Putrescine
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Basic Info
Common Name | Putrescine(F05253) |
2D Structure | |
Description | Putrescine 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 | F05253 |
CAS Number | 110-60-1 |
PubChem CID | 1045 |
Formula | C4H12N2 |
IUPAC Name | butane-1,4-diamine |
InChI Key | KIDHWZJUCRJVML-UHFFFAOYSA-N |
InChI | InChI=1S/C4H12N2/c5-3-1-2-4-6/h1-6H2 |
Canonical SMILES | C(CCN)CN |
Isomeric SMILES | C(CCN)CN |
Wikipedia | Putrescine |
Synonyms | 1,4-diaminobutane putrescine 1,4-butanediamine 110-60-1 tetramethylenediamine butane-1,4-diamine Butylenediamine Putrescin 1,4-Butylenediamine Tetramethyldiamine |
Classifies | Predicted: Veterinary Drug |
Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Organic nitrogen compounds |
Class | Organonitrogen compounds |
Subclass | Amines |
Intermediate Tree Nodes | Primary amines |
Direct Parent | Monoalkylamines |
Alternative Parents | |
Molecular Framework | Aliphatic acyclic compounds |
Substituents | Organopnictogen compound - Hydrocarbon derivative - Primary aliphatic amine - Aliphatic acyclic compound |
Description | This compound belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group. |
Properties
Property Name | Property Value |
---|---|
Molecular Weight | 88.154 |
Hydrogen Bond Donor Count | 2 |
Hydrogen Bond Acceptor Count | 2 |
Rotatable Bond Count | 3 |
Complexity | 17.5 |
Monoisotopic Mass | 88.1 |
Exact Mass | 88.1 |
XLogP | -0.9 |
Formal Charge | 0 |
Heavy Atom Count | 6 |
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+ | 0.8645 |
Human Intestinal Absorption | HIA+ | 0.8896 |
Caco-2 Permeability | Caco2+ | 0.8867 |
P-glycoprotein Substrate | Non-substrate | 0.5600 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.9692 |
Non-inhibitor | 0.8872 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.6470 |
Distribution | ||
Subcellular localization | Lysosome | 0.8762 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.8950 |
CYP450 2D6 Substrate | Substrate | 0.5153 |
CYP450 3A4 Substrate | Non-substrate | 0.8448 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.9045 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.9071 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9497 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.9084 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.9111 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8704 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8553 |
Non-inhibitor | 0.8449 | |
AMES Toxicity | Non AMES toxic | 0.9080 |
Carcinogens | Non-carcinogens | 0.5694 |
Fish Toxicity | Low FHMT | 0.8400 |
Tetrahymena Pyriformis Toxicity | Low TPT | 0.9336 |
Honey Bee Toxicity | Low HBT | 0.5728 |
Biodegradation | Not ready biodegradable | 0.5290 |
Acute Oral Toxicity | II | 0.7692 |
Carcinogenicity (Three-class) | Non-required | 0.6203 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -0.1344 | LogS |
Caco-2 Permeability | 1.1774 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 2.3026 | LD50, mol/kg |
Fish Toxicity | 3.0677 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | -0.2180 | pIGC50, ug/L |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
Detection of biogenic amines in pet food ingredients by RP-HPLC with automated dansyl chloride derivatisation. | J Sep Sci | 2018 Oct 14 | 30318732 |
Safety Evaluations of <i>Bifidobacterium bifidum</i> BGN4 and <i>Bifidobacterium longum</i> BORI. | Int J Mol Sci | 2018 May 9 | 29747442 |
Putrescine as indicator of manganese neurotoxicity: Dose-response study in human SH-SY5Y cells. | Food Chem Toxicol | 2018 Jun | 29684492 |
Varying the ratio of Lys:Met while maintaining the ratios of Thr:Phe, Lys:Thr,Lys:His, and Lys:Val alters mammary cellular metabolites, mammalian target ofrapamycin signaling, and gene transcription. | J Dairy Sci | 2018 Feb | 29248224 |
Comparative study on the effects of putrescine and spermidine pre-treatment oncadmium stress in wheat. | Ecotoxicol Environ Saf | 2018 Feb | 29127816 |
