Methylguanidine
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Basic Info
Common Name | Methylguanidine(F05254) |
2D Structure | |
Description | Methylguanidine 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 | F05254 |
CAS Number | 471-29-4 |
PubChem CID | 10111 |
Formula | C2H7N3 |
IUPAC Name | 2-methylguanidine |
InChI Key | CHJJGSNFBQVOTG-UHFFFAOYSA-N |
InChI | InChI=1S/C2H7N3/c1-5-2(3)4/h1H3,(H4,3,4,5) |
Canonical SMILES | CN=C(N)N |
Isomeric SMILES | CN=C(N)N |
Synonyms | 1-methylguanidine METHYLGUANIDINE N-Methylguanidine Methylguanidin Guanidine, methyl- Monomethylguanidine Monomethyl guanidin 471-29-4 N1-Methylguanidine Methylguanidin [German] |
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 | 73.099 |
Hydrogen Bond Donor Count | 2 |
Hydrogen Bond Acceptor Count | 1 |
Rotatable Bond Count | 0 |
Complexity | 42.9 |
Monoisotopic Mass | 73.064 |
Exact Mass | 73.064 |
XLogP | -1.3 |
Formal Charge | 0 |
Heavy Atom Count | 5 |
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+ | 0.7908 |
Human Intestinal Absorption | HIA+ | 0.9357 |
Caco-2 Permeability | Caco2- | 0.7638 |
P-glycoprotein Substrate | Non-substrate | 0.7429 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.9734 |
Non-inhibitor | 0.9177 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.7663 |
Distribution | ||
Subcellular localization | Lysosome | 0.5870 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.7949 |
CYP450 2D6 Substrate | Non-substrate | 0.6847 |
CYP450 3A4 Substrate | Non-substrate | 0.8071 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.9814 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.9739 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9462 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.9715 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.9715 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9818 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9694 |
Non-inhibitor | 0.9790 | |
AMES Toxicity | Non AMES toxic | 0.8907 |
Carcinogens | Non-carcinogens | 0.7445 |
Fish Toxicity | Low FHMT | 0.9202 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.5531 |
Honey Bee Toxicity | Low HBT | 0.5069 |
Biodegradation | Not ready biodegradable | 0.8456 |
Acute Oral Toxicity | III | 0.5366 |
Carcinogenicity (Three-class) | Non-required | 0.7209 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -0.0540 | LogS |
Caco-2 Permeability | 0.4624 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 2.0048 | LD50, mol/kg |
Fish Toxicity | 2.8932 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | -0.3812 | pIGC50, ug/L |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
Activity of (-)-epigallocatechin 3-O-gallate against oxidative stress in rats with adenine-induced renal failure. | J Agric Food Chem | 2004 Apr 7 | 15053559 |
Buckwheat extract inhibits progression of renal failure. | J Agric Food Chem | 2002 May 22 | 12010008 |
Comparison of renal effects of creatinine, creatol and methylguanidine in rats with adenine-induced chronic renal failure. | Nephron | 1993 | 8341388 |
Comparison of toxic effects of methylguanidine, guanidinosuccinic acid and creatinine in rats with adenine-induced chronic renal failure. | Nephron | 1989 | 2918950 |
[Chronic renal failure: present and future. Pathophysiology and metabolic abnormalities--uremic toxin, small molecular compounds]. | Nihon Naika Gakkai Zasshi | 1986 Nov | 2950190 |
Uraemic toxins. | Aust N Z J Med | 1981 | 6942801 |
Amino acid and protein metabolism in renal failure. | Am J Clin Nutr | 1978 Sep | 685869 |
Plasma concentration and urinary excretion of guanidine derivatives in normal subjects and patients with renal failure. | Clin Exp Pharmacol Physiol | 1975 Jan-Feb | 1126056 |
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:
- 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 ]