ECMDB: Thiamine monophosphate (ECMDB02666) (M2MDB000462)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (4)XML

Proteins (838)

Record Information

Version

2.0

Creation Date

2012-05-31 13:56:55 -0600

Update Date

2015-09-17 15:41:16 -0600

Secondary Accession Numbers

ECMDB02666

Identification

Name:

Thiamine monophosphate

Description

Thiamine dihydrogen phosphate ester. The monophosphate ester of thiamine. Synonyms: monophosphothiamine; vitamin B1 monophosphate. -- Pubchem

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms:

Aneurin-monophosphorsaeureester
Aneurine monophosphate
Aneurine monophosphoric acid
Monofosfotiamina
Monophosphoric ester of thiamine
Monophosphothiamine
Monophosphothiaminum
Phosphothiaminum
Thiamin dihydrogenphosphate
Thiamin dihydrogenphosphoric acid
Thiamin monophosphate
Thiamin monophosphoric acid
Thiamin phosphate
Thiamin phosphoric acid
Thiamin-P
Thiamine monophosphate
Thiamine monophosphate dihydrate
Thiamine monophosphoric acid
Thiamine monophosphoric acid dihydric acid
Thiamine phosphate
Thiamine phosphoric acid
Thiamine-phosphate
Thiamine-phosphoric acid
Thiamine-Pi
ThiamineP
ThP
Tiamina monofosfato
TMP

Chemical Formula:

C₁₂H₁₇N₄O₄PS

Weight:

Average: 344.327
Monoisotopic: 344.070812254

InChI Key:

HZSAJDVWZRBGIF-UHFFFAOYSA-N

InChI:

InChI=1S/C12H17N4O4PS/c1-8-11(3-4-20-21(17,18)19)22-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H3-,13,14,15,17,18,19)

CAS number:

495-23-8

IUPAC Name:

3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-5-[2-(phosphonooxy)ethyl]-1,3-thiazol-3-ium

Traditional IUPAC Name:

thiamin monophosphate

SMILES:

CC1=C(CCO[P@](O)([O-])=O)SC=[N+]1CC1=CN=C(C)N=C1N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as thiamine phosphates. These are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Thiamine phosphates

Alternative Parents

Substituents

Thiamine-phosphate
4,5-disubstituted 1,3-thiazole
Monoalkyl phosphate
Hydropyrimidine
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Imidolactam
Azole
Thiazole
Heteroaromatic compound
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organic cation
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

1,3-thiazolium cation (CHEBI:9533 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.046 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-5.7	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	1.66	ChemAxon
pKa (Strongest Basic)	5.51	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.44 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	84.27 m³·mol⁻¹	ChemAxon
Polarizability	32.59 Å³	ChemAxon
Number of Rings	2	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:

Thiamin diphosphate biosynthesis	PW002028
Vitamin B1/Thiamine	PW000892

KEGG Pathways:

Metabolic pathways eco01100
Thiamine metabolism ec00730

EcoCyc Pathways:

thiamin diphosphate biosynthesis I (E. coli) PWY-6894

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-00di-0900000000-113c390c4d19be64bd0d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00ec-9600000000-7ac71f27ba3ca0e2fe91	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-3cf7f44d89518227c630	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1900000000-135b9e1aef14efaa6b3e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0109000000-eaecb343c9ff0c6f060f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9148000000-58b0f8616c541d910c2a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-3900000000-cbb443e2c206edc550d7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-4109000000-1d9d048d26c541eac8d6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002b-9001000000-3b5f50e234444b8876e6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-8a23656944b47d54a23a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006t-0519000000-8f42bf528fe96c321951	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0930000000-7ae879f5468ac7078781	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0900000000-b2954ab23477c3f8bdbc	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	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
1D NMR	1H 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

Synthesis Reference:

Leder, Irwin G. Enzymic synthesis of thiamine monophosphate. Journal of Biological Chemistry (1961), 236 3066-71.

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	9533
HMDB ID	HMDB02666
Pubchem Compound ID	1131
Kegg ID	C01081
ChemSpider ID	2627905
Wikipedia	Thiamine monophosphate
BioCyc ID	THIAMINE-P
EcoCyc ID	THIAMINE-P
Ligand Expo	TPS

Enzymes

Protein Details

1. Phosphatase nudJ

General function:: Involved in hydrolase activity
Specific function:: Catalyzes the hydrolysis of 4-amino-2-methyl-5- hydroxymethylpyrimidine pyrophosphate (HMP-PP) to 4-amino-2- methyl-5-hydroxymethylpyrimidine phosphate (HMP-P), and hydrolysis of thiamine pyrophosphate (TPP) to thiamine monophosphate (TMP). Can hydrolyze other substrates such as MeO-HMP-PP, CF(3)-HMP-PP and MeO-TPP. Is also a non-specific nucleoside tri- and diphosphatase that releases inorganic orthophosphate
Gene Name:: nudJ
Uniprot ID:: P0AEI6
Molecular weight:: 17433

Protein Details

2. Thiamine-monophosphate kinase

General function:: Involved in catalytic activity
Specific function:: ATP + thiamine phosphate = ADP + thiamine diphosphate
Gene Name:: thiL
Uniprot ID:: P0AGG0
Molecular weight:: 35070

Reactions

ATP + thiamine phosphate = ADP + thiamine diphosphate.

Protein Details

3. Thiamine-phosphate pyrophosphorylase

General function:: Involved in catalytic activity
Specific function:: Condenses 4-methyl-5-(beta-hydroxyethyl)thiazole monophosphate (THZ-P) and 2-methyl-4-amino-5-hydroxymethyl pyrimidine pyrophosphate (HMP-PP) to form thiamine monophosphate (TMP)
Gene Name:: thiE
Uniprot ID:: P30137
Molecular weight:: 23015

Reactions

2-methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 4-methyl-5-(2-phosphono-oxyethyl)thiazole = diphosphate + thiamine phosphate.

Protein Details

4. Thiamine kinase

General function:: Involved in transferase activity, transferring phosphorus-containing groups
Specific function:: Catalyzes the phosphorylation of thiamine to thiamine phosphate
Gene Name:: thiK
Uniprot ID:: P75948
Molecular weight:: 32397

Reactions

ATP + thiamine = ADP + thiamine phosphate.

Thiamine monophosphate (ECMDB02666) (M2MDB000462)

Structure for #<Compound:0x92254c88>

Enzymes

Reactions

Reactions

Reactions