NP-MRD: Showing NP-Card for Disialosyl galactosyl globoside (NP0087563)

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Record Information

Version

2.0

Created at

2022-05-11 16:53:08 UTC

Updated at

2022-05-11 16:53:08 UTC

NP-MRD ID

NP0087563

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Disialosyl galactosyl globoside

Description

Disialosyl galactosyl globoside, also known as DSGG, belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. Disialosyl galactosyl globoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Antidisialosyl antibodies have been found in some patients with chronic idiopathic ataxic neuropathy (CIAN) (PMID: 12420092 ). Globosides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Biosynthesis of Disialosyl galactosyl globoside (DSGG)is mediated by sialyltransferases from MSGG (monosialylgalactosylgloboside) (PMID: 17123352 ). Disialosyl galactosyl globoside was first documented in 2000 (PMID: 10675485). Disialosyl galactosyl globoside is a renal cell carcinoma (RCC)-associated antigen which mediates adhesion of RCC TOS-1 cells to certain lung tissue target cells (PMID: 17123352).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231220442D          

 68 70  0  0  1  0            999 V2000
   15.1809  -11.7823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3080  -10.6553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4513   -9.4178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4842   -6.9428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1658  -10.6553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3243  -13.0197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7369  -11.4803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3080   -9.0054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3091   -7.7678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4665  -13.8447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7216   -4.7994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7520  -11.7823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6580  -10.6553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8342   -6.9428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8955   -9.9408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0224   -7.7678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1658   -9.0054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3091   -9.4178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8342   -4.6888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3231  -12.6072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7381   -6.9428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0237   -8.1804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3243  -13.8447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5967   -4.7994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3091   -4.0848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3160  -11.7933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4712  -12.1388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8955  -13.8447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0717   -4.7994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2230  -10.7315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8955  -11.3698    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.8955  -13.0197    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.1809  -12.6072    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.6099  -12.6072    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.0224  -10.2428    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.6099  -11.7823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7369  -10.6553    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.0224   -9.4178    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.4665  -13.0197    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.4513  -10.2428    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.7369   -9.0054    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.4842   -5.5138    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.0717   -6.2283    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.3091   -5.5138    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.3091   -6.9428    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.7216   -6.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7520  -12.6072    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.4830  -10.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2467   -6.2283    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.8803  -10.2428    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.7369   -8.1804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8803   -9.4178    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.5948   -9.0054    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.8342   -5.5138    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.4106  -10.8748    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.5948   -8.1804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0375  -13.0197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6099  -14.2572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0237   -7.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0092   -5.5138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4842   -4.0848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6099  -15.0823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1285  -11.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0717   -3.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7533  -11.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5658  -11.2202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6094  -12.2773    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.7417   -6.7999    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 31  1  0  0  0  0
  1 33  1  0  0  0  0
 31  2  1  6  0  0  0
 35  2  1  1  0  0  0
  3 40  1  0  0  0  0
  3 41  1  0  0  0  0
  4 43  1  0  0  0  0
  4 45  1  0  0  0  0
 40  5  1  1  0  0  0
 50  5  1  1  0  0  0
 34  6  1  6  0  0  0
 37  7  1  6  0  0  0
 38  8  1  1  0  0  0
 45  9  1  1  0  0  0
  9 56  1  0  0  0  0
 39 10  1  6  0  0  0
 44 11  1  1  0  0  0
 47 12  1  1  0  0  0
 13 48  1  0  0  0  0
 49 14  1  6  0  0  0
 15 48  2  0  0  0  0
 16 51  1  0  0  0  0
 52 17  1  1  0  0  0
 53 18  1  1  0  0  0
 54 19  1  1  0  0  0
 20 57  1  0  0  0  0
 21 59  1  0  0  0  0
 22 59  2  0  0  0  0
 23 58  2  0  0  0  0
 24 60  1  0  0  0  0
 25 61  2  0  0  0  0
 26 63  2  0  0  0  0
 27 65  2  0  0  0  0
 32 28  1  1  0  0  0
 28 58  1  0  0  0  0
 42 29  1  6  0  0  0
 29 61  1  0  0  0  0
 55 30  1  1  0  0  0
 30 65  1  0  0  0  0
 31 36  1  0  0  0  0
 31 48  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 33 39  1  0  0  0  0
 33 67  1  1  0  0  0
 34 36  1  0  0  0  0
 35 37  1  0  0  0  0
 35 38  1  0  0  0  0
 37 40  1  0  0  0  0
 38 41  1  0  0  0  0
 39 47  1  0  0  0  0
 41 51  1  1  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 43 49  1  0  0  0  0
 43 68  1  6  0  0  0
 44 46  1  0  0  0  0
 45 46  1  0  0  0  0
 45 59  1  0  0  0  0
 47 57  1  0  0  0  0
 49 54  1  0  0  0  0
 50 52  1  0  0  0  0
 50 55  1  0  0  0  0
 52 53  1  0  0  0  0
 53 56  1  0  0  0  0
 54 60  1  0  0  0  0
 55 63  1  0  0  0  0
 58 62  1  0  0  0  0
 61 64  1  0  0  0  0
 65 66  1  0  0  0  0
M  END

