5,6,7,8-Tetrahydrofolic acid

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for 5,6,7,8-Tetrahydrofolic acid are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the 5,6,7,8-Tetrahydrofolic acid?

The molecule 5,6,7,8-Tetrahydrofolic acid presents a molecular formula of C19H23N7O6 and its IUPAC name is (2S)-2-[[4-[[(6R)-2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridin-6-yl]methylamino]benzoyl]amino]pentanedioic acid.

Tetrahydrofolic acid is a molecule that is essential for the body to create new DNA and RNA. This molecule is also important for the metabolism of amino acids and for the synthesis of certain vitamins and minerals. Tetrahydrofolic acid belongs in food, but it is also produced by the body..

3D structure

Cartesian coordinates

Geometry of 5,6,7,8-Tetrahydrofolic acid in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

5,6,7,8-Tetrahydrofolic acid MSTNYGQPCMXVAQ-NEPJUHHUSA-N chemical compound 2D structure molecule svg
5,6,7,8-Tetrahydrofolic acid

 

Molecule descriptors

 
IUPAC name(2S)-2-[[4-[[(6R)-2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridin-6-yl]methylamino]benzoyl]amino]pentanedioic acid
InChI codeInChI=1S/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11-,12+/m1/s1
InChI KeyMSTNYGQPCMXVAQ-NEPJUHHUSA-N
SMILESNc1nc2c(c(=O)[nH]1)N[C@H](CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2

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.

  • (2S)-2-[(4-{[(6R)(2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
  • (2S)-2-[[4-[[(6R)-2-amino-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl]methylamino]benzoyl]amino]pentanedioic acid
  • (2S)-2-[[4-[[(6R)-2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridin-6-yl]methylamino]benzoyl]amino]pentanedioic acid
  • (2S,6R)-5,6,7,8-tetrahydrofolic acid
  • (6R)-tetrahydrofolic acid
  • 135-16-0
  • 5,6,7,8-Tetrahydrofolic acid
  • 5,6,7,8-tetrahydrofolic acid
  • 6R-Tetrahydrofolic acid
  • BDBM50391006
  • N-[4-({[(6r)-2-Amino-4-Oxo-3,4,5,6,7,8-Hexahydropteridin-6-Yl]methyl}amino)benzoyl]-L-Glutamic Acid
  • Q27452575
  • [6r]-tetrahydrofolic acid
  • folate-H4
  • th-folate

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4228235
  • CHEMBL2074655
  • CHEBI:166569
  • SCHEMBL8031

Physico-Chemical properties

IUPAC name(2S)-2-[[4-[[(6R)-2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridin-6-yl]methylamino]benzoyl]amino]pentanedioic acid
Molecular formulaC19H23N7O6
Molecular weight445.429
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity121.03
LogP1.0
Topological polar surface area211.6

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.