Basic information
- CAS
20559-16-4- Standard SMILES
CCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)([O-])OCC[N+](C)(C)C- InChIKey
VXUOFDJKYGDUJI-OAQYLSRUSA-N- Molecular formula
- C22H46NO7P
- Average molar mass
- 467.6 g/mol
- Monoisotopic mass
- 467.3011898
Overview
1-myristoyl-sn-glycero-3-phosphocholine is a lysophosphatidylcholine 14:0 in which the acyl group specified is myristoyl. The major species at pH 7.3. It is a 1-O-acyl-sn-glycero-3-phosphocholine, a lysophosphatidylcholine 14:0 and a tetradecanoate ester.
Names & identifiers
- Preferred name
- 1-Myristoyl-sn-glycero-3-phosphocholine
- IUPAC
- [(2R)-2-hydroxy-3-tetradecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
- English name
- 1-MYRISTOYL-SN-GLYCERO-3-PHOSPHOCHOLINE
- Molecular formula
- C22H46NO7P
- Molecular weight
- 467.58
Names & synonyms
1-Myristoyl-sn-glycero-3-phosphocholine20559-16-4LysoPC(14:0/0:0)1-tetradecanoyl-sn-glycero-3-phosphocholine(R)-2-Hydroxy-3-(tetradecanoyloxy)propyl (2-(trimethylammonio)ethyl) phosphate1-myristoyl-2-hydroxy-sn-glycero-3-phosphocholine14:0 Lyso PCMFCD00036902LPC 14:01-myristoyl-glycero-3-phosphocholineLPC(14:0)PC(14:0/0:0)
Show more names
M-LysoPCLYSOLECITHIN, MYRISTOYLL-A-lysophosphatidylcholineLysolecithin, tetradecanoylL-g-Myristoyl-a-lysolecithinL-γ-Myristoyl-α-lysolecithin1-myristoylglycerophosphocholineL-GAMMA-MYRISTOYL-ALPHA-LYSOLECITHIN
LPC(14:0/0:0)LyPC(14:0)CHEBI:64489DTXSID90942748Lysophosphatidylcholine(14:0/0:0)LyPC(14:0/0:0)1-Myristoyl-sn-glycero-3-phosphocolineCholine, hydroxide, dihydrogen phosphate, inner salt, 3-ester with 1-monomyristin, L-
Properties
Computed structural properties
- XLogP
- 4.5
- Topological polar surface area
- 105 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 22
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 488
Experimental & physicochemical properties
Lipids
Lipids -> Unambiguous Lipids
Lipids -> Glycerophospholipids [GP] -> Glycerophosphocholines [GP01] -> Monoacylglycerophosphocholines [GP0105]
Physical DescriptionSolid
Collision Cross Section
225.1 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Sample Type: Human plasma; Dataset: Unambiguous Lipids]
227 Ų [M+HCOO]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
227.56 Ų [M+Na]+ [CCS Type: TIMS; Method: single field calibrated]
222 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
231.3 Ų [M+HCOO]- [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]
220.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with phosphatidylcholines (ESI+) and phosphatidylethanolamines (ESI-)]
Physicochemical properties
- Melting point
- 142 °C · >142°C (dec.)
- storage temp.
- 20 °C · −20°C
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 10
- wgk
- 3
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS08
- target organs
- Central nervous system, Liver,Kidney
- Hazard statements
- H302-H315-H319-H331-H336-H351-H361d-H372-H412
- Hazard Classifications
- Acute Tox. 3 InhalationAcute Tox. 4 OralAquatic Chronic 3Carc. 2Eye Irrit. 2Repr. 2Skin Irrit. 2STOT RE 1STOT SE 3
- Precautionary statements
- P201-P273-P301+P312+P330-P302+P352-P304+P340+P311-P308+P313
Chemistry & industry
Pharmacology
Tissue LocationsAll Tissues
Cellular LocationsExtracellular
Metabolite PathwaysAcetaminophen Action Pathway
Applications
Description1-MYRISTOYL-SN-GLYCERO-3-PHOSPHOCHOLINE is a lysophospholipid (LyP), which is a monoglycerophospholipid in which the phosphorylcholine moiety occupies the glycerol substitution site. LysoPC(14:0/0:0) has a potent antispasmodic effect.
Uses1-Myristoyl-sn-glycero-3-phosphocholine is a derivative of sn-Glycero-3-phosphocholine (G598700) and can be used as a biomarker in biological studies.
Suppliers93 total
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]
湖北威德利化学试剂有限公司186-02735115 18062128043 · [email protected]
Shochem(Shanghai) Co.,Ltd86-21-50800795 · [email protected]
艾吉析科技（上海）有限公司17717235263 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
广州佳途科技股份有限公司81960175-877 18933936954 · [email protected]
Related reactions
0 records
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Compound notes
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