Thiamine (YMDB00220)

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Identification

YMDB ID

YMDB00220

Name

Thiamine

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Thiamine, also known as aneurin or vitamin B1, belongs to the class of organic compounds known as thiamines. Thiamines are compounds containing a thiamine moiety, which is structurally characterized by a 3-[(4-Amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-5-yl backbone. Thiamine is a very strong basic compound (based on its pKa). Thiamine exists in all living species, ranging from bacteria to humans. Thiamine is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Aneurin
Antiberiberi factor
Apate drops
Beatine
Bedome
Begiolan
Benerva
Bequin
Berin
Betalin s
Betaxin
Bethiazine
Beuion
Bevitex
Bevitine
Bewon
Biamine
Bithiamin
Biuno
Bivatin
Bivita
Cernevit-12
Clotiamina
Eskapen
Eskaphen
Hybee
Lixa-beta
Metabolin
Slowten
THD
Thiadoxine
Thiamin
Thiaminal
Thiaminium
Thiamol
Thiavit
Tiamidon
Tiaminal
Trophite
Vetalin S
VIB
Vinothiam
Vitamin B1
Vitaneuron
3-(4-AMINO-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-4-methyl-thiazol-3-ium
Thiamine(1+) ion
Mononitrate, thiamine
Thiamine mononitrate
Vitamin b 1

CAS number

59-43-8

Weight

Average: 265.355
Monoisotopic: 265.112306876

InChI Key

JZRWCGZRTZMZEH-UHFFFAOYSA-N

InChI

InChI=1S/C12H17N4OS/c1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15)/q+1

IUPAC Name

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

Traditional IUPAC Name

thiamine

Chemical Formula

C₁₂H₁₇N₄OS

SMILES

[H]OC([H])([H])C([H])([H])C1=C([N+](=C([H])S1)C([H])([H])C1=C(N=C(N=C1[H])C([H])([H])[H])N([H])[H])C([H])([H])[H]

Chemical Taxonomy

Description

belongs to the class of organic compounds known as thiamines. Thiamines are compounds containing a thiamine moiety, which is structurally characterized by a 3-[(4-Amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-5-yl backbone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Thiamines

Alternative Parents

Substituents

Thiamine
4,5-disubstituted 1,3-thiazole
Aminopyrimidine
Imidolactam
Azole
Thiazole
Heteroaromatic compound
Azacycle
Alcohol
Organopnictogen compound
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Amine
Organic cation
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

thiamine (CHEBI:18385 )
Water-soluble vitamins (C00378 )
a vitamin (THIAMINE )

Physical Properties

State

Solid

Charge

Melting point

248 °C

Experimental Properties

Property	Value	Reference
Water Solubility	500 mg/mL [MERCK INDEX (1996); approx.]	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.015 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-3.1	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	15.5	ChemAxon
pKa (Strongest Basic)	5.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	73.4 m³·mol⁻¹	ChemAxon
Polarizability	28.14 Å³	ChemAxon
Number of Rings	2	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

extracellular
cytoplasm

Organoleptic Properties

Flavour/Odour	Source
Bitter	FDB008424

SMPDB Pathways

Vitamin B1/Thiamine metabolism

PW002486

KEGG Pathways

Thiamine metabolism

ec00730

SMPDB Reactions

Thiamine monophosphate + water → Thiamine + phosphate

Thiamine + Adenosine triphosphate → hydron + Adenosine monophosphate + Thiamine pyrophosphate

KEGG Reactions

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
0.188 ± 0.0 µM	hops, malted barley	anaerobic	Baker's yeast	Alcoholic beverage, beer, regular, all - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
0.005 ± 0.0 µM	grape juice	anaerobic	Baker's yeast	Alcoholic beverage, wine, table, red - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
Conversion Details Here

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00e9-3890000000-9f8b525433ab279ad512	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9442000000-05ab93d3afb7b6f538e9	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-000i-0109000000-48864f31ba475645654b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-05o1-9200000000-2ec0f3e9e364cffde16e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0aou-9000000000-0184506492d9f5b68b97	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-03di-0090000000-872150be83cbd75d8ecf	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0002-0930000000-ecf71c75bdea859139d5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0002-0900000000-4d9113fdc633fb1ccbb5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0002-0900000000-4a8016299623af0c3027	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0002-1900000000-773912c9f325c419c77d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-014i-0390000000-95f3ca57c95542bdc7e7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-0900000000-e079d1fc1e06396dc524	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00di-0900000000-ebb16d4f204f291b9a3a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-00e9-4900000000-ad4d4779d76b9edb7ec5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-001i-9600000000-b631eed5be831527fc17	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-00di-0900000000-50f2f613f576814eb627	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-002b-0900000000-2f184bbfec6bc0ef00c6	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-001i-9000000000-35bc744495a2570a565f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-1900000000-d8a7ac327273c32b4524	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0002-0920000000-ca80ef6513c61be5b5e9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-03di-0090000000-872150be83cbd75d8ecf	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0190000000-183af2449d1439af9825	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0090000000-2230ebc7c6b73192c26f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-7920000000-75670df9647a475ca92c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-3090000000-d0ff9a733629a86b75c7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03dj-3690000000-db3f204af490d7e1722e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0005-9000000000-5196f2b4daab995967bf	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Kawasaki, Y., Onozuka, M., Mizote, T., Nosaka, K. (2005). "Biosynthesis of hydroxymethylpyrimidine pyrophosphate in Saccharomyces cerevisiae." Curr Genet 47:156-162.15614489
Alcoholic beverage, beer, regular, all - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
Alcoholic beverage, wine, table, red - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page

