   44   98                                                       
CONECT   42    3   74   82                                                  
CONECT   43    4   75   83                                                  
CONECT   44   41   45   76  110                                             
CONECT   45   33   44   84  111                                             
CONECT   46   35   53   85  112                                             
CONECT   47   36   55   86  113                                             
CONECT   48   37   56  100  114                                             
CONECT   49   38   57   99  115                                             
CONECT   50   39   63  101  116                                             
CONECT   51   40   64  102  117                                             
CONECT   52   34   76   87                                                  
CONECT   53   46   66   74  118                                             
CONECT   54   65   68   75  119                                             
CONECT   55   47   66   88  120                                             
CONECT   56   48   58   89  121                                             
CONECT   57   49   65   90  122                                             
CONECT   58   56   60   91  123                                             
CONECT   59   61   63   92  124                                             
CONECT   60   58   70   93  125                                             
CONECT   61   59   69   94  126                                             
CONECT   62   67   71   95  127                                             
CONECT   63   50   59  103  128                                             
CONECT   64   51   67  104  129                                             
CONECT   65   54   57  105  130                                             
CONECT   66   53   55  106  131                                             
CONECT   67   62   64  107  132                                             
CONECT   68   54   99  104  133                                             
CONECT   69   61   98  101  134                                             
CONECT   70   60  100  105  135                                             
CONECT   71   62  102  103  136                                             
CONECT   72   73   96   97                                                  
CONECT   73   35   72  106  107                                             
CONECT   74   42   53                                                       
CONECT   75   43   54                                                       
CONECT   76   44   52                                                       
CONECT   77   36                                                            
CONECT   78   37                                                            
CONECT   79   38                                                            
CONECT   80   39                                                            
CONECT   81   40                                                            
CONECT   82   42                                                            
CONECT   83   43                                                            
CONECT   84   45                                                            
CONECT   85   46                                                            
CONECT   86   47                                                            
CONECT   87   52                                                            
CONECT   88   55                                                            
CONECT   89   56                                                            
CONECT   90   57                                                            
CONECT   91   58                                                            
CONECT   92   59                                                            
CONECT   93   60                                                            
CONECT   94   61                                                            
CONECT   95   62                                                            
CONECT   96   72                                                            
CONECT   97   72                                                            
CONECT   98   41   69                                                       
CONECT   99   49   68                                                       
CONECT  100   48   70                                                       
CONECT  101   50   69                                                       
CONECT  102   51   71                                                       
CONECT  103   63   71                                                       
CONECT  104   64   68                                                       
CONECT  105   65   70                                                       
CONECT  106   66   73                                                       
CONECT  107   67   73                                                       
CONECT  108   31                                                            
CONECT  109   33                                                            
CONECT  110   44                                                            
CONECT  111   45                                                            
CONECT  112   46                                                            
CONECT  113   47                                                            
CONECT  114   48                                                            
CONECT  115   49                                                            
CONECT  116   50                                                            
CONECT  117   51                                                            
CONECT  118   53                                                            
CONECT  119   54                                                            
CONECT  120   55                                                            
CONECT  121   56                                                            
CONECT  122   57                                                            
CONECT  123   58                                                            
CONECT  124   59                                                            
CONECT  125   60                                                            
CONECT  126   61                                                            
CONECT  127   62                                                            
CONECT  128   63                                                            
CONECT  129   64                                                            
CONECT  130   65                                                            
CONECT  131   66                                                            
CONECT  132   67                                                            
CONECT  133   68                                                            
CONECT  134   69                                                            
CONECT  135   70                                                            
CONECT  136   71                                                            
MASTER        0    0    0    0    0    0    0    0  136    0  280    0
END

View in JSmol

Synonyms

Value	Source
(2S,4S,5R,6S)-2-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(4E)-3-hydroxy-2-[(1-hydroxyoctadecylidene)amino]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-3-hydroxy-5-{[(2S,3R,4R,5R,6R)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylate	Generator
Ceramide, monosialosyl tetraglycosyl	MeSH
g(m1) Ganglioside	MeSH
GM1a Monosialoganglioside	MeSH
Monosialoganglioside, GM1a	MeSH
Monosialosyl tetraglycosyl ceramide	MeSH
Tetraglycosyl ceramide, monosialosyl	MeSH

Chemical Formula

C₇₃H₁₃₁N₃O₃₁

Average Mass

1546.8410 Da

Monoisotopic Mass

1545.87665 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

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@]4([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]4([H])O)[C@@]3([H])N=C(C)O)[C@]([H])(O[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 Identifier

InChI=1S/C73H131N3O31/c1-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-52(87)76-44(45(84)33-31-29-27-25-23-21-18-16-14-12-10-8-6-2)41-98-69-61(94)59(92)63(50(39-80)101-69)103-71-62(95)67(107-73(72(96)97)35-46(85)53(74-42(3)82)66(106-73)55(88)47(86)36-77)64(51(40-81)102-71)104-68-54(75-43(4)83)65(57(90)49(38-79)99-68)105-70-60(93)58(91)56(89)48(37-78)100-70/h31,33,44-51,53-71,77-81,84-86,88-95H,5-30,32,34-41H2,1-4H3,(H,74,82)(H,75,83)(H,76,87)(H,96,97)/b33-31+/t44?,45?,46-,47?,48+,49+,50+,51+,53+,54+,55?,56-,57-,58-,59+,60+,61+,62+,63+,64-,65+,66-,67+,68-,69+,70-,71-,73-/m0/s1

InChI Key

QPJBWNIQKHGLAU-BVLUPYCXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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

sialotriaosylceramide (CHEBI:84989 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.67	ALOGPS
logP	3.84	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	2.98	ChemAxon
pKa (Strongest Basic)	2.37	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	34	ChemAxon
Hydrogen Donor Count	20	ChemAxon
Polar Surface Area	551.05 Å²	ChemAxon
Rotatable Bond Count	52	ChemAxon
Refractivity	377.57 m³·mol⁻¹	ChemAxon
Polarizability	170.44 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5497107

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Monosialoganglioside GM1 (NP0340052)

MOL for NP0340052 (Monosialoganglioside GM1)

3D MOL for NP0340052 (Monosialoganglioside GM1)

3D SDF for NP0340052 (Monosialoganglioside GM1)

3D-SDF for NP0340052 (Monosialoganglioside GM1)

PDB for NP0340052 (Monosialoganglioside GM1)

3D PDB for NP0340052 (Monosialoganglioside GM1)

SMILES for NP0340052 (Monosialoganglioside GM1)

INCHI for NP0340052 (Monosialoganglioside GM1)

Structure for NP0340052 (Monosialoganglioside GM1)

3D Structure for NP0340052 (Monosialoganglioside GM1)