NP-MRD: Showing NP-Card for Monosialoganglioside GM3 (NP0340053)

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Record Information

Version

2.0

Created at

2024-09-12 01:12:15 UTC

Updated at

2024-09-12 01:12:16 UTC

NP-MRD ID

NP0340053

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Monosialoganglioside GM3

Description

Ganglioside GM3, also known as g(m3) ganglioside or GM3, 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. It was first documented in 2014 (PMID: 24362891). Ganglioside GM3 is a moderately basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304032018352D          

109111  0  0  1  0            999 V2000
  -12.8605    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   22.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6208   13.3870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460   10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   22.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   21.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171   10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   21.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   20.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   19.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2868   18.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   18.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579   17.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579   16.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434   15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579   14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2440   11.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7477   14.5077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0905   14.0190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   12.7875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   13.6125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.5262   12.4685    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   12.0299   15.2830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   13.3727   14.7942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   14.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3386   12.6118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4050   14.9965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  4  1  1  0  0  0  0
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M  END


  Mrv1652304032018352D          

109111  0  0  1  0            999 V2000
  -12.8605    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   22.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6208   13.3870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460   10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   22.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   21.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2881   13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0905   14.0190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   12.7875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   13.6125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.5262   12.4685    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9353   14.3645    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881   12.7875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   11.1375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9959   13.1005    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.6531   13.5892    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0026   12.3750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   12.3750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   12.7875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881   11.1375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   11.5500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1834   12.9572    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0026   11.5500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   12.3750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737   11.5500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.7137   10.7748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   11.5500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.2780   13.8757    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   12.3750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0299   15.2830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   14.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3727   14.7942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   14.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3386   12.6118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4050   14.9965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8406   13.4460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   13.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5262   10.6315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1834   10.1428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9012   12.1820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   11.5500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   12.3750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   15.2625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   13.6125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   13.2000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   13.2000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8083   13.2438    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4656   13.7325    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   11.9625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   10.7250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7137   12.3252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1484   12.9366    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5211   11.7333    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   11.9625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   13.2000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   10.7250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   11.9625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3865   13.1708    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5901   12.2645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   13.2000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   10.7250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
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 11  9  1  0  0  0  0
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 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
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 26 17  1  0  0  0  0
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 35 33  1  0  0  0  0
 36 34  1  0  0  0  0
 37 35  1  0  0  0  0
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 39 37  1  0  0  0  0
 45  3  1  4  0  0  0
 46 44  1  0  0  0  0
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 47 46  1  0  0  0  0
 48 40  1  0  0  0  0
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 51 43  1  1  0  0  0
 52 39  1  0  0  0  0
 53 48  1  0  0  0  0
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 55 50  1  0  0  0  0
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 55101  1  1  0  0  0
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 60106  1  6  0  0  0
 61107  1  1  0  0  0
 62108  1  6  0  0  0
 63109  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0340053

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(CCCCCCCC)=C(/[H])CCCCCCCCCCCCCC(O)=N[C@@]([H])(CO[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O[C@]2([H])O[C@]([H])(CO)[C@]([H])(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)[C@]([H])(O)C(\[H])=C(/[H])CCCCCCCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C65H118N2O21/c1-4-6-8-10-12-14-16-18-19-20-21-22-23-24-25-27-29-31-33-35-37-39-52(75)67-46(47(72)38-36-34-32-30-28-26-17-15-13-11-9-7-5-2)44-83-62-57(79)56(78)59(51(43-70)85-62)86-63-58(80)61(55(77)50(42-69)84-63)88-65(64(81)82)40-48(73)53(66-45(3)71)60(87-65)54(76)49(74)41-68/h18-19,36,38,46-51,53-63,68-70,72-74,76-80H,4-17,20-35,37,39-44H2,1-3H3,(H,66,71)(H,67,75)(H,81,82)/b19-18-,38-36+/t46-,47+,48-,49+,50+,51+,53+,54+,55-,56+,57+,58+,59+,60+,61-,62+,63-,65-/m0/s1

