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8002-43-5 molecular structure
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(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 and InChIs

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

Cite this record

CBID:30 http://www.chembase.cn/molecule-30.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
8002-43-5
PubChem SID
46505650
160963493
PubChem CID
445141
6323481
Chemspider ID
13628254
DrugBank ID
DB00144
Wikipedia Title
Phosphatidylserine

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 1.468034  H Acceptors
H Donor LogD (pH = 5.5) -4.3265905 
LogD (pH = 7.4) -4.6020546  Log P -1.6207099 
Molar Refractivity 81.8088 cm3 Polarizability 33.800537 Å3
Polar Surface Area 171.68 Å2 Rotatable Bonds 15 
Lipinski's Rule of Five true 
Log P -1.02  LOG S -2.02 
Solubility (Water) 3.70e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Hydrophobicity(logP)
-3.5 expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia DrugBank DrugBank
DrugBank - DB00144 external link
Item Information
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

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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