Guanidine
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Basic Info
| Common Name | Guanidine(F05256) |
| 2D Structure | |
| Description | Guaniidine 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 | F05256 |
| CAS Number | 113-00-8 |
| PubChem CID | 3520 |
| Formula | CH5N3 |
| IUPAC Name | guanidine |
| InChI Key | ZRALSGWEFCBTJO-UHFFFAOYSA-N |
| InChI | InChI=1S/CH5N3/c2-1(3)4/h(H5,2,3,4) |
| Canonical SMILES | C(=N)(N)N |
| Isomeric SMILES | C(=N)(N)N |
| Wikipedia | Guanidine |
| Synonyms |
guanidine
Iminourea
Aminomethanamidine
Carbamidine
Carbamamidine
Guanidin
Imidourea
Aminoformamidine
113-00-8
UNII-JU58VJ6Y3B
|
| Classifies |
Predicted: Pollutant
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic nitrogen compounds |
| Class | Organonitrogen compounds |
| Subclass | Guanidines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Guanidines |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Guanidine - Carboximidamide - Organopnictogen compound - Hydrocarbon derivative - Imine - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as guanidines. These are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 59.072 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 0 |
| Complexity | 26.3 |
| Monoisotopic Mass | 59.048 |
| Exact Mass | 59.048 |
| XLogP | -1.3 |
| Formal Charge | 0 |
| Heavy Atom Count | 4 |
| 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+ | 0.8502 |
| Human Intestinal Absorption | HIA+ | 0.9378 |
| Caco-2 Permeability | Caco2- | 0.7527 |
| P-glycoprotein Substrate | Non-substrate | 0.8033 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9770 |
| Non-inhibitor | 0.9320 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7825 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.5748 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8402 |
| CYP450 2D6 Substrate | Non-substrate | 0.6619 |
| CYP450 3A4 Substrate | Non-substrate | 0.8447 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9843 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9588 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9695 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9772 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9763 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9789 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9733 |
| Non-inhibitor | 0.9798 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.7148 |
| Fish Toxicity | Low FHMT | 0.8795 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.5784 |
| Honey Bee Toxicity | Low HBT | 0.5000 |
| Biodegradation | Not ready biodegradable | 0.7652 |
| Acute Oral Toxicity | II | 0.5514 |
| Carcinogenicity (Three-class) | Non-required | 0.6807 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.0870 | LogS |
| Caco-2 Permeability | 0.4633 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.9367 | LD50, mol/kg |
| Fish Toxicity | 2.4000 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.0045 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Sensitivity enhancement of aminoglycosides in hydrophilic interaction liquidchromatography with tandem mass spectrometry by post-column addition of tracesodium acetate in methanol. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2018Jun | 29160759 |
| Novel photoluminescence enzyme immunoassay based on supramolecular host-guest recognition using L-arginine/6-aza-2-thiothymine-stabilized gold nanocluster. | Biosens Bioelectron | 2018 Jun 30 | 29529510 |
| Low-dose cadmium exposure exacerbates polyhexamethylene guanidine-induced lung fibrosis in mice. | J Toxicol Environ Health A | 2018 | 29590002 |
| Caesalpinia bonduc serine proteinase inhibitor CbTI-2: Exploring the conformational features and antimalarial activity. | Int J Biol Macromol | 2017 Oct | 28502855 |
| In vitro algicidal effect of guanidine on Prototheca zopfii genotype 2 strains isolated from clinical and subclinical bovine mastitis. | Lett Appl Microbiol | 2017 Jun | 28349671 |
| Interaction of free arginine and guanidine with glucose under thermal processing conditions and formation of Amadori-derived imidazolones. | Food Chem | 2017 Apr 1 | 27855939 |
| Synthesis of the Paralytic Shellfish Poisons (+)-Gonyautoxin 2, (+)-Gonyautoxin 3, and (+)-11,11-Dihydroxysaxitoxin. | J Am Chem Soc | 2016 May 11 | 27138488 |
| Cyclic Guanidine Compounds from Toxic Newts Support the Hypothesis that Tetrodotoxin is Derived from a Monoterpene. | Angew Chem Int Ed Engl | 2016 Jul 18 | 27248052 |
| A glucose-centric perspective of hyperglycemia. | Indian J Exp Biol | 2016 Feb | 26934776 |
| Synthesis of a tricyclic bisguanidine compound structurally related to saxitoxin and its identification in paralytic shellfish toxin-producing microorganisms. | Chemistry | 2015 May 18 | 25873235 |
| Guanidino groups greatly enhance the action of antimicrobial peptidomimetics against bacterial cytoplasmic membranes. | Biochim Biophys Acta | 2014 Oct | 24878450 |
| Lipopolysaccharide induced conversion of recombinant prion protein. | Prion | 2014 Mar-Apr | 24819168 |
| Effect of uremic serum and uremic toxins on drug metabolism in human microsomes. | Regul Toxicol Pharmacol | 2014 Mar | 24184159 |
| Medical treatment for botulism. | Cochrane Database Syst Rev | 2014 Feb 20 | 24558013 |
| Development of a rapid total nucleic acid extraction method for the isolation of hepatitis A virus from fresh produce. | Int J Food Microbiol | 2013 Feb 15 | 23334093 |
| Bilberry anthocyanins neutralize the cytotoxicity of co-chaperonin GroES fibrillation intermediates. | Biochemistry | 2013 Dec 23 | 24308332 |
| Akwaton, polyhexamethylene-guanidine hydrochloride-based sporicidal disinfectant: a novel tool to fight bacterial spores and nosocomial infections. | J Med Microbiol | 2012 Oct | 22871428 |
| Enhanced inhibition of foot-and-mouth disease virus by combinations of porcineinterferon-α and antiviral agents. | Antiviral Res | 2012 Nov | 23000495 |
| LogSpin: a simple, economical and fast method for RNA isolation from infected or healthy plants and other eukaryotic tissues. | BMC Res Notes | 2012 Jan 19 | 22260178 |
| Design, synthesis, and biological evaluation of bifunctional thyrointegrin inhibitors: new anti-angiogenesis analogs. | J Enzyme Inhib Med Chem | 2011 Dec | 21395488 |
Targets
- 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:
- 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:
- Ribonuclease a activity
- Specific Function:
- Endonuclease that catalyzes the cleavage of RNA on the 3' side of pyrimidine nucleotides. Acts on single-stranded and double-stranded RNA.
- Gene Name:
- RNASE1
- Uniprot ID:
- P07998
- Molecular Weight:
- 17644.125 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Scaffold protein binding
- Specific Function:
- Interacts with the cytoplasmic tail of NMDA receptor subunits and shaker-type potassium channels. Required for synaptic plasticity associated with NMDA receptor signaling. Overexpression or depletion of DLG4 changes the ratio of excitatory to inhibitory synapses in hippocampal neurons. May reduce the amplitude of ASIC3 acid-evoked currents by retaining the channel intracellularly. May regulate the intracellular trafficking of ADR1B (By similarity).
- Gene Name:
- DLG4
- Uniprot ID:
- P78352
- Molecular Weight:
- 80494.615 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- 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 ]