(6S)-5,6,7,8-Tetrahydrofolate

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

What is the (6S)-5,6,7,8-Tetrahydrofolate?

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

Folate, also known as vitamin B9, is a water-soluble vitamin that is naturally present in some foods, added to others, and available as a dietary supplement. Folate, as the natural form, refers to dietary folate while folic acid refers to the synthetic form of this vitamin. Your body needs folate to make DNA, RNA, and metabolize amino acids. Women who are pregnant or might become pregnant take folate to prevent neural tube defects in the baby. Everyone else needs folate to make healthy red blood cells and prevent anemia..

The recommended dietary allowance (RDA) for folate is 400 micrograms (mcg) per day for adults (including pregnant women). The RDA for pregnant women is 600 mcg per day, and the RDA for lactating women is 500 mcg per day..

The U.S. Food and Drug Administration (FDA) requires manufacturers to use the term "folic acid" on food and supplement labels, rather than "folate" or "folacin." This is because folic acid is the form of folate that is added to foods and supplements, and it is the form that your body can use best..

Folate is a generic term for a group of closely related compounds with similar chemical structures, including natural folates and synthetic folic acid. Folic acid is the synthetic form of folate that belongs in supplements and added to fortified foods. The natural form of folate belongs in leafy green vegetables and other foods..

Folate is important for the development of the neural tube. The neural tube is the precursor to the baby's brain and spinal cord. A pregnant woman needs 400 micrograms of folate (also called folic acid) a day to help prevent neural tube defects in her baby. The best way to get the recommended 400 micrograms of folate a day is to take a supplement that contains 400 micrograms of folate (also called folic acid) and to eat a diet that is rich in folate-containing foods..

Most people in the United States get enough folate from the foods they eat. The foods that are the best sources of folate are leafy green vegetables, legumes (beans and peas), and orange juice. You can also get folate from fortified foods, such as breakfast cereals, breads, and pastas..

Folate is a water-soluble vitamin and is mainly found in leafy green vegetables and fruits. It is also found in some legumes, nuts, and seeds. Folate is important for the development of the neural tube. The neural tube is the precursor to the baby's brain and spinal cord. A pregnant woman needs 400 micrograms of folate (also called folic acid) a day to help prevent neural tube defects in her baby..

Most people in the United States get enough folate from the foods they eat. The foods that are the best sources of folate are leafy green vegetables, legumes (beans and peas), and orange juice. You can also get folate from fortified foods, such as breakfast cereals, breads, and pastas..

Folate is a water-soluble vitamin and is mainly found in leafy green vegetables and fruits. It is also found in some legumes, nuts, and seeds. Folate is important for the development of the neural tube. The neural tube is the precursor to the baby's brain and spinal cord. A pregnant woman needs 400 micrograms of folate (also called folic acid) a day to help prevent neural tube defects in her baby..

Most people in the United States get enough folate from the foods they eat. The foods that are the best sources of folate are leafy green vegetables, legumes (beans and peas), and orange juice. You can also get folate from fortified foods, such as breakfast cereals, breads, and pastas..

Folate is a water-soluble vitamin and is mainly found in leafy green vegetables and fruits. It is also found in some legumes, nuts, and seeds. Folate is important for the development of the neural tube. The neural tube is the precursor to the baby's brain and spinal cord. A pregnant woman needs 400 micrograms of folate (also called folic acid) a day to help prevent neural tube defects in her baby..

Most people in the United States get enough folate from the foods they eat. The foods that are the best sources of folate are leafy green vegetables, legumes (beans and peas), and orange juice. You can also get folate from fortified foods, such as breakfast cereals, breads, and pastas..

3D structure

Cartesian coordinates

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

2D drawing

 

(6S)-5,6,7,8-Tetrahydrofolate MSTNYGQPCMXVAQ-RYUDHWBXSA-N chemical compound 2D structure molecule svg
(6S)-5,6,7,8-Tetrahydrofolate

 

Molecule descriptors

 
IUPAC name(2S)-2-[[4-[[(6S)-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-/m0/s1
InChI KeyMSTNYGQPCMXVAQ-RYUDHWBXSA-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,6S)-5,6,7,8-tetrahydrofolic acid
  • (6S)-5,6,7,8-TETRAHYDROFOLATE
  • (6S)-5,6,7,8-Tetrahydrofolate
  • (6S)-5,6,7,8-tetrahydrofolic acid
  • (6S)-5,6,7,8-tetrahydropteroylglutamate
  • (6S)-H4folate
  • (6S)-THFA
  • (6S)-Tetrahydrofolic acid
  • (6S)-tetrahydrofolate
  • 135-16-0
  • 5,6,7,8-tetrahydrofolate
  • 6S-tetrahydrofolic acid
  • C00101
  • DB02031
  • N-(5,6,7,8-tetrahydropteroyl)-L-glutamic acid
  • N-[4-({[(6S)-2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)benzoyl]-L-glutamic acid
  • N-{[4-({[(6S)-2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]carbonyl}-L-glutamic acid
  • Q27098158
  • tetrahydrofolic-acid

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4228237
  • CHEBI:15635
  • SCHEMBL6880950
  • SCHEMBL9879710

Physico-Chemical properties

IUPAC name(2S)-2-[[4-[[(6S)-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.