The <i>Aspergillus flavus</i> Spermidine Synthase (<i>spds</i>) Gene, Is Required for Normal Development, Aflatoxin Production, and Pathogenesis During Infection of Maize Kernels. | Front Plant Sci | 2018 | 29616053 |
[Content and Origin of Nonvolatile Amines in Various Commercial Pickles]. | Shokuhin Eiseigaku Zasshi | 2018 | 29743466 |
Potassium, not lepidimoide, is the principal 'allelochemical' of cress-seedexudate that promotes amaranth hypocotyl elongation. | Ann Bot | 2017 Oct 17 | 28981578 |
Food Quality Monitor: Paper-Based Plasmonic Sensors Prepared Through ReversalNanoimprinting for Rapid Detection of Biogenic Amine Odorants. | ACS Appl Mater Interfaces | 2017 May 24 | 28471650 |
Effect of lantibiotic gallidermin against biogenic amine-producing faecalstaphylococci from ostriches and pheasants. | Folia Microbiol (Praha) | 2017 May | 28084600 |
In vitro effects of sodium bicarbonate buffer on rumen fermentation, levels of lipopolysaccharide and biogenic amine, and composition of rumen microbiota. | J Sci Food Agric | 2017 Mar | 27339112 |
Determination of biogenic amines in licorice (Glycyrrhiza glabra) by ion-pairextraction and liquid chromatography-tandem mass spectrometry. | J Sci Food Agric | 2017 Mar | 27381870 |
Synergistic Effects of l-Arginine and Methyl Salicylate on AlleviatingPostharvest Disease Caused by Botrysis cinerea in Tomato Fruit. | J Agric Food Chem | 2017 Jun 21 | 28535671 |
Interactive effects of protein and carbohydrates on production of microbialmetabolites in the large intestine of growing pigs. | Arch Anim Nutr | 2017 Jun | 28429993 |
Assessment of virulence factors, antibiotic resistance and amino-decarboxylase activity in Enterococcus faecium MXVK29 isolated from Mexican chorizo. | Lett Appl Microbiol | 2017 Feb | 27930817 |
Exploring polyamine metabolism of Alternaria alternata to target new substances to control the fungal infection. | Food Microbiol | 2017 Aug | 28400003 |
Comparison of Biogenic Amines and Mycotoxins in Alfalfa and Red Clover Fodder Depending on Additives. | Int J Environ Res Public Health | 2017 Apr 14 | 28420109 |
Alteration of metabolomic markers of amino-acid metabolism in piglets within-feed antibiotics. | Amino Acids | 2017 Apr | 28101652 |
Improved fermentative production of gamma-aminobutyric acid via the putrescineroute: Systems metabolic engineering for production from glucose, amino sugars,and xylose. | Biotechnol Bioeng | 2017 Apr | 27800627 |
Safety assessment of Tetragenococcus halophilus isolates from doenjang, a Korean high-salt-fermented soybean paste. | Food Microbiol | 2017 Apr | 27889172 |
Targets
- General Function:
- Protein homodimerization activity
- Specific Function:
- Key enzyme of polyamine biosynthesis that converts ornithine into putrescine, which is the precursor for the polyamines, spermidine and spermine.
- Gene Name:
- ODC1
- Uniprot ID:
- P11926
- Molecular Weight:
- 51147.73 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:
- Putrescine binding
- Specific Function:
- Essential for biosynthesis of the polyamines spermidine and spermine. Promotes maintenance and self-renewal of embryonic stem cells, by maintaining spermine levels (By similarity).
- Gene Name:
- AMD1
- Uniprot ID:
- P17707
- Molecular Weight:
- 38339.335 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:
- Receptor signaling protein activity
- Specific Function:
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling.
- Gene Name:
- ADRB1
- Uniprot ID:
- P08588
- Molecular Weight:
- 51322.1 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:
- Protein homodimerization activity
- Specific Function:
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine.
- Gene Name:
- ADRB2
- Uniprot ID:
- P07550
- Molecular Weight:
- 46458.32 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 ]
- 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 ]