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Showing NP-Card for SM(d18:0/26:1(17Z)) (NP0339271)

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Record Information
Version2.0
Created at2024-09-11 20:48:06 UTC
Updated at2024-09-11 20:48:07 UTC
NP-MRD IDNP0339271
Secondary Accession NumbersNone
Natural Product Identification
Common NameSM(d18:0/26:1(17Z))
DescriptionSM(d18:1/26:1(17Z)), also known as C26:1 Sphingomyelin, belongs to the class of organic compounds known as phosphosphingolipids. These are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group. Thus, SM(D18:1/26:1(17Z)) is considered to be a phosphosphingolipid lipid molecule. Sphingomyelins are synthesized by the transfer of phosphorylcholine from phosphatidylcholine to a ceramide in a reaction catalyzed by SM(d18:1/26:1(17Z)) synthase. The plasma membrane of cells is highly enriched in SM(d18:1/26:1(17Z)) and is considered largely to be found in the exoplasmic leaflet of the cell membrane. SM(d18:1/26:1(17Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, SM(d18:1/26:1(17Z)) has been detected, but not quantified in, several different foods, such as cow milks, cow milks, cow milks, and cow milks. This could make SM(D18:1/26:1(17Z)) a potential biomarker for the consumption of these foods. SM(d18:1/26:1(17Z)) can accumulate in a rare hereditary disease called Niemann-Pick Disease, types A and B. Niemann-Pick disease is a genetically-inherited disease caused by a deficiency in the enzyme Sphingomyelinase, which causes the accumulation of SM(d18:1/26:1(17Z)) in spleen, liver, lungs, bone marrow, and the brain, causing irreversible neurological damage. In humans, SM(d18:1/26:1(17Z)) is the only membrane phospholipid not derived from glycerol. SM(d18:1/26:1(17Z)) (d18:0/26:1(17Z)) or SM(d18:0/26:1(17Z)) is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath which surrounds some nerve cell axons. SMs play a role in signal transduction.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0339271 (SM(d18:0/26:1(17Z)))


  Mrv1652303262014182D          

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M  CHG  2  25   1  27  -1
M  END
Download

3D MOL for NP0339271 (SM(d18:0/26:1(17Z)))

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3D SDF for NP0339271 (SM(d18:0/26:1(17Z)))

  Mrv1652303262014182D          

 58 57  0  0  1  0            999 V2000
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M  CHG  2  25   1  27  -1
M  END
> <DATABASE_ID>
NP0339271

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CCCCCCCCCCCCCCC\C=C/CCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C49H97N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-26-27-28-29-31-33-35-37-39-41-43-49(53)50-47(46-57-58(54,55)56-45-44-51(3,4)5)48(52)42-40-38-36-34-32-30-19-17-15-13-11-9-7-2/h20-21,40,42,47-48,52H,6-19,22-39,41,43-46H2,1-5H3,(H-,50,53,54,55)/b21-20-,42-40+/t47-,48+/m0/s1

> <INCHI_KEY>
YXEXWUZHFGYOHJ-UOJCCMJYSA-N

> <FORMULA>
C49H97N2O6P

> <MOLECULAR_WEIGHT>
841.278

> <EXACT_MASS>
840.708425358

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
155

> <JCHEM_AVERAGE_POLARIZABILITY>
108.04415124857749

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2S,3R,4E)-2-[(17Z)-hexacos-17-enamido]-3-hydroxyoctadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
6.53

> <JCHEM_LOGP>
11.059822734194924

> <ALOGPS_LOGS>
-7.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.49920132064026

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.865155035270682

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0502041460417337

> <JCHEM_POLAR_SURFACE_AREA>
107.91999999999999

> <JCHEM_REFRACTIVITY>
261.06850000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
45

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.59e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[(2S,3R,4E)-2-[(17Z)-hexacos-17-enamido]-3-hydroxyoctadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0339271 (SM(d18:0/26:1(17Z)))
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PDB for NP0339271 (SM(d18:0/26:1(17Z)))
HEADER    PROTEIN                                 26-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAR-20         0                                  
HETATM    1  C   UNK     0      11.657  -6.248   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      43.116  -4.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      41.555  -7.046   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      43.663  -6.499   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.996  -5.488   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.324  -6.269   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.664  -5.509   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.991  -6.290   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.331  -5.530   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.658  -6.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.998  -5.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.325  -6.331   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.665  -5.571   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.993  -6.352   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.332  -5.593   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      27.660  -6.373   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.999  -5.614   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      30.327  -6.394   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      41.008  -4.937   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      39.668  -5.697   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      34.334  -5.656   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      32.994  -6.415   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      31.667  -5.635   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      32.982  -7.954   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0      42.335  -5.718   0.000  0.00  0.00           N+1
HETATM   26  O   UNK     0      31.679  -4.095   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      36.241  -4.336   0.000  0.00  0.00           O-1
HETATM   28  O   UNK     0      37.760  -7.015   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      38.340  -4.916   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      35.661  -6.435   0.000  0.00  0.00           O+0
HETATM   31  P   UNK     0      37.001  -5.676   0.000  0.00  0.00           P+0
HETATM   32  C   UNK     0      14.310  -7.954   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.644  -8.724   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      16.978  -7.954   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      18.311  -8.724   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      19.645  -7.954   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      20.979  -8.724   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      22.312  -7.954   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      23.646  -8.724   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      24.980  -7.954   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      26.313  -8.724   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      27.647  -7.954   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      28.981  -8.724   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      30.314  -7.954   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      31.648  -8.724   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      31.648 -10.264   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      12.977  -8.724   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      11.643  -7.954   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      10.309  -8.724   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -1.694  -8.724   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -0.360  -7.954   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       0.973  -8.724   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       2.307  -7.954   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       3.641  -8.724   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       4.974  -7.954   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       6.308  -8.724   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       7.642  -7.954   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       8.975  -8.724   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2   25                                                            
CONECT    3   25                                                            
CONECT    4   25                                                            
CONECT    5    1    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   23                                                       
CONECT   19   20   25                                                       
CONECT   20   19   29                                                       
CONECT   21   22   30                                                       
CONECT   22   21   23   24                                                  
CONECT   23   18   22   26                                                  
CONECT   24   22   45                                                       
CONECT   25    2    3    4   19                                             
CONECT   26   23                                                            
CONECT   27   31                                                            
CONECT   28   31                                                            
CONECT   29   20   31                                                       
CONECT   30   21   31                                                       
CONECT   31   27   28   29   30                                             
CONECT   32   33   47                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   24   46                                                  
CONECT   46   45                                                            
CONECT   47   32   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   58                                                       
CONECT   50   51                                                            
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   49                                                       
MASTER        0    0    0    0    0    0    0    0   58    0  114    0
END

Download
3D PDB for NP0339271 (SM(d18:0/26:1(17Z)))
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SMILES for NP0339271 (SM(d18:0/26:1(17Z)))
CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CCCCCCCCCCCCCCC\C=C/CCCCCCCC
Download
INCHI for NP0339271 (SM(d18:0/26:1(17Z)))
InChI=1S/C49H97N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-26-27-28-29-31-33-35-37-39-41-43-49(53)50-47(46-57-58(54,55)56-45-44-51(3,4)5)48(52)42-40-38-36-34-32-30-19-17-15-13-11-9-7-2/h20-21,40,42,47-48,52H,6-19,22-39,41,43-46H2,1-5H3,(H-,50,53,54,55)/b21-20-,42-40+/t47-,48+/m0/s1
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View in JSmol
Synonyms
ValueSource
C26:1 SphingomyelinChEBI
N-(17Z-Hexacosenoyl)-sphing-4-enine-1-phosphocholineChEBI
N-(Tricosanoyl)-sphing-4-enine-1-phosphocholineHMDB
SphingomyelinHMDB
N-(17Z-Hexacosenoyl)-1-phosphocholine-sphing-4-enineMetBuilder
Sphingomyelin(D18:1/26:1(17Z))MetBuilder
N-(17Z-Hexacosenoyl)-1-phosphocholine-sphingosineMetBuilder
N-(17Z-Hexacosenoyl)-1-phosphocholine-D-erythro-sphingosineMetBuilder
N-(17Z-Hexacosenoyl)-1-phosphocholine-4-sphingenineMetBuilder
N-(17Z-Hexacosenoyl)-1-phosphocholine-D-sphingosineMetBuilder
N-(17Z-Hexacosenoyl)-1-phosphocholine-sphingenineMetBuilder
N-(17Z-Hexacosenoyl)-1-phosphocholine-erythro-4-sphingenineMetBuilder
SM(D18:1/26:1(17Z))ChEBI
N-(17Z-Hexacosenoyl)-1-phosphocholine-sphinganineMetBuilder
Sphingomyelin(D18:0/26:1(17Z))MetBuilder
N-(17Z-Hexacosenoyl)-1-phosphocholine-dihydrosphingosineMetBuilder
N-(17Z-Hexacosenoyl)-1-phosphocholine-D-erythro-sphinganineMetBuilder
Chemical FormulaC49H97N2O6P
Average Mass841.2780 Da
Monoisotopic Mass840.70843 Da
IUPAC Name(2-{[(2S,3R,4E)-2-[(17Z)-hexacos-17-enamido]-3-hydroxyoctadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2S,3R,4E)-2-[(17Z)-hexacos-17-enamido]-3-hydroxyoctadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CCCCCCCCCCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C49H97N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-26-27-28-29-31-33-35-37-39-41-43-49(53)50-47(46-57-58(54,55)56-45-44-51(3,4)5)48(52)42-40-38-36-34-32-30-19-17-15-13-11-9-7-2/h20-21,40,42,47-48,52H,6-19,22-39,41,43-46H2,1-5H3,(H-,50,53,54,55)/b21-20-,42-40+/t47-,48+/m0/s1
InChI KeyYXEXWUZHFGYOHJ-UOJCCMJYSA-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 phosphosphingolipids. These are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassSphingolipids  
Sub ClassPhosphosphingolipids  
Direct ParentPhosphosphingolipids  
Alternative Parents
Substituents
  • Sphingoid-1-phosphate or derivatives
    • 

  • Phosphocholine
    • 

  • Phosphoethanolamine
    • 

  • Dialkyl phosphate
    • 

  • Fatty amide
    • 

  • N-acyl-amine
    • 

  • Organic phosphoric acid derivative
    • 

  • Phosphoric acid ester
    • 

  • Fatty acyl
    • 

  • Alkyl phosphate
    • 

  • Tetraalkylammonium salt
    • 

  • Quaternary ammonium salt
    • 

  • Secondary carboxylic acid amide
    • 

  • Secondary alcohol
    • 

  • Carboxamide group
    • 

  • Carboxylic acid derivative
    • 

  • Organic zwitterion
    • 

  • Alcohol
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Amine
    • 

  • Organic salt
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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
logP6.53ALOGPS
logP11.06ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area107.92 ŲChemAxon
Rotatable Bond Count45ChemAxon
Refractivity261.07 m³·mol⁻¹ChemAxon
Polarizability108.04 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0013461  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029461  
KNApSAcK IDNot Available
Chemspider ID24846876  
KEGG Compound IDC00550  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44260128  
PDB IDNot Available
ChEBI ID84476  
Good Scents IDNot Available
References
General References