Basic information
- CAS
407-41-0- Standard SMILES
N[C@@H](COP(=O)(O)O)C(=O)O- InChIKey
BZQFBWGGLXLEPQ-REOHCLBHSA-N- Molecular formula
- C3H8NO6P
- Average molar mass
- 185.07 g/mol
- Monoisotopic mass
- 185.00892397
Overview
O-phospho-L-serine is the L-enantiomer of O-phosphoserine. It has a role as an EC 1.4.7.1 [glutamate synthase (ferredoxin)] inhibitor, a mouse metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, an EC 2.5.1.49 (O-acetylhomoserine aminocarboxypropyltransferase) inhibitor, an EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor and a human metabolite. It is a conjugate acid of an O-phosphonato-L-serine(2-). It is an enantiomer of an O-phospho-D-serine.
Names & identifiers
- Preferred name
- Phospho-L-serine
- IUPAC
- (2S)-2-amino-3-phosphonooxypropanoic acid
- English name
- O-Phospho-L-serine
- Molecular formula
- C3H8NO6P
- Molecular weight
- 185.07
Names & synonyms
O-phospho-L-serineDexfosfoserineL-O-Phosphoserine407-41-0FosforinaL-PhosphoserineseriphosL-O-Serine phosphateserine phosphateO-Phosphoryl-L-serinePhospho-L-serine(+)-L-Serine dihydrogen phosphate (ester)
Show more names
L OP-serL-SOPL-O-(RG)P-serine3-P-SERINEPhospho Ser
O-phosphoserine, l-DexfosfoserinaGNF-Pf-1028DTXSID1046348NSC-760136VI4F0K069V3-phospho-L-serineDTXCID9026348
Database identifiers
- CAS
407-41-0- PubChem CID
- 68841
- DTXSID
DTXSID1046348- ChEMBL
CHEMBL284377- ChEBI
CHEBI:15811- UNII
- VI4F0K069V
- EC Number
- 206-986-0
- Nikkaji
- J136.545B
Properties
Computed structural properties
- XLogP
- -5.1
- Topological polar surface area
- 130 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 4
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 186
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Solubility71 mg/mL
Melting Point170 - 171 °C
Physical DescriptionSolid
Collision Cross Section
135.1 Ų [M+Na-2H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
140.9 Ų [M+Na]+
Physicochemical properties
- Melting point
- 190 °C · 190 °C(lit.)
- alpha
- 20 · [α]D20 +14～+18°(c=5,dil.HCl)
- Boiling point
- 475.4 · 475.4±55.0 °C(Predicted)
- Density
- 1.809 · 1.809±0.06 g/cm3(Predicted)
- vapor pressure
- 0 Pa · 0Pa at 20℃
- storage temp.
- under inert gas
- solubility
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 92.7% (38 of 41) of all reports.
Not Classified
Aggregated GHS information provided per 41 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory InformationREACH registered substance: O-phosphoserine (EC: 206-986-0)
Hazard Classes and CategoriesNot Classified
Safety data
- F
- 10
- wgk
- 3
- ridadr
- UN 3261 8 / PGII
- hs_code
- 29225090
- risk_code
- 21/22
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- hazard_code
- Xn
- safety_code
- 36/37
- Storage Class
- 8B - Non-combustible corrosive hazardous materials
- Hazard statements
- H314
- REACH Registrations
- Active
- Hazard Classifications
- Skin Corr. 1B
- Precautionary statements
- P260-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338
Chemistry & industry
Pharmacology
Tissue LocationsProstate
Cellular LocationsCytoplasm
Metabolite Pathways3-Phosphoglycerate dehydrogenase deficiency
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >1000
Applications
DescriptionO-Phospho-L-Serine is an agonist of the group III metabotropic glutamate receptors mGluR4a and mGluR6 (EC50s = 2-5 μM). It mimics the phosphatidylserine head group and has been shown to inhibit the proliferation of microglia and to enhance neuronal differentiation of progenitor cells.
Usesroborant
UsesO-Phospho-L-Serine is an agonist of the group III metabotropic glutamate receptors mGluR4a and mGluR6 (EC50s = 2-5 μM). It mimics the phosphatidylserine head group and has been shown to inhibit the proliferation of microglia and to enhance neuronal differentiation of progenitor cells.
UsesL-O-Phosphoserine is the catalytic domain of human protein kinase C β II when complexed with a malemide inhibitor. It is also used in the purification of the Epstein-Barr virus nuclear antigen 2A.
General DescriptionMonoclonal Anti-Phosphoserine (mouse IgG1 isotype) is derived from the hybridoma produced by the fusion of mouse myeloma cells and splenocytes from an immunized mouse.
Upstream & downstream products
Downstream products
Related reactions
2 records
Compound notes
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