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Chemistry

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Also known as: 1,2-dimyristoyl-rac-glycero-3-phosphocholine, 18656-38-7, Dl-dimyristoylphosphatidylcholine, 13699-48-4, Dmpc, 2,3-di(tetradecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate

Molecular Formula

C₃₆H₇₂NO₈P

Molecular Weight

677.9 g/mol

InChI Key

CITHEXJVPOWHKC-UHFFFAOYSA-N

FDA UNII

U86ZGC74V5

A synthetic phospholipid used in liposomes and lipid bilayers for the study of biological membranes.

1 2D Structure

Dimyristoyl Lecithin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2,3-di(tetradecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate

2.1.2 InChI

InChI=1S/C36H72NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-35(38)42-32-34(33-44-46(40,41)43-31-30-37(3,4)5)45-36(39)29-27-25-23-21-19-17-15-13-11-9-7-2/h34H,6-33H2,1-5H3

2.1.3 InChI Key

CITHEXJVPOWHKC-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCCCCCCCCCCCCC(=O)OCC(COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCC

2.2 Other Identifiers

2.2.1 UNII

U86ZGC74V5

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1,2 Dimyristoyl Glycero 3 Phosphorylcholine

2. 1,2 Ditetradecanoyl Glycero 3 Phosphocholine

3. 1,2 Ditetradecyl Glycero 3 Phosphocholine

4. 1,2-dimyristoyl-glycero-3-phosphorylcholine

5. 1,2-ditetradecanoyl-glycero-3-phosphocholine

6. 1,2-ditetradecyl-glycero-3-phosphocholine

7. Dimyristoyllecithin

8. Dimyristoylphosphatidylcholine

9. Dmcp

10. Dmpc

2.3.2 Depositor-Supplied Synonyms

1. 1,2-dimyristoyl-rac-glycero-3-phosphocholine

2. 18656-38-7

3. Dl-dimyristoylphosphatidylcholine

4. 13699-48-4

5. Dmpc

6. 2,3-di(tetradecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl Phosphate

7. Dl-beta,gamma-dimyristoyl-alpha-lecithin

8. Dimyristoyl-phosphatidylcholine

9. U86zgc74v5

10. Chebi:241349

11. Dimyristoyllecithin

12. L-alpha-dimyristoylphosphatidylcholine

13. Ncgc00181029-01

14. (1)-(7-myristoyl-4-oxido-10-oxo-3,5,9-trioxa-4-phosphatricosyl)trimethylammonium 4-oxide

15. 3,5,9-trioxa-4-phosphatricosan-1-aminium, 4-hydroxy-n,n,n-trimethyl-10-oxo-7-((1-oxotetradecyl)oxy)-, Inner Salt, 4-oxide

16. Unii-u86zgc74v5

17. Einecs 242-481-1

18. Soy Bean Phospholipid

19. Dsstox_cid_26816

20. Dsstox_rid_81928

21. 1,2-ditetradecanoyl-rac-glycerol-3-phosphocholine

22. Dsstox_gsid_46816

23. Schembl244839

24. Chembl316257

25. Dtxsid4046816

26. Dimyristoyl-.alpha.-lecithin

27. Tox21_112679

28. Mfcd00066562

29. Akos024418777

30. Db11283

31. Hy-w142596

32. 1,2-dimyristoyl-phosphatidylcholine

33. Cas-18656-38-7

34. Cs-0204636

35. Ft-0625421

36. Ft-0627667

37. Ft-0627775

38. 1,2-dimyristoyl-dl-phosphatidylcholine

39. D-5665

40. D-5667

41. Dimyristoyl Phosphatidylcholine, (+/-)

42. 1,2-dimyristoyl-glycero-3-phosphocholine

43. A839808

44. 1,2-dimyristoyl-phosphatidylcholine, (+/-)

45. 1,2-dimyristoyl-glycero-3-phosphocholine, Dl-

46. 1,2-dimyristoyl-rac-glycero-3-phosphocholine, >=99%

47. Q27225712

48. 1,2-dimyristoyl-glycero-3-phosphocholine, (+/-)-

49. 2,3-bis(1-oxotetradecoxy)propyl 2-(trimethylammonio)ethyl Phosphate

50. 2,3-bis(tetradecanoyloxy)propyl 2-(trimethylammonio)ethyl Phosphate

51. 2,3-bis(tetradecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl Phosphate

52. [2-({[2,3-bis(tetradecanoyloxy)propyl] Phosphonato}oxy)ethyl]trimethylazanium

53. 3,5,9-trioxa-4-phosphatricosan-1-aminium,4-hydroxy-n,n,n-trimethyl-10-oxo-7-[(1-oxotetradecyl)oxy]-, Inner Salt, 4-oxide

54. 3,5,9-trioxa-4-phosphatricosan-1-aminium,4-hydroxy-n,n,n-trimethyl-10-oxo-7-[(1-oxotetradecyl)oxy]-,inner Salt,4-oxide

2.4 Create Date

2005-03-28

3 Chemical and Physical Properties

Molecular Formula	C₃₆H₇₂NO₈P
Molecular Weight	677.9 g/mol
XLogP3	11.3
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	36
Exact Mass	677.49955525 g/mol
Monoisotopic Mass	677.49955525 g/mol
Topological Polar Surface Area	111 Å²
Heavy Atom Count	46
Formal Charge	0
Complexity	765
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

DL-dimyristoylphosphatidylcholine is not an active pharmaceutical agent and has no indication.

5 Pharmacology and Biochemistry

5.1 Pharmacology

DL-dimyristoylphosphatidylcholine is a water soluble phospholipid used to solubilize drugs for injection.

5.2 MeSH Pharmacological Classification

Indicators and Reagents

Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant and Hackh's Chemical Dictionary, 5th ed, p301, p499) (See all compounds classified as Indicators and Reagents.)

5.3 Mechanism of Action

As a phospholipid, DL-dimyristoylphosphatidylcholine can form a micelle with a hydrophobic core to contain lipophilic drugs while maintaining a hyrophilic outer portion to allow increased solubility of the drug in the aqueous environment of the blood or gastrointestinal tract.

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