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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:14:46 UTC

HMDB ID

HMDB0000370

Secondary Accession Numbers

HMDB00370

Metabolite Identification

Common Name

2-Amino-3-phosphonopropionic acid

Description

2-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is a non-proteinogenc alpha-amino acid that is alanine in which one of the hydrogens of the terminal methyl group has been replaced by a dihydroxy(oxido)-lambda(5)-phosphanyl group.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‚Äôs disease (PMID: 7644542 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Amino-3-phosphono-propanoic acid	ChEBI
2-Amino-3-phosphono-propionic acid	ChEBI
2-Amino-3-phosphopropionic acid	ChEBI
2-Amino-3-phosprop	ChEBI
2-AP3	ChEBI
2-Azanyl-3-phosphono-propanoic acid	ChEBI
Phosphonoalanine	ChEBI
2-Amino-3-phosphono-propanoate	Generator
2-Amino-3-phosphono-propionate	Generator
2-Amino-3-phosphopropionate	Generator
2-Azanyl-3-phosphono-propanoate	Generator
2-Amino-3-phosphonopropionate	Generator
2-Amino-3-phosphonopropionic acid, (DL)-isomer	HMDB
2-Amino-3-phosphonopropionic acid, sodium salt	HMDB
3-Phosphono-L-alanine	HMDB
L-AP3	HMDB
1-Amino-3-(phosphohydroxy)propan-2-one	HMDB
1-Amino-propan-2-one-3-phosphate	HMDB
2-Amino-3-phosphonopropanoate	HMDB
2-Amino-3-phosphonopropanoic acid	HMDB
3-Amino-2-oxopropyl phosphate	HMDB
D-Alanyl-phosphate	HMDB
Glyphosate	HMDB

Chemical Formula

C₃H₈NO₅P

Average Molecular Weight

169.0731

Monoisotopic Molecular Weight

169.014008883

IUPAC Name

2-amino-3-phosphonopropanoic acid

Traditional Name

phosphonoalanine

CAS Registry Number

5652-28-8

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 Key

LBTABPSJONFLPO-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).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha 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 Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic alpha-amino acid (CHEBI:28388 )
alanine derivative (CHEBI:28388 )

Ontology

Not Available

Fibroblast (HMDB: HMDB0000370)

Fibroblasts (HMDB: HMDB0000370)

Organ

Tissue

Epithelium

Epidermis (HMDB: HMDB0000370)

