Basic Info

Common NamePutrescine(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.
Putrescine is a polyamine. Putrescine is related to cadaverine (another polyamine). Both are produced by the breakdown of amino acids in living and dead organisms and both are toxic in large doses. Putrescine and cadaverine are largely responsible for the foul odor of putrefying flesh, but also contribute to the odor of such processes as bad breath and bacterial vaginosis. Putrescine is also found in semen. Putrescine attacks s-adenosyl methionine and converts it to spermidine. Spermidine in turn attacks another s-adenosyl methionine and converts it to spermine. Putrescine is synthesized in small quantities by healthy living cells by the action of ornithine decarboxylase. The polyamines, of which putrescine is one of the simplest, appear to be growth factors necessary for cell division. Putrescine apparently has specific role in skin physiology and neuroprotection. Pharmacological interventions have demonstrated convincingly that a steady supply of polyamines is a prerequisite for cell proliferation to occur. Genetic engineering of polyamine metabolism in transgenic rodents has shown that polyamines play a role in spermatogenesis, skin physiology, promotion of tumorigenesis and organ hypertrophy as well as neuronal protection. Transgenic activation of polyamine catabolism not only profoundly disturbs polyamine homeostasis in most tissues, but also creates a complex phenotype affecting skin, female fertility, fat depots, pancreatic integrity and regenerative growth. Transgenic expression of ornithine decarboxylase antizyme has suggested that this unique protein may act as a general tumor suppressor. Homozygous deficiency of the key biosynthetic enzymes of the polyamines, ornithine and S-adenosylmethionine decarboxylase is not compatible with murine embryogenesis. (A3286, A3287).

FRCD IDF05253
CAS Number110-60-1
PubChem CID1045
FormulaC4H12N2
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

WikipediaPutrescine
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 DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic nitrogen compounds
ClassOrganonitrogen compounds
SubclassAmines
Intermediate Tree NodesPrimary amines
Direct ParentMonoalkylamines
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsOrganopnictogen compound - Hydrocarbon derivative - Primary aliphatic amine - Aliphatic acyclic compound
DescriptionThis compound belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.

Properties

Property NameProperty Value
Molecular Weight88.154
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count3
Complexity17.5
Monoisotopic Mass88.1
Exact Mass88.1
XLogP-0.9
Formal Charge0
Heavy Atom Count6
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.8645
Human Intestinal AbsorptionHIA+0.8896
Caco-2 PermeabilityCaco2+0.8867
P-glycoprotein SubstrateNon-substrate0.5600
P-glycoprotein InhibitorNon-inhibitor0.9692
Non-inhibitor0.8872
Renal Organic Cation TransporterNon-inhibitor0.6470
Distribution
Subcellular localizationLysosome0.8762
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8950
CYP450 2D6 SubstrateSubstrate0.5153
CYP450 3A4 SubstrateNon-substrate0.8448
CYP450 1A2 InhibitorNon-inhibitor0.9045
CYP450 2C9 InhibitorNon-inhibitor0.9071
CYP450 2D6 InhibitorNon-inhibitor0.9497
CYP450 2C19 InhibitorNon-inhibitor0.9084
CYP450 3A4 InhibitorNon-inhibitor0.9111
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8704
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8553
Non-inhibitor0.8449
AMES ToxicityNon AMES toxic0.9080
CarcinogensNon-carcinogens0.5694
Fish ToxicityLow FHMT0.8400
Tetrahymena Pyriformis ToxicityLow TPT0.9336
Honey Bee ToxicityLow HBT0.5728
BiodegradationNot ready biodegradable0.5290
Acute Oral ToxicityII0.7692
Carcinogenicity (Three-class)Non-required0.6203

Model Value Unit
Absorption
Aqueous solubility-0.1344LogS
Caco-2 Permeability1.1774LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.3026LD50, mol/kg
Fish Toxicity3.0677pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.2180pIGC50, ug/L

References

TitleJournalDatePubmed ID
Detection of biogenic amines in pet food ingredients by RP-HPLC with automated dansyl chloride derivatisation.J Sep Sci2018 Oct 1430318732
Safety Evaluations of <i>Bifidobacterium bifidum</i> BGN4 and <i>Bifidobacterium longum</i> BORI.Int J Mol Sci2018 May 929747442
Putrescine as indicator of manganese neurotoxicity: Dose-response study in human SH-SY5Y cells.Food Chem Toxicol2018 Jun29684492
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 Sci2018 Feb29248224
Comparative study on the effects of putrescine and spermidine pre-treatment oncadmium stress in wheat.Ecotoxicol Environ Saf2018 Feb29127816
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 Sci201829616053
[Content and Origin of Nonvolatile Amines in Various Commercial Pickles].Shokuhin Eiseigaku Zasshi201829743466
Potassium, not lepidimoide, is the principal 'allelochemical' of cress-seedexudate that promotes amaranth hypocotyl elongation.Ann Bot2017 Oct 1728981578
Food Quality Monitor: Paper-Based Plasmonic Sensors Prepared Through ReversalNanoimprinting for Rapid Detection of Biogenic Amine Odorants.ACS Appl Mater Interfaces2017 May 2428471650
Effect of lantibiotic gallidermin against biogenic amine-producing faecalstaphylococci from ostriches and pheasants.Folia Microbiol (Praha)2017 May28084600
In vitro effects of sodium bicarbonate buffer on rumen fermentation, levels of lipopolysaccharide and biogenic amine, and composition of rumen microbiota.J Sci Food Agric2017 Mar27339112
Determination of biogenic amines in licorice (Glycyrrhiza glabra) by ion-pairextraction and liquid chromatography-tandem mass spectrometry.J Sci Food Agric2017 Mar27381870
Synergistic Effects of l-Arginine and Methyl Salicylate on AlleviatingPostharvest Disease Caused by Botrysis cinerea in Tomato Fruit.J Agric Food Chem2017 Jun 2128535671
Interactive effects of protein and carbohydrates on production of microbialmetabolites in the large intestine of growing pigs.Arch Anim Nutr2017 Jun28429993
Assessment of virulence factors, antibiotic resistance and amino-decarboxylase activity in Enterococcus faecium MXVK29 isolated from Mexican chorizo.Lett Appl Microbiol2017 Feb27930817
Exploring polyamine metabolism of Alternaria alternata to target new substances to control the fungal infection.Food Microbiol2017 Aug28400003
Comparison of Biogenic Amines and Mycotoxins in Alfalfa and Red Clover Fodder Depending on Additives.Int J Environ Res Public Health2017 Apr 1428420109
Alteration of metabolomic markers of amino-acid metabolism in piglets within-feed antibiotics.Amino Acids2017 Apr28101652
Improved fermentative production of gamma-aminobutyric acid via the putrescineroute: Systems metabolic engineering for production from glucose, amino sugars,and xylose.Biotechnol Bioeng2017 Apr27800627
Safety assessment of Tetragenococcus halophilus isolates from doenjang, a Korean high-salt-fermented soybean paste.Food Microbiol2017 Apr27889172

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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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 ]