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Putrescine (M2MDB000378)
| Record Information | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Version | 2.0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 13:52:10 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-06-03 15:54:06 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| Identification | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | Putrescine | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | 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. 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. (Wikipedia) | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
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| Chemical Formula: | C4H12N2 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight: | Average: 88.1515 Monoisotopic: 88.100048394 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key: | KIDHWZJUCRJVML-UHFFFAOYSA-N | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI: | InChI=1S/C4H12N2/c5-3-1-2-4-6/h1-6H2 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS number: | 110-60-1 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name: | butane-1,4-diamine | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name: | putrescine | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES: | NCCCCN | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Organic nitrogen compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Organonitrogen compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Amines | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | Monoalkylamines | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Alternative Parents | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Substituents |
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| Molecular Framework | Aliphatic acyclic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors |
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| Physical Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State: | Solid | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Charge: | 2 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point: | 27.5 °C | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
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| Predicted Properties |
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| Biological Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations: | Cytoplasm | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Reactions: | Adenosine triphosphate + Water + Putrescine > ADP + Hydrogen ion + Phosphate + Putrescine Adenosine triphosphate + Water + Putrescine > ADP + Hydrogen ion + Phosphate + Putrescine Hydrogen ion + Ornithine + L-Ornithine <> Carbon dioxide + Putrescine + Ethylenediamine S-Adenosylmethioninamine + Putrescine + Ethylenediamine <> 5'-Methylthioadenosine + Hydrogen ion + Spermidine Adenosine triphosphate + L-Glutamate + Putrescine + Ethylenediamine <> ADP + gamma-Glutamyl-L-putrescine + Hydrogen ion + Phosphate Agmatine + Water <> Putrescine + Urea + Ethylenediamine alpha-Ketoglutarate + Putrescine > 4-Aminobutyraldehyde + L-Glutamate Ornithine <> Putrescine + Carbon dioxide Acetyl-CoA + Putrescine <> Coenzyme A + N-Acetylputrescine Putrescine + alpha-Ketoglutarate <> 4-Aminobutyraldehyde + L-Glutamate Agmatine + Water <> Putrescine + Urea S-Adenosylmethioninamine + Putrescine <> 5'-Methylthioadenosine + Spermidine Adenosine triphosphate + L-Glutamate + Putrescine <> ADP + Phosphate + gamma-Glutamyl-L-putrescine Adenosine triphosphate + Putrescine + Water > ADP + Phosphate + Putrescine + Hydrogen ion Adenosine triphosphate + Putrescine + Water > ADP + Phosphate + Putrescine + Hydrogen ion Water + Agmatine > Urea + Putrescine Hydrogen ion + Ornithine > Carbon dioxide + Putrescine Putrescine + Oxoglutaric acid <> 4-Aminobutyraldehyde + L-Glutamate Putrescine + L-Glutamate + Adenosine triphosphate > Hydrogen ion + gamma-Glutamyl-L-putrescine + ADP + Phosphate Putrescine + S-Adenosylmethioninamine > Hydrogen ion + Spermidine + 5'-Methylthioadenosine Ornithine > Putrescine + Carbon dioxide Putrescine + Oxoglutaric acid > L-Glutamate + 1-Pyrroline + Water Adenosine triphosphate + L-Glutamate + Putrescine > ADP + Inorganic phosphate + gamma-Glutamyl-L-putrescine S-Adenosylmethioninamine + Putrescine > 5'-Methylthioadenosine + Spermidine Putrescine + Adenosine triphosphate + L-Glutamic acid + L-Glutamate > Phosphate + Adenosine diphosphate + Hydrogen ion + gamma-Glutamyl-L-putrescine + ADP Putrescine + Oxoglutaric acid > L-Glutamic acid + 4-Aminobutyraldehyde + L-Glutamate More...Ornithine + Hydrogen ion + Ornithine > Putrescine + Carbon dioxide Putrescine + S-Adenosylmethioninamine > Spermidine + Hydrogen ion + 5'-S-methyl-5'-thioadenosine Putrescine + Oxoglutaric acid <> L-Glutamic acid + 1-Pyrroline + Water + L-Glutamate Decarboxy-SAM + Putrescine > 5'-Methylthioadenosine + Spermidine + Hydrogen ion S-Adenosylmethioninamine + Putrescine + Ethylenediamine <>5 5'-Methylthioadenosine + Hydrogen ion + Spermidine Hydrogen ion + Ornithine + L-Ornithine <> Carbon dioxide + Putrescine + Ethylenediamine Ornithine <> Putrescine + Carbon dioxide S-Adenosylmethioninamine + Putrescine + Ethylenediamine <>5 5'-Methylthioadenosine + Hydrogen ion + Spermidine | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMPDB Pathways: |
