MiMeDB: Showing metabocard for Thiamine monophosphate (MMDBc0029696)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:37:56 UTC

Update Date

2024-10-11 04:08:23 UTC

Metabolite ID

MMDBc0029696

Metabolite Identification

Common Name

Thiamine monophosphate

Description

Thiamine dihydrogen phosphate ester. The monophosphate ester of thiamine. Synonyms: monophosphothiamine; vitamin B1 monophosphate. -- Pubchem

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282021232D          

 22 23  0  0  0  0            999 V2000
10001.364010000.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.999710001.2799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3640 9998.7200    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.607310000.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8929 9999.9530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.2141 9998.7200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.180710000.3662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4682 9999.9530    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8804 9999.2406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.755810000.3662    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
 9996.0579 9999.2406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.982110000.4478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3147 9999.9628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5696 9999.1782    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10000.3946 9999.1782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6495 9999.9628    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
10002.790110000.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.0756 9999.9547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.0756 9999.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.7901 9998.7172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10003.5046 9999.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.5046 9999.9547    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 12 16  1  0  0  0  0
 15 16  2  0  0  0  0
  1 16  1  0  0  0  0
 12  2  1  0  0  0  0
 13  4  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 17 22  1  0  0  0  0
 21 22  2  0  0  0  0
  1 18  1  0  0  0  0
 19  3  1  0  0  0  0
 21  6  1  0  0  0  0
M  CHG  2  10  -1  16   1
M  END
> <DATABASE_ID>
MMDBc0029696

> <DATABASE_NAME>
MIME

> <SMILES>
CC1=C(CCOP(O)([O-])=O)SC=[N+]1CC1=CN=C(C)N=C1N

> <INCHI_IDENTIFIER>
InChI=1S/C12H17N4O4PS/c1-8-11(3-4-20-21(17,18)19)22-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H3-,13,14,15,17,18,19)

> <INCHI_KEY>
HZSAJDVWZRBGIF-UHFFFAOYSA-N

> <FORMULA>
C12H17N4O4PS

> <MOLECULAR_WEIGHT>
344.327

> <EXACT_MASS>
344.070812254

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
31.956487685608256

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-[2-(hydrogen phosphonooxy)ethyl]-4-methyl-1,3-thiazol-3-ium

> <ALOGPS_LOGP>
-1.68

> <JCHEM_LOGP>
-5.696316403219863

> <ALOGPS_LOGS>
-3.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.712600648963036

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.6589988406382288

> <JCHEM_PKA_STRONGEST_BASIC>
5.507552519532389

> <JCHEM_POLAR_SURFACE_AREA>
125.27000000000001

> <JCHEM_REFRACTIVITY>
83.15090000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.90e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-[2-(hydrogen phosphonooxy)ethyl]-4-methyl-1,3-thiazol-3-ium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-20         0                                  
HETATM    1  C   UNK     0    8669.2138667.350   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8666.6668669.056   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    8669.2138664.277   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    8664.0678667.350   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8662.7338666.579   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8674.5338664.277   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8661.4048667.350   0.000  0.00  0.00           O+0
HETATM    8  P   UNK     0    8660.0748666.579   0.000  0.00  0.00           P+0
HETATM    9  O   UNK     0    8660.8438665.249   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8658.7448667.350   0.000  0.00  0.00           O-1
HETATM   11  O   UNK     0    8659.3088665.249   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8666.6338667.503   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.3878666.597   0.000  0.00  0.00           C+0
HETATM   14  S   UNK     0    8665.8638665.133   0.000  0.00  0.00           S+0
HETATM   15  C   UNK     0    8667.4038665.133   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0    8667.8798666.597   0.000  0.00  0.00           N+1
HETATM   17  C   UNK     0    8671.8758667.352   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8670.5418666.582   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8670.5418665.042   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0    8671.8758664.272   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0    8673.2098665.042   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0    8673.2098666.582   0.000  0.00  0.00           N+0
CONECT    1   16   18                                                       
CONECT    2   12                                                            
CONECT    3   19                                                            
CONECT    4    5   13                                                       
CONECT    5    4    7                                                       
CONECT    6   21                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12   13   16    2                                                  
CONECT   13   12   14    4                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   12   15    1                                                  
CONECT   17   18   22                                                       
CONECT   18   17   19    1                                                  
CONECT   19   18   20    3                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22    6                                                  
CONECT   22   17   21                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

Synonyms

Value	Source
THIAMIN phosphATE	ChEBI
THIAMIN phosphoric acid	Generator
Thiamine monophosphoric acid	Generator
Aneurin-monophosphorsaeureester	HMDB
Aneurine monophosphate	HMDB
Monofosfotiamina	HMDB
monoPhosphoric ester OF thiamine	HMDB
Monophosphothiamine	HMDB
Monophosphothiaminum	HMDB
Phosphothiaminum	HMDB
Thiamin dihydrogenphosphate	HMDB
Thiamin monophosphate	HMDB
Thiamine monophosphate dihydrate	HMDB
Thiamine phosphate	HMDB
Tiamina monofosfato	HMDB
TMP	HMDB
monoPhosphate, thiamine	HMDB
Phosphoester, thiamine	HMDB
Thiamine phosphoester	HMDB

Molecular Formula

C₁₂H₁₇N₄O₄PS

Average Mass

344.327

Monoisotopic Mass

344.070812254

IUPAC Name

3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-[2-(hydrogen phosphonooxy)ethyl]-4-methyl-1,3-thiazol-3-ium

Traditional Name

3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-[2-(hydrogen phosphonooxy)ethyl]-4-methyl-1,3-thiazol-3-ium

CAS Registry Number

495-23-8

SMILES

CC1=C(CCOP(O)([O-])=O)SC=[N+]1CC1=CN=C(C)N=C1N

InChI Identifier

InChI=1S/C12H17N4O4PS/c1-8-11(3-4-20-21(17,18)19)22-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H3-,13,14,15,17,18,19)

InChI Key

HZSAJDVWZRBGIF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thiamine phosphates. These are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Thiamine phosphates

Alternative Parents

Substituents

Thiamine-phosphate
4,5-disubstituted 1,3-thiazole
Aminopyrimidine
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Imidolactam
Azole
Thiazole
Heteroaromatic compound
Azacycle
Amine
Hydrocarbon derivative
Primary amine
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Organic zwitterion
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

thiamine phosphate (CHEBI:37574 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.089 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-5.7	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	1.66	ChemAxon
pKa (Strongest Basic)	5.51	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	125.27 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	83.15 m³·mol⁻¹	ChemAxon
Polarizability	31.96 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane
Mitochondria

Biospecimen Locations

Cerebrospinal Fluid (CSF)
Feces

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

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0018459	2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate	Thiamine monophosphate	Thiamine-phosphate synthase	Synthesis	PathBank	31602464
MMDBr0018460	Thiamine monophosphate	Thiamine pyrophosphate	Thiamine-monophosphate kinase	Phosphorylation	PathBank	31602464
MMDBr0019201	2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate	Thiamine monophosphate	Thiamine-phosphate synthase	Synthesis	PathBank	31602464
MMDBr0019202	Thiamine monophosphate	Thiamine pyrophosphate	Thiamine-monophosphate kinase	Phosphorylation	PathBank	31602464
MMDBr0019945	2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate	Thiamine monophosphate	Thiamine biosynthetic bifunctional enzyme	Thiamine biosynthesis	PathBank	31602464
MMDBr0019948	Thiamine monophosphate	Thiamine	Repressible acid phosphatase	Dephosphorylation	PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Alzheimer's disease		Association	Human Cerebrospinal Fluid (CSF)	HMDB	12111441

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	8	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	327	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool	Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	174	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Actinobacteria	15	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	92	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	126	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Firmicutes	26	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	2		Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Tenericutes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.0035	0.0038	uM	Adult (>18 years old)	Both	Alzheimer's disease	HMDB	12111441
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.0043	0.0024	uM	Adult (>18 years old)	Both	Normal	HMDB	12111441

External Links

HMDB ID

Not Available

DrugBank ID

DB03416

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023043

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Thiamine monophosphate

METLIN ID

3488

PubChem Compound

3382778

PDB ID

Not Available

ChEBI ID

37574

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Tallaksen CM, Bohmer T, Bell H: Concentrations of the water-soluble vitamins thiamin, ascorbic acid, and folic acid in serum and cerebrospinal fluid of healthy individuals. Am J Clin Nutr. 1992 Sep;56(3):559-64. doi: 10.1093/ajcn/56.3.559. [PubMed:1503069 ]
Tallaksen CM, Bohmer T, Bell H, Karlsen J: Concomitant determination of thiamin and its phosphate esters in human blood and serum by high-performance liquid chromatography. J Chromatogr. 1991 Mar 8;564(1):127-36. doi: 10.1016/0378-4347(91)80075-n. [PubMed:1860908 ]
Kimura M, Itokawa Y: Determination of thiamine and its phosphate esters in human and rat blood by high-performance liquid chromatography with post-column derivatization. J Chromatogr. 1985 Sep 20;332:181-8. doi: 10.1016/s0021-9673(01)83295-7. [PubMed:4055941 ]
Tallaksen CM, Bell H, Bohmer T: Thiamin and thiamin phosphate ester deficiency assessed by high performance liquid chromatography in four clinical cases of Wernicke encephalopathy. Alcohol Clin Exp Res. 1993 Jun;17(3):712-6. doi: 10.1111/j.1530-0277.1993.tb00825.x. [PubMed:8333605 ]
Tallaksen CM, Sande A, Bohmer T, Bell H, Karlsen J: Kinetics of thiamin and thiamin phosphate esters in human blood, plasma and urine after 50 mg intravenously or orally. Eur J Clin Pharmacol. 1993;44(1):73-8. doi: 10.1007/BF00315284. [PubMed:8436160 ]
Lu W, Kimball E, Rabinowitz JD: A high-performance liquid chromatography-tandem mass spectrometry method for quantitation of nitrogen-containing intracellular metabolites. J Am Soc Mass Spectrom. 2006 Jan;17(1):37-50. doi: 10.1016/j.jasms.2005.09.001. Epub 2005 Dec 15. [PubMed:16352439 ]

Showing metabocard for Thiamine monophosphate (MMDBc0029696)

MOL for #<Metabolite:0x00007f9205f437d0>

3D MOL for #<Metabolite:0x00007f9205f437d0>

3D SDF for #<Metabolite:0x00007f9205f437d0>

3D-SDF for #<Metabolite:0x00007f9205f437d0>

PDB for #<Metabolite:0x00007f9205f437d0>

3D PDB for #<Metabolite:0x00007f9205f437d0>

SMILES for #<Metabolite:0x00007f9205f437d0>

INCHI for #<Metabolite:0x00007f9205f437d0>

Structure for #<Metabolite:0x00007f9205f437d0>

3D Structure for #<Metabolite:0x00007f9205f437d0>