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Showing Compound 2-Amino-3-phosphonopropionic acid (FDB021989)

Record Information
Version1.0
Creation date2011-09-21 00:06:36 UTC
Update date2015-10-09 22:32:15 UTC
Primary IDFDB021989
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Amino-3-phosphonopropionic acid
Description2-Amino-3-phosphonopropionic acid (AP-3)is a normal human metabolite found in diverse tissues, such as liver, intestine and spleen. (PMID 2627760) AP-3 is a metabotropic glutamate receptor agonist (PMID 8836635) 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 disease (PMID 7644542) [HMDB]
CAS Number5652-28-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
1-amino-3-(Ohydroxy)propan-2-oneHMDB
1-amino-Propan-2-one-3-ateHMDB
1-amino-propan-2-one-3-phosphatehmdb
2-amino-3-OnopropanoateHMDB
2-amino-3-Onopropanoic acidHMDB
2-amino-3-OnopropionateHMDB
2-amino-3-Onopropionic acidHMDB
2-Amino-3-phosphonopropionic acidhmdb
3-amino-2-Oxopropyl ateHMDB
D-Alanyl-ateHMDB
OnoalanineKegg
Predicted Properties
PropertyValueSource
Water Solubility34.7 g/LALOGPS
logP-2.5ALOGPS
logP-3.8ChemAxon
logS-0.69ALOGPS
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
Chemical FormulaC3H8NO5P
IUPAC name2-amino-3-phosphonopropanoic acid
InChI IdentifierInChI=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
Isomeric SMILESNC(CP(O)(O)=O)C(O)=O
Average Molecular Weight169.0731
Monoisotopic Molecular Weight169.014008883
Classification
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

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS2-Amino-3-phosphonopropionic acid, 4 TMS, GC-MS Spectrumsplash10-0006-0977300000-4d443df31909d1853a23Spectrum
GC-MS2-Amino-3-phosphonopropionic acid, non-derivatized, GC-MS Spectrumsplash10-0006-0977300000-4d443df31909d1853a23Spectrum
Predicted GC-MS2-Amino-3-phosphonopropionic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00e9-9500000000-25e7ef18b28da038081fSpectrum
Predicted GC-MS2-Amino-3-phosphonopropionic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-8910000000-350d551b33d8dcc00403Spectrum
Predicted GC-MS2-Amino-3-phosphonopropionic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Amino-3-phosphonopropionic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Amino-3-phosphonopropionic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Amino-3-phosphonopropionic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Amino-3-phosphonopropionic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Amino-3-phosphonopropionic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Amino-3-phosphonopropionic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-9200000000-08200d2cb234cf50b9162012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-3900000000-c9c889a41769a47adbb02012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9200000000-08200d2cb234cf50b9162012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-8b77aaf1b45a8474d0e82012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0ufr-4900000000-a387ee1964c407a1e3242012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-9000000000-d60e9dd01c1955aa2a292012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9000000000-bfdad272f458c80ee2402012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-d4bd00a29f208f0b6c4f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0fk9-0900000000-7849997de5f05d38e1072012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0fk9-0900000000-8a8d71c41991a12e2d3e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-052r-0900000000-44aa8996de047417f3132012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-053i-6900000000-59ba18558489e038f56c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-003u-9100000000-cdd1bec9118104602deb2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-8b77aaf1b45a8474d0e82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0ufr-4900000000-a387ee1964c407a1e3242017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-d60e9dd01c1955aa2a292017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-bfdad272f458c80ee2402017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-d4bd00a29f208f0b6c4f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0fk9-0900000000-7849997de5f05d38e1072017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1900000000-45d697c64347f275ee312016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-4900000000-6edd7e15764a7a402a222016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9200000000-4a8ae3dee523a44eb0dc2016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-5ff068071928da7730ad2016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00pj-8900000000-b93eb66e26a07668eb5d2016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-3a5413c9c3e2d6c726b42016-09-14View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID3723
ChEMBL IDCHEMBL88621
KEGG Compound IDC05672
Pubchem Compound ID3857
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00370
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGlyphosate
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference