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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-11-15 21:04:30 UTC
HMDB IDHMDB0000370
Secondary Accession Numbers
  • HMDB00370
Metabolite 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is a non-proteinogenc alpha-amino acid that is alanine in which one of the hydrogens of the terminal methyl group has been replaced by a dihydroxy(oxido)-lambda(5)-phosphanyl group.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
Data?1582752127
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 Molecular Weight169.0731
Monoisotopic Molecular Weight169.014008883
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
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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility34.7 g/LALOGPS
logP10(-2.5) g/LALOGPS
logP10(-3.8) g/LChemAxon
logS10(-0.69) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.91131661259
DarkChem[M-H]-127.90731661259
AllCCS[M+H]+136.1232859911
AllCCS[M-H]-125.24332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Amino-3-phosphonopropionic acidNC(CP(O)(O)=O)C(O)=O2585.8Standard polar33892256
2-Amino-3-phosphonopropionic acidNC(CP(O)(O)=O)C(O)=O1358.3Standard non polar33892256
2-Amino-3-phosphonopropionic acidNC(CP(O)(O)=O)C(O)=O1887.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Amino-3-phosphonopropionic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C(N)CP(=O)(O)O1672.3Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,1TMS,isomer #2C[Si](C)(C)OP(=O)(O)CC(N)C(=O)O1721.4Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,1TMS,isomer #3C[Si](C)(C)NC(CP(=O)(O)O)C(=O)O1749.2Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C(N)CP(=O)(O)O[Si](C)(C)C1715.6Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C(N)CP(=O)(O)O[Si](C)(C)C1645.3Standard non polar33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C(N)CP(=O)(O)O[Si](C)(C)C2803.7Standard polar33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #2C[Si](C)(C)NC(CP(=O)(O)O)C(=O)O[Si](C)(C)C1762.3Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #2C[Si](C)(C)NC(CP(=O)(O)O)C(=O)O[Si](C)(C)C1718.4Standard non polar33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #2C[Si](C)(C)NC(CP(=O)(O)O)C(=O)O[Si](C)(C)C2668.5Standard polar33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #3C[Si](C)(C)OP(=O)(CC(N)C(=O)O)O[Si](C)(C)C1750.3Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #3C[Si](C)(C)OP(=O)(CC(N)C(=O)O)O[Si](C)(C)C1680.6Standard non polar33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #3C[Si](C)(C)OP(=O)(CC(N)C(=O)O)O[Si](C)(C)C2822.5Standard polar33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #4C[Si](C)(C)NC(CP(=O)(O)O[Si](C)(C)C)C(=O)O1805.3Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #4C[Si](C)(C)NC(CP(=O)(O)O[Si](C)(C)C)C(=O)O1696.2Standard non polar33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #4C[Si](C)(C)NC(CP(=O)(O)O[Si](C)(C)C)C(=O)O2432.5Standard polar33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #5C[Si](C)(C)N(C(CP(=O)(O)O)C(=O)O)[Si](C)(C)C1891.6Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #5C[Si](C)(C)N(C(CP(=O)(O)O)C(=O)O)[Si](C)(C)C1946.8Standard non polar33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #5C[Si](C)(C)N(C(CP(=O)(O)O)C(=O)O)[Si](C)(C)C2706.7Standard polar33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C(N)CP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1731.3Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C(N)CP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1727.8Standard non polar33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C(N)CP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2611.2Standard polar33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #2C[Si](C)(C)NC(CP(=O)(O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1777.6Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #2C[Si](C)(C)NC(CP(=O)(O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1749.0Standard non polar33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #2C[Si](C)(C)NC(CP(=O)(O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C2207.3Standard polar33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #3C[Si](C)(C)OC(=O)C(CP(=O)(O)O)N([Si](C)(C)C)[Si](C)(C)C1880.8Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #3C[Si](C)(C)OC(=O)C(CP(=O)(O)O)N([Si](C)(C)C)[Si](C)(C)C1945.5Standard non polar33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #3C[Si](C)(C)OC(=O)C(CP(=O)(O)O)N([Si](C)(C)C)[Si](C)(C)C2389.5Standard polar33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #4C[Si](C)(C)NC(CP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O1805.2Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #4C[Si](C)(C)NC(CP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O1802.8Standard non polar33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #4C[Si](C)(C)NC(CP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O2098.0Standard polar33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #5C[Si](C)(C)OP(=O)(O)CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1937.8Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #5C[Si](C)(C)OP(=O)(O)CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1864.6Standard non polar33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #5C[Si](C)(C)OP(=O)(O)CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2244.5Standard polar33892256
2-Amino-3-phosphonopropionic acid,4TMS,isomer #1C[Si](C)(C)NC(CP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1784.6Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,4TMS,isomer #1C[Si](C)(C)NC(CP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1845.1Standard non polar33892256
