P. aeruginosa Metabolome Database: 2-[(2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate (PAMDB004543)

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

PAMDB004543

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 in thiamin diphosphate biosynthesis I in E.coli, where it is a substrate for the enzyme thiamine phosphate synthase which catalyzes the reaction 2-[(2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate + 4-amino-2-methyl-5-diphosphomethylpyrimidine + 2 H+ -> thiamin phosphate + CO2 + diphosphate. In thiazole biosynthesis I, it is a product for enzyme thiazole synthase which catalyzes reaction 1-deoxy-D-xylulose 5-phosphate + 2-iminoacetate + a thiocarboxy-[ThiS-Protein] -> 2-[(2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate + a ThiS sulfur-carrier protein + 2 H2O. (BioCyc compound: CPD-13575).

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

2-[(2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphoric acid

Chemical Formula:

C₇H₁₀NO₆PS

Average Molecular Weight:

267.19

Monoisotopic Molecular Weight:

266.996645218

InChI Key:

PQMCQNOVNFNPFJ-HYIMLASBSA-N

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)/b5-2-/t6-/m1/s1

CAS number:

Not Available

IUPAC Name:

(2R,5Z)-4-methyl-5-[2-(phosphonooxy)ethylidene]-2,5-dihydro-1,3-thiazole-2-carboxylic acid

Traditional IUPAC Name:

(2R,5Z)-4-methyl-5-[2-(phosphonooxy)ethylidene]-2H-1,3-thiazole-2-carboxylic acid

SMILES:

CC1=N[C@H](S\C1=C/COP(O)(O)=O)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
Monoalkyl phosphate
Organic phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Thiazole
Meta-thiazoline
Ketimine
Thioenolether
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid
Azacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Carbonyl group
Organic oxide
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	9.1 mg/mL	ALOGPS
logP	-0.55	ALOGPS
logP	-0.31	ChemAxon
logS	-1.5	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	3	ChemAxon
Polar Surface Area	116.42 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	58.03 m³·mol^-1	ChemAxon
Polarizability	22.5 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 <> 2-[(2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate +2 Water

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	splash10-00xr-1790000000-0a7d9b4ea406b0449856	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-2900000000-a32a0fdc34132c6aa90b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dm-5910000000-49d9bdb14276ad3abbd9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01dj-6190000000-3296b65b319323779c84	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9010000000-ae173c7cfad6e27b22e4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-9000000000-bd7f1c33e1c0ab4ee51f	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	53477655
Kegg ID	C20246
ChemSpider ID	30790801
Wikipedia ID	Not Available
BioCyc ID	Not Available

2-[(2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate (PAMDB004543)

Structure for 2-[(2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate (PAMDB004543)