MiMeDB: Showing metabocard for 2-[(2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate (MMDBc0031922)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:55:06 UTC

Update Date

2022-08-31 18:26:27 UTC

Metabolite ID

MMDBc0031922

Metabolite Identification

Common 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

 
  Mrv1533006041517172D          
 
 16 16  0  0  1  0            999 V2000
    9.2383   -9.5877    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.5017  -10.3701    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3272  -10.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5740   -9.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9011   -9.0955    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.2844   -9.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8173  -11.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4460   -9.3395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8529   -9.8848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2623   -8.5188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2844   -8.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9989   -7.9266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8239   -7.9266    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.8239   -8.7516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6489   -7.9266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8239   -7.1016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  4  6  2  0  0  0  0
  3  7  1  0  0  0  0
  1  8  1  1  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031922

> <DATABASE_NAME>
MIME

> <SMILES>
CC1=N[C@H](S\C1=C/COP(O)(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
PQMCQNOVNFNPFJ-HYIMLASBSA-N

> <FORMULA>
C7H10NO6PS

> <MOLECULAR_WEIGHT>
267.19

> <EXACT_MASS>
266.996645218

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
22.502932564686915

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
-0.55

> <JCHEM_LOGP>
-0.31433164845944983

> <ALOGPS_LOGS>
-1.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.546402830396778

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.6728032996394822

> <JCHEM_PKA_STRONGEST_BASIC>
0.314050036477303

> <JCHEM_POLAR_SURFACE_AREA>
116.42000000000002

> <JCHEM_REFRACTIVITY>
58.03210000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.10e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUN-15         0                                  
HETATM    1  C   UNK     0      17.245 -17.897   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      17.737 -19.358   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      19.277 -19.342   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.738 -17.871   0.000  0.00  0.00           C+0
HETATM    5  S   UNK     0      18.482 -16.978   0.000  0.00  0.00           S+0
HETATM    6  C   UNK     0      21.064 -17.106   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.192 -20.573   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.766 -17.434   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      14.659 -18.452   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      15.423 -15.902   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      21.064 -15.566   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      22.398 -14.796   0.000  0.00  0.00           O+0
HETATM   13  P   UNK     0      23.938 -14.796   0.000  0.00  0.00           P+0
HETATM   14  O   UNK     0      23.938 -16.336   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      25.478 -14.796   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      23.938 -13.256   0.000  0.00  0.00           O+0
CONECT    1    2    5    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4    1                                                       
CONECT    6    4   11                                                       
CONECT    7    3                                                            
CONECT    8    1    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

Synonyms

Value	Source
(R,Z)-2-(2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate	ChEBI
CThz*-p	ChEBI
(R,Z)-2-(2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphoric acid	Generator
2-[(2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphoric acid	Generator

Molecular Formula

C₇H₁₀NO₆PS

Average Mass

267.19

Monoisotopic Mass

266.996645218

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC1=N[C@H](S\C1=C/COP(O)(O)=O)C(O)=O

InChI Identifier

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

InChI Key

PQMCQNOVNFNPFJ-HYIMLASBSA-N

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

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00xr-1790000000-0a7d9b4ea406b0449856	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-2900000000-a32a0fdc34132c6aa90b	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dm-5910000000-49d9bdb14276ad3abbd9	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01dj-6190000000-3296b65b319323779c84	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9010000000-ae173c7cfad6e27b22e4	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-9000000000-bd7f1c33e1c0ab4ee51f	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0015043	2-[(2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate	2-(2-Carboxy-4-methylthiazol-5-yl)ethyl phosphate	Thiazole tautomerase	Cleavage of a thiamin molecule	RHEA	34755880
MMDBr0016358	2-[(2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate	Carbon dioxide	Probable thiamine biosynthetic bifunctional enzyme	Synthesis	RHEA	34755880
MMDBr0024808	1-Deoxy-D-xylulose 5-phosphate	Water	Thiazole synthase	Synthesis	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	130	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Pig ; Cattle ; Turkey ; Chicken	Unknown
Bacteria	Firmicutes	100	Human feces; Human ; Catfish ; Cattle
Eukaryota/Fungi	Ascomycota	2
Archaea/Archaea	Euryarchaeota	24
Bacteria	Thermotogae	1
Bacteria	Actinobacteria	31	Human ; Cattle ; Human feces
Bacteria	Bacteroidetes	7	Human ; Human feces
Archaea/Archaea	Crenarchaeota	1
Bacteria	Chloroflexi	4
Bacteria	Chlamydiae	2	Human ; Sheep
Bacteria	Chlorobi	6
Bacteria	Deinococcus-thermus	4
Bacteria	Dictyoglomi	2
Bacteria	Fusobacteria	1	Human ; Human feces
Bacteria	Cyanobacteria	13
Bacteria	Aquificae	3
Bacteria	Acidobacteria	1
Bacteria	Spirochaetes	2
Archaea	Euryarchaeota	1
Bacteria	Planctomycetes	1
Bacteria	nah	1
Bacteria/NULL	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Pig ; Cattle ; Turkey ; Chicken	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-13575

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

134196

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 2-[(2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate (MMDBc0031922)

MOL for #<Metabolite:0x00007f5a580304d0>

3D MOL for #<Metabolite:0x00007f5a580304d0>

3D SDF for #<Metabolite:0x00007f5a580304d0>

3D-SDF for #<Metabolite:0x00007f5a580304d0>

PDB for #<Metabolite:0x00007f5a580304d0>

3D PDB for #<Metabolite:0x00007f5a580304d0>

SMILES for #<Metabolite:0x00007f5a580304d0>

INCHI for #<Metabolite:0x00007f5a580304d0>

Structure for #<Metabolite:0x00007f5a580304d0>

3D Structure for #<Metabolite:0x00007f5a580304d0>