> <INCHI_KEY>
PFJKOHUKELZMLE-VEUXDRLPSA-N

> <FORMULA>
C65H118N2O21

> <MOLECULAR_WEIGHT>
1263.652

> <EXACT_MASS>
1262.822708828

> <JCHEM_ACCEPTOR_COUNT>
23

> <JCHEM_ATOM_COUNT>
206

> <JCHEM_AVERAGE_POLARIZABILITY>
146.68136847954696

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4S,5R,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R,4E)-3-hydroxy-2-{[(15Z)-1-hydroxytetracos-15-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-carboxylic acid

> <ALOGPS_LOGP>
5.23

> <JCHEM_LOGP>
9.158787484944249

> <ALOGPS_LOGS>
-4.85

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
5.349564611584274

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0638042350267387

> <JCHEM_PKA_STRONGEST_BASIC>
2.50895711689865

> <JCHEM_POLAR_SURFACE_AREA>
380.3900000000001

> <JCHEM_REFRACTIVITY>
329.84159999999974

> <JCHEM_ROTATABLE_BOND_COUNT>
50

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.77e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4S,5R,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R,4E)-3-hydroxy-2-{[(15Z)-1-hydroxytetracos-15-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-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     -24.006  18.480   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003  42.350   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.425  24.989   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -22.673  19.250   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669  41.580   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -21.339  18.480   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669  40.040   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -20.005  19.250   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  39.270   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -18.672  18.480   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  37.730   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -17.338  19.250   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  36.960   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -16.004  18.480   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  35.420   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -14.671  19.250   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  34.650   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -14.671  20.790   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -13.337  21.560   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -12.003  20.790   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -10.669  21.560   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -9.336  20.790   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -8.002  21.560   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.668  20.790   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.335  21.560   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668  33.110   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.001  20.790   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335  32.340   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.667  21.560   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335  30.800   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.334  20.790   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.001  30.030   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.000  21.560   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.001  28.490   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.334  20.790   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.335  27.720   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.667  21.560   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.335  26.180   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.001  20.790   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      22.855  21.827   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      21.929  27.081   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      17.338  25.410   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      12.003  19.250   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       8.002  23.100   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      24.436  26.169   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       6.668  23.870   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       6.668  25.410   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      23.382  23.275   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      20.413  26.814   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      17.338  23.870   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      12.003  20.790   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       5.335  21.560   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      22.392  24.454   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      19.886  25.367   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      18.672  23.100   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      13.337  23.100   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      12.003  23.870   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      17.338  20.790   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      13.337  21.560   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      20.876  24.187   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      18.672  21.560   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      10.669  23.100   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      16.004  21.560   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      21.866  20.113   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      21.339  21.560   0.000  0.00  0.00           C+0
HETATM   66  N   UNK     0      22.919  25.901   0.000  0.00  0.00           N+0
HETATM   67  N   UNK     0       5.335  23.100   0.000  0.00  0.00           N+0
HETATM   68  O   UNK     0      22.456  28.528   0.000  0.00  0.00           O+0
HETATM   69  O   UNK     0      18.672  26.180   0.000  0.00  0.00           O+0
HETATM   70  O   UNK     0      10.669  18.480   0.000  0.00  0.00           O+0
HETATM   71  O   UNK     0      24.962  27.616   0.000  0.00  0.00           O+0
HETATM   72  O   UNK     0       8.002  26.180   0.000  0.00  0.00           O+0
HETATM   73  O   UNK     0      24.899  23.542   0.000  0.00  0.00           O+0
HETATM   74  O   UNK     0      19.423  27.993   0.000  0.00  0.00           O+0
HETATM   75  O   UNK     0       6.668  20.790   0.000  0.00  0.00           O+0
HETATM   76  O   UNK     0      18.369  25.099   0.000  0.00  0.00           O+0
HETATM   77  O   UNK     0      20.005  23.870   0.000  0.00  0.00           O+0
HETATM   78  O   UNK     0      14.671  23.870   0.000  0.00  0.00           O+0
HETATM   79  O   UNK     0      12.003  25.410   0.000  0.00  0.00           O+0
HETATM   80  O   UNK     0      17.338  19.250   0.000  0.00  0.00           O+0
HETATM   81  O   UNK     0      23.382  19.845   0.000  0.00  0.00           O+0
HETATM   82  O   UNK     0      20.876  18.933   0.000  0.00  0.00           O+0
HETATM   83  O   UNK     0       9.336  23.870   0.000  0.00  0.00           O+0
HETATM   84  O   UNK     0      16.004  23.100   0.000  0.00  0.00           O+0
HETATM   85  O   UNK     0      10.669  21.560   0.000  0.00  0.00           O+0
HETATM   86  O   UNK     0      14.671  20.790   0.000  0.00  0.00           O+0
HETATM   87  O   UNK     0      20.349  22.740   0.000  0.00  0.00           O+0
HETATM   88  O   UNK     0      20.005  20.790   0.000  0.00  0.00           O+0
HETATM   89  H   UNK     0     -16.004  21.560   0.000  0.00  0.00           H+0
HETATM   90  H   UNK     0     -13.337  23.100   0.000  0.00  0.00           H+0
HETATM   91  H   UNK     0       6.668  28.490   0.000  0.00  0.00           H+0
HETATM   92  H   UNK     0       4.001  25.410   0.000  0.00  0.00           H+0
HETATM   93  H   UNK     0       8.002  24.640   0.000  0.00  0.00           H+0
HETATM   94  H   UNK     0       5.335  24.640   0.000  0.00  0.00           H+0
HETATM   95  H   UNK     0      23.909  24.722   0.000  0.00  0.00           H+0
HETATM   96  H   UNK     0      21.402  25.634   0.000  0.00  0.00           H+0
HETATM   97  H   UNK     0      17.338  22.330   0.000  0.00  0.00           H+0
HETATM   98  H   UNK     0      13.337  20.020   0.000  0.00  0.00           H+0
HETATM   99  H   UNK     0      21.866  23.007   0.000  0.00  0.00           H+0
HETATM  100  H   UNK     0      18.944  24.148   0.000  0.00  0.00           H+0
HETATM  101  H   UNK     0      19.639  21.902   0.000  0.00  0.00           H+0
HETATM  102  H   UNK     0      14.671  22.330   0.000  0.00  0.00           H+0
HETATM  103  H   UNK     0      13.337  24.640   0.000  0.00  0.00           H+0
HETATM  104  H   UNK     0      18.672  20.020   0.000  0.00  0.00           H+0
HETATM  105  H   UNK     0      12.003  22.330   0.000  0.00  0.00           H+0
HETATM  106  H   UNK     0      19.388  24.585   0.000  0.00  0.00           H+0
HETATM  107  H   UNK     0      17.902  22.894   0.000  0.00  0.00           H+0
HETATM  108  H   UNK     0      10.669  24.640   0.000  0.00  0.00           H+0
HETATM  109  H   UNK     0      16.004  20.020   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3   45                                                            
CONECT    4    1    6                                                       
CONECT    5    2    7                                                       
CONECT    6    4    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   26                                                       
CONECT   18   16   19   89                                                  
CONECT   19   18   20   90                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   27                                                       
CONECT   26   17   28                                                       
CONECT   27   25   29                                                       
CONECT   28   26   30                                                       
CONECT   29   27   31                                                       
CONECT   30   28   32                                                       
CONECT   31   29   33                                                       
CONECT   32   30   34                                                       
CONECT   33   31   35                                                       
CONECT   34   32   36                                                       
CONECT   35   33   37                                                       
CONECT   36   34   38   91                                                  
CONECT   37   35   39                                                       
CONECT   38   36   47   92                                                  
CONECT   39   37   52                                                       
CONECT   40   48   65                                                       
CONECT   41   49   68                                                       
CONECT   42   50   69                                                       
CONECT   43   51   70                                                       
CONECT   44   46   83                                                       
CONECT   45    3   66   71                                                  
CONECT   46   44   47   67   93                                             
CONECT   47   38   46   72   94                                             
CONECT   48   40   53   73   95                                             
CONECT   49   41   54   74   96                                             
CONECT   50   42   55   84   97                                             
CONECT   51   43   59   85   98                                             
CONECT   52   39   67   75                                                  
CONECT   53   48   60   66   99                                             
CONECT   54   49   60   76  100                                             
CONECT   55   50   61   77  101                                             
CONECT   56   57   59   78  102                                             
CONECT   57   56   62   79  103                                             
CONECT   58   61   63   80  104                                             
CONECT   59   51   56   86  105                                             
CONECT   60   53   54   87  106                                             
CONECT   61   55   58   88  107                                             
CONECT   62   57   83   85  108                                             
CONECT   63   58   84   86  109                                             
CONECT   64   65   81   82                                                  
CONECT   65   40   64   87   88                                             
CONECT   66   45   53                                                       
CONECT   67   46   52                                                       
CONECT   68   41                                                            
CONECT   69   42                                                            
CONECT   70   43                                                            
CONECT   71   45                                                            
CONECT   72   47                                                            
CONECT   73   48                                                            
CONECT   74   49                                                            
CONECT   75   52                                                            
CONECT   76   54                                                            
CONECT   77   55                                                            
CONECT   78   56                                                            
CONECT   79   57                                                            
CONECT   80   58                                                            
CONECT   81   64                                                            
CONECT   82   64                                                            
CONECT   83   44   62                                                       
CONECT   84   50   63                                                       
CONECT   85   51   62                                                       
CONECT   86   59   63                                                       
CONECT   87   60   65                                                       
CONECT   88   61   65                                                       
CONECT   89   18                                                            
CONECT   90   19                                                            
CONECT   91   36                                                            
CONECT   92   38                                                            
CONECT   93   46                                                            
CONECT   94   47                                                            
CONECT   95   48                                                            
CONECT   96   49                                                            
CONECT   97   50                                                            
CONECT   98   51                                                            
CONECT   99   53                                                            
CONECT  100   54                                                            
CONECT  101   55                                                            
CONECT  102   56                                                            
CONECT  103   57                                                            
CONECT  104   58                                                            
CONECT  105   59                                                            
CONECT  106   60                                                            
CONECT  107   61                                                            
CONECT  108   62                                                            
CONECT  109   63                                                            
MASTER        0    0    0    0    0    0    0    0  109    0  222    0
END

