Np mrd loader

Showing NP-Card for Glucosylceramide (NP0334620)

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Record Information
Version2.0
Created at2024-09-10 19:10:28 UTC
Updated at2024-09-10 19:10:28 UTC
NP-MRD IDNP0334620
Secondary Accession NumbersNone
Natural Product Identification
Common NameGlucosylceramide
DescriptionGlucosylceramide, also known as ganglioside GL1A or gaucher cerebroside, belongs to the class of organic compounds known as glycosyl-n-acylsphingosines. Glycosyl-N-acylsphingosines are compounds containing a sphingosine linked to a simple glucosyl moiety. Glucosylceramide is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, glucosylceramide is involved in globoid cell leukodystrophy. Glucosylceramide is a potentially toxic compound. Glucosylceramide, with regard to humans, has been linked to several inborn metabolic disorders including hypobetalipoproteinemia and abetalipoproteinemia.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334620 (Glucosylceramide)


  Mrv0541 02231218212D          

 57 57  0  0  1  0            999 V2000
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    9.6052  -16.2231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3196  -16.6356    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.0340  -16.2231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.7485  -14.9856    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   23.8941  -16.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6086  -16.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 56 57  1  1  0  0  0
M  END
Download

3D MOL for NP0334620 (Glucosylceramide)

Download
3D SDF for NP0334620 (Glucosylceramide)

  Mrv0541 02231218212D          

 57 57  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0334620

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C48H93NO8/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-44(52)49-41(40-56-48-47(55)46(54)45(53)43(39-50)57-48)42(51)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2/h35,37,41-43,45-48,50-51,53-55H,3-34,36,38-40H2,1-2H3,(H,49,52)/b37-35+/t41-,42+,43+,45?,46-,47+,48+/m0/s1

> <INCHI_KEY>
POQRWMRXUOPCLD-XNWFPASESA-N

> <FORMULA>
C48H93NO8

> <MOLECULAR_WEIGHT>
812.2539

> <EXACT_MASS>
811.690118957

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
105.49916790027729

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
9.15

> <JCHEM_LOGP>
12.651068818000004

> <ALOGPS_LOGS>
-6.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.015713374330051

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.181223595454894

> <JCHEM_PKA_STRONGEST_BASIC>
0.01939833913543909

> <JCHEM_POLAR_SURFACE_AREA>
148.71

> <JCHEM_REFRACTIVITY>
234.99700000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
41

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.86e-04 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0334620 (Glucosylceramide)
Download
PDB for NP0334620 (Glucosylceramide)
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      15.262 -33.363   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      16.596 -32.593   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.596 -31.053   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.262 -30.283   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      15.262 -28.743   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      17.930 -30.283   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      19.263 -31.053   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      20.597 -30.283   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      20.597 -28.743   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.931 -27.973   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      23.264 -28.743   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      23.264 -30.283   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.598 -31.053   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.932 -30.283   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.265 -31.053   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.599 -30.283   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.932 -31.053   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      31.266 -30.283   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      32.600 -31.053   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      33.933 -30.283   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      35.267 -31.053   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      36.600 -30.283   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      37.934 -31.053   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      39.268 -30.283   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      40.601 -31.053   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      41.935 -30.283   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      43.269 -31.053   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      44.602 -30.283   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      45.936 -31.053   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      47.270 -30.283   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      48.603 -31.053   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      49.937 -30.283   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      51.270 -31.053   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      52.604 -30.283   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      53.938 -31.053   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      21.931 -31.053   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      21.931 -26.433   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      23.264 -25.663   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      20.597 -25.663   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      20.597 -24.123   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      19.263 -23.353   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      19.263 -21.813   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      17.930 -21.043   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      17.930 -19.503   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      16.596 -18.733   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      16.596 -17.193   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      15.262 -16.423   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      15.262 -14.883   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      13.929 -14.114   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      13.929 -12.574   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      12.595 -11.804   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      12.595 -10.264   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      11.261  -9.494   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      19.263 -32.593   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      20.597 -33.363   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      17.930 -33.363   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      17.930 -34.903   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   56                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8   54                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   37                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   36                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   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   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   12                                                            
CONECT   37   10   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52                                                            
CONECT   54    7   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54    2   57                                                  
CONECT   57   56                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  114    0
END

Download
3D PDB for NP0334620 (Glucosylceramide)
Download
SMILES for NP0334620 (Glucosylceramide)
CCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1O[C@H](CO)C(O)[C@H](O)[C@H]1O)[C@H](O)\C=C\CCCCCCCCCCCCC
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INCHI for NP0334620 (Glucosylceramide)
InChI=1S/C48H93NO8/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-44(52)49-41(40-56-48-47(55)46(54)45(53)43(39-50)57-48)42(51)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2/h35,37,41-43,45-48,50-51,53-55H,3-34,36,38-40H2,1-2H3,(H,49,52)/b37-35+/t41-,42+,43+,45?,46-,47+,48+/m0/s1
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View in JSmol
Synonyms
ValueSource
1-O-b-D-Glucopyranosyl-ceramideHMDB
1-O-beta-delta-Glucopyranosyl-ceramideHMDB
Ganglioside GL1aHMDB
Gaucher cerebrosideHMDB
GLC-beta1->1'cerHMDB
GlcCeramideHMDB
GlucocerebrosideHMDB
Chemical FormulaC48H93NO8
Average Mass812.2539 Da
Monoisotopic Mass811.69012 Da
IUPAC NameN-[(2S,3R,4E)-3-hydroxy-1-{[(2R,3R,4S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]tetracosanamide
Traditional NameN-[(2S,3R,4E)-3-hydroxy-1-{[(2R,3R,4S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]tetracosanamide
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1O[C@H](CO)C(O)[C@H](O)[C@H]1O)[C@H](O)\C=C\CCCCCCCCCCCCC
InChI Identifier
InChI=1S/C48H93NO8/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-44(52)49-41(40-56-48-47(55)46(54)45(53)43(39-50)57-48)42(51)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2/h35,37,41-43,45-48,50-51,53-55H,3-34,36,38-40H2,1-2H3,(H,49,52)/b37-35+/t41-,42+,43+,45?,46-,47+,48+/m0/s1
InChI KeyPOQRWMRXUOPCLD-XNWFPASESA-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 glycosyl-n-acylsphingosines. Glycosyl-N-acylsphingosines are compounds containing a sphingosine linked to a simple glucosyl moiety.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassSphingolipids  
Sub ClassGlycosphingolipids  
Direct ParentGlycosyl-N-acylsphingosines  
Alternative Parents
Substituents
  • Glycosyl-n-acylsphingosine
    • 

  • Fatty acyl glycoside
    • 

  • Fatty acyl glycoside of mono- or disaccharide
    • 

  • Alkyl glycoside
    • 

  • Hexose monosaccharide
    • 

  • Glycosyl compound
    • 

  • O-glycosyl compound
    • 

  • Fatty amide
    • 

  • Fatty acyl
    • 

  • Monosaccharide
    • 

  • N-acyl-amine
    • 

  • Oxane
    • 

  • Carboxamide group
    • 

  • Secondary carboxylic acid amide
    • 

  • Secondary alcohol
    • 

  • Acetal
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Polyol
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Alcohol
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Primary alcohol
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • 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
logP9.15ALOGPS
logP12.65ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)12.18ChemAxon
pKa (Strongest Basic)0.019ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area148.71 ŲChemAxon
Rotatable Bond Count41ChemAxon
Refractivity235 m³·mol⁻¹ChemAxon
Polarizability105.5 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000140  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021900  
KNApSAcK IDNot Available
Chemspider ID24765741  
KEGG Compound IDC01190  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGlucocerebroside  
METLIN IDNot Available
PubChem Compound53477677  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available