Source

Endogenous

Endogenous (HMDB: HMDB0000370)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Vitamin B6 (PathBank: SMP0002387)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	34.7 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-3.8	ChemAxon
logS	-0.69	ALOGPS
pKa (Strongest Acidic)	1.4	ChemAxon
pKa (Strongest Basic)	9.83	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	120.85 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	31.08 m³·mol⁻¹	ChemAxon
Polarizability	12.85 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	134.911	31661259
DarkChem	[M-H]-	127.907	31661259
AllCCS	[M+H]+	136.12	32859911
AllCCS	[M-H]-	125.243	32859911
DeepCCS	[M+H]+	123.014	30932474
DeepCCS	[M-H]-	119.45	30932474
DeepCCS	[M-2H]-	156.805	30932474
DeepCCS	[M+Na]+	131.814	30932474
AllCCS	[M+H]+	136.1	32859911
AllCCS	[M+H-H2O]+	132.2	32859911
AllCCS	[M+NH4]+	139.7	32859911
AllCCS	[M+Na]+	140.8	32859911
AllCCS	[M-H]-	125.2	32859911
AllCCS	[M+Na-2H]-	127.4	32859911
AllCCS	[M+HCOO]-	129.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Amino-3-phosphonopropionic acid	NC(CP(O)(O)=O)C(O)=O	2585.8	Standard polar	33892256
2-Amino-3-phosphonopropionic acid	NC(CP(O)(O)=O)C(O)=O	1358.3	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid	NC(CP(O)(O)=O)C(O)=O	1887.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Amino-3-phosphonopropionic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C(N)CP(=O)(O)O	1672.3	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,1TMS,isomer #2	C[Si](C)(C)OP(=O)(O)CC(N)C(=O)O	1721.4	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,1TMS,isomer #3	C[Si](C)(C)NC(CP(=O)(O)O)C(=O)O	1749.2	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(N)CP(=O)(O)O[Si](C)(C)C	1715.6	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(N)CP(=O)(O)O[Si](C)(C)C	1645.3	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(N)CP(=O)(O)O[Si](C)(C)C	2803.7	Standard polar	33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #2	C[Si](C)(C)NC(CP(=O)(O)O)C(=O)O[Si](C)(C)C	1762.3	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #2	C[Si](C)(C)NC(CP(=O)(O)O)C(=O)O[Si](C)(C)C	1718.4	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #2	C[Si](C)(C)NC(CP(=O)(O)O)C(=O)O[Si](C)(C)C	2668.5	Standard polar	33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #3	C[Si](C)(C)OP(=O)(CC(N)C(=O)O)O[Si](C)(C)C	1750.3	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #3	C[Si](C)(C)OP(=O)(CC(N)C(=O)O)O[Si](C)(C)C	1680.6	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #3	C[Si](C)(C)OP(=O)(CC(N)C(=O)O)O[Si](C)(C)C	2822.5	Standard polar	33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #4	C[Si](C)(C)NC(CP(=O)(O)O[Si](C)(C)C)C(=O)O	1805.3	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #4	C[Si](C)(C)NC(CP(=O)(O)O[Si](C)(C)C)C(=O)O	1696.2	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #4	C[Si](C)(C)NC(CP(=O)(O)O[Si](C)(C)C)C(=O)O	2432.5	Standard polar	33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #5	C[Si](C)(C)N(C(CP(=O)(O)O)C(=O)O)[Si](C)(C)C	1891.6	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #5	C[Si](C)(C)N(C(CP(=O)(O)O)C(=O)O)[Si](C)(C)C	1946.8	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,2TMS,isomer #5	C[Si](C)(C)N(C(CP(=O)(O)O)C(=O)O)[Si](C)(C)C	2706.7	Standard polar	33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(N)CP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1731.3	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(N)CP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1727.8	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(N)CP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2611.2	Standard polar	33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #2	C[Si](C)(C)NC(CP(=O)(O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1777.6	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #2	C[Si](C)(C)NC(CP(=O)(O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1749.0	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #2	C[Si](C)(C)NC(CP(=O)(O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2207.3	Standard polar	33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(CP(=O)(O)O)N([Si](C)(C)C)[Si](C)(C)C	1880.8	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(CP(=O)(O)O)N([Si](C)(C)C)[Si](C)(C)C	1945.5	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(CP(=O)(O)O)N([Si](C)(C)C)[Si](C)(C)C	2389.5	Standard polar	33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #4	C[Si](C)(C)NC(CP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O	1805.2	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #4	C[Si](C)(C)NC(CP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O	1802.8	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #4	C[Si](C)(C)NC(CP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O	2098.0	Standard polar	33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #5	C[Si](C)(C)OP(=O)(O)CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1937.8	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #5	C[Si](C)(C)OP(=O)(O)CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1864.6	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,3TMS,isomer #5	C[Si](C)(C)OP(=O)(O)CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2244.5	Standard polar	33892256
2-Amino-3-phosphonopropionic acid,4TMS,isomer #1	C[Si](C)(C)NC(CP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1784.6	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,4TMS,isomer #1	C[Si](C)(C)NC(CP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1845.1	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,4TMS,isomer #1	C[Si](C)(C)NC(CP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1950.3	Standard polar	33892256
