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Details

Stereochemistry ABSOLUTE
Molecular Formula C42H82NO8P
Molecular Weight 760.0761
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of 1-PALMITOYL-2-OLEOYL-SN-GLYCERO-3-PHOSPHOCHOLINE

SMILES

CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC

InChI

InChIKey=WTJKGGKOPKCXLL-VYOBOKEXSA-N
InChI=1S/C42H82NO8P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h20-21,40H,6-19,22-39H2,1-5H3/b21-20-/t40-/m1/s1

HIDE SMILES / InChI

Molecular Formula C42H82NO8P
Molecular Weight 760.0761
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 1 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25817536

POPC is a 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine. It is an important phospholipid for biophysical experiments and has been used to study various subjects such as lipid rafts. POPC also used in systems mimicking the cell membrane. It was shown that endogenous lipid synthesis generates a discrete phosphatidylcholine species, 1-palmitoyl 2-oleyl phosphatidylcholine (16:0/18:1 PC), that serves as an endogenous ligand for PPARalpha. Myelin is a membrane characterized by high lipid content to facilitate impulse propagation. Changes in myelin fatty acid (FA) composition have been associated with peripheral neuropathy. It was also found that mice lacking sterol regulatory element-binding factor-1c (Srebf1c) have blunted peripheral nerve FA synthesis that results in development of peripheral neuropathy. Peripheral nerves lacking Srebf1c show decreased FA synthesis and glycolytic flux, but increased FA catabolism and mitochondrial function. These metabolic alterations are the result of local accumulation of two endogenous peroxisome proliferator-activated receptor-α (PARalpha) ligands, 1-palmitoyl-2-oleyl-sn-glycerol-3-phosphatidylcholine and 1-stearoyl-2-oleyl-sn-glycerol-3-phosphatidylcholine. Treatment with a PPARalpha antagonist rescues the neuropathy.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Structural analyses reveal phosphatidyl inositols as ligands for the NR5 orphan receptors SF-1 and LRH-1.
2005-02-11
Reconstitution of Ca2+-regulated membrane fusion by synaptotagmin and SNAREs.
2004-04-16
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:27:18 GMT 2025
Edited
by admin
on Mon Mar 31 18:27:18 GMT 2025
Record UNII
TE895536Y5
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
1-HEXADECANOYL-2-(9Z-OCTADECENOYL)-SN-GLYCERO-3-PHOSPHOCHOLINE
Preferred Name English
1-PALMITOYL-2-OLEOYL-SN-GLYCERO-3-PHOSPHOCHOLINE
Common Name English
3,5,8-TRIOXA-4-PHOSPHAHEXACOS-17-EN-1-AMINIUM, 4-HYDROXY-N,N,N-TRIMETHYL-9-OXO-7-(((1-OXOHEXADECYL)OXY)METHYL)-, INNER SALT, 4-OXIDE, (7R,17Z)-
Common Name English
1-PALMITOYL-2-OLEOYL-SN-GLYCERO-3-PHOSPHOCHOLINE (POPC)
Common Name English
Code System Code Type Description
PUBCHEM
5497103
Created by admin on Mon Mar 31 18:27:18 GMT 2025 , Edited by admin on Mon Mar 31 18:27:18 GMT 2025
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SMS_ID
100000093374
Created by admin on Mon Mar 31 18:27:18 GMT 2025 , Edited by admin on Mon Mar 31 18:27:18 GMT 2025
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EVMPD
SUB30396
Created by admin on Mon Mar 31 18:27:18 GMT 2025 , Edited by admin on Mon Mar 31 18:27:18 GMT 2025
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FDA UNII
TE895536Y5
Created by admin on Mon Mar 31 18:27:18 GMT 2025 , Edited by admin on Mon Mar 31 18:27:18 GMT 2025
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WIKIPEDIA
POPC
Created by admin on Mon Mar 31 18:27:18 GMT 2025 , Edited by admin on Mon Mar 31 18:27:18 GMT 2025
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EPA CompTox
DTXSID101029642
Created by admin on Mon Mar 31 18:27:18 GMT 2025 , Edited by admin on Mon Mar 31 18:27:18 GMT 2025
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ECHA (EC/EINECS)
248-056-7
Created by admin on Mon Mar 31 18:27:18 GMT 2025 , Edited by admin on Mon Mar 31 18:27:18 GMT 2025
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CHEBI
73001
Created by admin on Mon Mar 31 18:27:18 GMT 2025 , Edited by admin on Mon Mar 31 18:27:18 GMT 2025
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CAS
26853-31-6
Created by admin on Mon Mar 31 18:27:18 GMT 2025 , Edited by admin on Mon Mar 31 18:27:18 GMT 2025
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