2-Amino-3-phosphonopropionic acid,4TMS,isomer #1C[Si](C)(C)NC(CP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1950.3Standard polar33892256
2-Amino-3-phosphonopropionic acid,4TMS,isomer #2C[Si](C)(C)OC(=O)C(CP(=O)(O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1895.8Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,4TMS,isomer #2C[Si](C)(C)OC(=O)C(CP(=O)(O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1910.2Standard non polar33892256
2-Amino-3-phosphonopropionic acid,4TMS,isomer #2C[Si](C)(C)OC(=O)C(CP(=O)(O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2082.8Standard polar33892256
2-Amino-3-phosphonopropionic acid,4TMS,isomer #3C[Si](C)(C)OP(=O)(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C1919.0Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,4TMS,isomer #3C[Si](C)(C)OP(=O)(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C1937.7Standard non polar33892256
2-Amino-3-phosphonopropionic acid,4TMS,isomer #3C[Si](C)(C)OP(=O)(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C2006.2Standard polar33892256
2-Amino-3-phosphonopropionic acid,5TMS,isomer #1C[Si](C)(C)OC(=O)C(CP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1925.1Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,5TMS,isomer #1C[Si](C)(C)OC(=O)C(CP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1971.7Standard non polar33892256
2-Amino-3-phosphonopropionic acid,5TMS,isomer #1C[Si](C)(C)OC(=O)C(CP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1922.4Standard polar33892256
2-Amino-3-phosphonopropionic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(N)CP(=O)(O)O1932.4Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OP(=O)(O)CC(N)C(=O)O1960.8Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(CP(=O)(O)O)C(=O)O1997.5Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(N)CP(=O)(O)O[Si](C)(C)C(C)(C)C2153.9Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(N)CP(=O)(O)O[Si](C)(C)C(C)(C)C2075.9Standard non polar33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(N)CP(=O)(O)O[Si](C)(C)C(C)(C)C3078.8Standard polar33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(CP(=O)(O)O)C(=O)O[Si](C)(C)C(C)(C)C2205.2Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(CP(=O)(O)O)C(=O)O[Si](C)(C)C(C)(C)C2146.0Standard non polar33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(CP(=O)(O)O)C(=O)O[Si](C)(C)C(C)(C)C2809.9Standard polar33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(CC(N)C(=O)O)O[Si](C)(C)C(C)(C)C2196.8Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(CC(N)C(=O)O)O[Si](C)(C)C(C)(C)C2097.9Standard non polar33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(CC(N)C(=O)O)O[Si](C)(C)C(C)(C)C3031.5Standard polar33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(CP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)O2243.4Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(CP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)O2116.1Standard non polar33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(CP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)O2616.3Standard polar33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)N(C(CP(=O)(O)O)C(=O)O)[Si](C)(C)C(C)(C)C2318.0Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)N(C(CP(=O)(O)O)C(=O)O)[Si](C)(C)C(C)(C)C2327.0Standard non polar33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)N(C(CP(=O)(O)O)C(=O)O)[Si](C)(C)C(C)(C)C2755.5Standard polar33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(N)CP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2368.7Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(N)CP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2315.1Standard non polar33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(N)CP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2986.0Standard polar33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(CP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2393.5Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(CP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2348.2Standard non polar33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(CP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2514.1Standard polar33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(CP(=O)(O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2521.7Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(CP(=O)(O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2537.0Standard non polar33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(CP(=O)(O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2620.0Standard polar33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(CP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O2419.5Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(CP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O2360.3Standard non polar33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(CP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O2430.1Standard polar33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OP(=O)(O)CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2538.9Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OP(=O)(O)CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2469.8Standard non polar33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OP(=O)(O)CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2510.1Standard polar33892256
2-Amino-3-phosphonopropionic acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(CP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2585.6Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(CP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2530.5Standard non polar33892256
2-Amino-3-phosphonopropionic acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(CP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2394.5Standard polar33892256
2-Amino-3-phosphonopropionic acid,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(CP(=O)(O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2730.6Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(CP(=O)(O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2671.0Standard non polar33892256
2-Amino-3-phosphonopropionic acid,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(CP(=O)(O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2452.6Standard polar33892256
2-Amino-3-phosphonopropionic acid,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2747.1Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2622.6Standard non polar33892256
2-Amino-3-phosphonopropionic acid,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2398.5Standard polar33892256
2-Amino-3-phosphonopropionic acid,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(CP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2906.2Semi standard non polar33892256
2-Amino-3-phosphonopropionic acid,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(CP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2809.5Standard non polar33892256
2-Amino-3-phosphonopropionic acid,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(CP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2422.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2-Amino-3-phosphonopropionic acid GC-MS (4 TMS)splash10-0006-0977300000-4d443df31909d1853a232014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Amino-3-phosphonopropionic acid GC-MS (Non-derivatized)splash10-0006-0977300000-4d443df31909d1853a232017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Amino-3-phosphonopropionic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00e9-9500000000-25e7ef18b28da038081f2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Amino-3-phosphonopropionic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00di-8910000000-350d551b33d8dcc004032017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Amino-3-phosphonopropionic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Amino-3-phosphonopropionic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Amino-3-phosphonopropionic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Amino-3-phosphonopropionic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Amino-3-phosphonopropionic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Amino-3-phosphonopropionic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Amino-3-phosphonopropionic acid GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-001i-9200000000-08200d2cb234cf50b9162012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0a4i-3900000000-c9c889a41769a47adbb02012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-001i-9200000000-08200d2cb234cf50b9162012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-014i-0900000000-8b77aaf1b45a8474d0e82012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-0ufr-4900000000-a387ee1964c407a1e3242012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-004i-9000000000-d60e9dd01c1955aa2a292012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-004i-9000000000-bfdad272f458c80ee2402012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-004i-9000000000-d4bd00a29f208f0b6c4f2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-0fk9-0900000000-7849997de5f05d38e1072012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-0fk9-0900000000-8a8d71c41991a12e2d3e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-052r-0900000000-44aa8996de047417f3132012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-053i-6900000000-59ba18558489e038f56c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-003u-9100000000-cdd1bec9118104602deb2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ , negative-QTOFsplash10-014i-0900000000-8b77aaf1b45a8474d0e82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ , negative-QTOFsplash10-0ufr-4900000000-a387ee1964c407a1e3242017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ , negative-QTOFsplash10-004i-9000000000-d60e9dd01c1955aa2a292017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ , negative-QTOFsplash10-004i-9000000000-bfdad272f458c80ee2402017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ , negative-QTOFsplash10-004i-9000000000-d4bd00a29f208f0b6c4f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ , positive-QTOFsplash10-0fk9-0900000000-7849997de5f05d38e1072017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid 10V, Positive-QTOFsplash10-00di-1900000000-45d697c64347f275ee312016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid 20V, Positive-QTOFsplash10-00di-4900000000-6edd7e15764a7a402a222016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid 40V, Positive-QTOFsplash10-0007-9200000000-4a8ae3dee523a44eb0dc2016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid 10V, Negative-QTOFsplash10-014i-2900000000-5ff068071928da7730ad2016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid 20V, Negative-QTOFsplash10-00pj-8900000000-b93eb66e26a07668eb5d2016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid 40V, Negative-QTOFsplash10-004i-9100000000-3a5413c9c3e2d6c726b42016-09-14Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue Locations
  • Epidermis
  • Fibroblasts
  • Intestine
  • Liver
  • Spleen
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSmith, Edward C. R.; McQuaid, Loretta A.; Paschal, Jonathan W.; DeHoniesto, Juel. An enantioselective synthesis of D-(-)- and L-(+)-2-amino-3-phosphonopropanoic acid. Journal of Organic Chemistry (1990), 55(14), 4472-4.
Material Safety Data Sheet (MSDS)Download (PDF)
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 ]
  4. Thompson JA, Miles BS, Fennessey PV: Urinary organic acids quantitated by age groups in a healthy pediatric population. Clin Chem. 1977 Sep;23(9):1734-8. [PubMed:890917 ]
  5. Wester RC, Melendres J, Sarason R, McMaster J, Maibach HI: Glyphosate skin binding, absorption, residual tissue distribution, and skin decontamination. Fundam Appl Toxicol. 1991 May;16(4):725-32. [PubMed:1884912 ]
  6. Acquavella JF, Alexander BH, Mandel JS, Burns CJ, Gustin C: Exposure misclassification in studies of agricultural pesticides: insights from biomonitoring. Epidemiology. 2006 Jan;17(1):69-74. [PubMed:16357597 ]
  7. Kintzios S, Pistola E, Panagiotopoulos P, Bomsel M, Alexandropoulos N, Bem F, Ekonomou G, Biselis J, Levin R: Bioelectric recognition assay (BERA). Biosens Bioelectron. 2001 Jun;16(4-5):325-36. [PubMed:11390221 ]
  8. Tan SA, Tan LG: Distribution of ciliatine (2-aminoethylphosphonic acid) and phosphonoalanine (2-amino-3-phosphonopropionic acid) in human tissues. Clin Physiol Biochem. 1989;7(6):303-9. [PubMed:2627760 ]
  9. Sorrentino G, Singh IN, Massarelli R, Kanfer JN: Stimulation of phospholipase C activity by norepinephrine, t-ACPD and bombesin in LA-N-2 cells. Eur J Pharmacol. 1996 Jul 11;308(1):81-6. [PubMed:8836635 ]
  10. Lee RK, Wurtman RJ, Cox AJ, Nitsch RM: Amyloid precursor protein processing is stimulated by metabotropic glutamate receptors. Proc Natl Acad Sci U S A. 1995 Aug 15;92(17):8083-7. [PubMed:7644542 ]
  11. Wang S, Deng Y, Liu B, Li X, Lin X, Yuan D, Ma J: High-performance liquid chromatographic determination of 2-aminoethylphosphonic acid and 2-amino-3-phosphonopropionic acid in seawater matrix using precolumn fluorescence derivatization with o-phthalaldehyde-ethanethiol. J Chromatogr A. 2018 Oct 12;1571:147-154. doi: 10.1016/j.chroma.2018.08.016. Epub 2018 Aug 8. [PubMed:30119975 ]
  12. KITTREDGE JS, HUGHES RR: THE OCCURRENCE OF ALPHA-AMINO-BETA-PHOSPHONOPROPIONIC ACID IN THE ZOANTHID, ZOANTHUS SOCIATUS, AND THE CILIATE, TETRAHYMENA PYRIFORMIS. Biochemistry. 1964 Jul;3:991-6. doi: 10.1021/bi00895a026. [PubMed:14214094 ]
  13. Kulakova AN, Kulakov LA, Villarreal-Chiu JF, Gilbert JA, McGrath JW, Quinn JP: Expression of the phosphonoalanine-degradative gene cluster from Variovorax sp. Pal2 is induced by growth on phosphonoalanine and phosphonopyruvate. FEMS Microbiol Lett. 2009 Mar;292(1):100-6. doi: 10.1111/j.1574-6968.2008.01477.x. Epub 2009 Jan 13. [PubMed:19191873 ]