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Showing NP-Card for 2-Amino-3-phosphonopropionic acid (NP0000424)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-09 22:32:56 UTC
NP-MRD IDNP0000424
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Amino-3-phosphonopropionic acid
Description2-Amino-3-phosphonopropionic acid (AP-3 or 2-AP3), also known as 3-phosphonoalanine, is a non-proteinogenc alpha-amino acid that is alanine in which one of the hydrogens of the terminal methyl group has been replaced by a dihydroxy(oxido)-lambda(5)-phosphanyl group. It is found in many organisms ranging from microbes to invertebrates to animals. In humans AP-3 is found in diverse tissues, such as liver, intestine and spleen. (PMID: 2627760 ). 2-Amino-3-phosphonopropionic acid is a ubiquitous naturally occurring phosphonate used as a source of phosphorus by many prokaryotic organisms (PMID: 30119975 ). The natural occurrence of 2-amino-3-phosphonopropionic acid. The phosphonate analogue of aspartic acid, was first reported by Kittredge & Hughes (PMID: 14214094 ) In the sea anemone Zoanthus sociatus and the protozoon Tetrahymena pyriformis. It has since been established to be one of the most widely distributed of the biogenic C–P compounds, particularly among the lower marine invertebrates (PMID: 19191873 ). AP-3 has been determined to be a metabotropic glutamate receptor agonist (PMID: 8836635 ). It has been shown to block the amyloid precursor protein (APP) release evoked by glutamate receptor stimulation in neurons of the cortex and hippocampus. APP accumulation is believed to produce the damage in Alzheimer’s disease (PMID: 7644542 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000424 (2-Amino-3-phosphonopropionic acid)

2-Amino-3-phosphonopropionic acid.mol
  Mrv1652305261923532D          

 10  9  0  0  0  0            999 V2000
    1.0717    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.2063    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6592   -0.9207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4842    0.5082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.0313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  1  4  2  0  0  0  0
  1  5  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  3  6  1  0  0  0  0
  2 10  1  0  0  0  0
M  END
Download

3D MOL for NP0000424 (2-Amino-3-phosphonopropionic acid)

HMDB0000370
     RDKit          3D
2-Amino-3-phosphonopropionic acid
 18 17  0  0  0  0  0  0  0  0999 V2000
   -1.8554   -1.2837    0.0648 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7478   -0.4932   -0.4401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4396   -0.8590    0.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9535   -0.0388    0.0085 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.0950   -0.8758    0.6010 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667    0.1374   -1.6193 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0209    1.4382    0.8497 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1109    0.9180   -0.3803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3478    1.8445   -0.7523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3534    1.2832    0.1069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6852   -1.6259    1.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7351   -0.7109    0.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5902   -0.8277   -1.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1618   -0.6196    1.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5503   -1.9557    0.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5151    0.4027   -2.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6287    2.0496    0.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2058    1.2167   -0.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  4  7  1  0
  2  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  6 16  1  0
  7 17  1  0
 10 18  1  0
M  END
Download

3D SDF for NP0000424 (2-Amino-3-phosphonopropionic acid)

2-Amino-3-phosphonopropionic acid.mol
  Mrv1652305261923532D          

 10  9  0  0  0  0            999 V2000
    1.0717    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.2063    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6592   -0.9207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4842    0.5082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.0313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  1  4  2  0  0  0  0
  1  5  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  3  6  1  0  0  0  0
  2 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000424

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CP(O)(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C3H8NO5P/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)

> <INCHI_KEY>
LBTABPSJONFLPO-UHFFFAOYSA-N

> <FORMULA>
C3H8NO5P

> <MOLECULAR_WEIGHT>
169.0731

> <EXACT_MASS>
169.014008883

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
12.845471026789173

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-phosphonopropanoic acid

> <ALOGPS_LOGP>
-2.49

> <JCHEM_LOGP>
-3.825907258582544

> <ALOGPS_LOGS>
-0.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
2.303293526274112

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3962969931080478

> <JCHEM_PKA_STRONGEST_BASIC>
9.829618218775975

> <JCHEM_POLAR_SURFACE_AREA>
120.85

> <JCHEM_REFRACTIVITY>
31.081500000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.47e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phosphonoalanine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000424 (2-Amino-3-phosphonopropionic acid)

HMDB0000370
     RDKit          3D
2-Amino-3-phosphonopropionic acid
 18 17  0  0  0  0  0  0  0  0999 V2000
   -1.8554   -1.2837    0.0648 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7478   -0.4932   -0.4401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4396   -0.8590    0.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9535   -0.0388    0.0085 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.0950   -0.8758    0.6010 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667    0.1374   -1.6193 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0209    1.4382    0.8497 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1109    0.9180   -0.3803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3478    1.8445   -0.7523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3534    1.2832    0.1069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6852   -1.6259    1.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7351   -0.7109    0.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5902   -0.8277   -1.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1618   -0.6196    1.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5503   -1.9557    0.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5151    0.4027   -2.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6287    2.0496    0.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2058    1.2167   -0.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  4  7  1  0
  2  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  6 16  1  0
  7 17  1  0
 10 18  1  0
M  END
Download

PDB for NP0000424 (2-Amino-3-phosphonopropionic acid)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 2-Amino-3-phosphonopropionic acid.mol             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       2.001   0.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.667  -0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.667   0.385   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.001   1.925   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.334  -0.385   0.000  0.00  0.00           O+0
HETATM    6  P   UNK     0      -2.001  -0.385   0.000  0.00  0.00           P+0
HETATM    7  O   UNK     0      -1.231  -1.719   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -3.334  -1.155   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -2.771   0.949   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       0.667  -1.925   0.000  0.00  0.00           N+0
CONECT    1    2    4    5                                                  
CONECT    2    1    3   10                                                  
CONECT    3    2    6                                                       
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    7    8    9    3                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    2                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for NP0000424 (2-Amino-3-phosphonopropionic acid)

