Pyridoxine
(right click,save link as to download,it is a temp file,please download as soon as possible, you can also use CTRL+S to save the whole html page)
Basic Info
| Common Name | Pyridoxine(F04737) |
| 2D Structure | |
| Description | Pyridoxine is the 4-methanol form of vitamin B6 and is converted to pyridoxal 5-phosphate in the body. Pyridoxal 5-phosphate is a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. Although pyridoxine and vitamin B6 are still frequently used as synonyms, especially by medical researchers, this practice is erroneous and sometimes misleading. Pyridoxine is one of the compounds that can be called vitamin B6. Pyridoxine assists in the balancing of sodium and potassium as well as promoting red blood cell production. It is linked to cancer immunity and helps fight the formation of homocysteine. It has been suggested that Pyridoxine might help children with learning difficulties, and may also prevent dandruff, eczema, and psoriasis. In addition, pyridoxine can help balance hormonal changes in women and aid in immune system. Lack of pyridoxine may cause anemia, nerve damage, seizures, skin problems, and sores in the mouth. Deficiency, though rare because of widespread distribution in foods, leads to the development of peripheral neuritis in adults and affects the central nervous system in children. |
| FRCD ID | F04737 |
| CAS Number | 65-23-6 |
| PubChem CID | 1054 |
| Formula | C8H11NO3 |
| IUPAC Name | 4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol |
| InChI Key | LXNHXLLTXMVWPM-UHFFFAOYSA-N |
| InChI | InChI=1S/C8H11NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,10-12H,3-4H2,1H3 |
| Canonical SMILES | CC1=NC=C(C(=C1O)CO)CO |
| Isomeric SMILES | CC1=NC=C(C(=C1O)CO)CO |
| Wikipedia | Pyridoxine |
| Synonyms |
Gravidox
3-hydroxy-4,5-bis(hydroxymethyl)-2-methylpyridine
pyridoxine
65-23-6
Pyridoxol
vitamin B6
Pyridoxin
Hydoxin
Adermine
Pyridoxolum
|
| Classifies |
Predicted: Pollutant
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Pyridines and derivatives |
| Subclass | Pyridoxines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Pyridoxines |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Pyridoxine - Methylpyridine - Hydroxypyridine - Heteroaromatic compound - Azacycle - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Aromatic alcohol - Primary alcohol - Organooxygen compound - Organonitrogen compound - Alcohol - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as pyridoxines. These are pyridoxal derivatives in which the carbaldehyde group at position 2 of the pyridoxal moiety is replaced by a hydroxymethyl group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 169.18 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 2 |
| Complexity | 142 |
| Monoisotopic Mass | 169.074 |
| Exact Mass | 169.074 |
| XLogP | -0.8 |
| Formal Charge | 0 |
| Heavy Atom Count | 12 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.6889 |
| Human Intestinal Absorption | HIA+ | 0.9728 |
| Caco-2 Permeability | Caco2- | 0.8958 |
| P-glycoprotein Substrate | Non-substrate | 0.5579 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9723 |
| Non-inhibitor | 0.9221 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8177 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7589 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7386 |
| CYP450 2D6 Substrate | Non-substrate | 0.7810 |
| CYP450 3A4 Substrate | Non-substrate | 0.7104 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9046 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9071 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9230 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9025 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8648 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6950 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8454 |
| Non-inhibitor | 0.8734 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.9418 |
| Fish Toxicity | Low FHMT | 0.8792 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.8757 |
| Honey Bee Toxicity | Low HBT | 0.5988 |
| Biodegradation | Not ready biodegradable | 0.5678 |
| Acute Oral Toxicity | III | 0.8153 |
| Carcinogenicity (Three-class) | Non-required | 0.6568 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.9348 | LogS |
