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Human Metabolome Database Version 3.5

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Showing metabocard for Putrescine (HMDB01414)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:31:30 -0600
HMDB ID HMDB01414
Secondary Accession Numbers None
Metabolite Identification
Common 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, 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. (PMID: 15009201 Link_out, 16364196 Link_out). 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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1,4-Butanediamine
  2. 1,4-Butylenediamine
  3. 1,4-Diaminobutane
  4. 1,4-Tetramethylenediamine
  5. Butylenediamine
  6. Putrescin
  7. Tetramethyldiamine
  8. Tetramethylenediamine
Chemical Formula C4H12N2
Average Molecular Weight 88.1515
Monoisotopic Molecular Weight 88.100048394
IUPAC Name butane-1,4-diamine
Traditional IUPAC Name putrescine
CAS Registry Number 110-60-1
SMILES NCCCCN
InChI Identifier InChI=1S/C4H12N2/c5-3-1-2-4-6/h1-6H2
InChI Key KIDHWZJUCRJVML-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Acyclic Compounds
Class Alkylamines
Sub Class Polyamines
Other Descriptors
  • Alkylamines
  • Biogenic amines(KEGG)
  • alkane-alpha,omega-diamine(ChEBI)
Substituents
  • N/A
Direct Parent Polyamines
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Microbial
Biofunction
  • Component of Arginine and proline metabolism
  • Component of Glycine, serine and threonine metabolism
  • Component of Histidine metabolism
  • Component of Methane metabolism
  • Component of Phenylalanine metabolism
  • Component of Tryptophan metabolism
  • Component of Tyrosine metabolism
  • Component of beta-Alanine metabolism
  • RNA component
Application Not Available
Cellular locations
  • Mitochondria
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 27.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP -0.70 SANGSTER (1994)
Predicted Properties
Property Value Source
LogP -0.98 ALOGPS
LogP -0.85 ChemAxon
LogS 0.43 ALOGPS
pKa (strongest basic) 10.51 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 52.04 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 27.38 ChemAxon
Polarizability 11.07 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 2 ChemAxon
Spectra
Gas-MS Spectrum
13C NMR Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI RMU-6L)
MS/MS Spectrum EI-B (HITACHI RMU-6M)
MS/MS Spectrum CI-B (HITACHI M-80)
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Muscle
  • Fibroblasts
  • Neuron
  • Placenta
  • Testes
  • Erythrocyte
  • Liver
  • Brain
  • Prostate
  • Skin
  • Platelet
Pathways
Name SMPDB Link KEGG Link
Methionine Metabolism SMP00033 map00270 Link_out
Spermidine and Spermine Biosynthesis SMP00445 Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.214 +/- 0.08 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
0.23 +/- 0.05 uM Adult (>18 years old) Both Normal
Saliva Detected and Quantified
0.06 uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.35 (0.08-1.06) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.032 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.20 (0.04-0.40) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
  • Bouatra, S. ...
