Structure Database (LMSD)

Common Name
PC(18:0(11cp)/0:0)
Systematic Name
1-(cis-11,12-methylene-octadecanoyl)-sn-glycero-3-phosphocholine
Synonyms
LM ID
LMGP01050145
Status
Active
Exact Mass
Calculate m/z
535.363792
Formula
Abbrev


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MDLMOL SDF CSV TSV
MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".

Main

Classification

String Representations

InChiKey (Click to copy)
JMNXFZCXVGEDAC-NRUKRLKBSA-N
InChi (Click to copy)
InChI=1S/C27H54NO7P/c1-5-6-7-13-16-24-21-25(24)17-14-11-9-8-10-12-15-18-27(30)33-22-26(29)23-35-36(31,32)34-20-19-28(2,3)4/h24-26,29H,5-23H2,1-4H3/t24?,25?,26-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(O)COC(CCCCCCCCCC1CC1CCCCCC)=O

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Spirastrella (#283506)
Demospongiae (#6042)
Lyso-PAF analogues and lysophosphatidylcholines from the marine sponge Spirastrella abata as inhibitors of cholesterol biosynthesis.,
J Nat Prod, 1999
Pubmed ID: 10579872

Other Databases

PubChem CID

Calculated Physicochemical Properties

Heavy Atoms 36
Rings 1
Aromatic Rings 0
Rotatable Bonds 25
Van der Waals Molecular Volume 553.02
Topological Polar Surface Area 105.12
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 8
logP 6.64
Molar Refractivity 143.76

Reactions

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Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
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Reactions graph legend

Admin

Created at
27th Oct 2020
Updated at
25th Apr 2022
LIPID MAPS® abbreviations for glycerophospholipids (GP)

The LIPID MAPS® glycerophospholipid abbreviations (PC, PE, etc.) are used here to refer to species with one or two radyl side-chains where the structures of the side chains are indicated within parentheses in the 'Headgroup(sn1/sn2)' format (e.g. PC(16:0/18:1(9Z)). By default, R stereochemistry at the C-2 carbon of glycerol and attachment of the headgroup at the sn3 position is assumed. Also, acyl chains are assumed by default. The 'O-' prefix is used to indicate the presence of an alkyl ether substituent e.g. PC(O-16:0/18:1(9Z)), whereas the 'P-' prefix is used for the 1Z-alkenyl ether (Plasmalogen) substituent e.g. PC(P-16:0/18:1(9Z)).

For molecules with opposite (S) stereochemistry at C2 of the glycerol group and attachment of the headgroup at the sn1 position, the stereochemistry specification of [S] is appended to the abbreviation. The 'Headgroup(sn3/sn2)' abbreviation format is used.

For molecules with unknown stereochemistry at the C-2 carbon of the glycerol group, the stereochemistry specification of [U] is appended to the abbreviation and the structure is drawn with C-2 stereochemistry unspecified.