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Record Information

Version

2.0

Creation Date

2015-06-04 16:14:45 -0600

Update Date

2015-09-14 16:46:22 -0600

Secondary Accession Numbers

ECMDB23825

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

Synonyms:

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

Chemical Formula:

C₇H₁₀NO₆PS

Weight:

Average: 267.19
Monoisotopic: 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

Description

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 or derivatives
Monoalkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Thiazole
Meta-thiazoline
Ketimine
Thioenolether
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Imine
Organic oxygen compound
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 g/L	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
1-Deoxy-D-xylulose 5-phosphate + 2 2-iminoacetate <>2 2-[(2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate +2 Water

SMPDB Pathways:

Not Available

KEGG Pathways:

Metabolic pathways eco01100
Thiamine metabolism ec00730

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	View in JSpectraViewer
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
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:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	134196
HMDB ID	Not Available
Pubchem Compound ID	Not Available
Kegg ID	C20246
ChemSpider ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. Thiazole synthase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the rearrangement of 1-deoxy-D-xylulose 5- phosphate (DXP) to produce the thiazole phosphate moiety of thiamine. Sulfur is provided by the thiocarboxylate moiety of the carrier protein ThiS. In vitro, sulfur can be provided by H(2)S
Gene Name:: thiG
Uniprot ID:: P30139
Molecular weight:: 26896

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 H(2)O.

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2-[(2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate (M2MDB004543)

Structure for #<Compound:0x88e9527c>

Enzymes

Reactions