     RDKit          3D

125127  0  0  0  0  0  0  0  0999 V2000
    2.1436    3.7966    0.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8311    3.1228    0.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3218    3.4294   -1.0289 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2524    2.2189    0.9491 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0000    1.5520    0.7319 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8275    2.5247   -0.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7917    3.7008    0.2417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8378    0.2591    0.0508 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0218   -0.5828    0.7964 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2346   -0.6053    0.1718 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3748   -1.6321   -0.8160 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2868   -1.0740   -1.7307 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1486   -2.1971   -2.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8237   -2.8226   -1.2142 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0829    0.0870   -1.2506 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2698    0.0858   -2.0441 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.9496   -0.4579   -0.4613 C   0  0  2  0  0  0  0  0  0  0  0  0
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    6.9057   -1.4380   -2.3991 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1199   -1.5940    0.8653 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0670   -0.6403    0.6968 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -5.7821    0.1487   -1.5812 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.5323    3.6341   -0.7968 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2003    2.5491    1.1883 O   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.5830   -2.0061    1.0890 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.4922    1.5486    1.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9879   -1.9769    3.4175 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0783    1.4236    1.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4333    3.3284   -0.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8689    1.0157   -1.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 02231220442D          

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M  END
> <DATABASE_ID>
NP0087563

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(O[C@@](C[C@H](O)[C@H]1NC(C)=O)(OC[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O[C@@]2(C[C@H](O)[C@@H](NC(C)=O)[C@@]([H])(O2)[C@H](O)[C@H](O)CO)C(O)=O)[C@H]1O)[C@@H](NC(C)=O)C=O)C(O)=O)[C@H](O)[C@H](O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C36H59N3O27/c1-11(44)37-14(6-40)28(25(54)19(51)10-61-35(33(57)58)4-15(47)21(38-12(2)45)29(64-35)23(52)17(49)7-41)63-32-27(56)31(26(55)20(9-43)62-32)66-36(34(59)60)5-16(48)22(39-13(3)46)30(65-36)24(53)18(50)8-42/h6,14-32,41-43,47-56H,4-5,7-10H2,1-3H3,(H,37,44)(H,38,45)(H,39,46)(H,57,58)(H,59,60)/t14-,15-,16-,17+,18+,19+,20+,21+,22+,23+,24+,25-,26-,27+,28+,29+,30+,31-,32-,35+,36-/m0/s1

> <INCHI_KEY>
SKJCZIMWAATHMG-CZYIXMLQSA-N

> <FORMULA>
C36H59N3O27

> <MOLECULAR_WEIGHT>
965.8576

> <EXACT_MASS>
965.333593697

> <JCHEM_ACCEPTOR_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
90.52737606672908

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
18

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,4S,5R,6R)-2-{[(2R,3S,4R,5R)-4-{[(2R,3R,4S,5S,6R)-4-{[(2S,4S,5R,6R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-acetamido-2,3-dihydroxy-6-oxohexyl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

> <ALOGPS_LOGP>
-2.53

> <JCHEM_LOGP>
-10.431699295666666

> <ALOGPS_LOGS>
-1.45

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.20080319779832

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5984396235431393

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6558033954201417

> <JCHEM_POLAR_SURFACE_AREA>
497.3399999999999

> <JCHEM_REFRACTIVITY>
201.40279999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
23

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.44e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4S,5R,6R)-2-{[(2R,3S,4R,5R)-4-{[(2R,3R,4S,5S,6R)-4-{[(2S,4S,5R,6R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-acetamido-2,3-dihydroxy-6-oxohexyl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      28.338 -21.994   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      30.442 -19.890   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      34.442 -17.580   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      38.237 -12.960   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      35.776 -19.890   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      32.339 -24.303   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      33.109 -21.430   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      30.442 -16.810   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      39.777 -14.500   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      27.004 -25.843   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      40.547  -8.959   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      25.670 -21.994   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      27.362 -19.890   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      35.157 -12.960   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      29.672 -18.556   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      31.775 -14.500   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      35.776 -16.810   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      39.777 -17.580   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      35.157  -8.752   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      23.003 -23.533   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      42.444 -12.960   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      41.111 -15.270   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      32.339 -25.843   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      32.847  -8.959   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      39.777  -7.625   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      36.057 -22.014   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      40.080 -22.659   0.000  0.00  0.00           O+0
HETATM   28  N   UNK     0      29.672 -25.843   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0      37.467  -8.959   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0      39.616 -20.032   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0      29.672 -21.224   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      29.672 -24.303   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      28.338 -23.533   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      31.005 -23.533   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      31.775 -19.120   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      31.005 -21.994   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      33.109 -19.890   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      31.775 -17.580   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      27.004 -24.303   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      34.442 -19.120   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      33.109 -16.810   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      38.237 -10.292   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      37.467 -11.626   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      39.777 -10.292   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      39.777 -12.960   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      40.547 -11.626   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      25.670 -23.533   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      28.902 -19.890   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      35.927 -11.626   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      37.110 -19.120   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      33.109 -15.270   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      37.110 -17.580   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      38.444 -16.810   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      35.157 -10.292   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      38.100 -20.300   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      38.444 -15.270   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      24.337 -24.303   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      31.005 -26.613   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      41.111 -13.730   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      33.617 -10.292   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      38.237  -7.625   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      31.005 -28.154   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      37.573 -21.747   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      37.467  -6.291   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      40.606 -21.212   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      42.123 -20.944   0.000  0.00  0.00           C+0
HETATM   67  H   UNK     0      27.271 -22.918   0.000  0.00  0.00           H+0
HETATM   68  H   UNK     0      36.851 -12.693   0.000  0.00  0.00           H+0
CONECT    1   31   33                                                       
CONECT    2   31   35                                                       
CONECT    3   40   41                                                       
CONECT    4   43   45                                                       
CONECT    5   40   50                                                       
CONECT    6   34                                                            
CONECT    7   37                                                            
CONECT    8   38                                                            
CONECT    9   45   56                                                       
CONECT   10   39                                                            
CONECT   11   44                                                            
CONECT   12   47                                                            
CONECT   13   48                                                            
CONECT   14   49                                                            
CONECT   15   48                                                            
CONECT   16   51                                                            
CONECT   17   52                                                            
CONECT   18   53                                                            
CONECT   19   54                                                            
CONECT   20   57                                                            
CONECT   21   59                                                            
CONECT   22   59                                                            
CONECT   23   58                                                            
CONECT   24   60                                                            
CONECT   25   61                                                            
CONECT   26   63                                                            
CONECT   27   65                                                            
CONECT   28   32   58                                                       
CONECT   29   42   61                                                       
CONECT   30   55   65                                                       
CONECT   31    1    2   36   48                                             
CONECT   32   28   33   34                                                  
CONECT   33    1   32   39   67                                             
CONECT   34    6   32   36                                                  
CONECT   35    2   37   38                                                  
CONECT   36   31   34                                                       
CONECT   37    7   35   40                                                  
CONECT   38    8   35   41                                                  
CONECT   39   10   33   47                                                  
CONECT   40    3    5   37                                                  
CONECT   41    3   38   51                                                  
CONECT   42   29   43   44                                                  
CONECT   43    4   42   49   68                                             
CONECT   44   11   42   46                                                  
CONECT   45    4    9   46   59                                             
CONECT   46   44   45                                                       
CONECT   47   12   39   57                                                  
CONECT   48   13   15   31                                                  
CONECT   49   14   43   54                                                  
CONECT   50    5   52   55                                                  
CONECT   51   16   41                                                       
CONECT   52   17   50   53                                                  
CONECT   53   18   52   56                                                  
CONECT   54   19   49   60                                                  
CONECT   55   30   50   63                                                  
CONECT   56    9   53                                                       
CONECT   57   20   47                                                       
CONECT   58   23   28   62                                                  
CONECT   59   21   22   45                                                  
CONECT   60   24   54                                                       
CONECT   61   25   29   64                                                  
CONECT   62   58                                                            
CONECT   63   26   55                                                       
CONECT   64   61                                                            
CONECT   65   27   30   66                                                  
CONECT   66   65                                                            
CONECT   67   33                                                            
CONECT   68   43                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  140    0
END

View in JSmol

Synonyms

Value	Source
Disialosylgalactosylgloboside	HMDB
DSGG	HMDB
Neuacalpha2-3galbeta1-3(neuacalpha2-6)galnac	HMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->6)-O-[O-(N-acetyl-alpha-neuraminosyl)-(2->3)-beta-D-galactopyranosyl-(1->3)]-2-(acetylamino)-2-deoxy-D-galactose	HMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->6)-O-[O-(N-acetyl-alpha-neuraminosyl)-(2->3)-beta-delta-galactopyranosyl-(1->3)]-2-(acetylamino)-2-deoxy-delta-galactose	HMDB
Disialylgalactosylgloboside	HMDB
(2R,4S,5R,6R)-2-{[(2R,3S,4R,5R)-4-{[(2R,3R,4S,5S,6R)-4-{[(2S,4S,5R,6R)-2-carboxy-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroxy-5-[(1-hydroxyethylidene)amino]-6-oxohexyl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate	HMDB
Disialosyl galactosyl globoside	MeSH

Chemical Formula

C₃₆H₅₉N₃O₂₇

Average Mass

965.8576 Da

Monoisotopic Mass

965.33359 Da

IUPAC Name

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

Traditional Name

CAS Registry Number

Not Available

SMILES

[H][C@]1(O[C@@](C[C@H](O)[C@H]1NC(C)=O)(OC[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O[C@@]2(C[C@H](O)[C@@H](NC(C)=O)[C@@]([H])(O2)[C@H](O)[C@H](O)CO)C(O)=O)[C@H]1O)[C@@H](NC(C)=O)C=O)C(O)=O)[C@H](O)[C@H](O)CO

InChI Identifier

InChI=1S/C36H59N3O27/c1-11(44)37-14(6-40)28(25(54)19(51)10-61-35(33(57)58)4-15(47)21(38-12(2)45)29(64-35)23(52)17(49)7-41)63-32-27(56)31(26(55)20(9-43)62-32)66-36(34(59)60)5-16(48)22(39-13(3)46)30(65-36)24(53)18(50)8-42/h6,14-32,41-43,47-56H,4-5,7-10H2,1-3H3,(H,37,44)(H,38,45)(H,39,46)(H,57,58)(H,59,60)/t14-,15-,16-,17+,18+,19+,20+,21+,22+,23+,24+,25-,26-,27+,28+,29+,30+,31-,32-,35+,36-/m0/s1

InChI Key

SKJCZIMWAATHMG-CZYIXMLQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-acylneuraminic acids

Alternative Parents

Substituents

N-acylneuraminic acid
Neuraminic acid
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
C-glucuronide
Alkyl glycoside
C-glycosyl compound
O-glycosyl compound
Glycosyl compound
Ketal
Amino saccharide
Pyran
Dicarboxylic acid or derivatives
Oxane
Monosaccharide
Fatty acyl
Acetamide
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Acetal
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aldehyde
Organic nitrogen compound
Primary alcohol
Organopnictogen compound
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

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	-2.5	ALOGPS
logP	-10	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	2.6	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	27	ChemAxon
Hydrogen Donor Count	18	ChemAxon
Polar Surface Area	497.34 Å²	ChemAxon
Rotatable Bond Count	23	ChemAxon
Refractivity	201.4 m³·mol⁻¹	ChemAxon
Polarizability	90.53 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

HMDB0006588

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023988

KNApSAcK ID

Not Available

Chemspider ID

112280

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

126334

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Satoh M, Nejad FM, Ohtani H, Ito A, Ohyama C, Saito S, Orikasa S, Hakomori S: Association of renal cell carcinoma antigen, disialylgalactosylgloboside, with c-Src and Rho A in clustered domains at the surface membrane. Int J Oncol. 2000 Mar;16(3):529-36. doi: 10.3892/ijo.16.3.529. [PubMed:10675485 ]
Senda M, Ito A, Tsuchida A, Hagiwara T, Kaneda T, Nakamura Y, Kasama K, Kiso M, Yoshikawa K, Katagiri Y, Ono Y, Ogiso M, Urano T, Furukawa K, Oshima S, Furukawa K: Identification and expression of a sialyltransferase responsible for the synthesis of disialylgalactosylgloboside in normal and malignant kidney cells: downregulation of ST6GalNAc VI in renal cancers. Biochem J. 2007 Mar 15;402(3):459-70. doi: 10.1042/BJ20061118. [PubMed:17123352 ]

Showing NP-Card for Disialosyl galactosyl globoside (NP0087563)

MOL for NP0087563 (Disialosyl galactosyl globoside)

3D MOL for NP0087563 (Disialosyl galactosyl globoside)

3D SDF for NP0087563 (Disialosyl galactosyl globoside)

3D-SDF for NP0087563 (Disialosyl galactosyl globoside)

PDB for NP0087563 (Disialosyl galactosyl globoside)

3D PDB for NP0087563 (Disialosyl galactosyl globoside)

SMILES for NP0087563 (Disialosyl galactosyl globoside)

INCHI for NP0087563 (Disialosyl galactosyl globoside)

Structure for NP0087563 (Disialosyl galactosyl globoside)

3D Structure for NP0087563 (Disialosyl galactosyl globoside)