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| KEGG Pathways: | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| EcoCyc Pathways: |
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| Concentrations | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Find out more about how we convert literature concentrations. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Spectra: | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References: |
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| Synthesis Reference: | Dudley, H. W.; Thorpe, W. V. Synthesis of N-methylputrescine and of putrescine. Biochemical Journal (1925), 19 845-9. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Enzymes
- General function:
- Involved in catalytic activity
- Specific function:
- Catalyzes the production of spermidine from putrescine and decarboxylated S-adenosylmethionine (dcSAM), which serves as an aminopropyl donor
- Gene Name:
- speE
- Uniprot ID:
- P09158
- Molecular weight:
- 32321
Reactions
| S-adenosylmethioninamine + putrescine = 5'-S-methyl-5'-thioadenosine + spermidine. |
- General function:
- Involved in N-acetyltransferase activity
- Specific function:
- Regulates polyamine concentration by their degradation. Acts on spermidine, forming N(1)- and N(8)-acetylspermidine
- Gene Name:
- speG
- Uniprot ID:
- P0A951
- Molecular weight:
- 21887
Reactions
| Acetyl-CoA + an alkane-alpha,omega-diamine = CoA + an N-acetyldiamine. |
- General function:
- Involved in carboxy-lyase activity
- Specific function:
- L-ornithine = putrescine + CO(2)
- Gene Name:
- speC
- Uniprot ID:
- P21169
- Molecular weight:
- 79416
Reactions
| L-ornithine = putrescine + CO(2). |
- General function:
- Involved in carboxy-lyase activity
- Specific function:
- L-ornithine = putrescine + CO(2)
- Gene Name:
- speF
- Uniprot ID:
- P24169
- Molecular weight:
- 82415
Reactions
| L-ornithine = putrescine + CO(2). |
- General function:
- Involved in transaminase activity
- Specific function:
- Catalyzes the aminotransferase reaction from putrescine to 2-oxoglutarate, leading to glutamate and 4-aminobutanal, which spontaneously cyclizes to form 1-pyrroline. Is also able to transaminate cadaverine and, in lower extent, spermidine, but not ornithine. Alpha-ketobutyrate and pyruvate can also act as amino acceptors, although much less efficiently
- Gene Name:
- patA
- Uniprot ID:
- P42588
- Molecular weight:
- 49661
Reactions
| Putrescine + 2-oxoglutarate = L-glutamate + 1-pyrroline + H(2)O. |
- General function:
- Involved in agmatinase activity
- Specific function:
- Catalyzes the formation of putrescine from agmatine
- Gene Name:
- speB
- Uniprot ID:
- P60651
- Molecular weight:
- 33557
Reactions
| Agmatine + H(2)O = putrescine + urea. |
- General function:
- Involved in nucleotide binding
- Specific function:
- Part of the ABC transporter complex PotABCD involved in spermidine/putrescine import. Responsible for energy coupling to the transport system
- Gene Name:
- potA
- Uniprot ID:
- P69874
- Molecular weight:
- 43028
Reactions
| ATP + H(2)O + polyamine(Out) = ADP + phosphate + polyamine(In). |
- General function:
- Involved in glutamate-ammonia ligase activity
- Specific function:
- Involved in the breakdown of putrescine via the biosynthesis of gamma-L-glutamylputrescine
- Gene Name:
- puuA
- Uniprot ID:
- P78061
- Molecular weight:
- 53177
Reactions
| ATP + L-glutamate + putrescine = ADP + phosphate + gamma-L-glutamylputrescine. |
- General function:
- Involved in transporter activity
- Specific function:
- Probably part of the binding-protein-dependent transport system ydcSTUV
- Gene Name:
- ydcS
- Uniprot ID:
- P76108
- Molecular weight:
- 42295
- General function:
- Involved in nucleotide binding
- Specific function:
- Probably part of a binding-protein-dependent transport system ydcSTUV. Probably responsible for energy coupling to the transport system
- Gene Name:
- ydcT
- Uniprot ID:
- P77795
- Molecular weight:
- 37040
- General function:
- Involved in transporter activity
- Specific function:
- Probably part of the binding-protein-dependent transport system ydcSTUV; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- ydcU
- Uniprot ID:
- P77156
- Molecular weight:
- 34360
- General function:
- Involved in transporter activity
- Specific function:
- Probably part of the binding-protein-dependent transport system ydcSTUV; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- ydcV
- Uniprot ID:
- P0AFR9
- Molecular weight:
- 28722
- General function:
- Involved in transporter activity
- Specific function:
- Required for the activity of the bacterial periplasmic transport system of putrescine and spermidine
- Gene Name:
- potB
- Uniprot ID:
- P0AFK4
- Molecular weight:
- 31062
- General function:
- Involved in transporter activity
- Specific function:
- Required for the activity of the bacterial periplasmic transport system of putrescine and spermidine
- Gene Name:
- potC
- Uniprot ID:
- P0AFK6
- Molecular weight:
- 29111
- General function:
- Involved in transporter activity
- Specific function:
- Required for the activity of the bacterial periplasmic transport system of putrescine
- Gene Name:
- potI
- Uniprot ID:
- P0AFL1
- Molecular weight:
- 30540
- General function:
- Involved in transporter activity
- Specific function:
