Neopterin
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Basic Info
| Common Name | Neopterin(F05246) |
| 2D Structure | |
| Description | Neopterin is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. |
| FRCD ID | F05246 |
| CAS Number | 2009-64-5 |
| PubChem CID | 4455 |
| Formula | C9H11N5O4 |
| IUPAC Name | 2-amino-6-(1,2,3-trihydroxypropyl)-1H-pteridin-4-one |
| InChI Key | BMQYVXCPAOLZOK-UHFFFAOYSA-N |
| InChI | InChI=1S/C9H11N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h1,4,6,15-17H,2H2,(H3,10,11,13,14,18) |
| Canonical SMILES | C1=C(N=C2C(=N1)NC(=NC2=O)N)C(C(CO)O)O |
| Isomeric SMILES | C1=C(N=C2C(=N1)NC(=NC2=O)N)C(C(CO)O)O |
| Wikipedia | Neopterin |
| Synonyms |
2-Amino-6-(1,2,3-trihydroxypropyl)-4(3H)-pteridinone
[S-(R*,S*)]-2-amino-6-(1,2,3-trihydroxypropyl)-1H-pteridine-4-one
neopterin
Monapterin
neopterine
AC1Q6INQ
AC1L1I7D
SCHEMBL2304401
[S-(R*,S*)]-2-Amino-6-(1,2,3-trihydroxypropyl)-1H-pteridin-4-on
SCHEMBL11301495
|
| Classifies |
Predicted: Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Pteridines and derivatives |
| Subclass | Pterins and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Biopterins and derivatives |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Biopterin - Aminopyrimidine - Pyrimidone - Pyrazine - Pyrimidine - Heteroaromatic compound - Vinylogous amide - Secondary alcohol - Polyol - Azacycle - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Primary amine - Primary alcohol - Alcohol - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Organic nitrogen compound - Amine - Aromatic alcohol - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 253.218 |
| Hydrogen Bond Donor Count | 5 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 3 |
| Complexity | 363 |
| Monoisotopic Mass | 253.081 |
| Exact Mass | 253.081 |
| XLogP | -3.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 18 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 2 |
| 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+ | 0.7800 |
| Human Intestinal Absorption | HIA+ | 0.9673 |
| Caco-2 Permeability | Caco2- | 0.7695 |
| P-glycoprotein Substrate | Substrate | 0.5466 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9729 |
| Non-inhibitor | 0.9949 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9417 |
| Distribution | ||
| Subcellular localization | Nucleus | 0.4420 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8613 |
| CYP450 2D6 Substrate | Non-substrate | 0.8000 |
| CYP450 3A4 Substrate | Non-substrate | 0.6416 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8400 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9052 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9236 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9046 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9209 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9763 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9893 |
| Non-inhibitor | 0.9128 | |
| AMES Toxicity | Non AMES toxic | 0.7360 |
| Carcinogens | Non-carcinogens | 0.9233 |
| Fish Toxicity | Low FHMT | 0.8754 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8806 |
| Honey Bee Toxicity | Low HBT | 0.7482 |
| Biodegradation | Not ready biodegradable | 0.9706 |
| Acute Oral Toxicity | III | 0.6658 |
| Carcinogenicity (Three-class) | Non-required | 0.6505 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.9668 | LogS |
| Caco-2 Permeability | -0.4978 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.1247 | LD50, mol/kg |
| Fish Toxicity | 1.7502 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.1876 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Impact of High-Dose Multi-Strain Probiotic Supplementation on NeurocognitivePerformance and Central Nervous System Immune Activation of HIV-1 InfectedIndividuals. | Nutrients | 2017 Nov 21 | 29160817 |
| Effect of Coffee in Lipopolysaccharide-Induced Indoleamine 2,3-Dioxygenase Activation and Depressive-like Behavior in Mice. | J Agric Food Chem | 2016 Nov 23 | 27690418 |
| Mildly compromised tetrahydrobiopterin cofactor biosynthesis due to Pts variants leads to unusual body fat distribution and abdominal obesity in mice. | J Inherit Metab Dis | 2016 Mar | 26830550 |
| TiO(2) nanoparticles and bulk material stimulate human peripheral bloodmononuclear cells. | Food Chem Toxicol | 2014 Mar | 24361406 |
| Cacao extracts suppress tryptophan degradation of mitogen-stimulated peripheral blood mononuclear cells. | J Ethnopharmacol | 2009 Mar 18 | 19330924 |
| Effect of multiple micronutrient supplementation during pregnancy on inflammatorymarkers in Nepalese women. | Am J Clin Nutr | 2006 Nov | 17093161 |
| Food preservatives sodium sulfite and sorbic acid suppress mitogen-stimulatedperipheral blood mononuclear cells. | Food Chem Toxicol | 2006 Dec | 16904801 |
| Inflammatory mediator production in swine following endotoxin challenge with or without co-administration of dexamethasone. | Int Immunopharmacol | 2003 Apr | 12689661 |
| [Transmission of HIV infection]. | Wien Klin Wochenschr | 1995 | 7886967 |
Targets
- General Function:
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function:
- Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
- Gene Name:
- SLC22A8
- Uniprot ID:
- Q8TCC7
- Molecular Weight:
- 59855.585 Da
References
- Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
- General Function:
- Vitamin d binding
- Specific Function:
- May have weak glycosidase activity towards glucuronylated steroids. However, it lacks essential active site Glu residues at positions 239 and 872, suggesting it may be inactive as a glycosidase in vivo. May be involved in the regulation of calcium and phosphorus homeostasis by inhibiting the synthesis of active vitamin D (By similarity). Essential factor for the specific interaction between FGF23 and FGFR1 (By similarity).The Klotho peptide generated by cleavage of the membrane-bound isoform may be an anti-aging circulating hormone which would extend life span by inhibiting insulin/IGF1 signaling.
- Gene Name:
- KL
- Uniprot ID:
- Q9UEF7
- Molecular Weight:
- 116179.815 Da
References
- Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
- General Function:
- Superoxide-generating nadph oxidase activity
- Specific Function:
- Constitutive NADPH oxidase which generates superoxide intracellularly upon formation of a complex with CYBA/p22phox. Regulates signaling cascades probably through phosphatases inhibition. May function as an oxygen sensor regulating the KCNK3/TASK-1 potassium channel and HIF1A activity. May regulate insulin signaling cascade. May play a role in apoptosis, bone resorption and lipolysaccharide-mediated activation of NFKB. May produce superoxide in the nucleus and play a role in regulating gene expression upon cell stimulation. Isoform 3 is not functional. Isoform 5 and isoform 6 display reduced activity.Isoform 4: Involved in redox signaling in vascular cells. Constitutively and NADPH-dependently generates reactive oxygen species (ROS). Modulates the nuclear activation of ERK1/2 and the ELK1 transcription factor, and is capable of inducing nuclear DNA damage. Displays an increased activity relative to isoform 1.
- Gene Name:
- NOX4
- Uniprot ID:
- Q9NPH5
- Molecular Weight:
- 66930.995 Da
References
- Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]