2-Amino-3-phosphonopropionic acid,4TMS,isomer #2	C[Si](C)(C)OC(=O)C(CP(=O)(O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1895.8	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,4TMS,isomer #2	C[Si](C)(C)OC(=O)C(CP(=O)(O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1910.2	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,4TMS,isomer #2	C[Si](C)(C)OC(=O)C(CP(=O)(O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2082.8	Standard polar	33892256
2-Amino-3-phosphonopropionic acid,4TMS,isomer #3	C[Si](C)(C)OP(=O)(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	1919.0	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,4TMS,isomer #3	C[Si](C)(C)OP(=O)(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	1937.7	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,4TMS,isomer #3	C[Si](C)(C)OP(=O)(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	2006.2	Standard polar	33892256
2-Amino-3-phosphonopropionic acid,5TMS,isomer #1	C[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)C	1925.1	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,5TMS,isomer #1	C[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)C	1971.7	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,5TMS,isomer #1	C[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)C	1922.4	Standard polar	33892256
2-Amino-3-phosphonopropionic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(N)CP(=O)(O)O	1932.4	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O)CC(N)C(=O)O	1960.8	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(CP(=O)(O)O)C(=O)O	1997.5	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(N)CP(=O)(O)O[Si](C)(C)C(C)(C)C	2153.9	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(N)CP(=O)(O)O[Si](C)(C)C(C)(C)C	2075.9	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(N)CP(=O)(O)O[Si](C)(C)C(C)(C)C	3078.8	Standard polar	33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CP(=O)(O)O)C(=O)O[Si](C)(C)C(C)(C)C	2205.2	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CP(=O)(O)O)C(=O)O[Si](C)(C)C(C)(C)C	2146.0	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CP(=O)(O)O)C(=O)O[Si](C)(C)C(C)(C)C	2809.9	Standard polar	33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(CC(N)C(=O)O)O[Si](C)(C)C(C)(C)C	2196.8	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(CC(N)C(=O)O)O[Si](C)(C)C(C)(C)C	2097.9	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(CC(N)C(=O)O)O[Si](C)(C)C(C)(C)C	3031.5	Standard polar	33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(CP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)O	2243.4	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(CP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)O	2116.1	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(CP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)O	2616.3	Standard polar	33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C(CP(=O)(O)O)C(=O)O)[Si](C)(C)C(C)(C)C	2318.0	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C(CP(=O)(O)O)C(=O)O)[Si](C)(C)C(C)(C)C	2327.0	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C(CP(=O)(O)O)C(=O)O)[Si](C)(C)C(C)(C)C	2755.5	Standard polar	33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #1	CC(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)C	2368.7	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #1	CC(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)C	2315.1	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #1	CC(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)C	2986.0	Standard polar	33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #2	CC(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)C	2393.5	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #2	CC(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)C	2348.2	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #2	CC(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)C	2514.1	Standard polar	33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #3	CC(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)C	2521.7	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #3	CC(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)C	2537.0	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #3	CC(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)C	2620.0	Standard polar	33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #4	CC(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	2419.5	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #4	CC(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	2360.3	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #4	CC(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	2430.1	Standard polar	33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #5	CC(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)C	2538.9	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #5	CC(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)C	2469.8	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,3TBDMS,isomer #5	CC(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)C	2510.1	Standard polar	33892256
2-Amino-3-phosphonopropionic acid,4TBDMS,isomer #1	CC(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)C	2585.6	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,4TBDMS,isomer #1	CC(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)C	2530.5	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,4TBDMS,isomer #1	CC(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)C	2394.5	Standard polar	33892256
2-Amino-3-phosphonopropionic acid,4TBDMS,isomer #2	CC(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)C	2730.6	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,4TBDMS,isomer #2	CC(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)C	2671.0	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,4TBDMS,isomer #2	CC(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)C	2452.6	Standard polar	33892256
