MiMeDB: Showing metabocard for 2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate (MMDBc0031740)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:47:16 UTC

Update Date

2022-08-31 18:24:08 UTC

MiMeDB ID

MMDBc0031740

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 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


  Mrv0541 10101211142D          

 17 17  0  0  0  0            999 V2000
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -1.5764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.5757    4.0018    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.4487    4.3038    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.2737    2.8748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    3.5893    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  2  2  0  0  0  0
  5  4  1  0  0  0  0
  7  6  1  0  0  0  0
  8  4  2  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  7  1  0  0  0  0
 14  3  1  0  0  0  0
 15 11  1  0  0  0  0
 15 12  1  0  0  0  0
 15 13  2  0  0  0  0
 15 14  1  0  0  0  0
 16  5  1  0  0  0  0
 16  6  1  0  0  0  0
 17  2  1  0  0  0  0
M  CHG  3  10  -1  11  -1  12  -1
M  END
> <DATABASE_ID>
MMDBc0031740

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(COP([O-])([O-])=O)=C1\SC(N=C1C)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)/p-3/b5-2-

> <INCHI_KEY>
PQMCQNOVNFNPFJ-DJWKRKHSSA-K

> <FORMULA>
C7H7NO6PS

> <MOLECULAR_WEIGHT>
264.172

> <EXACT_MASS>
263.973169163

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
21.865223959652305

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-3

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.52

> <JCHEM_LOGP>
-0.31433164845944983

> <ALOGPS_LOGS>
-1.08

> <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>
124.91000000000001

> <JCHEM_REFRACTIVITY>
66.6258

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.65e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-OCT-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   15  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   16  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+0
HETATM   17  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2    3    5   17                                                  
CONECT    3    2   14                                                       
CONECT    4    1    5    8                                                  
CONECT    5    2    4   16                                                  
CONECT    6    7    8   16                                                  
CONECT    7    6    9   10                                                  
CONECT    8    4    6                                                       
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11   15                                                            
CONECT   12   15                                                            
CONECT   13   15                                                            
CONECT   14    3   15                                                       
CONECT   15   11   12   13   14                                             
CONECT   16    5    6                                                       
CONECT   17    2                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

Synonyms

Value	Source
2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphoric acid	Generator

Chemical Formula

C₇H₇NO₆PS

Average Molecular Weight

264.172

Monoisotopic Molecular Weight

263.973169163

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H]\C(COP([O-])([O-])=O)=C1\SC(N=C1C)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)/p-3/b5-2-

InChI Key

PQMCQNOVNFNPFJ-DJWKRKHSSA-K

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
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Meta-thiazoline
Thiazole
Thioenolether
Ketimine
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Carbonyl group
Organic anion
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	26.5 g/L	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	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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0090000000-5fa092b3be7a77455418	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-08i0-0490000000-06b6cebfee5c4e2d5c79	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0005-9400000000-1e8ab834145bed1e26ec	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1190000000-6641d94d92d2d80c99c5	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-5090000000-d7626709d04c13dcc86c	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-9000000000-e8812202b947d2d2d123	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		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

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
	Proteobacteria	1	Human	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

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

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

90659326

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for 2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate (MMDBc0031740)

MOL for #<Metabolite:0x000055b76e055ea8>

3D MOL for #<Metabolite:0x000055b76e055ea8>

3D SDF for #<Metabolite:0x000055b76e055ea8>

3D-SDF for #<Metabolite:0x000055b76e055ea8>

PDB for #<Metabolite:0x000055b76e055ea8>

3D PDB for #<Metabolite:0x000055b76e055ea8>

SMILES for #<Metabolite:0x000055b76e055ea8>

INCHI for #<Metabolite:0x000055b76e055ea8>

Structure for #<Metabolite:0x000055b76e055ea8>

3D Structure for #<Metabolite:0x000055b76e055ea8>