Milk Composition Database: Showing metabocard for Thiamine (BMDB0000235)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:27:10 UTC

Update Date

2020-06-04 20:45:42 UTC

MCDB ID

BMDB0000235

Secondary Accession Numbers

BMDB00235

Metabolite Identification

Common Name

Thiamine

Description

Thiamine, also known as vitamin B1 or aneurin, 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 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 exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Thiamine exists in all living species, ranging from bacteria to humans. In cattle, thiamine is involved in the metabolic pathway called the valine, leucine, and isoleucine degradation pathway. Thiamine is a potentially toxic compound.

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	248 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	500 mg/mL	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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00e9-3890000000-9f8b525433ab279ad512	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9442000000-05ab93d3afb7b6f538e9	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-000i-0109000000-48864f31ba475645654b	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-05o1-9200000000-2ec0f3e9e364cffde16e	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0aou-9000000000-0184506492d9f5b68b97	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-03di-0090000000-872150be83cbd75d8ecf	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0002-0930000000-ecf71c75bdea859139d5	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0002-0900000000-4d9113fdc633fb1ccbb5	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0002-0900000000-4a8016299623af0c3027	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0002-1900000000-773912c9f325c419c77d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-014i-0390000000-95f3ca57c95542bdc7e7	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-0900000000-e079d1fc1e06396dc524	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00di-0900000000-ebb16d4f204f291b9a3a	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-00e9-4900000000-ad4d4779d76b9edb7ec5	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-001i-9600000000-b631eed5be831527fc17	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-00di-0900000000-50f2f613f576814eb627	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-002b-0900000000-2f184bbfec6bc0ef00c6	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-001i-9000000000-35bc744495a2570a565f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-1900000000-d8a7ac327273c32b4524	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0002-0920000000-ca80ef6513c61be5b5e9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-03di-0090000000-872150be83cbd75d8ecf	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0190000000-183af2449d1439af9825	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0090000000-2230ebc7c6b73192c26f	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-7920000000-75670df9647a475ca92c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-3090000000-d0ff9a733629a86b75c7	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03dj-3690000000-db3f204af490d7e1722e	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0005-9000000000-5196f2b4daab995967bf	2016-09-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Not Available	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	1.131 uM	USDA Food Co...	details
Detected and Quantified	1.131 uM	USDA Food Co...	details
Detected and Quantified	0.754 uM	USDA Food Co...	details
Detected and Quantified	1.357 uM	USDA Food Co...	details
Detected and Quantified	0.754 uM	USDA Food Co...	details
Detected and Quantified	1.696 uM	USDA Food Co...	details
Detected and Quantified	1.507 uM	USDA Food Co...	details
Detected and Quantified	0.754 uM	USDA Food Co...	details
Detected and Quantified	1.696 uM	USDA Food Co...	details
Detected and Quantified	1.545 uM	USDA Food Co...	details
Detected and Quantified	1.696 uM	USDA Food Co...	details
Detected and Quantified	1.696 uM	USDA Food Co...	details
Detected and Quantified	1.432 uM	USDA Food Co...	details
Detected and Quantified	1.696 uM	USDA Food Co...	details
Detected and Quantified	1.507 uM	USDA Food Co...	details
Detected and Quantified	1.696 uM	USDA Food Co...	details
Detected and Quantified	1.47 uM	USDA Food Co...	details
Detected and Quantified	1.47 uM	USDA Food Co...	details
Detected and Quantified	1.734 uM	USDA Food Co...	details
Detected and Quantified	1.734 uM	USDA Food Co...	details
Detected and Quantified	1.696 uM	Park, Y. W; Juáre...	details
Detected and Quantified	9 - 52 uM	PMID: 17558655	details
Detected and Quantified	1.36 - 1.47 uM	PMID: 22081685	details
Detected and Quantified	1.6 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	1.6 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	1.8 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	1.53 +/- 0.04 uM	PMID: 30994344	details

External Links

HMDB ID

HMDB0000235

DrugBank ID

DB00152

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Thiamine

METLIN ID

Not Available

PubChem Compound

1130

PDB ID

Not Available

ChEBI ID

18385

References

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.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Agostini TS, Scherer R, Godoy HT: Simultaneous determination of B-group vitamins in enriched Brazilian dairy products. Crit Rev Food Sci Nutr. 2007;47(5):435-9. doi: 10.1080/10408390600846309. [PubMed:17558655 ]
Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S. [PubMed:22081685 ]
Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W. (2007). Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113 doi: 10.1016/j.smallrumres.2006.09.013. Small Ruminant Research.
A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
USDA Food Composition Databases [Link]

Showing metabocard for Thiamine (BMDB0000235)

Structure for BMDB0000235 (Thiamine)