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Showing NP-Card for Glucosylceramide (d18:1/26:1(17Z)) (NP0334119)

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Record Information
Version2.0
Created at2024-09-09 22:16:22 UTC
Updated at2024-09-09 22:16:22 UTC
NP-MRD IDNP0334119
Secondary Accession NumbersNone
Natural Product Identification
Common NameGlucosylceramide (d18:1/26:1(17Z))
DescriptionA glycosphingolipid (ceramide and oligosaccharide)or oligoglycosylceramide with one or more sialic acids (i.E. N-acetylneuraminic acid) linked on the sugar chain. It is a component the cell plasma membrane which modulates cell signal transduction events. Gangliosides have been found to be highly important in immunology. Ganglioside GL1a carries a net-negative charge at pH 7.0 And is acidic. Gangliosides can amount to 6% of the weight of lipids from brain, but they are found at low levels in all animal tissues. Cerebrosides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Cerebrosides have a single sugar group linked to ceramide. The most common are galactocerebrosides (containing galactose), the least common are glucocerebrosides (containing glucose). Galactocerebrosides are found predominantly in neuronal cell membranes. In contrast glucocerebrosides are not normally found in membranes. Instead, they are typically intermediates in the synthesis or degradation of more complex glycosphingolipids. Galactocerebrosides are synthesized from ceramide and UDP-galactose. Excess lysosomal accumulation of glucocerebrosides is found in Gaucher disease. [HMDB]
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0334119 (Glucosylceramide (d18:1/26:1(17Z)))


  Mrv2104 05252300482D          

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M  END
Download

3D MOL for NP0334119 (Glucosylceramide (d18:1/26:1(17Z)))

Download
3D SDF for NP0334119 (Glucosylceramide (d18:1/26:1(17Z)))

  Mrv2104 05252300482D          

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M  END
> <DATABASE_ID>
NP0334119

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C50H95NO8/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-28-30-32-34-36-38-40-46(54)51-43(42-58-50-49(57)48(56)47(55)45(41-52)59-50)44(53)39-37-35-33-31-29-27-16-14-12-10-8-6-4-2/h17-18,37,39,43-45,47-50,52-53,55-57H,3-16,19-36,38,40-42H2,1-2H3,(H,51,54)/b18-17+,39-37+/t43-,44+,45+,47+,48-,49+,50+/m0/s1

> <INCHI_KEY>
LVROXDRMMJVBGH-MVCHRRFKSA-N

> <FORMULA>
C50H95NO8

> <MOLECULAR_WEIGHT>
838.309

> <EXACT_MASS>
837.705769023

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
154

> <JCHEM_AVERAGE_POLARIZABILITY>
107.95828622806553

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(Z,17E)-N-[(2S,3R,4E)-3-hydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]hexacos-17-enimidic acid

> <JCHEM_LOGP>
13.997888618333338

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.20613392405592

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.813854553241642

> <JCHEM_PKA_STRONGEST_BASIC>
2.7207933676967873

> <JCHEM_POLAR_SURFACE_AREA>
152.2

> <JCHEM_REFRACTIVITY>
245.83730000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
42

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(Z,17E)-N-[(2S,3R,4E)-3-hydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]hexacos-17-enimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0334119 (Glucosylceramide (d18:1/26:1(17Z)))
Download
PDB for NP0334119 (Glucosylceramide (d18:1/26:1(17Z)))
HEADER    PROTEIN                                 25-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAY-23         0                                  
HETATM    1  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      61.349 -13.860   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      60.016 -14.630   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      58.682 -13.860   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      57.348 -14.630   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      56.015 -13.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      54.681 -14.630   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      53.347 -13.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      52.013 -14.630   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.004 -13.860   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.338 -14.630   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.672 -13.860   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      20.005 -14.630   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      21.339 -13.860   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      22.673 -14.630   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      24.006 -13.860   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      25.340 -14.630   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      26.674 -13.860   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      50.680 -13.860   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      28.007 -14.630   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      49.346 -14.630   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      29.341 -13.860   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      48.012 -13.860   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      30.675 -14.630   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      46.679 -14.630   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      32.008 -13.860   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      45.345 -13.860   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      33.342 -14.630   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      44.011 -14.630   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      34.676 -13.860   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      42.678 -13.860   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      36.009 -14.630   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      36.009  -6.930   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      40.010 -12.320   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      40.010 -13.860   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      41.344 -14.630   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      37.343  -7.700   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      37.343 -13.860   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      38.677  -6.930   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      40.010  -7.700   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      40.010  -9.240   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      38.677 -10.010   0.000  0.00  0.00           C+0
HETATM   51  N   UNK     0      38.677 -14.630   0.000  0.00  0.00           N+0
HETATM   52  O   UNK     0      34.676  -7.700   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      41.344 -16.170   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      37.343 -12.320   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      38.677  -5.390   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      41.344  -6.930   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      41.344 -10.010   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      38.677 -11.550   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  H   UNK     0      41.344 -13.090   0.000  0.00  0.00           H+0
HETATM   61  H   UNK     0      40.010 -15.400   0.000  0.00  0.00           H+0
HETATM   62  H   UNK     0      36.009  -8.470   0.000  0.00  0.00           H+0
HETATM   63  H   UNK     0      37.343  -6.160   0.000  0.00  0.00           H+0
HETATM   64  H   UNK     0      41.344  -8.470   0.000  0.00  0.00           H+0
HETATM   65  H   UNK     0      40.010 -10.780   0.000  0.00  0.00           H+0
HETATM   66  H   UNK     0      37.343 -10.780   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   27                                                       
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   28                                                       
CONECT   27   16   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                                                       
CONECT   37   35   39                                                       
CONECT   38   36   40                                                       
CONECT   39   37   44                                                       
CONECT   40   38   46                                                       
CONECT   41   45   52                                                       
CONECT   42   43   58                                                       
CONECT   43   42   60   44   51                                             
CONECT   44   39   43   61   53                                             
CONECT   45   41   62   47   59                                             
CONECT   46   40   51   54                                                  
CONECT   47   45   63   48   55                                             
CONECT   48   47   64   49   56                                             
CONECT   49   48   65   50   57                                             
CONECT   50   49   66   58   59                                             
CONECT   51   43   46                                                       
CONECT   52   41                                                            
CONECT   53   44                                                            
CONECT   54   46                                                            
CONECT   55   47                                                            
CONECT   56   48                                                            
CONECT   57   49                                                            
CONECT   58   42   50                                                       
CONECT   59   45   50                                                       
CONECT   60   43                                                            
CONECT   61   44                                                            
CONECT   62   45                                                            
CONECT   63   47                                                            
CONECT   64   48                                                            
CONECT   65   49                                                            
CONECT   66   50                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  132    0
END

Download
3D PDB for NP0334119 (Glucosylceramide (d18:1/26:1(17Z)))
Download
SMILES for NP0334119 (Glucosylceramide (d18:1/26:1(17Z)))
[H][C@@](O)(\C=C\CCCCCCCCCCCCC)[C@]([H])(CO[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O)\N=C(/O)CCCCCCCCCCCCCCC\C=C\CCCCCCCC
Download
INCHI for NP0334119 (Glucosylceramide (d18:1/26:1(17Z)))
InChI=1S/C50H95NO8/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-28-30-32-34-36-38-40-46(54)51-43(42-58-50-49(57)48(56)47(55)45(41-52)59-50)44(53)39-37-35-33-31-29-27-16-14-12-10-8-6-4-2/h17-18,37,39,43-45,47-50,52-53,55-57H,3-16,19-36,38,40-42H2,1-2H3,(H,51,54)/b18-17+,39-37+/t43-,44+,45+,47+,48-,49+,50+/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC50H95NO8
Average Mass838.3090 Da
Monoisotopic Mass837.70577 Da
IUPAC Name(Z,17E)-N-[(2S,3R,4E)-3-hydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]hexacos-17-enimidic acid
Traditional Name(Z,17E)-N-[(2S,3R,4E)-3-hydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]hexacos-17-enimidic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(\C=C\CCCCCCCCCCCCC)[C@]([H])(CO[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O)\N=C(/O)CCCCCCCCCCCCCCC\C=C\CCCCCCCC
InChI Identifier
InChI=1S/C50H95NO8/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-28-30-32-34-36-38-40-46(54)51-43(42-58-50-49(57)48(56)47(55)45(41-52)59-50)44(53)39-37-35-33-31-29-27-16-14-12-10-8-6-4-2/h17-18,37,39,43-45,47-50,52-53,55-57H,3-16,19-36,38,40-42H2,1-2H3,(H,51,54)/b18-17+,39-37+/t43-,44+,45+,47+,48-,49+,50+/m0/s1
InChI KeyLVROXDRMMJVBGH-MVCHRRFKSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot 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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassSphingolipids  
Sub ClassGlycosphingolipids  
Direct ParentGlycosphingolipids  
Alternative Parents
Substituents
  • Glycosphingolipid
    • 

  • Fatty acyl glycoside of mono- or disaccharide
    • 

  • Fatty acyl glycoside
    • 

  • Alkyl glycoside
    • 

  • Fatty acyl
    • 

  • Oxane
    • 

  • Monosaccharide
    • 

  • Secondary alcohol
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organic 1,3-dipolar compound
    • 

  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Carboximidic acid
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Alcohol
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP14ChemAxon
pKa (Strongest Acidic)5.81ChemAxon
pKa (Strongest Basic)2.72ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area152.2 ŲChemAxon
Rotatable Bond Count42ChemAxon
Refractivity245.84 m³·mol⁻¹ChemAxon
Polarizability107.96 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available