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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 07:51:27 UTC

Update Date

2021-09-24 07:51:27 UTC

HMDB ID

HMDB0304185

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-methyl-5-(2-phosphonooxyethyl)thiazole

Description

4-metyl-5-(beta-hydroxyethyl)thiazole phosphate, also known as 4-methyl-5-(2-phosphono-oxyethyl)-thiazole, is a member of the class of compounds known as 4,5-disubstituted thiazoles. 4,5-disubstituted thiazoles are compounds containing a thiazole ring substituted at positions 4 and 5 only. 4-metyl-5-(beta-hydroxyethyl)thiazole phosphate is slightly soluble (in water) and a moderately acidic compound (based on its pKa). 4-metyl-5-(beta-hydroxyethyl)thiazole phosphate can be found in a number of food items such as black-eyed pea, chinese chestnut, fireweed, and japanese pumpkin, which makes 4-metyl-5-(beta-hydroxyethyl)thiazole phosphate a potential biomarker for the consumption of these food products. 4-metyl-5-(beta-hydroxyethyl)thiazole phosphate may be a unique S.cerevisiae (yeast) metabolite.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02231216432D          

 13 13  0  0  0  0            999 V2000
   -2.3232    2.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9363    1.7948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8501    0.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1356    0.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211    0.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7066    0.5619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0078    0.9744    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.7223    1.3869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4203    0.2599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4047    1.6888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6037    0.6388    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1558    1.2519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7433    1.9664    0.0000 N   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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  2  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  2 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0304185

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(CCOP(O)(O)=O)SC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C6H10NO4PS/c1-5-6(13-4-7-5)2-3-11-12(8,9)10/h4H,2-3H2,1H3,(H2,8,9,10)

> <INCHI_KEY>
OCYMERZCMYJQQO-UHFFFAOYSA-N

> <FORMULA>
C6H10NO4PS

> <MOLECULAR_WEIGHT>
223.187

> <EXACT_MASS>
223.006815015

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
19.249996361885728

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[2-(4-methyl-1,3-thiazol-5-yl)ethoxy]phosphonic acid

> <ALOGPS_LOGP>
0.09

> <JCHEM_LOGP>
-0.5138435736727225

> <ALOGPS_LOGS>
-1.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.694128920504482

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.6125248307259508

> <JCHEM_PKA_STRONGEST_BASIC>
2.5753901399321957

> <JCHEM_POLAR_SURFACE_AREA>
79.64999999999999

> <JCHEM_REFRACTIVITY>
48.1962

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-methyl-1,3-thiazol-5-yl)ethoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.337   4.381   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.481   3.350   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.320   1.819   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.986   1.049   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.653   1.819   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.319   1.049   0.000  0.00  0.00           O+0
HETATM    7  P   UNK     0       0.015   1.819   0.000  0.00  0.00           P+0
HETATM    8  O   UNK     0       1.348   2.589   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.785   0.485   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -0.755   3.152   0.000  0.00  0.00           O+0
HETATM   11  S   UNK     0      -6.727   1.192   0.000  0.00  0.00           S+0
HETATM   12  C   UNK     0      -7.757   2.337   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -6.987   3.671   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    3   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    2                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Methyl-5-(2-phosphoethyl)-thiazole	ChEBI
4-Methyl-5-(2-phosphono-oxyethyl)-thiazole	ChEBI
4-Methyl-5-(2-phosphonooxyethyl)-thiazole	ChEBI
PHOSPHORIC ACID mono-[2-(4-methyl-thiazol-5-yl)-ethyl] ester	ChEBI
4-Methyl-5-(2-phosphonooxyethyl)thiazole	Kegg
5-(2-Hydroxyethyl)-4-methylthiazole phosphate	Kegg
HET-p	Kegg
PHOSPHate mono-[2-(4-methyl-thiazol-5-yl)-ethyl] ester	Generator
5-(2-Hydroxyethyl)-4-methylthiazole phosphoric acid	Generator
4-Methyl-5-hydroxyethylthiazole phosphoric acid	Generator
4-METHYL-5-hydroxyethylthiazole phosphATE	ChEBI
4-Metyl-5-(b-hydroxyethyl)thiazole phosphate	Generator
4-Metyl-5-(b-hydroxyethyl)thiazole phosphoric acid	Generator
4-Metyl-5-(beta-hydroxyethyl)thiazole phosphoric acid	Generator
4-Metyl-5-(β-hydroxyethyl)thiazole phosphate	Generator
4-Metyl-5-(β-hydroxyethyl)thiazole phosphoric acid	Generator

Chemical Formula

C₆H₁₀NO₄PS

Average Molecular Weight

223.187

Monoisotopic Molecular Weight

223.006815015

IUPAC Name

[2-(4-methyl-1,3-thiazol-5-yl)ethoxy]phosphonic acid

Traditional Name

2-(4-methyl-1,3-thiazol-5-yl)ethoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CC1=C(CCOP(O)(O)=O)SC=N1

InChI Identifier

InChI=1S/C6H10NO4PS/c1-5-6(13-4-7-5)2-3-11-12(8,9)10/h4H,2-3H2,1H3,(H2,8,9,10)

InChI Key

OCYMERZCMYJQQO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4,5-disubstituted thiazoles. 4,5-Disubstituted thiazoles are compounds containing a thiazole ring substituted at positions 4 and 5 only.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Thiazoles

Direct Parent

4,5-disubstituted thiazoles

Alternative Parents

Substituents

Monoalkyl phosphate
4,5-disubstituted 1,3-thiazole
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Heteroaromatic compound
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

1,3-thiazole (CHEBI:17857 )
monoalkyl phosphate (CHEBI:17857 )
Thiazole alkaloids (C04327 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.09	ALOGPS
logP	-0.51	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	1.61	ChemAxon
pKa (Strongest Basic)	2.58	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.65 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	48.2 m³·mol⁻¹	ChemAxon
Polarizability	19.25 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	146.135	32859911
AllCCS	[M+H-H2O]+	142.283	32859911
AllCCS	[M+Na]+	150.747	32859911
AllCCS	[M+NH4]+	149.716	32859911
AllCCS	[M-H]-	143.309	32859911
AllCCS	[M+Na-2H]-	144.341	32859911
AllCCS	[M+HCOO]-	145.551	32859911
DeepCCS	[M+H]+	136.531	30932474
DeepCCS	[M-H]-	133.714	30932474
DeepCCS	[M-2H]-	170.363	30932474
DeepCCS	[M+Na]+	145.832	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-methyl-5-(2-phosphonooxyethyl)thiazole,1TMS,isomer #1	CC1=C(CCOP(=O)(O)O[Si](C)(C)C)SC=N1	1970.3	Semi standard non polar	33892256
4-methyl-5-(2-phosphonooxyethyl)thiazole,1TMS,isomer #1	CC1=C(CCOP(=O)(O)O[Si](C)(C)C)SC=N1	1825.4	Standard non polar	33892256
4-methyl-5-(2-phosphonooxyethyl)thiazole,1TMS,isomer #1	CC1=C(CCOP(=O)(O)O[Si](C)(C)C)SC=N1	2648.2	Standard polar	33892256
4-methyl-5-(2-phosphonooxyethyl)thiazole,2TMS,isomer #1	CC1=C(CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)SC=N1	1979.7	Semi standard non polar	33892256
4-methyl-5-(2-phosphonooxyethyl)thiazole,2TMS,isomer #1	CC1=C(CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)SC=N1	1949.3	Standard non polar	33892256
4-methyl-5-(2-phosphonooxyethyl)thiazole,2TMS,isomer #1	CC1=C(CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)SC=N1	2221.8	Standard polar	33892256
4-methyl-5-(2-phosphonooxyethyl)thiazole,1TBDMS,isomer #1	CC1=C(CCOP(=O)(O)O[Si](C)(C)C(C)(C)C)SC=N1	2210.0	Semi standard non polar	33892256
4-methyl-5-(2-phosphonooxyethyl)thiazole,1TBDMS,isomer #1	CC1=C(CCOP(=O)(O)O[Si](C)(C)C(C)(C)C)SC=N1	2074.8	Standard non polar	33892256
4-methyl-5-(2-phosphonooxyethyl)thiazole,1TBDMS,isomer #1	CC1=C(CCOP(=O)(O)O[Si](C)(C)C(C)(C)C)SC=N1	2781.1	Standard polar	33892256
4-methyl-5-(2-phosphonooxyethyl)thiazole,2TBDMS,isomer #1	CC1=C(CCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)SC=N1	2434.4	Semi standard non polar	33892256
4-methyl-5-(2-phosphonooxyethyl)thiazole,2TBDMS,isomer #1	CC1=C(CCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)SC=N1	2380.0	Standard non polar	33892256
4-methyl-5-(2-phosphonooxyethyl)thiazole,2TBDMS,isomer #1	CC1=C(CCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)SC=N1	2483.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-methyl-5-(2-phosphonooxyethyl)thiazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9300000000-4b265fbb33f5d2a284a5	2016-09-22	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-methyl-5-(2-phosphonooxyethyl)thiazole 10V, Positive-QTOF	splash10-00fr-1970000000-6d53ae2ae5cf22f5c35d	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-methyl-5-(2-phosphonooxyethyl)thiazole 20V, Positive-QTOF	splash10-004i-1900000000-2a7dfc383c0b8f0bc737	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-methyl-5-(2-phosphonooxyethyl)thiazole 40V, Positive-QTOF	splash10-01ta-8900000000-f80f35678c9e0a53bfdf	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-methyl-5-(2-phosphonooxyethyl)thiazole 10V, Negative-QTOF	splash10-00fr-9170000000-0f15ea5b2875cc1966c8	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-methyl-5-(2-phosphonooxyethyl)thiazole 20V, Negative-QTOF	splash10-004i-9000000000-9be355f278967310c343	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-methyl-5-(2-phosphonooxyethyl)thiazole 40V, Negative-QTOF	splash10-004i-9000000000-3af10cdc8386468900f8	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-methyl-5-(2-phosphonooxyethyl)thiazole 10V, Positive-QTOF	splash10-00fr-0690000000-c5a85288f3c0ae83b359	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-methyl-5-(2-phosphonooxyethyl)thiazole 20V, Positive-QTOF	splash10-004i-4900000000-5a3ba3a8afe5cee644b5	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-methyl-5-(2-phosphonooxyethyl)thiazole 40V, Positive-QTOF	splash10-03gi-9600000000-47caa828201211845c2b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-methyl-5-(2-phosphonooxyethyl)thiazole 10V, Negative-QTOF	splash10-00fs-9050000000-392915fcb08678ef8065	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-methyl-5-(2-phosphonooxyethyl)thiazole 20V, Negative-QTOF	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-methyl-5-(2-phosphonooxyethyl)thiazole 40V, Negative-QTOF	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB03145

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

17857

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 4-methyl-5-(2-phosphonooxyethyl)thiazole (HMDB0304185)

MOL for HMDB0304185 (4-methyl-5-(2-phosphonooxyethyl)thiazole)

3D MOL for HMDB0304185 (4-methyl-5-(2-phosphonooxyethyl)thiazole)

3D SDF for HMDB0304185 (4-methyl-5-(2-phosphonooxyethyl)thiazole)

3D-SDF for HMDB0304185 (4-methyl-5-(2-phosphonooxyethyl)thiazole)

PDB for HMDB0304185 (4-methyl-5-(2-phosphonooxyethyl)thiazole)

3D PDB for HMDB0304185 (4-methyl-5-(2-phosphonooxyethyl)thiazole)

SMILES for HMDB0304185 (4-methyl-5-(2-phosphonooxyethyl)thiazole)

INCHI for HMDB0304185 (4-methyl-5-(2-phosphonooxyethyl)thiazole)

Structure for HMDB0304185 (4-methyl-5-(2-phosphonooxyethyl)thiazole)

3D Structure for HMDB0304185 (4-methyl-5-(2-phosphonooxyethyl)thiazole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra