Thiamine

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Thiamine are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Thiamine?

The molecule Thiamine presents a molecular formula of C12H17N4OS+ and its IUPAC name is 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethanol.

Thiamine is a water-soluble vitamin and is part of the vitamin B complex. It is also known as vitamin B1. Thiamine is essential for the body to use carbohydrates as fuel. It is also needed for proper muscle and nerve function. Thiamine belongs in many foods, including pork, whole grains, and fortified foods..

Thiamine is needed for the body to use carbohydrates as fuel. It is also needed for proper muscle and nerve function. Thiamine belongs in many foods, including pork, whole grains, and fortified foods..

Thiamine is important for energy metabolism and nerve function. It participes in the breakdown of carbohydrates and in the synthesis of neurotransmitters. Thiamine belongs in food, especially in pork, whole grains, and fortified foods. A thiamine deficiency can cause beriberi, a disease that affects the nervous system and the heart..

3D structure

Cartesian coordinates

Geometry of Thiamine in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Thiamine JZRWCGZRTZMZEH-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Thiamine

 

Molecule descriptors

 
IUPAC name2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethanol
InChI codeInChI=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 KeyJZRWCGZRTZMZEH-UHFFFAOYSA-N
SMILESCc1ncc(C[n+]2csc(CCO)c2C)c(N)n1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • 1sbr
  • 2-[3-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-3-ium-5-yl]ethanol
  • 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethanol
  • 3-((4-Amino-2-methylpyrimidin-5-yl)methyl)-5-(2-hydroxyethyl)-4-methylthiazol-3-ium
  • 3-(2-Methyl-4-aminopyrimidine-5-ylmethyl)-4-methylthiazolium-5-ethanol
  • 3-(4-AMINO-2-METHYL-PYRIMIDIN-5-YLMETHYL)-5-(2-HYDROXY-ETHYL)-4-METHYL-THIAZOL-3-IUM
  • 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium
  • 3[(4-Amino-2-methyl-5-pyrimidinyl)-methyl]-5-(2-hydroxyethyl)-4-methylthiazolium chloride
  • 3rlb
  • 4ABT0J945J
  • 70-16-6
  • Aneurin
  • Antiberiberi factor
  • BDBM50373877
  • BPBio1_000686
  • BSPBio_000622
  • Bequin
  • Betaxin
  • Biamine
  • C00378
  • DB00152
  • GTPL4628
  • GTPL4629
  • NCGC00017013-06
  • NCGC00188957-01
  • NCGC00188957-02
  • NSC36226
  • Prestwick0_000631
  • Prestwick1_000631
  • Prestwick2_000631
  • Prestwick3_000631
  • Q83187
  • SMP1_000084
  • STL301841
  • THD
  • THIAMIN; VITAMIN B1
  • ThOH
  • Thiadoxine
  • Thiamine
  • Thiamine (Vit B1)
  • Thiamine ion
  • Thiazolium, 3-((4-amino-2-methyl-5-pyrimidinyl)methyl)-5-(2-hydroxyethyl)-4-methyl-
  • TimTec1_000613
  • VIB
  • Vitamin B 1
  • [3H]-thiamine
  • [3H]thiamine
  • [3H]vitamin B1
  • bmse000274
  • thiamin
  • thiamine
  • thiamine(1+)
  • thiamine(1+) ion
  • thiaminium
  • vitamin B1

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC49153
  • UNII-4ABT0J945J
  • AKOS000668650
  • DTXSID50220251
  • CHEMBL1547
  • CHEBI:18385
  • SPBio_002841
  • SCHEMBL10075
  • SCHEMBL22129283

Physico-Chemical properties

IUPAC name2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethanol
Molecular formulaC12H17N4OS+
Molecular weight265.355
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity73.26
LogP1.2
Topological polar surface area104.2

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.