P. aeruginosa Metabolome Database: 2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate (PAMDB003443)

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

PAMDB003443

Identification

Name:

2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate

Description:

2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate is an intermediate involved in thiamine diphosphate biosynthesis. Thiamine diphosphate, also known as vitamin B1, is known to play a fundamental role in energy metabolism. It is an essential cofactor for a variety of enzymes such as transketolase, pyruvate dehydrogenase, pyruvate decarboxylase, and alpha-ketoglutarate dehydrogenase. Thiamine is synthesized de novo by microorganisms, plants and some lower eukaryotes (e.g. Plasmodium), but not by higher eukaryotes, which must obtain it through their diet.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

(5Z)-4-Methyl-5-(2-phosphonatooxyethylidene)-2H-1,3-thiazole-2-carboxylate
(5Z)-4-Methyl-5-(2-phosphonatooxyethylidene)-2H-1,3-thiazole-2-carboxylic acid
(R,Z)-2-(2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate
(R,Z)-2-(2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphoric acid
2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphoric acid
CThz*-P
Thiazole tautomer

Chemical Formula:

C₇H₇NO₆PS

Average Molecular Weight:

264.172

Monoisotopic Molecular Weight:

263.973169163

InChI Key:

PQMCQNOVNFNPFJ-DJWKRKHSSA-K

InChI:

InChI=1S/C7H10NO6PS/c1-4-5(2-3-14-15(11,12)13)16-6(8-4)7(9)10/h2,6H,3H2,1H3,(H,9,10)(H2,11,12,13)/p-3/b5-2-

CAS number:

Not Available

IUPAC Name:

(5Z)-4-methyl-5-[2-(phosphonatooxy)ethylidene]-2,5-dihydro-1,3-thiazole-2-carboxylate

Traditional IUPAC Name:

(5Z)-4-methyl-5-[2-(phosphonatooxy)ethylidene]-2H-1,3-thiazole-2-carboxylate

SMILES:

[H]\C(COP([O-])([O-])=O)=C1\SC(N=C1C)C([O-])=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Thiazolecarboxylic acid
Thiazolecarboxylic acid or derivatives
Organic phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Meta-thiazoline
Thiazole
Carboxylic acid salt
Thioenolether
Ketimine
Azacycle
Organoheterocyclic compound
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Imine
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic anion
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Not Available

Charge:

-3

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	26.5 mg/mL	ALOGPS
logP	0.52	ALOGPS
logP	-0.31	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	1.67	ChemAxon
pKa (Strongest Basic)	0.31	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	124.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	66.63 m³·mol^-1	ChemAxon
Polarizability	21.87 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:

1-Deoxy-D-xylulose 5-phosphate + 2-iminoacetate + thiocarboxy-adenylate-[sulfur-carrier protein ThiS] > 2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate + [sulfur-carrier protein ThiS] +2 Water
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

Pathways:

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0090000000-5fa092b3be7a77455418	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-08i0-0490000000-06b6cebfee5c4e2d5c79	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0005-9400000000-1e8ab834145bed1e26ec	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1190000000-6641d94d92d2d80c99c5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-5090000000-d7626709d04c13dcc86c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-9000000000-e8812202b947d2d2d123	View in MoNA

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	Not Available
HMDB ID	Not Available
Pubchem Compound ID	90659326
Kegg ID	Not Available
ChemSpider ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate (PAMDB003443)

Structure for 2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate (PAMDB003443)