Urine Detected and Quantified
0.076 +/- 0.011 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
1.8 +/- 0.46 umol/mmol creatinine Adult (>18 years old) Both Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Urine Detected but not Quantified Not Applicable Adult (>18 years old) Both Leukemia
Urine Detected and Quantified 0.46 +/- 0.067 umol/mmol creatinine Adult (>18 years old) Both Pancreatic cancer
Associated Disorders and Diseases
Disease References
Pancreatic cancer
  • Loser C, Folsch UR, Paprotny C, Creutzfeldt W: Polyamine concentrations in pancreatic tissue, serum, and urine of patients with pancreatic cancer. Pancreas. 1990 Mar;5(2):119-27. Pubmed: 2315288 Link_out
    Associated OMIM IDs
    DrugBank ID DB01917 Link_out
    DrugBank Metabolite ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB001494
    KNApSAcK ID C00001428 Link_out
    Chemspider ID 13837702 Link_out
    KEGG Compound ID C00134 Link_out
    BioCyc ID PUTRESCINE Link_out
    BiGG ID 33980 Link_out
    Wikipedia Link Putrescine Link_out
    NuGOwiki Link HMDB01414 Link_out
    Metagene Link HMDB01414 Link_out
    METLIN ID 3226 Link_out
    PubChem Compound 1045 Link_out
    PDB ID PUT Link_out
    ChEBI ID 17148 Link_out
    References
    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
    General References
    1. Reeben M, Arbatova J, Palgi J, Miettinen R, Halmekyto M, Alhonen L, Janne J, Riekkinen P Sr, Saarma M: Induced expression of neurotrophins in transgenic mice overexpressing ornithine decarboxylase and overproducing putrescine. J Neurosci Res. 1996 Sep 1;45(5):542-8. Pubmed: 8875319 Link_out
    2. Takagi K, Tatsumi Y, Kitaichi K, Iwase M, Shibata E, Nakao M, Matsumoto T, Takagi K, Hasegawa T: A sensitive colorimetric assay for polyamines in erythrocytes using oat seedling polyamine oxidase. Clin Chim Acta. 2004 Feb;340(1-2):219-27. Pubmed: 14734216 Link_out
    3. Harik SI, Sutton CH: Putrescine as a biochemical marker of malignant brain tumors. Cancer Res. 1979 Dec;39(12):5010-5. Pubmed: 227593 Link_out
    4. Gimelli G, Giglio S, Zuffardi O, Alhonen L, Suppola S, Cusano R, Lo Nigro C, Gatti R, Ravazzolo R, Seri M: Gene dosage of the spermidine/spermine N(1)-acetyltransferase ( SSAT) gene with putrescine accumulation in a patient with a Xp21.1p22.12 duplication and keratosis follicularis spinulosa decalvans (KFSD). Hum Genet. 2002 Sep;111(3):235-41. Epub 2002 Aug 1. Pubmed: 12215835 Link_out
    5. Venza M, Visalli M, Cicciu D, Teti D: Determination of polyamines in human saliva by high-performance liquid chromatography with fluorescence detection. J Chromatogr B Biomed Sci Appl. 2001 Jun 5;757(1):111-7. Pubmed: 11419735 Link_out
    6. Halmekyto M, Alhonen L, Alakuijala L, Janne J: Transgenic mice over-producing putrescine in their tissues do not convert the diamine into higher polyamines. Biochem J. 1993 Apr 15;291 ( Pt 2):505-8. Pubmed: 8484731 Link_out
    7. Goldman SS, Volkow ND, Brodie J, Flamm ES: Putrescine metabolism in human brain tumors. J Neurooncol. 1986;4(1):23-9. Pubmed: 3746382 Link_out
    8. El Baze P, Milano G, Verrando P, Renee N, Ortonne JP: Polyamine levels in normal human skin. A comparative study of pure epidermis, pure dermis, and suction blister fluid. Arch Dermatol Res. 1983;275(4):218-21. Pubmed: 6625645 Link_out
    9. Yamazaki H, Tsukahara T, Uki J, Matsuzaki S: Elevated levels of free putrescine and N1-acetylspermidine in cyst fluids of malignant brain tumours. J Neurol Neurosurg Psychiatry. 1986 Feb;49(2):209-10. Pubmed: 3950641 Link_out
    10. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411 Link_out
    11. Janne J, Alhonen L, Pietila M, Keinanen TA: Genetic approaches to the cellular functions of polyamines in mammals. Eur J Biochem. 2004 Mar;271(5):877-94. Pubmed: 15009201 Link_out
    12. Janne J, Alhonen L, Keinanen TA, Pietila M, Uimari A, Pirinen E, Hyvonen MT, Jarvinen A: Animal disease models generated by genetic engineering of polyamine metabolism. J Cell Mol Med. 2005 Oct-Dec;9(4):865-82. Pubmed: 16364196 Link_out
    Enzymes
    Name: Diamine acetyltransferase 2
    Reactions:
    Acetyl-CoA + Putrescine unknown Coenzyme A + N-Acetylputrescine details
    Gene Name: SAT2
    Uniprot ID: Q96F10 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Diamine acetyltransferase 1
    Reactions:
    Acetyl-CoA + Putrescine unknown Coenzyme A + N-Acetylputrescine details
    Gene Name: SAT1
    Uniprot ID: P21673 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Peroxisomal N(1)-acetyl-spermine/spermidine oxidase
    Reactions:
    N1-Acetylspermidine + Oxygen + Water unknown Putrescine + Acetamidopropanal + Hydrogen peroxide details
    Gene Name: PAOX
    Uniprot ID: Q6QHF9 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Choline dehydrogenase, mitochondrial
    Reactions: Not Available
    Gene Name: CHDH
    Uniprot ID: Q8NE62 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Dimethylglycine dehydrogenase, mitochondrial
    Reactions: Not Available
    Gene Name: DMGDH
    Uniprot ID: Q9UI17 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Spermine synthase
    Reactions: Not Available
    Gene Name: SMS
    Uniprot ID: P52788 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Spermidine synthase
    Reactions:
    S-Adenosylmethioninamine + Putrescine unknown 5'-Methylthioadenosine + Spermidine details
    Gene Name: SRM
    Uniprot ID: P19623 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: 4-trimethylaminobutyraldehyde dehydrogenase
    Reactions: Not Available
    Gene Name: ALDH9A1
    Uniprot ID: P49189 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Gamma-butyrobetaine dioxygenase
    Reactions: Not Available
    Gene Name: BBOX1
    Uniprot ID: O75936 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Amiloride-sensitive amine oxidase [copper-containing]
    Reactions:
    Putrescine + Oxygen + Water unknown 4-Aminobutyraldehyde + Ammonia + Hydrogen peroxide details
    Gene Name: ABP1
    Uniprot ID: P19801 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: S-methyl-5'-thioadenosine phosphorylase
    Reactions: Not Available
    Gene Name: MTAP
    Uniprot ID: Q13126 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: S-adenosylmethionine decarboxylase proenzyme
    Reactions: Not Available
    Gene Name: AMD1
    Uniprot ID: P17707 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Glycine amidinotransferase, mitochondrial
    Reactions: Not Available
    Gene Name: GATM
    Uniprot ID: P50440 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Betaine--homocysteine S-methyltransferase 1
    Reactions: Not Available
    Gene Name: BHMT
    Uniprot ID: Q93088 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Sarcosine dehydrogenase, mitochondrial
    Reactions: Not Available
    Gene Name: SARDH
    Uniprot ID: Q9UL12 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Histidine decarboxylase
    Reactions: Not Available
    Gene Name: HDC
    Uniprot ID: P19113 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Ornithine decarboxylase
    Reactions:
    Ornithine unknown Putrescine + CO(2) details
    Ornithine unknown Putrescine + Carbon dioxide details
    Gene Name: ODC1
    Uniprot ID: P11926 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Spermine oxidase
    Reactions: Not Available
    Gene Name: SMOX
    Uniprot ID: Q9NWM0 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Agmatinase, mitochondrial
    Reactions:
    Agmatine + Water unknown Putrescine + Urea details
    Gene Name: AGMAT
    Uniprot ID: Q9BSE5 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Trimethyllysine dioxygenase, mitochondrial
    Reactions: Not Available
    Gene Name: TMLHE
    Uniprot ID: Q9NVH6 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: S-methylmethionine--homocysteine S-methyltransferase BHMT2
    Reactions: Not Available
    Gene Name: BHMT2
    Uniprot ID: Q9H2M3 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Pyruvate dehydrogenase phosphatase regulatory subunit, mitochondrial
    Reactions: Not Available
    Gene Name: PDPR
    Uniprot ID: Q8NCN5 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Ornithine decarboxylase antizyme 1
    Reactions: Not Available
    Gene Name: OAZ1
    Uniprot ID: P54368 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Polyamine-modulated factor 1
    Reactions: Not Available
    Gene Name: PMF1
    Uniprot ID: Q6P1K2 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Transporters
    Name: Solute carrier family 22 member 4
    Reactions: Not Available
    Gene Name: SLC22A4
    Uniprot ID: Q9H015 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA