Np mrd loader

Showing NP-Card for PC(o-22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (NP0339267)

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Record Information
Version2.0
Created at2024-09-11 20:46:55 UTC
Updated at2024-09-11 20:46:55 UTC
NP-MRD IDNP0339267
Secondary Accession NumbersNone
Natural Product Identification
Common NamePC(o-22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
DescriptionPC(O-22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), also known as phosphatidylcholine(22:0/22:6) Or gpcho(22:0/22:6), Belongs to the class of organic compounds known as 1-alkyl,2-acylglycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one alkyl chain attached through an ether linkage at the O1-position. PC(O-22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is an extremely weak basic (essentially neutral) compound (based on its pKa). Fatty acids containing 16, 18 and 20 carbons are the most common. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. The Behenyl alcohol moiety is derived from Rice bran, while the docosahexaenoic acid moiety is derived from fish oils. PCs can be synthesized via three different routes. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0339267 (PC(o-22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))


  Mrv1652303252017062D          

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M  CHG  2   8  -1  13   1
M  END
Download

3D MOL for NP0339267 (PC(o-22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

Download
3D SDF for NP0339267 (PC(o-22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

  Mrv1652303252017062D          

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M  CHG  2   8  -1  13   1
M  END
> <DATABASE_ID>
NP0339267

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@](COCCCCCCCCCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC

> <INCHI_IDENTIFIER>
InChI=1S/C52H94NO7P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-42-44-47-57-49-51(50-59-61(55,56)58-48-46-53(3,4)5)60-52(54)45-43-41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h9,11,15,17,21,23,27,29,33,35,39,41,51H,6-8,10,12-14,16,18-20,22,24-26,28,30-32,34,36-38,40,42-50H2,1-5H3/b11-9-,17-15-,23-21-,29-27-,35-33-,41-39-/t51-/m1/s1

> <INCHI_KEY>
YLLDQHGIGWZVQP-ITBHSSNISA-N

> <FORMULA>
C52H94NO7P

> <MOLECULAR_WEIGHT>
876.279

> <EXACT_MASS>
875.676790879

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
155

> <JCHEM_AVERAGE_POLARIZABILITY>
108.55629062589566

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(docosyloxy)propyl phosphono]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
7.25

> <JCHEM_LOGP>
11.657886015194917

> <ALOGPS_LOGS>
-7.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8550607478746306

> <JCHEM_PKA_STRONGEST_BASIC>
-4.141005511601818

> <JCHEM_POLAR_SURFACE_AREA>
94.12

> <JCHEM_REFRACTIVITY>
278.02209999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
46

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.23e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(docosyloxy)propyl phosphono]oxy}ethyl)trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0339267 (PC(o-22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))
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PDB for NP0339267 (PC(o-22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))
HEADER    PROTEIN                                 25-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAR-20         0                                  
HETATM    1  O   UNK     0      31.651  -6.682   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      35.652  -5.911   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      34.615  -6.682   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      32.985  -5.911   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      36.986  -6.682   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      33.613  -8.054   0.000  0.00  0.00           O+0
HETATM    7  P   UNK     0      38.319  -5.911   0.000  0.00  0.00           P+0
HETATM    8  O   UNK     0      39.090  -7.245   0.000  0.00  0.00           O-1
HETATM    9  O   UNK     0      37.549  -4.577   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      39.653  -5.141   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      40.987  -5.911   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      42.321  -5.141   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      43.654  -5.911   0.000  0.00  0.00           N+1
HETATM   14  C   UNK     0      42.884  -7.245   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      44.721  -3.965   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      44.988  -6.682   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0      35.787  -8.082   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0      12.980  -6.682   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.314  -5.911   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.647  -6.682   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.981  -5.911   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.315  -6.682   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      19.648  -5.911   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      20.982  -6.682   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      22.316  -5.911   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      23.649  -6.682   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      24.983  -5.911   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      26.316  -6.682   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      27.650  -5.911   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      28.984  -6.682   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      30.317  -5.911   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.646  -5.912   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.313  -6.682   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.979  -5.912   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.645  -6.682   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.312  -5.911   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.978  -6.681   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.644  -5.911   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.311  -6.681   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.272  -8.054   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.606  -8.824   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       6.940  -8.054   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       8.273  -8.054   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       9.607  -8.824   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      10.941  -8.054   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      12.274  -8.054   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      13.608  -8.824   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      14.942  -8.054   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      16.275  -8.054   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      17.609  -8.824   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      18.943  -8.054   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      20.276  -8.054   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      21.610  -8.824   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      22.944  -8.054   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      24.277  -8.054   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      25.611  -8.824   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      26.945  -8.054   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      28.279  -8.054   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      29.612  -8.824   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      30.946  -8.054   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      32.280  -8.824   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0      32.280 -10.364   0.000  0.00  0.00           O+0
CONECT    1    4   31                                                       
CONECT    2    3    5                                                       
CONECT    3    2    4    6   17                                             
CONECT    4    3    1                                                       
CONECT    5    2    7                                                       
CONECT    6    3   61                                                       
CONECT    7    5    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13                                                            
CONECT   17    3                                                            
CONECT   18   19   32                                                       
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    1                                                       
CONECT   32   18   33                                                       
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                                                            
CONECT   40   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   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60    6   62                                                  
CONECT   62   61                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  122    0
END