| Caco-2 Permeability | 0.9728 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.6573 | LD50, mol/kg |
| Fish Toxicity | 2.4357 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.3762 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Rice flakes produced from commercial wild rice: Chemical compositions, vitamin B compounds, mineral and trace element contents and their dietary intake evaluation. | Food Chem | 2018 Oct 30 | 29853391 |
| Effect of heat treatment on 4'-O-methylpyridoxine (MPN) content in Ginkgo biloba seed extract solution. | J Sci Food Agric | 2018 Oct | 29572951 |
| Deficiency of dietary pyridoxine disturbed the intestinal physical barrierfunction of young grass carp (Ctenopharyngodon idella). | Fish Shellfish Immunol | 2018 Mar | 29339045 |
| Influence of vitamin intake and MTHFR polymorphism on the levels of DNA damage intobacco farmers. | Int J Occup Environ Health | 2018 Jul 27:1-8 | 30052162 |
| Enhanced Prophylaxis plus Antiretroviral Therapy for Advanced HIV Infection in Africa. | N Engl J Med | 2017 Jul 20 | 28723333 |
| Chemically modified cellulose strips with pyridoxal conjugated red fluorescentgold nanoclusters for nanomolar detection of mercuric ions. | Biosens Bioelectron | 2017 Apr 15 | 27940235 |
| High-concentrate diets based on forages harvested at different maturity stagesaffect ruminal synthesis of B vitamins in lactating dairy cows. | Animal | 2017 Apr | 27573890 |
| Protective Effects of Pyridoxamine Supplementation in the Early Stages ofDiet-Induced Kidney Dysfunction. | Biomed Res Int | 2017 | 29214163 |
| Bioavailability of Cu, Zn and Mn from Mineral Chelates or Blends of InorganicSalts in Growing Turkeys Fed with Supplemental Riboflavin and/or Pyridoxine. | Biol Trace Elem Res | 2016 Sep | 26781955 |
| Dietary Pyridoxine Protects against Stress and Maintains ImmunohaematologicalStatus in Chanos chanos Exposed to Endosulfan. | Basic Clin Pharmacol Toxicol | 2016 Sep | 27038044 |
| The effects of magnesium supplementation on subjective anxiety. | Magnes Res | 2016 Mar 1 | 27869100 |
| Methylating micronutrient supplementation during pregnancy influences foetalhepatic gene expression and IGF signalling and increases foetal weight. | Eur J Nutr | 2016 Jun | 26169873 |
| Nutraceutical approaches to homocysteine lowering in hypertensive subjects at lowcardiovascular risk: a multicenter, randomized clinical trial. | J Biol Regul Homeost Agents | 2016 Jul-Sep | 27655522 |
| Effect of dietary lysine restriction and arginine supplementation in two patients with pyridoxine-dependent epilepsy. | Mol Genet Metab | 2016 Jul | 27324284 |
| Mutations in PROSC Disrupt Cellular Pyridoxal Phosphate Homeostasis and Cause Vitamin-B<sub>6</sub>-Dependent Epilepsy. | Am J Hum Genet | 2016 Dec 1 | 27912044 |
| Decoration of multi-walled carbon nanotubes with metal nanoparticles insupercritical carbon dioxide medium as a novel approach for the modification ofscreen-printed electrodes. | Talanta | 2016 Dec 1 | 27769480 |
| Complementary Feeding Diets Made of Local Foods Can Be Optimized, but Additional Interventions Will Be Needed to Meet Iron and Zinc Requirements in 6- to23-Month-Old Children in Low- and Middle-Income Countries. | Food Nutr Bull | 2016 Dec | 27334774 |
| Dietary B Vitamins and Serum C-Reactive Protein in Persons With HumanImmunodeficiency Virus Infection: The Positive Living With HIV (POLH) Study. | Food Nutr Bull | 2016 Dec | 27370977 |
| Feeding pyridoxine prevents Saprolegnia parasitica infection in fish Labeorohita. | Fish Shellfish Immunol | 2016 Dec | 27670085 |
| Effect and mechanism of pyridoxamine on the lipid peroxidation and stability of polyunsaturated fatty acids in beef patties. | J Sci Food Agric | 2016 Aug | 26538517 |
Targets
- General Function:
- Ubiquitin protein ligase binding
- Specific Function:
- Hydro-lyase catalyzing the first step of the transsulfuration pathway, where the hydroxyl group of L-serine is displaced by L-homocysteine in a beta-replacement reaction to form L-cystathionine, the precursor of L-cysteine. This catabolic route allows the elimination of L-methionine and the toxic metabolite L-homocysteine (PubMed:23981774, PubMed:20506325, PubMed:23974653). Also involved in the production of hydrogen sulfide, a gasotransmitter with signaling and cytoprotective effects on neurons (By similarity).
- Gene Name:
- CBS
- Uniprot ID:
- P35520
- Molecular Weight:
- 60586.05 Da
- Mechanism of Action:
- Vitamin B6 is the collective term for a group of three related compounds, pyridoxine (PN), pyridoxal (PL) and pyridoxamine (PM), and their phosphorylated derivatives, pyridoxine 5'-phosphate (PNP), pyridoxal 5'-phosphate (PLP) and pyridoxamine 5'-phosphate (PMP). Although all six of these compounds should technically be referred to as vitamin B6, the term vitamin B6 is commonly used interchangeably with just one of them, pyridoxine. Vitamin B6, principally in the form of the coenzyme pyridoxal 5'-phosphate, is involved in a wide range of biochemical reactions, including the metabolism of amino acids and glycogen, the synthesis of nucleic acids, hemogloblin, sphingomyelin and other sphingolipids, and the synthesis of the neurotransmitters serotonin, dopamine, norepinephrine and gamma-aminobutyric acid (GABA).
- General Function:
- O-phospho-l-serine:2-oxoglutarate aminotransferase activity
- Specific Function:
- Catalyzes the reversible conversion of 3-phosphohydroxypyruvate to phosphoserine and of 3-hydroxy-2-oxo-4-phosphonooxybutanoate to phosphohydroxythreonine.
- Gene Name:
- PSAT1
- Uniprot ID:
- Q9Y617
- Molecular Weight:
- 40422.355 Da
- Mechanism of Action:
- Vitamin B6 is the collective term for a group of three related compounds, pyridoxine (PN), pyridoxal (PL) and pyridoxamine (PM), and their phosphorylated derivatives, pyridoxine 5'-phosphate (PNP), pyridoxal 5'-phosphate (PLP) and pyridoxamine 5'-phosphate (PMP). Although all six of these compounds should technically be referred to as vitamin B6, the term vitamin B6 is commonly used interchangeably with just one of them, pyridoxine. Vitamin B6, principally in the form of the coenzyme pyridoxal 5'-phosphate, is involved in a wide range of biochemical reactions, including the metabolism of amino acids and glycogen, the synthesis of nucleic acids, hemogloblin, sphingomyelin and other sphingolipids, and the synthesis of the neurotransmitters serotonin, dopamine, norepinephrine and gamma-aminobutyric acid (GABA).
- General Function:
- Zinc ion binding
- Specific Function:
- Required for synthesis of pyridoxal-5-phosphate from vitamin B6.
- Gene Name:
- PDXK
- Uniprot ID:
- O00764
- Molecular Weight:
- 35102.105 Da
- Mechanism of Action:
- Vitamin B6 is the collective term for a group of three related compounds, pyridoxine (PN), pyridoxal (PL) and pyridoxamine (PM), and their phosphorylated derivatives, pyridoxine 5'-phosphate (PNP), pyridoxal 5'-phosphate (PLP) and pyridoxamine 5'-phosphate (PMP). Although all six of these compounds should technically be referred to as vitamin B6, the term vitamin B6 is commonly used interchangeably with just one of them, pyridoxine. Vitamin B6, principally in the form of the coenzyme pyridoxal 5'-phosphate, is involved in a wide range of biochemical reactions, including the metabolism of amino acids and glycogen, the synthesis of nucleic acids, hemogloblin, sphingomyelin and other sphingolipids, and the synthesis of the neurotransmitters serotonin, dopamine, norepinephrine and gamma-aminobutyric acid (GABA).
- General Function:
- Pyridoxal phosphatase activity
- Specific Function:
- Protein serine phosphatase that dephosphorylates 'Ser-3' in cofilin and probably also dephosphorylates phospho-serine residues in DSTN. Regulates cofilin-dependent actin cytoskeleton reorganization. Required for normal progress through mitosis and normal cytokinesis. Does not dephosphorylate phospho-threonines in LIMK1. Does not dephosphorylate peptides containing phospho-tyrosine. Pyridoxal phosphate phosphatase. Has some activity towards pyridoxal 5'-phosphate (PLP), pyridoxine 5'-phosphate (PMP) and pyridoxine 5'-phosphate (PNP), with a highest activity with PLP followed by PNP.
- Gene Name:
- PDXP
- Uniprot ID:
- Q96GD0
- Molecular Weight:
- 31697.735 Da
- Mechanism of Action:
- Vitamin B6 is the collective term for a group of three related compounds, pyridoxine (PN), pyridoxal (PL) and pyridoxamine (PM), and their phosphorylated derivatives, pyridoxine 5'-phosphate (PNP), pyridoxal 5'-phosphate (PLP) and pyridoxamine 5'-phosphate (PMP). Although all six of these compounds should technically be referred to as vitamin B6, the term vitamin B6 is commonly used interchangeably with just one of them, pyridoxine. Vitamin B6, principally in the form of the coenzyme pyridoxal 5'-phosphate, is involved in a wide range of biochemical reactions, including the metabolism of amino acids and glycogen, the synthesis of nucleic acids, hemogloblin, sphingomyelin and other sphingolipids, and the synthesis of the neurotransmitters serotonin, dopamine, norepinephrine and gamma-aminobutyric acid (GABA).
- General Function:
- Toxic substance binding
- Specific Function:
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
- Gene Name:
- ALB
- Uniprot ID:
- P02768
- Molecular Weight:
- 69365.94 Da
- Mechanism of Action:
- Vitamin B6 is the collective term for a group of three related compounds, pyridoxine (PN), pyridoxal (PL) and pyridoxamine (PM), and their phosphorylated derivatives, pyridoxine 5'-phosphate (PNP), pyridoxal 5'-phosphate (PLP) and pyridoxamine 5'-phosphate (PMP). Although all six of these compounds should technically be referred to as vitamin B6, the term vitamin B6 is commonly used interchangeably with just one of them, pyridoxine. Vitamin B6, principally in the form of the coenzyme pyridoxal 5'-phosphate, is involved in a wide range of biochemical reactions, including the metabolism of amino acids and glycogen, the synthesis of nucleic acids, hemogloblin, sphingomyelin and other sphingolipids, and the synthesis of the neurotransmitters serotonin, dopamine, norepinephrine and gamma-aminobutyric acid (GABA).
- General Function:
- L-aminoadipate-semialdehyde dehydrogenase activity
- Specific Function:
- Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
- Gene Name:
- ALDH7A1
- Uniprot ID:
- P49419
- Molecular Weight:
- 58486.74 Da
- Mechanism of Action:
- Vitamin B6 is the collective term for a group of three related compounds, pyridoxine (PN), pyridoxal (PL) and pyridoxamine (PM), and their phosphorylated derivatives, pyridoxine 5'-phosphate (PNP), pyridoxal 5'-phosphate (PLP) and pyridoxamine 5'-phosphate (PMP). Although all six of these compounds should technically be referred to as vitamin B6, the term vitamin B6 is commonly used interchangeably with just one of them, pyridoxine. Vitamin B6, principally in the form of the coenzyme pyridoxal 5'-phosphate, is involved in a wide range of biochemical reactions, including the metabolism of amino acids and glycogen, the synthesis of nucleic acids, hemogloblin, sphingomyelin and other sphingolipids, and the synthesis of the neurotransmitters serotonin, dopamine, norepinephrine and gamma-aminobutyric acid (GABA).