Pyridoxine

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

What is the Pyridoxine?

The molecule Pyridoxine presents a molecular formula of C15H18N8O5 and its IUPAC name is 4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol.

Pyridoxine is a water-soluble vitamin that is part of the B-vitamin family. Pyridoxine is needed for the proper metabolism of carbohydrates, fats, and proteins. Pyridoxine is also needed for the proper function of the nervous system and for red blood cell production. Pyridoxine belongs in many foods, including meat, poultry, fish, vegetables, and grains. Pyridoxine can be found as a dietary supplement..

Pyridoxine was first isolated from rice bran in 1938. The chemical structure of pyridoxine was determined in 1953. Pyridoxine is a colorless to yellowish-brown crystal that is odorless and has a bitter taste. Pyridoxine is soluble in water and insoluble in alcohol..

Pyridoxine is converted in the body to pyridoxal 5'-phosphate (PLP), which is a coenzyme for many enzymes involved in amino acid metabolism. PLP is also needed for the proper function of the nervous system..

Pyridoxine deficiency is rare, but can occur in people with malabsorption disorders, such as celiac disease and Crohn's disease. Pyridoxine deficiency can also occur in people with alcoholism, anorexia nervosa, and certain types of cancer. Symptoms of pyridoxine deficiency include anemia, convulsions, dermatitis, depression, and mouth and tongue sores..

Pyridoxine supplementation is used to treat or prevent pyridoxine deficiency. Pyridoxine is also used to treat premenstrual syndrome (PMS), carpal tunnel syndrome, and some types of seizure disorders. Pyridoxine is sometimes used to treat side effects of isoniazid (a medication used to treat tuberculosis)..

Pyridoxine is generally considered safe when taken by mouth in recommended doses. Pyridoxine can cause stomach upset and vomiting when taken in large doses. When pyridoxine is injected into a vein, it can cause low blood pressure, headache, and dizziness..

Pregnant women should not take pyridoxine supplements unless directed to do so by their healthcare provider. Pyridoxine can cause birth defects when taken in high doses. Pyridoxine should be used with caution in people with kidney disease or liver disease..

3D structure

Cartesian coordinates

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

2D drawing

 

Pyridoxine LZPZPHGJDAGEJZ-AKAIJSEGSA-N chemical compound 2D structure molecule svg
Pyridoxine

 

Molecule descriptors

 
IUPAC name4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol
InChI codeInChI=1S/C15H18N8O5/c1-17-13(27)6-2-19-23(3-6)15-20-11(16)8-12(21-15)22(5-18-8)14-10(26)9(25)7(4-24)28-14/h2-3,5,7,9-10,14,24-26H,4H2,1H3,(H,17,27)(H2,16,20,21)/t7-,9-,10-,14-/m1/s1
InChI KeyLZPZPHGJDAGEJZ-AKAIJSEGSA-N
SMILESCNC(=O)c1cnn(-c2nc(N)c3ncn([C@@H]4O[C@H](CO)[C@@H](O)[C@H]4O)c3n2)c1

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.

  • (5-Hydroxy-6-methylpyridine-3,4-diyl)dimethanol
  • 12001-77-3
  • 2-Methyl-3-hydroxy-4,5-bis(hydroxymethyl)pyridine
  • 2-Methyl-3-hydroxy-4,5-di(hydroxymethyl)pyridine
  • 2-Methyl-3-hydroxy-4,5-dihydroxymethyl-pyridin
  • 2-Methyl-3-oxylato-4,5-bis(hydroxymethyl)pyridinium
  • 2-Methyl-4,5-bis(hydroxymethyl)-3-hydroxypyridine
  • 2-Picoline-4,5-dimethanol, 3-hydroxy-
  • 2-methyl-3-hydroxy-4,5-bis(hydroxy-methyl) pyridine
  • 2-methyl-3-hydroxy-4,5-dihydroxymethylpyridine
  • 2-methyl-3-hydroxy-4-hydroxymethyl-5-hydroxymethyl pyridine
  • 2B3E07D2-E4CC-4CC5-B085-6070BA01F9F0
  • 3,4-Pyridinedimethanol, 5-hydroxy-6-methyl-
  • 3-Hydroxy-4,5-dimethylol-.alpha.-picoline
  • 3-Hydroxy-4,5-dimethylol-alpha-picoline
  • 3-hydroxy-2-Picoline-4,5-dimethanol
  • 3-hydroxy-4,5-bis(hydroxymethyl)-2-methylpyridine
  • 4,5-Bis(hydroxymethyl)-2-methyl-3-pyridinol
  • 4,5-Bis(hydroxymethyl)-2-methyl-3-pyridinol #
  • 4,5-bis(hydroxymethyl)-2-methyl-pyridin-3-ol
  • 4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol
  • 4,5-bis(hydroxymethyl)-2-methylpyridine-3-ol
  • 5-Hydroxy-6-methyl-3,4-pyridinedimethanol
  • 58-56-0 (HCL)
  • 65-23-6
  • 65-23-6 (FREE BASE)
  • A835033
  • AC-14512
  • AC-907/25014218
  • AIDS-006784
  • AIDS006784
  • AM20070169
  • Adermin
  • Adermin hydrochloride
  • Adermine
  • Aderoxine
  • BBL005552
  • BCP27975
  • BDBM50103505
  • BIDD:PXR0180
  • BPBio1_000646
  • BSPBio_000586
  • Bezatin
  • C00314
  • CBDivE_015627
  • CCG-213453
  • CS-W019950
  • D08454
  • DB-073595
  • DB00165
  • DS-11013
  • DSSTox_CID_3541
  • DSSTox_GSID_23541
  • DSSTox_RID_77070
  • EN300-39851
  • FT-0631288
  • FT-0674200
  • Gravidox
  • HMS2093L07
  • HY-B1328
  • Hexabione
  • Hydoxin
  • Infuvite Pediatric
  • KSC-11-207-23
  • KUC106691N
  • KV2JZ1BI6Z
  • LS-134393
  • M.V.I.-12
  • M.V.I.-12 Lyophilized
  • MFCD00006335
  • NCGC00016261-01
  • NCGC00016261-02
  • NCGC00016261-03
  • NCGC00016261-04
  • NCGC00016261-05
  • NCGC00016261-08
  • NCGC00164317-01
  • NCGC00164317-02
  • NCGC00254340-01
  • NSC 759148
  • NSC-759148
  • NSC36225
  • NSC36225 (HCL)
  • NSC759148
  • O10129
  • Oprea1_061614
  • P5669_SIGMA
  • PN
  • Pharmakon1600-01505453
  • Piridossina
  • Piridoxina
  • Pirivitol
  • Prestwick0_000623
  • Prestwick1_000623
  • Prestwick2_000623
  • Prestwick3_000623
  • Pridoxine
  • Pyridoxin
  • Pyridoxin hydrochloride
  • Pyridoxine
  • Pyridoxine free base
  • Pyridoxine (INN)
  • Pyridoxine (Vit B6)
  • Pyridoxine hydrogen chloride
  • Pyridoxinum
  • Pyridoxol
  • Pyridoxol, Vitamin B6, Gravidox
  • Pyridoxol; Vitamin B6
  • Pyridoxolum
  • Q-201646
  • Q423746
  • SBI-0206844.P001
  • SMP2_000230
  • SR-05000001644
  • SR-05000001644-1
  • SR-05000001644-3
  • STK177324
  • TimTec1_000657
  • Vitamin V6
  • Vitamin b6,hydrochloride
  • VitaminB6
  • Z955123748
  • bmse000288
  • c1302
  • nchembio.93-comp1
  • pyridoxine
  • s3980
  • vitamin B-6
  • vitamin B6

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC49154
  • ZINC00049154
  • CAS-58-56-0
  • CAS-65-23-6
  • UNII-KV2JZ1BI6Z
  • AKOS005410791
  • ALBB-022452
  • DTXSID4023541
  • CHEMBL1364
  • CHEBI:16709
  • Tox21_113644
  • Tox21_300365
  • Tox21_113644_1
  • EINECS 200-603-0
  • SPBio_002805
  • SCHEMBL3506

Physico-Chemical properties

IUPAC name4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol
Molecular formulaC15H18N8O5
Molecular weight390.354
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity92.79
LogP-1.5
Topological polar surface area186.5

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.