NP-MRD: Showing NP-Card for Lactosylceramide (d18:1/24:1(15Z)) (NP0334113)

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Record Information

Version

2.0

Created at

2024-09-09 22:14:55 UTC

Updated at

2024-09-09 22:14:55 UTC

NP-MRD ID

NP0334113

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lactosylceramide (d18:1/24:1(15Z))

Description

Lactosylceramide (d18:1/24:1(15Z)) is a lactosylceramide or LacCer. Lactosylceramides are the most important and abundant of the diosylceramides. Lactosylceramides (LacCer) were originally called 'cytolipin H'. It is found in small amounts only in most animal tissues, but it has a number of significant biological functions and it is of great importance as the biosynthetic precursor of most of the neutral oligoglycosylceramides, sulfatides and gangliosides. In animal tissues, biosynthesis of lactosylceramide involves addition of the second monosaccharides unit (galactose) as its nucleotide derivative to monoglucosylceramide, catalysed by a specific beta-1,4-galactosyltransferase on the lumenal side of the Golgi apparatus. The glucosylceramide precursor must first cross from the cytosolic side of the membrane, possibly via the action of a flippase. The lactosylceramide produced can be further glycosylated or transferred to the plasma membrane. Lactosylceramide may assist in stabilizing the plasma membrane and activating receptor molecules in the special micro-domains or rafts, as with the cerebrosides. It may also have its own specialized function in the immunological system in that it is known to bind to specific bacteria. In addition, it is believed that a number of pro-inflammatory factors activate lactosylceramide synthase to generate lactosylceramide, which in turn activates "oxygen-sensitive" signalling pathways that affect such cellular processes as proliferation, adhesion, migration and angiogenesis. Dysfunctions in these pathways can affect several diseases of the cardiovascular system, cancer and inflammatory states, so lactosylceramide metabolism is a potential target for new therapeutic treatments. Beta-D-Galactosyl-1,4-beta-D-glucosylceramide is the second to last step in the synthesis of N-Acylsphingosine and is converted from Glucosylceramide via the enzyme beta-1,4-galactosyltransferase 6(EC:2.4.1.-). It can be converted to Glucosylceramide via the enzyme beta-galactosidase (EC:3.2.1.23). [HMDB]

Structure

MOL SDF PDB SMILES InChI


  Mrv1572004261605502D          

 84 85  0  0  1  0            999 V2000
    7.1447    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8657    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   32.1512    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4367    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7223    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0078    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2933    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5788    4.1250    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
   27.8644    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.7171    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   20.7197   10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   21.4341    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2881    3.7125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
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  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
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 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
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 17 15  1  0  0  0  0
 18 17  2  0  0  0  0
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 25 16  1  0  0  0  0
 26 24  1  0  0  0  0
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 35 33  1  0  0  0  0
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M  END


  Mrv1572004261605502D          

 84 85  0  0  1  0            999 V2000
    7.1447    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8657    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1512    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4367    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7223    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0078    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2933    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5788    4.1250    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
   27.8644    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   27.1499    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.7184    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   18.5762    4.1250    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
   19.2907    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   22.1486    7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   22.1486    3.7125    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
   21.4341    7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.0052    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   20.0052    9.0750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.7197    3.7125    0.0000 N   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
   22.8631    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   20.0052    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   19.2907   11.1375    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
   20.7197   10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    5.3625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    3.7125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.5775    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.8631    4.9500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486    4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618    9.4875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341    8.2500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762   10.7250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052   10.7250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052    8.2500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907    9.4875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907    7.0125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197    7.0125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052    5.7750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197    9.4875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  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
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18 17  2  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 16  1  0  0  0  0
 26 24  1  0  0  0  0
 27 25  1  0  0  0  0
 28 26  1  0  0  0  0
 29 27  1  0  0  0  0
 30 28  1  0  0  0  0
 31 29  1  0  0  0  0
 32 30  1  0  0  0  0
 33 31  1  0  0  0  0
 34 32  1  0  0  0  0
 35 33  1  0  0  0  0
 36 34  1  0  0  0  0
 37 35  2  0  0  0  0
 38 36  1  0  0  0  0
 42 41  1  0  0  0  0
 43 37  1  0  0  0  0
 43 42  1  0  0  0  0
 44 39  1  6  0  0  0
 45 40  1  1  0  0  0
 46 38  1  0  0  0  0
 47 44  1  0  0  0  0
 48 47  1  0  0  0  0
 50 48  1  0  0  0  0
 51 49  1  0  0  0  0
 52 45  1  0  0  0  0
 52 49  1  0  0  0  0
 53 51  1  0  0  0  0
 54 50  1  0  0  0  0
 42 55  1  6  0  0  0
 55 46  2  0  0  0  0
 56 39  1  0  0  0  0
 57 40  1  0  0  0  0
 43 58  1  1  0  0  0
 46 59  1  4  0  0  0
 47 60  1  6  0  0  0
 48 61  1  6  0  0  0
 49 62  1  1  0  0  0
 50 63  1  6  0  0  0
 64 51  1  0  0  0  0
 65 41  1  0  0  0  0
 53 65  1  1  0  0  0
 66 44  1  0  0  0  0
 66 54  1  0  0  0  0
 67 45  1  0  0  0  0
 67 53  1  0  0  0  0
 52 68  1  1  0  0  0
 54 68  1  6  0  0  0
 69 17  1  0  0  0  0
 70 18  1  0  0  0  0
 71 35  1  0  0  0  0
 72 37  1  0  0  0  0
 42 73  1  6  0  0  0
 43 74  1  6  0  0  0
 44 75  1  1  0  0  0
 45 76  1  6  0  0  0
 47 77  1  1  0  0  0
 48 78  1  1  0  0  0
 49 79  1  6  0  0  0
 50 80  1  6  0  0  0
 81 51  1  0  0  0  0
 52 82  1  1  0  0  0
 53 83  1  6  0  0  0
 54 84  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0334113

> <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@@]2([H])O)[C@]([H])(O)C1([H])O)[C@]([H])(O)C(\[H])=C(/[H])CCCCCCCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C54H101NO13/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-46(59)55-42(43(58)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2)41-65-53-51(64)49(62)52(45(40-57)67-53)68-54-50(63)48(61)47(60)44(39-56)66-54/h17-18,35,37,42-45,47-54,56-58,60-64H,3-16,19-34,36,38-41H2,1-2H3,(H,55,59)/b18-17+,37-35+/t42-,43+,44+,45+,47-,48-,49+,50+,51?,52+,53+,54-/m0/s1

> <INCHI_KEY>
MKOKWBRPIBQYJJ-AMCOFLHFSA-N

> <FORMULA>
C54H101NO13

> <MOLECULAR_WEIGHT>
972.396

> <EXACT_MASS>
971.727292316

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
169

> <JCHEM_AVERAGE_POLARIZABILITY>
118.86969380437878

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(15E)-N-[(2S,3R,4E)-1-{[(2R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]tetracos-15-enimidic acid

> <ALOGPS_LOGP>
7.36

> <JCHEM_LOGP>
11.337915642666665

> <ALOGPS_LOGS>
-5.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.939338000391112

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.8112932365856915

> <JCHEM_PKA_STRONGEST_BASIC>
2.59996375782802

> <JCHEM_POLAR_SURFACE_AREA>
231.34999999999994

> <JCHEM_REFRACTIVITY>
269.0486

> <JCHEM_ROTATABLE_BOND_COUNT>
43

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.59e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(15E)-N-[(2S,3R,4E)-1-{[(2R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]tetracos-15-enimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-16         0                                  
HETATM    1  C   UNK     0      13.337  18.480   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      61.349   7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.337  16.940   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      60.016   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.670  16.170   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      58.682   7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.670  14.630   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      57.348   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.004  13.860   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      56.015   7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.004  12.320   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      54.681   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.338  11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      53.347   7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.338  10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      52.013   6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.672   9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.672   7.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.005   6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      21.339   7.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      22.673   6.930   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      24.006   7.700   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      25.340   6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      26.674   7.700   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      50.680   7.700   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      28.007   6.930   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      49.346   6.930   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      29.341   7.700   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      48.012   7.700   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      30.675   6.930   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      46.679   6.930   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      32.008   7.700   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      45.345   7.700   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      33.342   6.930   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      44.011   6.930   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      34.676   7.700   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      42.678   7.700   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      36.009   6.930   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      33.342  16.170   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      41.344  14.630   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      40.010   9.240   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      40.010   7.700   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      41.344   6.930   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      34.676  16.940   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      40.010  13.860   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      37.343   7.700   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      34.676  18.480   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      36.009  19.250   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      37.343  13.860   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      37.343  18.480   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      37.343  12.320   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      38.677  14.630   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      38.677  11.550   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      37.343  16.940   0.000  0.00  0.00           C+0
HETATM   55  N   UNK     0      38.677   6.930   0.000  0.00  0.00           N+0
HETATM   56  O   UNK     0      33.342  14.630   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      42.678  13.860   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      41.344   5.390   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      37.343   9.240   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      33.342  19.250   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      36.009  20.790   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      36.009  14.630   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      38.677  19.250   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      36.009  11.550   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0      38.677  10.010   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0      36.009  16.170   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0      40.010  12.320   0.000  0.00  0.00           O+0
HETATM   68  O   UNK     0      38.677  16.170   0.000  0.00  0.00           O+0
HETATM   69  H   UNK     0      20.005  10.010   0.000  0.00  0.00           H+0
HETATM   70  H   UNK     0      17.338   6.930   0.000  0.00  0.00           H+0
HETATM   71  H   UNK     0      44.011   5.390   0.000  0.00  0.00           H+0
HETATM   72  H   UNK     0      42.678   9.240   0.000  0.00  0.00           H+0
HETATM   73  H   UNK     0      41.344   8.470   0.000  0.00  0.00           H+0
HETATM   74  H   UNK     0      40.010   6.160   0.000  0.00  0.00           H+0
HETATM   75  H   UNK     0      33.342  17.710   0.000  0.00  0.00           H+0
HETATM   76  H   UNK     0      40.010  15.400   0.000  0.00  0.00           H+0
HETATM   77  H   UNK     0      34.676  20.020   0.000  0.00  0.00           H+0
HETATM   78  H   UNK     0      37.343  20.020   0.000  0.00  0.00           H+0
HETATM   79  H   UNK     0      37.343  15.400   0.000  0.00  0.00           H+0
HETATM   80  H   UNK     0      36.009  17.710   0.000  0.00  0.00           H+0
HETATM   81  H   UNK     0      36.009  13.090   0.000  0.00  0.00           H+0
HETATM   82  H   UNK     0      38.677  13.090   0.000  0.00  0.00           H+0
HETATM   83  H   UNK     0      37.343  10.780   0.000  0.00  0.00           H+0
HETATM   84  H   UNK     0      38.677  17.710   0.000  0.00  0.00           H+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    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   25                                                       
CONECT   17   15   18   69                                                  
CONECT   18   17   19   70                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   26                                                       
CONECT   25   16   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                                                       
CONECT   32   30   34                                                       
CONECT   33   31   35                                                       
CONECT   34   32   36                                                       
CONECT   35   33   37   71                                                  
CONECT   36   34   38                                                       
CONECT   37   35   43   72                                                  
CONECT   38   36   46                                                       
CONECT   39   44   56                                                       
CONECT   40   45   57                                                       
CONECT   41   42   65                                                       
CONECT   42   41   43   55   73                                             
CONECT   43   37   42   58   74                                             
CONECT   44   39   47   66   75                                             
CONECT   45   40   52   67   76                                             
CONECT   46   38   55   59                                                  
CONECT   47   44   48   60   77                                             
CONECT   48   47   50   61   78                                             
CONECT   49   51   52   62   79                                             
CONECT   50   48   54   63   80                                             
CONECT   51   49   53   64   81                                             
CONECT   52   45   49   68   82                                             
CONECT   53   51   65   67   83                                             
CONECT   54   50   66   68   84                                             
CONECT   55   42   46                                                       
CONECT   56   39                                                            
CONECT   57   40                                                            
CONECT   58   43                                                            
CONECT   59   46                                                            
CONECT   60   47                                                            
CONECT   61   48                                                            
CONECT   62   49                                                            
CONECT   63   50                                                            
CONECT   64   51                                                            
CONECT   65   41   53                                                       
CONECT   66   44   54                                                       
CONECT   67   45   53                                                       
CONECT   68   52   54                                                       
CONECT   69   17                                                            
CONECT   70   18                                                            
CONECT   71   35                                                            
CONECT   72   37                                                            
CONECT   73   42                                                            
CONECT   74   43                                                            
CONECT   75   44                                                            
CONECT   76   45                                                            
CONECT   77   47                                                            
CONECT   78   48                                                            
CONECT   79   49                                                            
CONECT   80   50                                                            
CONECT   81   51                                                            
CONECT   82   52                                                            
CONECT   83   53                                                            
CONECT   84   54                                                            
MASTER        0    0    0    0    0    0    0    0   84    0  170    0
END

View in JSmol

Synonyms

Value	Source
(15E)-N-[(2S,3R,4E)-1-{[(2R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]tetracos-15-enimidate	Generator

Chemical Formula

C₅₄H₁₀₁NO₁₃

Average Mass

972.3960 Da

Monoisotopic Mass

971.72729 Da

IUPAC Name

(15E)-N-[(2S,3R,4E)-1-{[(2R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]tetracos-15-enimidic 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@@]2([H])O)[C@]([H])(O)C1([H])O)[C@]([H])(O)C(\[H])=C(/[H])CCCCCCCCCCCCC

InChI Identifier

InChI=1S/C54H101NO13/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-46(59)55-42(43(58)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2)41-65-53-51(64)49(62)52(45(40-57)67-53)68-54-50(63)48(61)47(60)44(39-56)66-54/h17-18,35,37,42-45,47-54,56-58,60-64H,3-16,19-34,36,38-41H2,1-2H3,(H,55,59)/b18-17+,37-35+/t42-,43+,44+,45+,47-,48-,49+,50+,51?,52+,53+,54-/m0/s1

InChI Key

MKOKWBRPIBQYJJ-AMCOFLHFSA-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 glycosphingolipids. These are sphingolipids containing a saccharide moiety glycosidically attached to the sphingoid base. Although saccharide moieties are mostly O-glycosidically linked to the ceramide moiety, other sphingolipids with glycosidic bonds of other types (e.G. S-,C-, or N-type) has been reported.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Glycosphingolipids

Direct Parent

Glycosphingolipids

Alternative Parents

Substituents

Glycosphingolipid
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Disaccharide
Fatty acyl
Oxane
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Carboximidic acid derivative
Carboximidic acid
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Alcohol
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	7.36	ALOGPS
logP	11.34	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	5.81	ChemAxon
pKa (Strongest Basic)	2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	231.35 Å²	ChemAxon
Rotatable Bond Count	43	ChemAxon
Refractivity	269.05 m³·mol⁻¹	ChemAxon
Polarizability	118.87 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Lactosylceramide (d18:1/24:1(15Z)) (NP0334113)

MOL for NP0334113 (Lactosylceramide (d18:1/24:1(15Z)))

3D MOL for NP0334113 (Lactosylceramide (d18:1/24:1(15Z)))

3D SDF for NP0334113 (Lactosylceramide (d18:1/24:1(15Z)))

3D-SDF for NP0334113 (Lactosylceramide (d18:1/24:1(15Z)))

PDB for NP0334113 (Lactosylceramide (d18:1/24:1(15Z)))

3D PDB for NP0334113 (Lactosylceramide (d18:1/24:1(15Z)))

SMILES for NP0334113 (Lactosylceramide (d18:1/24:1(15Z)))

INCHI for NP0334113 (Lactosylceramide (d18:1/24:1(15Z)))

Structure for NP0334113 (Lactosylceramide (d18:1/24:1(15Z)))

3D Structure for NP0334113 (Lactosylceramide (d18:1/24:1(15Z)))