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3-Aminopropylphosphonate (M2MDB001163)

Record Information
Version2.0
Creation Date2012-05-31 14:39:35 -0600
Update Date2015-06-03 17:19:48 -0600
Secondary Accession Numbers
  • ECMDB20329
Identification
Name:3-Aminopropylphosphonate
Description3-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
Thumb
MOLSDFPDBSMILESInChI
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphonic acids and derivatives
Sub ClassOrganic phosphonic acids
Direct ParentOrganic 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 FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility38.9 g/LALOGPS
logP-1.4ALOGPS
logP-3ChemAxon
logS-0.55ALOGPS
pKa (Strongest Acidic)1.79ChemAxon
pKa (Strongest Basic)10.22ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity30.12 m³·mol⁻¹ChemAxon
Polarizability12.15 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
3-Aminopropylphosphonate + Adenosine triphosphate + Water > ADP + Phosphate + Hydrogen ion
SMPDB Pathways:
inner membrane transportPW000786 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9100000000-f33d044bf0ef49a29b01View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-2900000000-54e80a9c9dd1fd29014cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-5900000000-82ca9588ae1674b13621View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-d7a1cd031b0c3cb98a10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-2900000000-899bd5450325157b56beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00gr-7900000000-8ff9cf93395d1123cb78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-b873b9a363954c750a4bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-2900000000-bc5dd3221a51a53ca9e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fdo-7900000000-e9619ddbb282c949d22eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-67494485e8ac2fdcab9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-16331886731ab6564dc0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-91c494057c53e760d7f9View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView 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
External Links:
ResourceLink
CHEBI ID142993
HMDB IDHMDB0245822
Pubchem Compound ID4868255
Kegg IDNot Available
ChemSpider ID88080
Wikipedia IDNot Available
BioCyc IDCPD0-1077
EcoCyc IDCPD0-1077

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