Structure Database (LMSD)
Common Name
NAPE(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)
Systematic Name
1-(hexadecanoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine
Synonyms
- N-arachidonoyl-1-palmitoyl-2-oleoyl-3-phosphatidylethanolamine
- NAPE(34:1)
LM ID
LMGP02011263
Formula
Exact Mass
Calculate m/z
1003.760522
Sum Composition
Abbrev Chains
NAPE 16:0_18:1_20:4
Status
Curated
3D model of NAPE(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
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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References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Homo sapiens
(#9606)
Mammalia
(#40674)
Endocannabinoid Oxygenation by Cyclooxygenases, Lipoxygenases, and Cytochromes P450: Cross-Talk between the Eicosanoid and Endocannabinoid Signaling Pathways,
Chem Rev, 2011
Chem Rev, 2011
Pubmed ID:
21923193
DOI:
10.1021/cr2002799
String Representations
InChiKey (Click to copy)
NAGMTBUTZNPNAF-OVUVQYNQSA-N
InChi (Click to copy)
InChI=1S/C59H106NO9P/c1-4-7-10-13-16-19-22-25-27-28-30-32-34-37-40-43-46-49-57(61)60-52-53-67-70(64,65)68-55-56(54-66-58(62)50-47-44-41-38-35-31-24-21-18-15-12-9-6-3)69-59(63)51-48-45-42-39-36-33-29-26-23-20-17-14-11-8-5-2/h16,19,25-27,29-30,32,37,40,56H,4-15,17-18,20-24,28,31,33-36,38-39,41-55H2,1-3H3,(H,60,61)(H,64,65)/b19-16-,27-25-,29-26-,32-30-,40-37-/t56-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)(O)OCCNC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)([H])(OC(CCCCCCC/C=C\CCCCCCCC)=O)COC(CCCCCCCCCCCCCCC)=O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
70
Rings
0
Aromatic Rings
0
Rotatable Bonds
55
Van der Waals Molecular Volume
1118.08
Topological Polar Surface Area
137.46
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
10
logP
18.95
Molar Refractivity
296.08
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.