View in JSmol

Synonyms

Value	Source
alpha-Neu5ac-(2->3)-beta-D-gal-(1->4)-beta-D-GLC-(11)-N-(15Z)-tetracos-15-enoylsphingosine	ChEBI
alpha-Neu5ac-(2->3)-beta-D-gal-(1->4)-beta-D-GLC-(11)-N-cis-tetracos-15-enoylsphingosine	ChEBI
g(m3) Ganglioside	ChEBI
GM3	ChEBI
Monosialodihexosylganglioside	ChEBI
Monosialoganglioside GM3	ChEBI
NANA-gal-GLC-ceramide	ChEBI
a-Neu5ac-(2->3)-b-D-gal-(1->4)-b-D-GLC-(11)-N-(15Z)-tetracos-15-enoylsphingosine	Generator
Α-neu5ac-(2->3)-β-D-gal-(1->4)-β-D-GLC-(11)-N-(15Z)-tetracos-15-enoylsphingosine	Generator
a-Neu5ac-(2->3)-b-D-gal-(1->4)-b-D-GLC-(11)-N-cis-tetracos-15-enoylsphingosine	Generator
Α-neu5ac-(2->3)-β-D-gal-(1->4)-β-D-GLC-(11)-N-cis-tetracos-15-enoylsphingosine	Generator
GM3, Ganglioside	MeSH
Hematoside	MeSH
II3neuaclaccer	MeSH
Lactosylceramide, sialyl	MeSH
Sialyl lactosylceramide	MeSH
Sialyllactosylceramide	MeSH
Ganglioside GM3	MeSH

