(6S)-Tetrahydrobiopterin

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for (6S)-Tetrahydrobiopterin are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the (6S)-Tetrahydrobiopterin?

The molecule (6S)-Tetrahydrobiopterin presents a molecular formula of C9H15N5O3 and its IUPAC name is (6S)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-3H-pteridin-4-one.

Tetrahydrobiopterin (BH4) is a molecule that participes in the production of nitric oxide (NO) and other important biological functions. BH4 is essential for the function of the enzyme nitric oxide synthase (NOS), which is responsible for the production of NO. NO is a important signaling molecule that participes in a variety of physiological processes, including blood pressure regulation, cell proliferation, and neuroprotection. BH4 is also involved in the metabolism of phenylalanine and tyrosine, two amino acids that are important for the synthesis of neurotransmitters. BH4 is produced in the body by the enzyme GTP cyclohydrolase I (GTPCH1). Mutations in the GTPCH1 gene can lead to reduced levels of BH4, which can lead to a variety of disorders, including hypertension, depression, and autism..

3D structure

Cartesian coordinates

Geometry of (6S)-Tetrahydrobiopterin in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

(6S)-Tetrahydrobiopterin FNKQXYHWGSIFBK-FKZODXBYSA-N chemical compound 2D structure molecule svg
(6S)-Tetrahydrobiopterin

 

Molecule descriptors

 
IUPAC name(6S)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-3H-pteridin-4-one
InChI codeInChI=1S/C9H15N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,4-,6-/m0/s1
InChI KeyFNKQXYHWGSIFBK-FKZODXBYSA-N
SMILESC[C@H](O)[C@H](O)[C@@H]1CNc2[nH]c(N)nc(=O)c2N1

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.

  • (6S)-2-AMINO-6-[(1R,2S)-1,2-DIHYDROXYPROPYL]-5,6,7,8-TETRAHYDRO-3H-PTERIDIN-4-ONE
  • (6S)-L-erythro-Tetrahydrobiopterin
  • (6S)-Tetrahydrobiopterin
  • 4(3H)-Pteridinone, 2-amino-6-((1R,2S)-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-, (6S)-
  • 62961-57-3
  • 8ES3LB438S
  • CS-0091968
  • Lopac-T-4425
  • NCGC00016021-01

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC2539827
  • UNII-8ES3LB438S
  • DTXSID10860778
  • CHEMBL1315516

Physico-Chemical properties

IUPAC name(6S)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-3H-pteridin-4-one
Molecular formulaC9H15N5O3
Molecular weight241.247
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity68.37
LogP-0.8
Topological polar surface area136.3

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.