COMPND    HMDB0000370
HETATM    1  N1  UNL     1      -1.855  -1.284   0.065  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.748  -0.493  -0.440  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.440  -0.859   0.402  1.00  0.00           C  
HETATM    4  P1  UNL     1       1.953  -0.039   0.009  1.00  0.00           P  
HETATM    5  O1  UNL     1       3.095  -0.876   0.601  1.00  0.00           O  
HETATM    6  O2  UNL     1       2.267   0.137  -1.619  1.00  0.00           O  
HETATM    7  O3  UNL     1       2.021   1.438   0.850  1.00  0.00           O  
HETATM    8  C3  UNL     1      -1.111   0.918  -0.380  1.00  0.00           C  
HETATM    9  O4  UNL     1      -0.348   1.845  -0.752  1.00  0.00           O  
HETATM   10  O5  UNL     1      -2.353   1.283   0.107  1.00  0.00           O  
HETATM   11  H1  UNL     1      -1.685  -1.626   1.038  1.00  0.00           H  
HETATM   12  H2  UNL     1      -2.735  -0.711   0.123  1.00  0.00           H  
HETATM   13  H3  UNL     1      -0.590  -0.828  -1.492  1.00  0.00           H  
HETATM   14  H4  UNL     1       0.162  -0.620   1.465  1.00  0.00           H  
HETATM   15  H5  UNL     1       0.550  -1.956   0.368  1.00  0.00           H  
HETATM   16  H6  UNL     1       1.515   0.403  -2.171  1.00  0.00           H  
HETATM   17  H7  UNL     1       2.629   2.050   0.378  1.00  0.00           H  
HETATM   18  H8  UNL     1      -3.206   1.217  -0.448  1.00  0.00           H  
CONECT    1    2   11   12
CONECT    2    3    8   13
CONECT    3    4   14   15
CONECT    4    5    5    6    7
CONECT    6   16
CONECT    7   17
CONECT    8    9    9   10
CONECT   10   18
END
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SMILES for NP0000424 (2-Amino-3-phosphonopropionic acid)

NC(CP(O)(O)=O)C(O)=O
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INCHI for NP0000424 (2-Amino-3-phosphonopropionic acid)

InChI=1S/C3H8NO5P/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)
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Synonyms
ValueSource
2-Amino-3-phosphono-propanoic acidChEBI
2-Amino-3-phosphono-propionic acidChEBI
2-Amino-3-phosphopropionic acidChEBI
2-Amino-3-phospropChEBI
2-AP3ChEBI
2-Azanyl-3-phosphono-propanoic acidChEBI
PhosphonoalanineChEBI
2-Amino-3-phosphono-propanoateGenerator
2-Amino-3-phosphono-propionateGenerator
2-Amino-3-phosphopropionateGenerator
2-Azanyl-3-phosphono-propanoateGenerator
2-Amino-3-phosphonopropionateGenerator
2-Amino-3-phosphonopropionic acid, (DL)-isomerHMDB
2-Amino-3-phosphonopropionic acid, sodium saltHMDB
3-Phosphono-L-alanineHMDB
L-AP3HMDB
1-Amino-3-(phosphohydroxy)propan-2-oneHMDB
1-Amino-propan-2-one-3-phosphateHMDB
2-Amino-3-phosphonopropanoateHMDB
2-Amino-3-phosphonopropanoic acidHMDB
3-Amino-2-oxopropyl phosphateHMDB
D-Alanyl-phosphateHMDB
GlyphosateHMDB
Chemical FormulaC3H8NO5P
Average Mass169.0731 Da
Monoisotopic Mass169.01401 Da
IUPAC Name2-amino-3-phosphonopropanoic acid
Traditional Namephosphonoalanine
CAS Registry Number5652-28-8
SMILES
NC(CP(O)(O)=O)C(O)=O
InChI Identifier
InChI=1S/C3H8NO5P/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)
InChI KeyLBTABPSJONFLPO-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Varshavi.d262021-08-08View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Organophosphonic acid
  • Organophosphonic acid derivative
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Primary amine
  • Organophosphorus compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility34.7 g/LALOGPS
logP-2.5ALOGPS
logP-3.8ChemAxon
logS-0.69ALOGPS
pKa (Strongest Acidic)1.4ChemAxon
pKa (Strongest Basic)9.83ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area120.85 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity31.08 m³·mol⁻¹ChemAxon
Polarizability12.85 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000370
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021989
KNApSAcK IDNot Available
Chemspider ID3723
KEGG Compound IDC05672
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5359
PubChem Compound3857
PDB IDNot Available
ChEBI ID28388
Good Scents IDNot Available
References
General References
  1. Lueken A, Juhl-Strauss U, Krieger G, Witte I: Synergistic DNA damage by oxidative stress (induced by H2O2) and nongenotoxic environmental chemicals in human fibroblasts. Toxicol Lett. 2004 Feb 28;147(1):35-43. [PubMed:14700526 ]
  2. Chan P, Mahler J: NTP technical report on the toxicity studies of Glyphosate (CAS No. 1071-83-6) Administered In Dosed Feed To F344/N Rats And B6C3F1 Mice. Toxic Rep Ser. 1992 Jul;16:1-D3. [PubMed:12209170 ]
  3. Dickson SJ, Meinhold RH, Beer ID, Koelmeyer TD: Rapid determination of glyphosate in postmortem specimens using 31P NMR. J Anal Toxicol. 1988 Sep-Oct;12(5):284-6. [PubMed:3226127 ]
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