Download
3D PDB for NP0339267 (PC(o-22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))
Download
SMILES for NP0339267 (PC(o-22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))
[H][C@@](COCCCCCCCCCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
Download
INCHI for NP0339267 (PC(o-22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))
InChI=1S/C52H94NO7P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-42-44-47-57-49-51(50-59-61(55,56)58-48-46-53(3,4)5)60-52(54)45-43-41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h9,11,15,17,21,23,27,29,33,35,39,41,51H,6-8,10,12-14,16,18-20,22,24-26,28,30-32,34,36-38,40,42-50H2,1-5H3/b11-9-,17-15-,23-21-,29-27-,35-33-,41-39-/t51-/m1/s1
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View in JSmol
Synonyms
ValueSource
1-Behenyl-2-docosahexaenoyl-sn-glycero-3-phosphocholineHMDB
Gpcho(22:0/22:6)HMDB
Gpcho(22:0/22:6n3)HMDB
Gpcho(22:0/22:6W3)HMDB
Gpcho(44:6)HMDB
LecithinHMDB
PC Ae C44:6HMDB
PC(22:0/22:6)HMDB
PC(22:0/22:6n3)HMDB
PC(22:0/22:6W3)HMDB
PC(44:6)HMDB
PC(O-44:6)HMDB
Phosphatidylcholine(22:0/22:6)HMDB
Phosphatidylcholine(22:0/22:6n3)HMDB
Phosphatidylcholine(22:0/22:6W3)HMDB
Phosphatidylcholine(44:6)HMDB
1-Docosanyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholineHMDB
PC(o-22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))Lipid Annotator
Chemical FormulaC52H94NO7P
Average Mass876.2790 Da
Monoisotopic Mass875.67679 Da
IUPAC Name(2-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(docosyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(docosyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
[H][C@@](COCCCCCCCCCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C52H94NO7P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-42-44-47-57-49-51(50-59-61(55,56)58-48-46-53(3,4)5)60-52(54)45-43-41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h9,11,15,17,21,23,27,29,33,35,39,41,51H,6-8,10,12-14,16,18-20,22,24-26,28,30-32,34,36-38,40,42-50H2,1-5H3/b11-9-,17-15-,23-21-,29-27-,35-33-,41-39-/t51-/m1/s1
InChI KeyYLLDQHGIGWZVQP-ITBHSSNISA-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 1-alkyl,2-acylglycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position,  and one alkyl chain attached through an ether linkage at the O1-position.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassGlycerophospholipids  
Sub ClassGlycerophosphocholines  
Direct Parent1-alkyl,2-acylglycero-3-phosphocholines  
Alternative Parents
Substituents
  • 1-alkyl,2-acylglycero-3-phosphocholine
    • 

  • Phosphocholine
    • 

  • Fatty acid ester
    • 

  • Dialkyl phosphate
    • 

  • Glycerol ether
    • 

  • Organic phosphoric acid derivative
    • 

  • Phosphoric acid ester
    • 

  • Fatty acyl
    • 

  • Alkyl phosphate
    • 

  • Tetraalkylammonium salt
    • 

  • Quaternary ammonium salt
    • 

  • Carboxylic acid ester
    • 

  • Carboxylic acid derivative
    • 

  • Dialkyl ether
    • 

  • Ether
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organonitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Amine
    • 

  • Organic nitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organic salt
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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
logP7.25ALOGPS
logP11.66ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area94.12 ŲChemAxon
Rotatable Bond Count46ChemAxon
Refractivity278.02 m³·mol⁻¹ChemAxon
Polarizability108.56 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0013450  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029450  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481755  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References