P. aeruginosa Metabolome Database: Pyridoxamine 5'-phosphate (PAMDB000420)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000420

Identification

Name:

Pyridoxamine 5'-phosphate

Description:

Pyradoxamine 5' phosphate or Vitamin B6 is a water-soluble compound that was discovered in 1930s during nutrition studies on rats. The vitamin was named pyridoxine to indicate its structural homology to pyridine. Later it was shown that vitamin B6 could exist in two other, slightly different, chemical forms, termed pyridoxal and pyridoxamine. All three forms of vitamin B6 are precursors of an activated compound known as pyridoxal 5-phosphate (PLP), which plays a vital role as the cofactor of a large number of essential enzymes.Vitamin B6 is a water-soluble vitamin. The three major forms of vitamin B6 are pyridoxine (also known as pyridoxol), pyridoxal, and pyridoxamine, which are all converted in to pyridoxal 5-phosphate (PLP) a cofactor in many reactions of amino acid metabolism. PLP also is necessary for the enzymatic reaction governing the release of glucose from glycogen.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

PMP
PX5'P
Pyridoxamine 5'-phosphate
Pyridoxamine 5'-phosphoric acid
Pyridoxamine phosphate
Pyridoxamine phosphoric acid

Chemical Formula:

C₈H₁₃N₂O₅P

Average Molecular Weight:

248.173

Monoisotopic Molecular Weight:

248.056208048

InChI Key:

ZMJGSOSNSPKHNH-UHFFFAOYSA-N

InChI:

InChI=1S/C8H13N2O5P/c1-5-8(11)7(2-9)6(3-10-5)4-15-16(12,13)14/h3,11H,2,4,9H2,1H3,(H2,12,13,14)

CAS number:

529-96-4

IUPAC Name:

{[4-(aminomethyl)-5-hydroxy-6-methylpyridin-3-yl]methoxy}phosphonic acid

Traditional IUPAC Name:

pyridoxamine-5'-phosphate

SMILES:

CC1=NC=C(COP(O)(O)=O)C(CN)=C1O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as pyridoxamines. These are pyridoxal derivatives in which the pyridoxal moiety is substituted at position 2 by an amine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridoxamines

Direct Parent

Pyridoxamines

Alternative Parents

Substituents

Pyridoxamine
Methylpyridine
Hydroxypyridine
Aralkylamine
Monoalkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic phosphate
Heteroaromatic compound
Azacycle
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monohydroxypyridine (CHEBI:18335 )
methylpyridines (CHEBI:18335 )
aminoalkylpyridine (CHEBI:18335 )
vitamin B6 phosphate (CHEBI:18335 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	6.61 mg/mL	ALOGPS
logP	-0.99	ALOGPS
logP	-2.2	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.74	ChemAxon
pKa (Strongest Basic)	10.11	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	56.64 m³·mol^-1	ChemAxon
Polarizability	22.14 Å³	ChemAxon
Number of Rings	1	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:

Pathways:

Metabolic pathways pae01100
Microbial metabolism in diverse environments pae01120
Vitamin B6 metabolism pae00750

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001j-0590000000-f2e78df6839a1a6c3c53	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f89-0900000000-45ff9c035fa30cea77bf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-2900000000-96d22fb2e9dd035fa2e5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9080000000-908c35d20c168506f92c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9010000000-97480b70e97796d59101	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-c77bbc411daf4c046f20	View in MoNA
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
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
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195

Synthesis Reference:

Katsunishi, Masatoshi; Kondo, Osamu. Pyridoxamine-5'-phosphate. Jpn. Tokkyo Koho (1972), 2 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	18335
HMDB ID	HMDB01555
Pubchem Compound ID	1053
Kegg ID	C00647
ChemSpider ID	1024
Wikipedia ID	Not Available
BioCyc ID	PYRIDOXAMINE-5P
EcoCyc ID	PYRIDOXAMINE-5P
Ligand Expo	PMP

Pyridoxamine 5'-phosphate (PAMDB000420)

Structure for Pyridoxamine 5'-phosphate (PAMDB000420)