1,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine

HCID 445468
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Substructure searchFind similar structures

Basic information

CAS
923-61-5
Standard SMILES
CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN)OC(=O)CCCCCCCCCCCCCCC
InChIKey
SLKDGVPOSSLUAI-PGUFJCEWSA-N
Molecular formula
C37H74NO8P
Average molar mass
692 g/mol
Monoisotopic mass
691.51520496

Overview

1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine is a 1,2-diacyl-sn-glycero-3-phosphoethanolamine in which the 1- and 2-acyl groups are both specified as hexadecanoyl (palmitoyl). It has a role as a mouse metabolite. It is functionally related to a hexadecanoic acid. It is a tautomer of a 1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine zwitterion.

Names & identifiers

Preferred name
1,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine
IUPAC
[(2R)-3-[2-aminoethoxy(hydroxy)phosphoryl]oxy-2-hexadecanoyloxypropyl] hexadecanoate
English name
1,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine
Molecular formula
C37H74NO8P
Molecular weight
691.97

Names & synonyms

923-61-51,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine4FWH120Z1ZCHEBI:731271,2-Dihexadecanoyl-sn-glycerol-3-phosphorylethanolamine2-aminoethyl (2R)-2,3-bis(palmitoyloxy)propyl hydrogen phosphate2-aminoethyl (2R)-2,3-bis(hexadecanoyloxy)propyl hydrogen phosphateRefChem:411644213-097-1C37H74NO8PPE(16:0/16:0)
Show more names
16:0 PEL-DPPESGX145SGX-145dipalmitoylDPPE L-2116beta-L-OddCCAS_923-61-5
Dipalmitoyl phosphatidylethanolamineMFCD00036776EINECS 213-097-11,2-Dipalmitoyl-sn-glycero-3-phosphorylethanolamineGPEtn(32:0)Phophatidylethanolamine(32:0)DI-PALMITOYL-3-SN-PHOSPHATIDYLETHANOLAMINEGPEtn(16:0/16:0)

Database identifiers

CAS
923-61-5
PubChem CID
445468
DTXSID
DTXSID90919258
ChEBI
CHEBI:73127
UNII
4FWH120Z1Z
EC Number
213-097-1
Nikkaji
J76.013G

Properties

Computed structural properties

XLogP
10.3
Topological polar surface area
134 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
9
Rotatable bonds
39
Heavy atoms
47

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
Lipids · 2 items

Lipids -> Unambiguous Lipids

Lipids -> Glycerophospholipids [GP] -> Glycerophosphoethanolamines [GP02] -> Diacylglycerophosphoethanolamines [GP0201]

Physical DescriptionSolid
Collision Cross Section · 2 items

260.5 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Sample Type: Human bronchoalveolar lavage fluid (BALF); Dataset: Unambiguous Lipids]

262.5 Ų [M-H]-

Physicochemical properties

Melting point
195 to · 195.0 to 199.0 °C
Boiling point
723.6 · 723.6±70.0 °C(Predicted)
Density
1.01 · 1.010±0.06 g/cm3(Predicted)
storage temp.
-20 °C · -20°C
solubility
Methanol (Slightly)
form
Solid

Safety & regulation

Hazard information

Regulatory Information · 1 item

Hexadecanoic acid, (1R)-1-(2-aminoethoxy)hydroxyphosphinyloxymethyl-1,2-ethanediyl ester: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
hs_code
29232000
Signal word
Warning
Symbol(GHS)
GHS07
Storage Class
11 - Combustible Solids

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 1 item

Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.

Tissue LocationsAll Tissues
Cellular LocationsExtracellular
Metabolite PathwaysPhosphatidylcholine Biosynthesis PC(16:0/16:0)
Applications · 4 items

Description1,2-Dipalmitoyl-sn-glycero-3-PE (1,2-DPPE) is a naturally occurring PE containing C16:0 fatty acids at the sn-1 and sn-2 positions. It belongs to a class of phospholipids that are the most abundant lipids in the inner leaflet of the plasma membrane. 1,2-DPPE interacts with cholesterol to form a condensed lipid monolayer with tight hydrogen bonding of the 1,2-DPPE interheadgroups, resulting in a more fluid membrane that may aid in transport and signaling across the bilayer.1,2-Dipalmitoyl-sn-glycero-3-PE MaxSpec® standard is a quantitative grade standard of 1,2-dipalmitoyl-sn-glycero-3-PE that has been prepared specifically for mass spectrometry and related applications where quantitative reproducibility is required. The solution has been prepared gravimetrically and is supplied in a deactivated glass ampule sealed under argon. The concentration was verified by comparison to an independently prepared calibration standard. This 1,2-dipalmitoyl-sn-glycero-3-PE MaxSpec® standard is guaranteed to meet identity, purity, stability, and concentration specifications and is provided with a batch-specific certificate of analysis. Ongoing stability testing is performed to ensure the concentration remains accurate throughout the shelf life of the product. Note: The amount of solution added to the vial is in excess of the listed amount. Therefore, it is necessary to accurately measure volumes for preparation of calibration standards. Follow recommended storage and handling conditions to maintain product quality.

Uses16:0 PE has been used:for the preparation of perfluorocarbon (PFC) nanoparticlesfor lipid binding by liposome flotation assaysto characterize the metabolic fate of synaptamide in a dopaminergic cell line

Uses1,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine is used in model membrane .

General DescriptionPhosphatidylethanolamine is an aminophospholipid. It is present in eukaryotic and prokaryotic cells. Phosphatidylethanolamine is one of the most abundant glycerophospholipids in biological membranes. It is found in nervous tissue.

Upstream & downstream products

Suppliers103 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
Shochem(Shanghai) Co.,Ltd86-21-50800795 · [email protected]
Additional notes · 1 item

DefinitionChEBI: 1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine is a 1,2-diacyl-sn-glycero-3-phosphoethanolamine in which the 1- and 2-acyl groups are both specified as hexadecanoyl (palmitoyl). It has a role as a mouse metabolite. It is functionally related to a hexadecanoic acid. It is a tautomer of a 1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine zwitterion.

Related reactions

1 records
New reaction record

Compound notes

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