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| cadaverine |
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| CHEBI:18127 |
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| An alkane-α,ω-diamine comprising a straight-chain pentane core with amino substitutents at positions 1 and 5. A colourless syrupy liquid diamine with a distinctive unpleasant odour, it is a homologue of putresceine and is formed by the bacterial decarboxylation of lysine that occurs during protein hydrolysis during putrefaction of animal tissue. It is also found in plants such as soyabean. |
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This entity has been manually annotated by the ChEBI Team.
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CHEBI:44370, CHEBI:3288, CHEBI:13928, CHEBI:22974
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| ChemicalBook:CB7853643, eMolecules:498259, ZINC000001529253 |
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Molfile
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SDF
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more structures >>
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| Cadaverine is an organic compound with the formula (CH2)5(NH2)2. Classified as a diamine, it is a colorless liquid with an unpleasant odor. It is present in small quantities in living organisms but is often associated with the putrefaction of animal tissue. Together with putrescine, it is largely responsible for the foul odor of putrefying flesh, but also contributes to other unpleasant odors.
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Read full article at Wikipedia
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| InChI=1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2 |
| VHRGRCVQAFMJIZ-UHFFFAOYSA-N |
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Mus musculus
(NCBI:txid10090)
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Source: BioModels - MODEL1507180067
See:
PubMed
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Daphnia magna
(NCBI:txid35525)
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See:
PubMed
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Glycine max
(NCBI:txid3847)
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See:
PubMed
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Escherichia coli
(NCBI:txid562)
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See:
PubMed
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Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
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Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
Daphnia magna metabolite
A Daphnia metabolite produced by the species Daphnia magna.
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View more via ChEBI Ontology
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1,5-Diaminopentane
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KEGG COMPOUND
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1,5-pentamethylenediamine
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NIST Chemistry WebBook
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1,5-Pentanediamine
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KEGG COMPOUND
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Cadaverine
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KEGG COMPOUND
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DAPE
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ChEBI
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Pentamethylenediamine
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KEGG COMPOUND
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PENTANE-1,5-DIAMINE
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PDBeChem
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1697256
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Reaxys Registry Number
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Reaxys
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2310
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Gmelin Registry Number
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Gmelin
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462-94-2
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CAS Registry Number
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KEGG COMPOUND
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462-94-2
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CAS Registry Number
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ChemIDplus
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462-94-2
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CAS Registry Number
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NIST Chemistry WebBook
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Zare D, Muhammad K, Bejo MH, Ghazali HM (2013)
Changes in urocanic acid, histamine, putrescine and cadaverine levels in Indian mackerel (Rastrelliger kanagurta) during storage at different temperatures.
Food chemistry 139, 320-325 [PubMed:23561112]
[show Abstract]
Histamine, putrescine cadaverine and cis-urocanic acid (UCA) have all been implicated or suggested in scombroid fish poisoning. However, there is little information on UCA especially during storage. Changes in their contents during storage of whole Indian mackerel at 0, 3±1, 10±1 for up to 15 days and 23±2°C for up to 2 days were monitored. Fresh muscles contained 14.83 mg/kg trans-UCA, 2.23 mg/kg cis-UCA and 1.86 mg/kg cadaverine. Histamine and putrescine were not detected. After 15 days at 0 and 3°C, trans-UCA content increased to 52.83 and 189.51 mg/kg, respectively, and decreased to <2 mg/kg at the other two temperatures. Storage at 10°C also resulted in an increase in trans-UCA after 3 days, only to decrease after 6 days. The concentration of cis-UCA increased nearly 13-fold after 15 days at 0 and 3°C, decreased at 10°C and remained unchanged at 23°C. Histamine, putrescine and cadaverine levels increased significantly (P value<0.05) at all temperatures especially at 23°C. | De Filippis F, Pennacchia C, Di Pasqua R, Fiore A, Fogliano V, Villani F, Ercolini D (2013)
Decarboxylase gene expression and cadaverine and putrescine production by Serratia proteamaculans in vitro and in beef.
