Basic information
- CAS
20263-06-3- Standard SMILES
NC(CP(=O)(O)O)C(=O)O- InChIKey
LBTABPSJONFLPO-UHFFFAOYSA-N- Molecular formula
- C3H8NO5P
- Average molar mass
- 169.07 g/mol
- Monoisotopic mass
- 169.01400899
Overview
2-amino-3-phosphonopropanoic acid is a non-proteinogenc alpha-amino acid that is alanine in which one of the hydrogens of the terminal methyl group has been replaced by a dihydroxy(oxido)-5-phosphanyl group. It has a role as a metabotropic glutamate receptor antagonist and a human metabolite. It is an alanine derivative, a member of phosphonic acids and a non-proteinogenic alpha-amino acid.
Names & identifiers
- Preferred name
- 2-Amino-3-phosphonopropionic acid
- IUPAC
- 2-amino-3-phosphonopropanoic acid
- English name
- (+-)-2-Amino-3-phosphonopropionic acid ( AP-3)NMDA antagonist
- Molecular formula
- C3H8NO5P
- Molecular weight
- 169.07
Names & synonyms
5652-28-82-amino-3-phosphonopropanoic acid2-Amino-3-phosphonopropionic acid3-phosphonoalaninePhosphonoalanine2-Amino-3-phosprop2-Amino-3-phosphopropionic acid2-Amino-3-phosphono-propionic acid2-AP3NSC-300780H89G8110OCHEBI:28388
Show more names
(+-)-2-Amino-3-phosphonopropionic acid ( AP-3)NMDA antagonist
DTXSID40863590RefChem:463956DTXCID80812183DL-AP320263-06-3DL-2-Amino-3-phosphonopropionic acidAlanine, 3-phosphono-2-Amino-3-phosphonopropionate
Database identifiers
- CAS
20263-06-3、23052-80-4、5652-28-8- PubChem CID
- 3857
- DTXSID
DTXSID40863590- ChEMBL
CHEMBL88621- ChEBI
CHEBI:28388- UNII
- 0H89G8110O
- EC Number
- 633-843-3
- Nikkaji
- J81.069J
Properties
Computed structural properties
- XLogP
- -5.2
- Topological polar surface area
- 121 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 3
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 174
Experimental & physicochemical properties
Physical DescriptionSolid
Physicochemical properties
- Boiling point
- 481.6 · 481.6±55.0 °C(Predicted)
- Density
- 1.763 · 1.763±0.06 g/cm3(Predicted)
- solubility
- PBS (pH 7.2): 2 mg/ml
- form
- White powder.
- pka
- 1.22 · 1.22±0.10(Predicted)
- color
- White to off-white
- FDA UNII
- 0 H89G8110O · 0H89G8110O
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P321-P362+P364-P332+P313-P337+P313-P403+P233-P405-P501
- HS Code
- 2931499090 · 2931499090
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- hs_code
- 2931499090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P321-P362+P364-P332+P313-P337+P313-P403+P233-P405-P501
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationDrugs that bind to but do not activate excitatory amino acid receptors, thereby blocking the actions of agonists.
Tissue LocationsEpidermis
Applications
DescriptionMetabotropic glutamate receptors (mGluR1-8) are G protein-coupled receptors that function to modulate brain excitatory signaling via presynaptic, postsynaptic, and glial mechanisms. DL-AP3 is a competitive mGluR1 antagonist that demonstrates a Ki value of 298 μM and an IC50 value of 1mM for rat mGluR1α when challenged with glutamate. DL-AP3 can antagonize excitatory amino acid-induced phosphoinositide hydrolysis, induce Ca2+ mobilization in rat hippocampal slices, and inhibit phosphoserine phosphatase in rat brain cortex. At concentrations from 10-300 μM DL-AP3 has been used to characterize the role of mGluR in long-term potentiation in the hippocampus in a model of learning and memory, the release of glutamate in Parkinson’s disease, and the increased activity of mGluR implicated in fragile X syndrome.
UsesDL-2-Amino-3-phosphonopropionic acid (AP3) is an inhibitor of phosphoserine phosphatase and mGluR. Also known as the antagonist of a receptor that is coupled to phosphoinositide metabolism in brain slices. D,L-2-Amino-3-phosphonopropionic acid is also an inhibitor of metabotropic glutamate receptors in rat brain.
Suppliers17 total
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]
河南阿尔法化工有限公司0371-55013243 15324716602 · [email protected]
Related reactions
0 records
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Compound notes
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