Structure Database (LMSD)

Common Name
CPA(18:1(9Z))
Systematic Name
1-(9Z-octadecenoyl)-sn-glycero-2,3-cyclic phosphate
Synonyms
  • 1-oleoyl-cyclic phosphatidic acid
  • cLPA(18:1)
LM ID
LMGP00000056
Status
Active
Exact Mass
Calculate m/z
418.248428
Formula
Abbrev
Abbrev Chains
CPA 18:1


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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)
ZUUIRLHAEZAVCP-GDCKJWNLSA-N
InChi (Click to copy)
InChI=1S/C21H39O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(22)25-18-20-19-26-28(23,24)27-20/h9-10,20H,2-8,11-19H2,1H3,(H,23,24)/b10-9-/t20-/m1/s1
SMILES (Click to copy)
[C@]1(COP(O1)(=O)O)([H])COC(CCCCCCC/C=C\CCCCCCCC)=O

References

Reference
Kobayashi T, Tanaka-Ishii R, Taguchi R, Ikezawa H, Murakami-Murofushi K.
Existence of a bioactive lipid, cyclic phosphatidic acid, bound to human serum albumin.
Life Sci. 1999;65:2185?91.

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Existence of a bioactive lipid, cyclic phosphatidic acid, bound to human serum albumin.,
Life Sci, 1999
Pubmed ID: 10576590

Other Databases

CHEBI ID
PubChem CID

Calculated Physicochemical Properties

Heavy Atoms 28
Rings 1
Aromatic Rings 0
Rotatable Bonds 18
Van der Waals Molecular Volume 426.79
Topological Polar Surface Area 86.20
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 6
logP 7.11
Molar Refractivity 112.42

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Created at
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Updated at
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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.