Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C8H8NO6P.2Na |
| Molecular Weight | 291.1055 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[Na+].CC1=NC=C(COP([O-])([O-])=O)C(C=O)=C1O
InChI
InChIKey=QLCHMRQQHVLZNQ-UHFFFAOYSA-L
InChI=1S/C8H10NO6P.2Na/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14;;/h2-3,11H,4H2,1H3,(H2,12,13,14);;/q;2*+1/p-2
| Molecular Formula | Na |
| Molecular Weight | 22.9898 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C8H8NO6P |
| Molecular Weight | 245.126 |
| Charge | -2 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20532028 | https://clinicaltrials.gov/ct2/show/NCT00157729 | https://clinicaltrials.gov/ct2/show/NCT00917293 | https://www.ncbi.nlm.nih.gov/pubmed/12213051 | https://www.ncbi.nlm.nih.gov/pubmed/23510563
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20532028 | https://clinicaltrials.gov/ct2/show/NCT00157729 | https://clinicaltrials.gov/ct2/show/NCT00917293 | https://www.ncbi.nlm.nih.gov/pubmed/12213051 | https://www.ncbi.nlm.nih.gov/pubmed/23510563
Pyridoxal phosphate (PLP, pyridoxal 5'-phosphate, P5P) is a coenzyme, the active form of vitamin B6. Pyridoxal 5′-phosphate (PLP) is used as a cofactor for a wide range of enzymes including mitochondrial cysteine desulfurase, cystathionine γ-synthase (CGS), ornithine 4,5-aminomutase (OAM), and d-serine dehydratase. The versatility of PLP arises from its ability to covalently bind the substrate, and then to act as an electrophilic catalyst, thereby stabilizing different types of carbanionic reaction intermediates. PLP acts as a coenzyme in all transamination reactions, in various beta-elimination reactions, in the condensation reaction in heme synthesis.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2530 |
3000.0 nM [EC50] | ||
Target ID: CHEMBL2531 |
39500.0 nM [EC50] | ||
Target ID: CHEMBL2094 |
10.0 µM [EC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Correlation of MRI and CT findings with histopathology in hepatic angiomyolipoma. | 2001 |
|
| Testing the tyrosine/catecholamine hypothesis of oral contraceptive-induced psychological side-effects: a controlled study on triphasil. | 2001 |
|
| Determination of mangafodipir trisodium and related impurities in bulk substance and pharmaceutical formulation by ion-pair high-performance liquid chromatography. | 2001 Apr |
|
| Crystal structure of maltose phosphorylase from Lactobacillus brevis: unexpected evolutionary relationship with glucoamylases. | 2001 Aug |
|
| Production of pyridoxal phosphate by a mutant strain of Schizosaccharomyces pombe. | 2001 Aug |
|
| Clinical and cost effectiveness of a new hepatocellular MRI contrast agent, mangafodipir trisodium, in the preoperative assessment of liver resectability. | 2001 Aug |
|
| A bioinformatical approach suggests the function of the autoimmune hepatitis target antigen soluble liver antigen/liver pancreas. | 2001 Aug |
|
| Structure of human cystathionine beta-synthase: a unique pyridoxal 5'-phosphate-dependent heme protein. | 2001 Aug 1 |
|
| P2X3 knock-out mice reveal a major sensory role for urothelially released ATP. | 2001 Aug 1 |
|
| Crystal structure of histidinol phosphate aminotransferase (HisC) from Escherichia coli, and its covalent complex with pyridoxal-5'-phosphate and l-histidinol phosphate. | 2001 Aug 24 |
|
| Inhibitory effect of glycation on catalytic activity of alanine aminotransferase. | 2001 Feb |
|
| Structure-activity relationships of pyridoxal phosphate derivatives as potent and selective antagonists of P2X1 receptors. | 2001 Feb 1 |
|
| Inhibitors of advanced glycation end product-associated protein cross-linking. | 2001 Feb 14 |
|
| Identification and characterization of an aromatic amino acid decarboxylase from the filarial nematode, Dirofilaria immitis. | 2001 Jan |
|
| Metal ion inhibition of nonenzymatic pyridoxal phosphate catalyzed decarboxylation and transamination. | 2001 Jan 17 |
|
| Long-term effects of vitamin B(12), folate, and vitamin B(6) supplements in elderly people with normal serum vitamin B(12) concentrations. | 2001 Jan-Feb |
|
| Serum cystatin C is an independent predictor of total homocysteine levels in stable Korean renal transplant recipients with normal serum creatinine. | 2001 Jul |
|
| Influence of pyridoxal 5'-phosphate alone and in combination with vigabatrin on brain GABA measured by 1H-NMR-spectroscopy. | 2001 Jul 1 |
|
| The human cDNA for a homologue of the plant enzyme 1-aminocyclopropane-1-carboxylate synthase encodes a protein lacking that activity. | 2001 Jul 11 |
|
| X-ray structure of Escherichia coli pyridoxine 5'-phosphate oxidase complexed with pyridoxal 5'-phosphate at 2.0 A resolution. | 2001 Jul 20 |
|
| Effect of vitamin B6 deficiency on the synthesis and accumulation of S-adenosylhomocysteine and S-adenosylmethionine in rat tissues. | 2001 Jun |
|
| Effect of feeding on circulating micronutrient concentrations in the Burmese python (Python molurus). | 2001 Jun |
|
| Stimulation of P2 receptors in the ventral tegmental area enhances dopaminergic mechanisms in vivo. | 2001 Jun |
|
| Cassette mutagenesis of lysine 130 of human glutamate dehydrogenase. An essential residue in catalysis. | 2001 Jun |
|
| Sensitivity to meat protein intake and hyperoxaluria in idiopathic calcium stone formers. | 2001 Jun |
|
| PPADS, an ATP antagonist, attenuates the effects of a moderately intense sound on cochlear mechanics. | 2001 Jun |
|
| Dephosphorylation of MnDPDP and related compounds by acid and alkaline phosphatase. | 2001 Jun |
|
| Pyridoxal phosphate binding sites are similar in human heme-dependent and yeast heme-independent cystathionine beta-synthases. Evidence from 31P NMR and pulsed EPR spectroscopy that heme and PLP cofactors are not proximal in the human enzyme. | 2001 Jun 1 |
|
| Low circulating vitamin B(6) is associated with elevation of the inflammation marker C-reactive protein independently of plasma homocysteine levels. | 2001 Jun 12 |
|
| Role of endogenous ATP at the incision area in a rat model of postoperative pain. | 2001 Jun 13 |
|
| Nucleotide-evoked relaxation of rat vas deferens--a possible role for endogenous ATP released upon alpha(1)-adrenoceptor stimulation. | 2001 Jun 22 |
|
| Homocyst(e)ine metabolism in hemodialysis patients treated with vitamins B6, B12 and folate. | 2001 Mar |
|
| Crystal structure of threonine synthase from Arabidopsis thaliana. | 2001 Mar |
|
| Adult hypophosphatasia. Current aspects. | 2001 Mar |
|
| Effect of phosphate on stability of pyridoxal in the presence of lysine. | 2001 Mar |
|
| [Comparison of biphasic spiral CT and MnDPDP-enhanced MRI in the detection and characterization of liver lesions]. | 2001 Mar |
|
| Molecular cloning and characterization of the mouse P2Y4 nucleotide receptor. | 2001 Mar 30 |
|
| Structural basis for the function of pyridoxine 5'-phosphate synthase. | 2001 Mar 7 |
|
| Three-dimensional structure of 2-amino-3-ketobutyrate CoA ligase from Escherichia coli complexed with a PLP-substrate intermediate: inferred reaction mechanism. | 2001 May 1 |
|
| Accelerated functional recovery after neuronal injury by P2 receptor blockade. | 2001 May 25 |
|
| ABA3 is a molybdenum cofactor sulfurase required for activation of aldehyde oxidase and xanthine dehydrogenase in Arabidopsis thaliana. | 2001 Nov 2 |
|
| Cloning, sequencing, heterologous expression, purification, and characterization of adenosylcobalamin-dependent D-ornithine aminomutase from Clostridium sticklandii. | 2001 Nov 30 |
|
| COMT genotype, micronutrients in the folate metabolic pathway and breast cancer risk. | 2001 Oct |
|
| Crystal structures of 1-aminocyclopropane-1-carboxylate (ACC) synthase in complex with aminoethoxyvinylglycine and pyridoxal-5'-phosphate provide new insight into catalytic mechanisms. | 2001 Oct 12 |
|
| P2Y(AC)(-)-receptor agonists enhance the proliferation of rat C6 glioma cells through activation of the p42/44 mitogen-activated protein kinase. | 2001 Sep |
|
| Cloning and characterization of a functional P2X receptor from larval bullfrog skin. | 2001 Sep |
|
| ATP P2X receptor-mediated enhancement of glutamate release and evoked EPSCs in dorsal horn neurons of the rat spinal cord. | 2001 Sep 1 |
|
| Properties and interaction of heterologously expressed glutamate decarboxylase isoenzymes GAD(65kDa) and GAD(67kDa) from human brain with ginkgotoxin and its 5'-phosphate. | 2001 Sep 13 |
|
| Smooth muscle does not have a common P2x receptor phenotype: expression, ontogeny and function of P2x1 receptors in mouse ileum, bladder and reproductive systems. | 2001 Sep 17 |
|
| Plants synthesize ethanolamine by direct decarboxylation of serine using a pyridoxal phosphate enzyme. | 2001 Sep 21 |
Sample Use Guides
Male Wistar rat (body weight -200 g) was sacrificed by bleeding from the right femoral artery under diethyl ether anesthesia. A thoracic aorta was removed and washed with RPMI 1640 medium to avoid contamination with blood. It was then turned inside out, and cut into short segments of about 1-1.5 mm. Each aortic segment was placed in the center of a well on a 6-well culture plate and covered with 0.5 ml of gel matrix solution reconstituted as described. The solution was allowed to gel at 37°C for 20 min, and then overlaid with 2 ml of RPMI 1640 medium (Gibco, New York, USA) containing 1% of ITS+ (Becton Dickinson Labware, MA, USA). PLP (Pyridoxal phosphate ) was reconstituted in phosphate buffered saline and added on day 1. Incubation was carried out for 10 days in a fully humidified system of 5% C02 in the air at 37°C. The medium was changed on day 7 of the culture.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:25:24 GMT 2023
by
admin
on
Fri Dec 15 15:25:24 GMT 2023
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| Record UNII |
ERZ74D7E6J
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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181317-75-9
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ERZ74D7E6J
Created by
admin on Fri Dec 15 15:25:24 GMT 2023 , Edited by admin on Fri Dec 15 15:25:24 GMT 2023
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PARENT -> SALT/SOLVATE |
