P. aeruginosa Metabolome Database: Thiamine monophosphate (PAMDB000462)

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

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB000462

Identification

Name:

Thiamine monophosphate

Description:

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

Structure

🔍MOL SDF PDB SMILES InChI View 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

Average Molecular Weight:

344.327

Monoisotopic Molecular Weight:

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

Taxonomy Description

This compound 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
Monoalkyl phosphate
Aminopyrimidine
4,5-disubstituted 1,3-thiazole
Imidolactam
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic phosphate
Hydropyrimidine
Heteroaromatic compound
Thiazole
Azole
Azacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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	0.0456 mg/mL	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	32.87 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:

Adenosine triphosphate + Thiamine monophosphate <> ADP + Thiamine pyrophosphate
Adenosine triphosphate + Thiamine <> ADP + Hydrogen ion + Thiamine monophosphate
Water + Thiamine pyrophosphate > Hydrogen ion + Phosphate + Thiamine monophosphate
2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 4-Methyl-5-(2-phosphoethyl)-thiazole + Hydrogen ion <> Pyrophosphate + Thiamine monophosphate
Adenosine triphosphate + Thiamine <> ADP + Thiamine monophosphate
2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 4-Methyl-5-(2-phosphoethyl)-thiazole <> Pyrophosphate + Thiamine monophosphate
2-[(2R,5Z)-(2-carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate + 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + Hydrogen ion > Thiamine monophosphate + Carbon dioxide + Pyrophosphate
4-amino-2-methyl-5-diphosphomethylpyrimidine + 2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate + 2 Hydrogen ion + 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate > Thiamine monophosphate + Carbon dioxide + diphosphate + Thiamine monophosphate + Pyrophosphate
Thiamine monophosphate + Adenosine triphosphate + Thiamine monophosphate > Thiamine pyrophosphate + Adenosine diphosphate + ADP

Pathways:

Metabolic pathways pae01100
Thiamine metabolism pae00730

Spectra

Spectra:

Spectrum Type	Description	Splash Key
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
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:

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

Material Safety Data Sheet (MSDS)

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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

Thiamine monophosphate (PAMDB000462)

Structure for Thiamine monophosphate (PAMDB000462)