Chemical Formula

C₆₅H₁₁₈N₂O₂₁

Average Mass

1263.6520 Da

Monoisotopic Mass

1262.82271 Da

IUPAC Name

(2S,4S,5R,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R,4E)-3-hydroxy-2-{[(15Z)-1-hydroxytetracos-15-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-carboxylic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCCCCC)=C(/[H])CCCCCCCCCCCCCC(O)=N[C@@]([H])(CO[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O[C@]2([H])O[C@]([H])(CO)[C@]([H])(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)[C@]([H])(O)C(\[H])=C(/[H])CCCCCCCCCCCCC

InChI Identifier

InChI=1S/C65H118N2O21/c1-4-6-8-10-12-14-16-18-19-20-21-22-23-24-25-27-29-31-33-35-37-39-52(75)67-46(47(72)38-36-34-32-30-28-26-17-15-13-11-9-7-5-2)44-83-62-57(79)56(78)59(51(43-70)85-62)86-63-58(80)61(55(77)50(42-69)84-63)88-65(64(81)82)40-48(73)53(66-45(3)71)60(87-65)54(76)49(74)41-68/h18-19,36,38,46-51,53-63,68-70,72-74,76-80H,4-17,20-35,37,39-44H2,1-3H3,(H,66,71)(H,67,75)(H,81,82)/b19-18-,38-36+/t46-,47+,48-,49+,50+,51+,53+,54+,55-,56+,57+,58+,59+,60+,61-,62+,63-,65-/m0/s1

InChI Key

PFJKOHUKELZMLE-VEUXDRLPSA-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	5.23	ALOGPS
logP	9.16	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	3.06	ChemAxon
pKa (Strongest Basic)	2.51	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	23	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	380.39 Å²	ChemAxon
Rotatable Bond Count	50	ChemAxon
Refractivity	329.84 m³·mol⁻¹	ChemAxon
Polarizability	146.68 Å³	ChemAxon
Number of Rings	3	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

86583360

PDB ID

Not Available

ChEBI ID

84118

Good Scents ID

Not Available

References

General References

de Jong A, Cheng TY, Huang S, Gras S, Birkinshaw RW, Kasmar AG, Van Rhijn I, Pena-Cruz V, Ruan DT, Altman JD, Rossjohn J, Moody DB: CD1a-autoreactive T cells recognize natural skin oils that function as headless antigens. Nat Immunol. 2014 Feb;15(2):177-85. doi: 10.1038/ni.2790. Epub 2013 Dec 22. [PubMed:24362891 ]

Showing NP-Card for Monosialoganglioside GM3 (NP0340053)

MOL for NP0340053 (Monosialoganglioside GM3)

3D MOL for NP0340053 (Monosialoganglioside GM3)

3D SDF for NP0340053 (Monosialoganglioside GM3)

3D-SDF for NP0340053 (Monosialoganglioside GM3)

PDB for NP0340053 (Monosialoganglioside GM3)

3D PDB for NP0340053 (Monosialoganglioside GM3)

SMILES for NP0340053 (Monosialoganglioside GM3)

INCHI for NP0340053 (Monosialoganglioside GM3)

Structure for NP0340053 (Monosialoganglioside GM3)

3D Structure for NP0340053 (Monosialoganglioside GM3)