- Required for the activity of the bacterial periplasmic transport system of putrescine
- Gene Name:
- potH
- Uniprot ID:
- P31135
- Molecular weight:
- 35489
- General function:
- Amino acid transport and metabolism
- Specific function:
- Part of the binding-protein-dependent transport system for putrescine. Probably responsible for energy coupling to the transport system
- Gene Name:
- potG
- Uniprot ID:
- P31134
- Molecular weight:
- 41930
- General function:
- Involved in transporter activity
- Specific function:
- Required for the activity of the bacterial periplasmic transport system of putrescine. Polyamine binding protein
- Gene Name:
- potF
- Uniprot ID:
- P31133
- Molecular weight:
- 40839
- General function:
- Involved in transporter activity
- Specific function:
- Required for the activity of the bacterial periplasmic transport system of putrescine and spermidine. Polyamine binding protein
- Gene Name:
- potD
- Uniprot ID:
- P0AFK9
- Molecular weight:
- 38867
Transporters
- General function:
- Involved in nucleotide binding
- Specific function:
- Part of the ABC transporter complex PotABCD involved in spermidine/putrescine import. Responsible for energy coupling to the transport system
- Gene Name:
- potA
- Uniprot ID:
- P69874
- Molecular weight:
- 43028
Reactions
| ATP + H(2)O + polyamine(Out) = ADP + phosphate + polyamine(In). |
- General function:
- Involved in transporter activity
- Specific function:
- Probably part of the binding-protein-dependent transport system ydcSTUV
- Gene Name:
- ydcS
- Uniprot ID:
- P76108
- Molecular weight:
- 42295
- General function:
- Involved in nucleotide binding
- Specific function:
- Probably part of a binding-protein-dependent transport system ydcSTUV. Probably responsible for energy coupling to the transport system
- Gene Name:
- ydcT
- Uniprot ID:
- P77795
- Molecular weight:
- 37040
- General function:
- Involved in transporter activity
- Specific function:
- Probably part of the binding-protein-dependent transport system ydcSTUV; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- ydcU
- Uniprot ID:
- P77156
- Molecular weight:
- 34360
- General function:
- Involved in transporter activity
- Specific function:
- Probably part of the binding-protein-dependent transport system ydcSTUV; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- ydcV
- Uniprot ID:
- P0AFR9
- Molecular weight:
- 28722
- General function:
- Involved in transporter activity
- Specific function:
- Required for the activity of the bacterial periplasmic transport system of putrescine and spermidine
- Gene Name:
- potB
- Uniprot ID:
- P0AFK4
- Molecular weight:
- 31062
- General function:
- Involved in transporter activity
- Specific function:
- Required for the activity of the bacterial periplasmic transport system of putrescine and spermidine
- Gene Name:
- potC
- Uniprot ID:
- P0AFK6
- Molecular weight:
- 29111
- General function:
- Involved in transporter activity
- Specific function:
- Required for the activity of the bacterial periplasmic transport system of putrescine
- Gene Name:
- potI
- Uniprot ID:
- P0AFL1
- Molecular weight:
- 30540
- General function:
- Involved in transporter activity
- Specific function:
- Required for the activity of the bacterial periplasmic transport system of putrescine
- Gene Name:
- potH
- Uniprot ID:
- P31135
- Molecular weight:
- 35489
- General function:
- Involved in transport
- Specific function:
- Imports putrescine
- Gene Name:
- puuP
- Uniprot ID:
- P76037
- Molecular weight:
- 50853
- General function:
- Involved in transporter activity
- Specific function:
- Non-specific porin
- Gene Name:
- ompN
- Uniprot ID:
- P77747
- Molecular weight:
- 41220
- General function:
- Involved in transporter activity
- Specific function:
- Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
- Gene Name:
- phoE
- Uniprot ID:
- P02932
- Molecular weight:
- 38922
- General function:
- Involved in transporter activity
- Specific function:
- OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
- Gene Name:
- ompF
- Uniprot ID:
- P02931
- Molecular weight:
- 39333
- General function:
- Involved in amino acid transmembrane transporter activity
- Specific function:
- Probable putrescine-ornithine antiporter
- Gene Name:
- potE
- Uniprot ID:
- P0AAF1
- Molecular weight:
- 46495
- General function:
- Amino acid transport and metabolism
- Specific function:
- Part of the binding-protein-dependent transport system for putrescine. Probably responsible for energy coupling to the transport system
- Gene Name:
- potG
- Uniprot ID:
- P31134
- Molecular weight:
- 41930
- General function:
- Involved in transporter activity
- Specific function:
- Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
- Gene Name:
- ompC
- Uniprot ID:
- P06996
- Molecular weight:
- 40368
- General function:
- Involved in transporter activity
- Specific function:
- Required for the activity of the bacterial periplasmic transport system of putrescine. Polyamine binding protein
- Gene Name:
- potF
- Uniprot ID:
- P31133
- Molecular weight:
- 40839
- General function:
- Involved in transporter activity
- Specific function:
- Required for the activity of the bacterial periplasmic transport system of putrescine and spermidine. Polyamine binding protein
- Gene Name:
- potD
- Uniprot ID:
- P0AFK9
- Molecular weight:
- 38867