Structure Database (LMSD)
Common Name
PE(16:0/18:1(9Z))-15-isoLG lactam
Systematic Name
Synonyms
- PE(34:1)-isoK lactam
3D model of PE(16:0/18:1(9Z))-15-isoLG lactam
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Homo sapiens
(#9606)
Mammalia
(#40674)
Isoketals form cytotoxic phosphatidylethanolamine adducts in cells.,
J Lipid Res, 2010
J Lipid Res, 2010
Pubmed ID:
19965577
DOI:
10.1194/jlr.M001040
String Representations
InChiKey (Click to copy)
VVYVGBXNIXUCDE-ORZYWFCSSA-N
InChi (Click to copy)
InChI=1S/C59H104NO12P/c1-5-8-11-13-15-17-19-21-22-24-26-28-30-32-39-44-58(65)72-53(49-69-57(64)43-38-31-29-27-25-23-20-18-16-14-12-9-6-2)50-71-73(67,68)70-48-47-60-51(4)54(41-36-33-34-37-42-56(62)63)55(59(60)66)46-45-52(61)40-35-10-7-3/h21-22,33,36,45-46,52-53,55,61H,5-20,23-32,34-35,37-44,47-50H2,1-4H3,(H,62,63)(H,67,68)/b22-21-,36-33-,46-45+/t52?,53-,55?/m1/s1
SMILES (Click to copy)
[C@](COP(=O)(O)OCCN1C(=O)C(/C=C/C(O)CCCCC)C(=C1C)C/C=C\CCCC(O)=O)([H])(OC(CCCCCCC/C=C\CCCCCCCC)=O)COC(CCCCCCCCCCCCCCC)=O
Other Databases
PubChem CID
Calculated Physicochemical Properties
Heavy Atoms
73
Rings
1
Aromatic Rings
0
Rotatable Bonds
53
Van der Waals Molecular Volume
1132.09
Topological Polar Surface Area
186.20
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
13
logP
17.41
Molar Refractivity
297.61
Admin
Created at
-
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.
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.