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Record Information

Version

2.0

Creation Date

2012-05-31 13:49:55 -0600

Update Date

2015-06-03 15:53:56 -0600

Secondary Accession Numbers

ECMDB01319

Identification

Name:

Pyridoxine 5'-phosphate

Description

Pyridoxine 5'-phosphate is a substrate for Pyridoxine-5'-phosphate oxidase and Pyridoxal kinase.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

5-Hydroxy-4-(hydroxymethyl)-6-methyl-3-pyridylmethyl dihydrogen phosphate
5-Hydroxy-4-(hydroxymethyl)-6-methyl-3-pyridylmethyl dihydrogen phosphoric acid
5-Hydroxy-6-methyl-3,4-pyridinedimethanol a( 3)-(dihydrogen phosphate)
5-Hydroxy-6-methyl-3,4-pyridinedimethanol a( 3)-(dihydrogen phosphoric acid)
5-Hydroxy-6-methyl-3,4-Pyridinedimethanol alpha( 3)-(dihydrogen phosphate)
5-Hydroxy-6-methyl-3,4-pyridinedimethanol alpha( 3)-(dihydrogen phosphoric acid)
5-Hydroxy-6-methyl-3,4-pyridinedimethanol α( 3)-(dihydrogen phosphate)
5-Hydroxy-6-methyl-3,4-pyridinedimethanol α( 3)-(dihydrogen phosphoric acid)
Pyn5'P
Pyridoxine 5'-phosphate
Pyridoxine 5'-phosphoric acid
Pyridoxine 5-phosphate
Pyridoxine 5-phosphoric acid
Pyridoxine-5'-phosphate
Pyridoxine-5'-phosphoric acid
Pyridoxine-5-phosphate
Pyridoxine-5-phosphoric acid
Pyridoxine-5P
Pyridoxine-P
Pyridoxine-phosphate
Pyridoxine-phosphoric acid
Pyridoxol 5-phosphate
Pyridoxol 5-phosphoric acid
Pyridoxol-5'-phosphate
Pyridoxol-5'-phosphoric acid
Pyridoxyl-5-phosphate
Pyridoxyl-5-phosphoric acid
[5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]methyl phosphate
[5-Hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]methyl phosphoric acid

Chemical Formula:

C₈H₁₂NO₆P

Weight:

Average: 249.1577
Monoisotopic: 249.040223633

InChI Key:

WHOMFKWHIQZTHY-UHFFFAOYSA-N

InChI:

InChI=1S/C8H12NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2,10-11H,3-4H2,1H3,(H2,12,13,14)

CAS number:

447-05-2

IUPAC Name:

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

Traditional IUPAC Name:

pyridoxine-5'-phosphate

SMILES:

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

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pyridoxine-5'-phosphates. These are pyridoxines that carry a phosphate group at the 5-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridoxines

Direct Parent

Pyridoxine-5'-phosphates

Alternative Parents

Substituents

Pyridoxine-5'-phosphate
Monoalkyl phosphate
Hydroxypyridine
Methylpyridine
Organic phosphoric acid derivative
Alkyl phosphate
Phosphoric acid ester
Heteroaromatic compound
Azacycle
Hydrocarbon derivative
Alcohol
Aromatic alcohol
Organic nitrogen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

vitamin B6 phosphate (CHEBI:28803 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	9.41 g/L	ALOGPS
logP	-0.8	ALOGPS
logP	-3.6	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	1.74	ChemAxon
pKa (Strongest Basic)	5.55	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	120.11 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	54.98 m³·mol⁻¹	ChemAxon
Polarizability	21.73 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:

SMPDB Pathways:

Vitamin B6 1430936196

PW000891

KEGG Pathways:

Metabolic pathways eco01100
Microbial metabolism in diverse environments ec01120
Vitamin B6 metabolism ec00750

EcoCyc Pathways:

pyridoxal 5'-phosphate biosynthesis I PYRIDOXSYN-PWY
pyridoxal 5'-phosphate salvage pathway PLPSAL-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9530000000-1e967afad92165e82bee	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9226000000-49f5293644ca681d401b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
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	splash10-0ue9-0590000000-68640055ed308d852fd0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f89-0900000000-1450b9f084acf6421d59	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-4900000000-8fd6492e6f2a6bea9879	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-8090000000-65f73f2c7a460a3fca23	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9010000000-5b0859a6a40a458fcc9f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a6fead236e12d88986b8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0290000000-da88c1789911b79c0362	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ff0-0910000000-366dc9237952c888f4b8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-2900000000-cd37cb30cd544c5f866a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002b-9010000000-64a9d47104102ec4486f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-ef724d5177083af378f0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	View in MoNA
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	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	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	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer

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
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Argoudelis, Chris J. Preparation of crystalline pyridoxine 5'-phosphate and some of its properties. Journal of Agricultural and Food Chemistry (1986), 34(6), 995-8.