2-Amino-3-phosphonopropionic acid,4TBDMS,isomer #3	CC(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)C	2747.1	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,4TBDMS,isomer #3	CC(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)C	2622.6	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,4TBDMS,isomer #3	CC(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)C	2398.5	Standard polar	33892256
2-Amino-3-phosphonopropionic acid,5TBDMS,isomer #1	CC(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)C	2906.2	Semi standard non polar	33892256
2-Amino-3-phosphonopropionic acid,5TBDMS,isomer #1	CC(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)C	2809.5	Standard non polar	33892256
2-Amino-3-phosphonopropionic acid,5TBDMS,isomer #1	CC(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)C	2422.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2-Amino-3-phosphonopropionic acid GC-MS (4 TMS)	splash10-0006-0977300000-4d443df31909d1853a23	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Amino-3-phosphonopropionic acid GC-MS (Non-derivatized)	splash10-0006-0977300000-4d443df31909d1853a23	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Amino-3-phosphonopropionic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00e9-9500000000-25e7ef18b28da038081f	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Amino-3-phosphonopropionic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00di-8910000000-350d551b33d8dcc00403	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Amino-3-phosphonopropionic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Amino-3-phosphonopropionic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Amino-3-phosphonopropionic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Amino-3-phosphonopropionic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Amino-3-phosphonopropionic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Amino-3-phosphonopropionic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Amino-3-phosphonopropionic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-001i-9200000000-08200d2cb234cf50b916	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0a4i-3900000000-c9c889a41769a47adbb0	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-001i-9200000000-08200d2cb234cf50b916	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-014i-0900000000-8b77aaf1b45a8474d0e8	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-0ufr-4900000000-a387ee1964c407a1e324	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-004i-9000000000-d60e9dd01c1955aa2a29	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-004i-9000000000-bfdad272f458c80ee240	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-004i-9000000000-d4bd00a29f208f0b6c4f	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-0fk9-0900000000-7849997de5f05d38e107	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-0fk9-0900000000-8a8d71c41991a12e2d3e	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-052r-0900000000-44aa8996de047417f313	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-053i-6900000000-59ba18558489e038f56c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF	splash10-003u-9100000000-cdd1bec9118104602deb	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ , negative-QTOF	splash10-014i-0900000000-8b77aaf1b45a8474d0e8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ , negative-QTOF	splash10-0ufr-4900000000-a387ee1964c407a1e324	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ , negative-QTOF	splash10-004i-9000000000-d60e9dd01c1955aa2a29	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ , negative-QTOF	splash10-004i-9000000000-bfdad272f458c80ee240	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ , negative-QTOF	splash10-004i-9000000000-d4bd00a29f208f0b6c4f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid LC-ESI-QQ , positive-QTOF	splash10-0fk9-0900000000-7849997de5f05d38e107	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid 10V, Positive-QTOF	splash10-00di-1900000000-45d697c64347f275ee31	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid 20V, Positive-QTOF	splash10-00di-4900000000-6edd7e15764a7a402a22	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid 40V, Positive-QTOF	splash10-0007-9200000000-4a8ae3dee523a44eb0dc	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid 10V, Negative-QTOF	splash10-014i-2900000000-5ff068071928da7730ad	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid 20V, Negative-QTOF	splash10-00pj-8900000000-b93eb66e26a07668eb5d	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3-phosphonopropionic acid 40V, Negative-QTOF	splash10-004i-9100000000-3a5413c9c3e2d6c726b4	2016-09-14	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Epidermis
Fibroblasts
Intestine
Liver
Spleen

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021989

KNApSAcK ID

Not Available

Chemspider ID

3723

KEGG Compound ID

C05672

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5359

PubChem Compound

3857

PDB ID

Not Available

ChEBI ID

28388

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Smith, 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)

Not Available

General References

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]

Showing metabocard for 2-Amino-3-phosphonopropionic acid (HMDB0000370)

MOL for HMDB0000370 (2-Amino-3-phosphonopropionic acid)

3D MOL for HMDB0000370 (2-Amino-3-phosphonopropionic acid)

3D SDF for HMDB0000370 (2-Amino-3-phosphonopropionic acid)

3D-SDF for HMDB0000370 (2-Amino-3-phosphonopropionic acid)

PDB for HMDB0000370 (2-Amino-3-phosphonopropionic acid)

3D PDB for HMDB0000370 (2-Amino-3-phosphonopropionic acid)

SMILES for HMDB0000370 (2-Amino-3-phosphonopropionic acid)

INCHI for HMDB0000370 (2-Amino-3-phosphonopropionic acid)

Structure for HMDB0000370 (2-Amino-3-phosphonopropionic acid)

3D Structure for HMDB0000370 (2-Amino-3-phosphonopropionic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra