(2S)-2-amino-3-({[(2R)-2-(butanoyloxy)-3-(propanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid

• ChemBase ID: 30
• Molecular Formular: C13H24NO10P
• Molecular Mass: 385.304121
• Monoisotopic Mass: 385.1137826
• SMILES: P(=O)(OC[C@H](OC(=O)CCC)COC(=O)CC)(OC[C@H](N)C(=O)O)O
• Canonical SMILES: CCCC(=O)O[C@@H](COP(=O)(OC[C@@H](C(=O)O)N)O)COC(=O)CC
• InChI: InChI=1S/C13H24NO10P/c1-3-5-12(16)24-9(6-21-11(15)4-2)7-22-25(19,20)23-8-10(14)13(17)18/h9-10H,3-8,14H2,1-2H3,(H,17,18)(H,19,20)/t9-,10+/m1/s1
• InChIKey: UNJJBGNPUUVVFQ-ZJUUUORDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-({[(2R)-2-(butanoyloxy)-3-(propanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid
• IUPAC Traditional name: phosphatidylserine
• Brand Name: LifeExtension PS Caps
• Synonyms: 3-O-sn-Phosphatidyl-L-serine; O3-Phosphatidyl-L-serine; Phosphatidyl-L-serine; Phosphatidylserine

Database IDs

• CAS Number: 8002-43-5
• PubChem SID: 46505650; 160963493
• PubChem CID: 445141; 6323481
• Chemspider ID: 13628254
• DrugBank ID: DB00144
• Wikipedia Title: Phosphatidylserine

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.468034
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -4.3265905
• LogD (pH = 7.4): -4.6020546
• Log P: -1.6207099
• Molar Refractivity: 81.8088 cm^3
• Polarizability: 33.800537 Å^3
• Polar Surface Area: 171.68 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.02
• LOG S: -2.02
• Solubility (Water): 3.70e+00 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): -3.5

DETAILS

DrugBank - DB00144

• Drug Groups: approved; nutraceutical
• Description: Phosphatidylserine (PS) is a phospholipid nutrient found in fish, green leafy vegetables, soybeans and rice, and is essential for the normal functioning of neuronal cell membranes and activates Protein kinase C (PKC) which has been shown to be involved in memory function. In apoptosis, phosphatidylserine is transferred to the outer leaflet of the plasma membrane. This is part of the process by which the cell is targeted for phagocytosis. PS has been shown to slow cognitive decline in animal models. PS has been investigated in a small number of double-blind placebo trials and has been shown to increase memory performance in the elderly. Because of the potentail cognitive benefits of phosphatidylserine, the substance is sold as a dietary supplement to people who believe they can benefit from an increased intake.; ; The dietary supplement was originally processed from bovine sources however Prion disease scares in the 1990s outlawed this process, and a soy-based alternative was adopted.
• Indication: Phosphatidylserine has demonstrated some usefulness in treating cognitive impairment, including Alzheimer's disease, age-associated memory impairment and some non-Alzheimer's dementias. More research is needed before phosphatidylserine can be indicated for immune enhancement or for reduction of exercise stress.
• Pharmacology: Phosphatidylserine is indicated in the treatment of cognitive impairment, including Alzheimer's disease, age-associated memory impairment and some non-Alzheimer's dementias. Further research is required before phosphatidylserine can be indicated for immune enhancement or for reduction of exercise stress. Phosphatidylserine was first isolated from brain lipids called cephalins. The major cephalins are phosphatidylserine and phophatidylethanolamine. Phosphatidylserine is involved in signal transduction activity as well as being a basic structural component of biologic membranes.
• Toxicity: There are no reports of overdosage. LD₅₀ in rats is more than 5g/kg, and in rabbits is more than 2g/kg.
• Affected Organisms: Humans and other mammals
• Biotransformation: Following absorption, lysophosphatidylserine is metabolized in intestinal mucosa cells, and its metabolites, which include some phosphatidylserine, enter the lymphatics draining the small intestine.
• Absorption: Absorbed in the small intestine.
• External Links: Wikipedia; PDRhealth