ECMDB: 3-Aminopropylphosphonate (ECMDB20329) (M2MDB001163)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (1)Transporters (3)XML

Proteins (3)

Record Information

Version

2.0

Creation Date

2012-05-31 14:39:35 -0600

Update Date

2015-06-03 17:19:48 -0600

Secondary Accession Numbers

ECMDB20329

Identification

Name:

3-Aminopropylphosphonate

Description

3-aminopropylphosphonate is a member of the chemical class known as Organic Phosphonic Acids and Derivatives. These are organic compounds containing phosphonic acid or a derivative thereof. . Phosphonates (Pn) are a large class of organophosphorus molecules that have direct carbon-phosphorus (C-P) bonds in place of the carbon-oxygen-phosphorus ester bond. In bacteria two pathways exist for Pn breakdown for use as a P source: the phosphonatase and C-P lyase pathways. These pathways differ both in regard to their substrate specificity and their cleavage mechanism. The phosphonatase pathway acts on the natural Pn alpha-aminoethylphosphonate (AEPn). In a two-step process it leads to cleavage of the C-P bond by a hydrolysis reaction requiring an adjacent carbonyl group. In contrast the C-P lyase pathway has a broad substrate specificity. It leads to cleavage of substituted Pn (such as AEPn) as well as unsubstituted Pn by a mechanism involving redox or radical chemistry. Due to its broad substrate specificity, the C-P lyase pathway is generally thought to be responsible for the breakdown of Pn herbicides (such as glyphosate) by bacteria.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

3-(Hydroxy-oxido-phosphoryl)propylazanium
3-Aminopropylphosphonate
3-Aminopropylphosphonic acid
3-APPn

Chemical Formula:

C₃H₁₀NO₃P

Weight:

Average: 139.0902
Monoisotopic: 139.039829703

InChI Key:

GSZQTIFGANBTNF-UHFFFAOYSA-N

InChI:

InChI=1S/C3H10NO3P/c4-2-1-3-8(5,6)7/h1-4H2,(H2,5,6,7)

CAS number:

Not Available

IUPAC Name:

(3-aminopropyl)phosphonic acid

Traditional IUPAC Name:

3-aminopropylphosphonic acid

SMILES:

NCCCP(O)(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphonic acids and derivatives

Sub Class

Organic phosphonic acids

Direct Parent

Organic phosphonic acids

Alternative Parents

Substituents

Organophosphonic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organophosphorus compound
Organonitrogen compound
Primary aliphatic amine
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Not Available

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	38.9 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-3	ChemAxon
logS	-0.55	ALOGPS
pKa (Strongest Acidic)	1.79	ChemAxon
pKa (Strongest Basic)	10.22	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	83.55 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	30.12 m³·mol⁻¹	ChemAxon
Polarizability	12.15 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

3-Aminopropylphosphonate + Adenosine triphosphate + Water > ADP + Phosphate + Hydrogen ion

SMPDB Pathways:

inner membrane transport

PW000786

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9100000000-f33d044bf0ef49a29b01	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006x-2900000000-54e80a9c9dd1fd29014c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-5900000000-82ca9588ae1674b13621	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-d7a1cd031b0c3cb98a10	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-2900000000-899bd5450325157b56be	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00gr-7900000000-8ff9cf93395d1123cb78	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-b873b9a363954c750a4b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-2900000000-bc5dd3221a51a53ca9e9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fdo-7900000000-e9619ddbb282c949d22e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9100000000-67494485e8ac2fdcab9c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-16331886731ab6564dc0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-91c494057c53e760d7f9	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	142993
HMDB ID	HMDB0245822
Pubchem Compound ID	4868255
Kegg ID	Not Available
ChemSpider ID	88080
Wikipedia ID	Not Available
BioCyc ID	CPD0-1077
EcoCyc ID	CPD0-1077

Enzymes

Protein Details

1. Phosphonates import ATP-binding protein PhnC

General function:: Inorganic ion transport and metabolism
Specific function:: Part of the ABC transporter complex PhnCDE involved in phosphonates, phosphate esters, phosphite and phosphate import. Responsible for energy coupling to the transport system
Gene Name:: phnC
Uniprot ID:: P16677
Molecular weight:: 29430

Reactions

ATP + H(2)O + phosphonate(Out) = ADP + phosphate + phosphonate(In).

Transporters

Protein Details

1. Putative phosphonates transport system permease protein phnE

General function:: Involved in transporter activity
Specific function:: Part of the binding-protein-dependent transport system for phosphonates; probably responsible for the translocation of the substrate across the membrane
Gene Name:: phnE
Uniprot ID:: P16683
Molecular weight:: 28383

Protein Details

2. Phosphonates import ATP-binding protein PhnC

General function:: Inorganic ion transport and metabolism
Specific function:: Part of the ABC transporter complex PhnCDE involved in phosphonates, phosphate esters, phosphite and phosphate import. Responsible for energy coupling to the transport system
Gene Name:: phnC
Uniprot ID:: P16677
Molecular weight:: 29430

Reactions

ATP + H(2)O + phosphonate(Out) = ADP + phosphate + phosphonate(In).

Protein Details

3. Phosphonates-binding periplasmic protein

General function:: alkylphosphonate transport
Specific function:: Phosphonate binding protein that is part of the phosphonate uptake system. Exhibits high affinity for 2-aminoethylphosphonate, and somewhat less affinity to ethylphosphonate, methylphosphonate, phosphonoacetate and phenylphosphonate.
Gene Name:: phnD
Uniprot ID:: P16682
Molecular weight:: 37370

3-Aminopropylphosphonate (ECMDB20329) (M2MDB001163)

Structure for #<Compound:0xabe1c084>

Enzymes

Reactions

Transporters

Reactions