International journal of food microbiology 165, 332-338 [PubMed:23811038]
[show Abstract]
Studies of the molecular basis of microbial metabolic activities that are important for the changes in food quality are valuable in order to help in understanding the behavior of spoiling bacteria in food. The growth of a psychrotrophic Serratia proteamaculans strain was monitored in vitro and in artificially inoculated raw beef. Two growth temperatures (25°C and 4°C) were tested in vitro, while growth at 15°C and 4°C was monitored in beef. During growth, the expression of inducible lysine and ornithine-decarboxylase genes was evaluated by quantitative reverse transcription-PCR (qRT-PCR), while the presence of cadaverine and putrescine was quantified by LC-ESI-MS/MS. The expression of the decarboxylase genes, and the consequent production of cadaverine and putrescine were shown to be influenced by the temperature, as well as by the complexity of the growth medium. Generally, the maximum gene expression and amine production took place during the exponential and early stationary phase, respectively. In addition, lower temperatures caused slower growth and gene downregulation. Higher amounts of cadaverine compared to putrescine were found during growth in beef with the highest concentrations corresponding to microbial loads of ca. 9CFU/g. The differences found in gene expression evaluated in vitro and in beef suggested that such activities are more reliably investigated in situ in specific food matrices. | Chou HT, Li JY, Peng YC, Lu CD (2013)
Molecular characterization of PauR and its role in control of putrescine and cadaverine catabolism through the γ-glutamylation pathway in Pseudomonas aeruginosa PAO1.
Journal of bacteriology 195, 3906-3913 [PubMed:23794626]
[show Abstract]
Pseudomonas aeruginosa PAO1 grows on a variety of polyamines as the sole source of carbon and nitrogen. Catabolism of polyamines is mediated by the γ-glutamylation pathway, which is complicated by the existence of multiple homologous enzymes with redundant specificities toward different polyamines for a more diverse metabolic capacity in this organism. Through a series of markerless gene knockout mutants and complementation tests, specific combinations of pauABCD (polyamine utilization) genes were deciphered for catabolism of different polyamines. Among six pauA genes, expression of pauA1, pauA2, pauA4, and pauA5 was found to be inducible by diamines putrescine (PUT) and cadaverine (CAD) but not by diaminopropane. Activation of these promoters was regulated by the PauR repressor, as evidenced by constitutively active promoters in the pauR mutant. The activities of these promoters were further enhanced by exogenous PUT or CAD in the mutant devoid of all six pauA genes. The recombinant PauR protein with a hexahistidine tag at its N terminus was purified, and specific bindings of PauR to the promoter regions of most pau operons were demonstrated by electromobility shift assays. Potential interactions of PUT and CAD with PauR were also suggested by chemical cross-linkage analysis with glutaraldehyde. In comparison, growth on PUT was more proficient than that on CAD, and this observed growth phenotype was reflected in a strong catabolite repression of pauA promoter activation by CAD but was completely absent as reflected by activation by PUT. In summary, this study clearly establishes the function of PauR in control of pau promoters in response to PUT and CAD for their catabolism through the γ-glutamylation pathway. | Tomar PC, Lakra N, Mishra SN (2013)
Cadaverine: a lysine catabolite involved in plant growth and development.
Plant signaling & behavior 8, doi: 10.4161/psb.25850 [PubMed:23887488]
[show Abstract]
The cadaverine (Cad) a diamine, imino compound produced as a lysine catabolite is also implicated in growth and development of plants depending on environmental condition. This lysine catabolism is catalyzed by lysine decarboxylase, which is developmentally regulated. However, the limited role of Cad in plants is reported, this review is tempted to focus the metabolism and its regulation, transport and responses, interaction and cross talks in higher plants. The Cad varied presence in plant parts/products suggests it as a potential candidate for taxonomic marker as well as for commercial exploitation along with growth and development. | Castrillo JI, Zeef LA, Hoyle DC, Zhang N, Hayes A, Gardner DC, Cornell MJ, Petty J, Hakes L, Wardleworth L, Rash B, Brown M, Dunn WB, Broadhurst D, O'Donoghue K, Hester SS, Dunkley TP, Hart SR, Swainston N, Li P, Gaskell SJ, Paton NW, Lilley KS, Kell DB, Oliver SG (2007)
Growth control of the eukaryote cell: a systems biology study in yeast.
Journal of biology 6, 4 [PubMed:17439666]
[show Abstract]
BackgroundCell growth underlies many key cellular and developmental processes, yet a limited number of studies have been carried out on cell-growth regulation. Comprehensive studies at the transcriptional, proteomic and metabolic levels under defined controlled conditions are currently lacking.ResultsMetabolic control analysis is being exploited in a systems biology study of the eukaryotic cell. Using chemostat culture, we have measured the impact of changes in flux (growth rate) on the transcriptome, proteome, endometabolome and exometabolome of the yeast Saccharomyces cerevisiae. Each functional genomic level shows clear growth-rate-associated trends and discriminates between carbon-sufficient and carbon-limited conditions. Genes consistently and significantly upregulated with increasing growth rate are frequently essential and encode evolutionarily conserved proteins of known function that participate in many protein-protein interactions. In contrast, more unknown, and fewer essential, genes are downregulated with increasing growth rate; their protein products rarely interact with one another. A large proportion of yeast genes under positive growth-rate control share orthologs with other eukaryotes, including humans. Significantly, transcription of genes encoding components of the TOR complex (a major controller of eukaryotic cell growth) is not subject to growth-rate regulation. Moreover, integrative studies reveal the extent and importance of post-transcriptional control, patterns of control of metabolic fluxes at the level of enzyme synthesis, and the relevance of specific enzymatic reactions in the control of metabolic fluxes during cell growth.ConclusionThis work constitutes a first comprehensive systems biology study on growth-rate control in the eukaryotic cell. The results have direct implications for advanced studies on cell growth, in vivo regulation of metabolic fluxes for comprehensive metabolic engineering, and for the design of genome-scale systems biology models of the eukaryotic cell. | Carrizo CN, Pitta-Alvarez SI, Kogan MJ, Giulietti AM, Tomaro ML (2001)
Occurrence of cadaverine in hairy roots of Brugmansia candida.
Phytochemistry 57, 759-763 [PubMed:11397445]
[show Abstract]
The polyamine, cadaverine, was detected in transformed root cultures of Brugmansia candida (syn. Datura candida), a Solanaceae which produces the tropane alkaloids scopolamine and hyoscyamine. To the best of our knowledge, this is the first time that the existence of this uncommon polyamine has been detected in a Datura species. Cadaverine, however, could not be found in the whole plant. The occurrence of cadaverine in hairy roots could be a consequence of either the transformation or a response to stress. Also, cadaverine could be participating in other secondary pathways rather than to the tropane alkaloids. The common polyamines, putrescine, spermidine and spermine were also observed. | Fernandez IM, Silva M, Schuch R, Walker WA, Siber AM, Maurelli AT, McCormick BA (2001)
Cadaverine prevents the escape of Shigella flexneri from the phagolysosome: a connection between bacterial dissemination and neutrophil transepithelial signaling.
The Journal of infectious diseases 184, 743-753 [PubMed:11517436]
[show Abstract]
Shigella flexneri causes bacillary dysentery in humans by invading epithelial cells of the colon, which is characterized by an acute polymorphonuclear leukocyte (PMNL)-rich inflammation. Our recent studies demonstrated that cadaverine, a polyamine, specifically acts to abrogate transepithelial signaling to PMNL induced by S. flexneri. Here, insight is provided into the cellular mechanisms by which cadaverine attenuates the ability of Shigella species to induce PMNL signaling. It was found that cadaverine retards the lysis of the Shigella species-containing vacuole, suggesting that a blockade is established, in which the pathogen is prevented from adequately interacting with the cytoskeleton. Furthermore, an IcsA mutant of S. flexneri that cannot interact with the cytoskeleton and spreads intercellularly fails to induce transmigration of PMNL. Results indicate that cadaverine-induced compartmentalization of Shigella species to the phagolysosome might be a protective response of the host that directly contributes to the diminished ability of PMNL to transmigrate across model intestinal epithelia. | Zhao Z, Baldo BA, O'Brien RM, Plomley RF (2000)
Reaction with, and fine structural recognition of polyamines by human IgE antibodies.
Molecular immunology 37, 233-240 [PubMed:10930630]
[show Abstract]
Human IgE antibodies from nine allergic subjects were found to react with poly-L-lysine (PLL) and other polyamines. Radioimmunoassay inhibition studies indicated that the two amino groups, but not the carboxyl, in lysine contributed to the antibody binding and 4-aminomethyl-1,8-octanediamine, a compound containing three primary amino groups, was a better inhibitor than compounds containing only two primary amino groups. Ethylamine showed weak but clear inhibition indicating that even a single amino group could bind to the antibody combining site. Substituted ethanolamine and quaternary ammonium compounds were well recognized by some sera but with others, substitution hampered recognition. Inhibition studies with compounds containing an amino and a carboxyl group at different distances revealed that an adjacent carboxyl group interfered with recognition of the amino group by some IgE antibodies. IgE binding to PLL was examined at different pHs and ionic strengths. Binding was greatest at pH 5-6 to 8 and decreased markedly outside this range. Ionic strengths higher than 0.3 M significantly diminished the binding. These results indicated that binding of specific antibody to polyamine was due to electrostatic interactions of positively charged amino groups in the polyamine with the antibody combining site. These results may be relevant to mechanisms underlying recognition of some allergens in some atopic conditions. | Gamarnik A, Frydman RB (1991)
Cadaverine, an Essential Diamine for the Normal Root Development of Germinating Soybean (Glycine max) Seeds.
Plant physiology 97, 778-785 [PubMed:16668466]
[show Abstract]
When the polyamine content of soybean (Glycine max) seeds was examined during the early stages of germination, the major polyamine in the cotyledons was found to be spermidine, followed by spermine; while very low concentrations of cadaverine were found. In the embryonic axes, however, cadaverine was the main polyamine and its content markedly increased 24 hours after the start of germination. When the germination of the seeds was performed in the presence of 1 millimolar alpha-difluoromethylornithine (DFMO), a marked decrease in the cadaverine content was found, while the other polyamines were not affected. This decrease of the cadaverine content was already noticeable after the first hours of germination. In the presence of DFMO, a pronounced elongation in the roots of the seedlings and a marked decrease in the appearance of secondary roots as compared with controls, was observed. This abnormal rooting of the seedlings caused by DFMO was almost completely reverted by the addition of 1 millimolar cadaverine. The latter also increased the appearance of secondary roots in the seedlings. The decrease in the cadaverine content produced by DFMO could be traced to a strong inhibition of lysine decarboxylase. A temporal correlation between the increase in cadaverine content and the increase in lysine decarboxylase activity was found. Both reached a maximum at the second day of germination. The activity of diamine oxidase, the cadaverine degrading enzyme, started to increase at the third day and reached a maximum between the fourth and fifth day of germination. DFMO increased the activity of diamine oxidase by about 25%. Hence, the large decrease in cadaverine content produced by DFMO has to be attributed to the in vivo suppression of lysine decarboxylase activity. Ornithine decarboxylase activity was also suppressed by DFMO, but putrescine and spermidine contents were not affected, except in the meristematic tissues. The obtained results suggest an important role for cadaverine in the normal rooting process of soybean seedlings. | Höfle MG (1984)
Degradation of putrescine and cadaverine in seawater cultures by marine bacteria.
Applied and environmental microbiology 47, 843-849 [PubMed:16346523]
[show Abstract]
Marine bacteria removed two diamines, putrescine and cadaverine, from coastal seawater supplemented only with these compounds. Batch cultures of natural bacterial communities were grown in filtered seawater (0.05 mum) supplemented with 500 mug of putrescine or cadaverine per liter. Increases in bacterial cell number were counted with an epifluorescence microscope after acridine orange staining. Removal of diamines from seawater was monitored by high-performance liquid chromatography. Diamines were removed from the seawater cultures within 48 h with no corresponding increase in bacterial yield, growth rate, or viability relative to control (unsupplemented) cultures. Shipboard experiments with open-ocean deep water (1,500 m) showed similar, if slower, removal of putrescine from seawater. Unlike uptake experiments with amino acids, labeled putrescine experiments indicated that most putrescine carbon is mineralized to CO(2) rather than assimilated by the bacteria. After growth in unsupplemented control cultures, the bacteria showed a significant potential to mineralize putrescine, indicating a general degradation potential for this compound by marine bacteria even if the compound was not present during growth. Indicators of metabolic activity such as glucose and glutamic acid uptake and mineralization were not affected by the presence of putrescine. This shows that at the concentrations added, the diamines are not toxic, and therefore detoxification was not the reason for degradation of the diamines by the bacteria. |
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