Synthesis Reference:

Sugimoto, Hirohiko; Ishiba, Teruyuki; Sato, Tomohiro; Nakai, Hiroshi; Hirai, Kentaro. Novel S-alkylation products from "isolated thiamin ylide" via thiaminium neothiaminthiolate ion pair. Journal of Organic Chemistry (1990), 55(2), 467-70.

External Links:

Resource	Link
CHEBI ID	18385
HMDB ID	HMDB00235
Pubchem Compound ID	1130
Kegg ID	C00378
ChemSpider ID	73580
FOODB ID	FDB008424
Wikipedia	Thiamine
BioCyc ID	THIAMINE

Enzymes

Protein Details

1. Acid phosphatase PHO11

General function:: Involved in acid phosphatase activity
Specific function:: A phosphate monoester + H(2)O = an alcohol + phosphate
Gene Name:: PHO11
Uniprot ID:: P35842
Molecular weight:: 52757.39844

Reactions

A phosphate monoester + H(2)O → an alcohol + phosphate.

Protein Details

2. Repressible acid phosphatase

General function:: Involved in acid phosphatase activity
Specific function:: Partially mediates extracellular nucleotide derived phosphate hydrolysis along with NPP1 and NPP2
Gene Name:: PHO5
Uniprot ID:: P00635
Molecular weight:: 52858.10156

Reactions

A phosphate monoester + H(2)O → an alcohol + phosphate.

Protein Details

3. Thiamine pyrophosphokinase

General function:: Involved in thiamine diphosphokinase activity
Specific function:: Essential protein, it is the only enzyme in yeast capable of synthesizing thiamine pyrophosphate (TPP)
Gene Name:: THI80
Uniprot ID:: P35202
Molecular weight:: 36615.69922

Reactions

ATP + thiamine → AMP + thiamine diphosphate.

Protein Details

4. Hydroxymethylpyrimidine/phosphomethylpyrimidine kinase THI20

General function:: Involved in phosphomethylpyrimidine kinase activity
Specific function:: Catalyzes the phosphorylation of hydroxymethylpyrimidine phosphate (HMP-P) to HMP-PP, and also probaby that of HMP to HMP- P
Gene Name:: THI20
Uniprot ID:: Q08224
Molecular weight:: 61268.89844

Reactions

ATP + 4-amino-5-hydroxymethyl-2-methylpyrimidine → ADP + 4-amino-5-phosphonooxymethyl-2-methylpyrimidine.
ATP + 4-amino-2-methyl-5-phosphomethylpyrimidine → ADP + 4-amino-2-methyl-5-diphosphomethylpyrimidine.
thiamine + H2O → 4-amino-5-hydroxymethyl-2-methylpyrimidine + 5-(2-hydroxyethyl)-4-methylthiazole.

Protein Details

5. Transposon Ty2-OR1 Gag-Pol polyprotein

General function:: Involved in DNA binding
Specific function:: Integrase (IN) targets the VLP to the nucleus, where a subparticle preintegration complex (PIC) containing at least integrase and the newly synthesized dsDNA copy of the retrotransposon must transit the nuclear membrane. Once in the nucleus, integrase performs the integration of the dsDNA into the host genome
Gene Name:: TY2B-OR1
Uniprot ID:: Q12113
Molecular weight:: 201982.0

Reactions

Deoxynucleoside triphosphate + DNA(n) → diphosphate + DNA(n+1).

Protein Details

6. Constitutive acid phosphatase

General function:: Involved in acid phosphatase activity
Specific function:: A phosphate monoester + H(2)O = an alcohol + phosphate
Gene Name:: PHO3
Uniprot ID:: P24031
Molecular weight:: 52776.10156

Reactions

A phosphate monoester + H(2)O → an alcohol + phosphate.

Protein Details

7. Acid phosphatase PHO12

General function:: Involved in acid phosphatase activity
Specific function:: A phosphate monoester + H(2)O = an alcohol + phosphate
Gene Name:: PHO12
Uniprot ID:: P38693
Molecular weight:: 52699.30078

Reactions

A phosphate monoester + H(2)O → an alcohol + phosphate.

Transporters

Protein Details

1. Thiamine transporter

General function:: Involved in nucleobase transmembrane transporter activity
Specific function:: Responsible for intake of thiamine
Gene Name:: THI7
Uniprot ID:: Q05998
Molecular weight:: 66903.29688

Protein Details

2. Putative thiamine transporter YOR071C

General function:: Involved in nucleobase transmembrane transporter activity
Specific function:: Responsible for intake of thiamine
Gene Name:: Not Available
Uniprot ID:: Q08485
Molecular weight:: 67192.89844

Structure for #<Compound:0xab60d280>

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Transporters