Livestock Metabolome Database: Showing metabocard for Thiamine (LMDB00109)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:42:33 UTC

Update Date

2016-07-19 23:35:51 UTC

Lmdb

LMDB00109

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Thiamine

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. Natural derivatives of thiamine phosphate, such as thiamine monophosphate (ThMP), thiamine diphosphate (ThDP), also sometimes called thiamine pyrophosphate (TPP), thiamine triphosphate (ThTP), and thiamine triphosphate (AThTP), that act as coenzymes in addition to their each unique biological functions. There are five known natural thiamine phosphate derivatives: thiamine monophosphate (ThMP), thiamine diphosphate (ThDP), also sometimes called thiamine pyrophosphate (TPP), thiamine triphosphate (ThTP), and the recently discovered adenosine thiamine triphosphate (AThTP), and adenosine thiamine diphosphate. Thiamine is a drug which is used for the treatment of thiamine and niacin deficiency states, korsakov's alcoholic psychosis, wernicke-korsakov syndrome, delirium, and peripheral neuritis. Thiamine is a very strong basic compound (based on its pKa). Thiamine has been shown to inhibit this effect of glucose on endothelial cells. Thiamine exists in all living species, ranging from bacteria to humans. In humans, thiamine is involved in the metabolic disorder called the 2-methyl-3-hydroxybutyryl-coa dehydrogenase deficiency pathway. Thiamine is a bitter tasting compound. Outside of the human body, Thiamine is found, on average, in the highest concentration within a few different foods, such as spread, leavening agents, and meat bouillons and in a lower concentration in cow milks, sharks, and vegetable juices. Thiamine has also been detected, but not quantified in, several different foods, such as chewing gums, walnuts, celery leaves, ascidians, and waters. This could make thiamine a potential biomarker for the consumption of these foods. Thiamine is a potentially toxic compound. Inhibition of endothelial cell proliferation may also promote atherosclerosis. Thiamine is a vitamin with antioxidant, erythropoietic, cognition-and mood-modulatory, antiatherosclerotic, putative ergogenic, and detoxification activities. The neuronal death is associated with increased free radical production, suggesting that oxidative stress may play an important early role in brain damage associated with thiamine deficiency. Oral mouse LD50 = 8224 mg/kg, oral rat LD50 = 3710 mg/kg.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-(4-AMINO-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-4-methyl-thiazol-3-ium	ChEBI
Aneurin	ChEBI
Antiberiberi factor	ChEBI
Thiamin	ChEBI
Thiamine(1+) ion	ChEBI
Thiaminium	ChEBI
Vitamin b1	ChEBI
Apate drops	HMDB
Beatine	HMDB
Bedome	HMDB
Begiolan	HMDB
Benerva	HMDB
Bequin	HMDB
Berin	HMDB
Betalin S	HMDB
Betaxin	HMDB
Bethiazine	HMDB
Beuion	HMDB
Bevitex	HMDB
Bevitine	HMDB
Bewon	HMDB
Biamine	HMDB
Bithiamin	HMDB
Biuno	HMDB
Bivatin	HMDB
Bivita	HMDB
Cernevit-12	HMDB
Clotiamina	HMDB
Eskapen	HMDB
Eskaphen	HMDB
Hybee	HMDB
Lixa-beta	HMDB
Metabolin	HMDB
Slowten	HMDB
THD	HMDB
Thiadoxine	HMDB
Thiaminal	HMDB
Thiamol	HMDB
Thiavit	HMDB
Tiamidon	HMDB
Tiaminal	HMDB
Trophite	HMDB
Vetalin S	HMDB
VIB	HMDB
Vinothiam	HMDB
Vitaneuron	HMDB
Mononitrate, thiamine	MeSH, HMDB
Thiamine mononitrate	MeSH, HMDB
Vitamin b 1	MeSH, HMDB

Chemical Formula

C₁₂H₁₇N₄OS

Average Molecular Weight

265.355

Monoisotopic Molecular Weight

265.112306876

IUPAC Name

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

Traditional Name

thiamine

CAS Registry Number

59-43-8

SMILES

CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N

InChI Identifier

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

InChI Key

JZRWCGZRTZMZEH-UHFFFAOYSA-N

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 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

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

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Milk

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Milk	Detected and Quantified	0.45 mg/kg	Not Available	Bovine	Park, Y. W; Juáre...	details
Milk	Detected and Quantified	0.8 mg/kg	Not Available	Ovine	Park, Y. W; Juáre...	details
Milk	Detected and Quantified	0.68 mg/kg	Not Available	Caprine	Park, Y. W; Juáre...	details