ChemFOnt: Showing chemical card for 2-Amino-3-phosphonopropionic acid (CFc000000270)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:37 UTC

Chemfont ID

CFc000000270

Molecule Identification

Common Name

2-Amino-3-phosphonopropionic acid

Definition

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is a non-proteinogenc alpha-amino acid that is alanine in which one of the hydrogens of the terminal methyl group has been replaced by a dihydroxy(oxido)-lambda(5)-phosphanyl group.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 SDF PDB SMILES InChI

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 )

Functional 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

Predicted 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

External Links

HMDB ID

HMDB0000370

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

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.

Showing chemical card for 2-Amino-3-phosphonopropionic acid (CFc000000270)

MOL for CFc000000270 (2-Amino-3-phosphonopropionic acid)

3D MOL for CFc000000270 (2-Amino-3-phosphonopropionic acid)

3D SDF for CFc000000270 (2-Amino-3-phosphonopropionic acid)

3D-SDF for CFc000000270 (2-Amino-3-phosphonopropionic acid)

PDB for CFc000000270 (2-Amino-3-phosphonopropionic acid)

3D PDB for CFc000000270 (2-Amino-3-phosphonopropionic acid)

SMILES for CFc000000270 (2-Amino-3-phosphonopropionic acid)

INCHI for CFc000000270 (2-Amino-3-phosphonopropionic acid)

Structure for CFc000000270 (2-Amino-3-phosphonopropionic acid)

3D Structure for CFc000000270 (2-Amino-3-phosphonopropionic acid)