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	28803
HMDB ID	HMDB01319
Pubchem Compound ID	1055
Kegg ID	C00627
ChemSpider ID	1026
Wikipedia ID	Not Available
BioCyc ID	PYRIDOXINE-5P
EcoCyc ID	PYRIDOXINE-5P
Ligand Expo	PXP

Enzymes

Protein Details

1. Pyridoxine 5'-phosphate synthase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the complicated ring closure reaction between the two acyclic compounds 1-deoxy-D-xylulose-5-phosphate (DXP) and 3-amino-2-oxopropyl phosphate (1-amino-acetone-3-phosphate or AAP) to form pyridoxine 5'-phosphate (PNP) and inorganic phosphate
Gene Name:: pdxJ
Uniprot ID:: P0A794
Molecular weight:: 26384

Reactions

1-deoxy-D-xylulose 5-phosphate + 3-amino-2-oxopropyl phosphate = pyridoxine 5'-phosphate + phosphate + 2 H(2)O.

Protein Details

2. 4-hydroxythreonine-4-phosphate dehydrogenase

General function:: Involved in 4-hydroxythreonine-4-phosphate dehydrogenase activity
Specific function:: Catalyzes the NAD(P)-dependent oxidation of 4- (phosphohydroxy)-L-threonine (HTP) into 2-amino-3-oxo-4- (phosphohydroxy)butyric acid which spontaneously decarboxylates to form 3-amino-2-oxopropyl phosphate (AHAP)
Gene Name:: pdxA
Uniprot ID:: P19624
Molecular weight:: 35114

Reactions

4-(phosphonooxy)-L-threonine + NAD(+) = (2S)-2-amino-3-oxo-4-phosphonooxybutanoate + NADH.

Protein Details

3. Phosphatase ybhA

General function:: Involved in catalytic activity
Specific function:: Catalyzes the dephosphorylation of the artificial chromogenic substrate p-nitrophenyl phosphate (pNPP) and of the natural substrates pyridoxalphosphate and erythrose 4-phosphate
Gene Name:: ybhA
Uniprot ID:: P21829
Molecular weight:: 30201

Protein Details

4. Pyridoxine kinase

General function:: Involved in pyridoxal kinase activity
Specific function:: Phosphorylates B6 vitamers; functions in a salvage pathway. Uses pyridoxal, pyridoxine, and pyridoxamine as substrates
Gene Name:: pdxK
Uniprot ID:: P40191
Molecular weight:: 30847

Reactions

ATP + pyridoxal = ADP + pyridoxal 5'-phosphate.

Protein Details

5. Pyridoxamine kinase

General function:: Involved in pyridoxal kinase activity
Specific function:: Phosphorylates B6 vitamers; functions in a salvage pathway. Uses pyridoxamine, but has negligible activity toward pyridoxal and pyridoxine as substrates
Gene Name:: pdxY
Uniprot ID:: P77150
Molecular weight:: 31322

Reactions

ATP + pyridoxal = ADP + pyridoxal 5'-phosphate.

Protein Details

6. Pyridoxine/pyridoxamine 5'-phosphate oxidase

General function:: Coenzyme transport and metabolism
Specific function:: Catalyzes the oxidation of either pyridoxine 5'- phosphate (PNP) or pyridoxamine 5'-phosphate (PMP) into pyridoxal 5'-phosphate (PLP)
Gene Name:: pdxH
Uniprot ID:: P0AFI7
Molecular weight:: 25545

Reactions

Pyridoxamine 5'-phosphate + H(2)O + O(2) = pyridoxal 5'-phosphate + NH(3) + H(2)O(2).
Pyridoxine 5'-phosphate + O(2) = pyridoxal 5'-phosphate + H(2)O(2).

Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.

Pyridoxine 5'-phosphate (M2MDB000338)

Structure for #<Compound:0xa94e8244>

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions