Benfotiamine

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

What is the Benfotiamine?

The molecule Benfotiamine presents a molecular formula of C19H23N4O6PS and its IUPAC name is S-[(Z)-2-[(4-amino-2-methylpyrimidin-5-yl)methyl-formylamino]-5-phosphonooxypent-2-en-3-yl] benzenecarbothioate.

Benfotiamine is a molecule that is closely related to thiamine, or vitamin B1. Benfotiamine is sometimes used as a supplement to treat thiamine deficiency and related conditions..

Benfotiamine is structurally similar to thiamine, and like thiamine, it participes in carbohydrate metabolism. Benfotiamine is thought to work by increasing levels of thiamine in the body..

Benfotiamine has been studied as a treatment for several conditions related to thiamine deficiency, including beriberi, Wernicke-Korsakoff syndrome, and diabetic neuropathy..

Benfotiamine has also been studied as a potential treatment for Alzheimer's disease, although the results of these studies have been mixed..

Benfotiamine is generally considered safe, although there is some concern that it may interact with certain medications. People with diabetes should be especially cautious about taking benfotiamine, as it may affect blood sugar levels..

3D structure

Cartesian coordinates

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

2D drawing

 

Benfotiamine BTNNPSLJPBRMLZ-LGMDPLHJSA-N chemical compound 2D structure molecule svg
Benfotiamine

 

Molecule descriptors

 
IUPAC nameS-[(Z)-2-[(4-amino-2-methylpyrimidin-5-yl)methyl-formylamino]-5-phosphonooxypent-2-en-3-yl] benzenecarbothioate
InChI codeInChI=1S/C19H23N4O6PS/c1-13(23(12-24)11-16-10-21-14(2)22-18(16)20)17(8-9-29-30(26,27)28)31-19(25)15-6-4-3-5-7-15/h3-7,10,12H,8-9,11H2,1-2H3,(H2,20,21,22)(H2,26,27,28)/b17-13-
InChI KeyBTNNPSLJPBRMLZ-LGMDPLHJSA-N
SMILESC/C(=C(\CCOP(=O)(O)O)SC(=O)c1ccccc1)N(C=O)Cc1cnc(C)nc1N

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.

  • (3Z)-4-{N-[(4-amino-2-methylpyrimidin-5-yl)methyl]carbonylamino}-3-(phenylcarb onylthio)pent-3-enyl dihydrogen phosphate
  • (Z)-S-(2-(N-((4-amino-2-methylpyrimidin-5-yl)methyl)formamido)-5-(phosphonooxy)pent-2-en-3-yl) benzothioate
  • 137-74-6
  • 22457-89-2
  • 22457-89-2 (free acid)
  • 57B892
  • A15020
  • AC-8280
  • BPBio1_000757
  • BSPBio_000687
  • Benfotamine
  • Benfotiamina
  • Benfotiamine
  • Benfotiamine (JAN/INN)
  • Benfotiaminum
  • Benphothiamine
  • Benzoylthiamine monophosphate
  • CCG-220654
  • D01255
  • DB11748
  • HMS1570C09
  • HMS2097C09
  • HMS3714C09
  • MFCD00057343
  • N-((4-Amino-2-methyl-5-pyrimidinyl)methyl)-N-(4-hydroxy-2-mercapto-1-methyl-1-butenyl)formamide S-benzoate O-phosphate
  • NCGC00179477-01
  • Prestwick2_000654
  • Prestwick3_000654
  • Prestwick_68
  • S-Benzoylthiamine O-monophosphate
  • S-Benzoylthiamine monophosphate
  • S-[(2Z)-2-{[(4-amino-2-methylpyrimidin-5-yl)methyl](formyl)amino}-5-(phosphonooxy)pent-2-en-3-yl] benzenecarbothioate
  • S-[(Z)-2-[(4-amino-2-methylpyrimidin-5-yl)methyl-formylamino]-5-phosphonooxypent-2-en-3-yl] benzenecarbothioate
  • S-{(1Z)-2-[[(4-Amino-2-methyl-5-pyrimidinyl)methyl](formyl)amino]-1-[2-(phosphonooxy)ethyl]-1-propenyl} benzenecarbothioate, AldrichCPR
  • SR-01000872627
  • SR-01000872627-1
  • SR-01000872627-2
  • STL453586
  • benfotiamine
  • s-[2-{[(4-amino-2-methylpyrimidin-5-yl)methyl](formyl)amino}-5-(phosphonooxy)pent-2-en-3-yl] benzenecarbothioate
  • s-{(1z)-2-[[(4-amino-2-methyl-5-pyrimidinyl)methyl](formyl)amino]-1-[2-(phosphonooxy)ethyl]-1-propenyl} benzenecarbothioate

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC2015559
  • AKOS015920320
  • CHEMBL4303665
  • CHEBI:41039
  • SCHEMBL188070
  • SCHEMBL19184708

Physico-Chemical properties

IUPAC nameS-[(Z)-2-[(4-amino-2-methylpyrimidin-5-yl)methyl-formylamino]-5-phosphonooxypent-2-en-3-yl] benzenecarbothioate
Molecular formulaC19H23N4O6PS
Molecular weight466.448
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity117.60
LogP3.8
Topological polar surface area191.1

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.