Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:28 UTC
NP-MRD IDNP0000792
Secondary Accession NumbersNone
Natural Product Identification
Common NamePutrescine
DescriptionPutrescine 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 has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ). It 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 , 16364196 ). 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. Putrescine can be found in Citrobacter, Corynebacterium, Cronobacter and Enterobacter (PMID: 27872963 ) (Https://Onlinelibrary.Wiley.Com/doi/full/10.1111/1541-4337.12099).
Structure
Thumb
Synonyms
ValueSource
1,4-ButanediamineChEBI
1,4-ButylenediamineChEBI
1,4-DIAMINOBUTANEChEBI
1,4-TetramethylenediamineChEBI
Butane-1,4-diamineChEBI
ButylenediamineChEBI
H2N(CH2)4nh2ChEBI
PutrescinChEBI
PutrescinaChEBI
PutreszinChEBI
TetramethylendiaminChEBI
TetramethylenediamineChEBI
1,4 ButanediamineMeSH
1,4 DiaminobutaneMeSH
1,4-ButanediammoniumHMDB
TetramethyldiamineHMDB
Chemical FormulaC4H12N2
Average Mass88.1515 Da
Monoisotopic Mass88.10005 Da
IUPAC Namebutane-1,4-diamine
Traditional Nameputrescine
CAS Registry Number110-60-1
SMILES
NCCCCN
InChI Identifier
InChI=1S/C4H12N2/c5-3-1-2-4-6/h1-6H2
InChI KeyKIDHWZJUCRJVML-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 1H] 2D NMR Spectrum (experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)Varshavi.d262021-08-02View Spectrum
Species
Species of Origin
Species NameSourceReference
Anisodus belladonnaKNApSAcK Database
Arabidopsis thalianaKNApSAcK Database
Capsicum annuumKNApSAcK Database
Citrus sinensisKNApSAcK Database
Corydalis yanhusuoKNApSAcK Database
Datura metelKNApSAcK Database
Datura stramoniumKNApSAcK Database
Glycine maxKNApSAcK Database
Glycine sojaKNApSAcK Database
Hordeum vulgareKNApSAcK Database
Lyallia kerguelensisKNApSAcK Database
Murraya paniculataKNApSAcK Database
Nicotiana tabacumKNApSAcK Database
Panax ginsengKNApSAcK Database
Prunus aviumKNApSAcK Database
Santalum albumKNApSAcK Database
Solanum lycopersicum L.KNApSAcK Database
Triticum aestivumKNApSAcK Database
Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
Homo sapiens (Urine)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentMonoalkylamines
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point27.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.70SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility236 g/LALOGPS
logP-0.98ALOGPS
logP-0.85ChemAxon
logS0.43ALOGPS
pKa (Strongest Basic)10.51ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.04 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.38 m³·mol⁻¹ChemAxon
Polarizability11.07 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
External Links
HMDB IDHMDB0060243
DrugBank IDDB01917
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001494
KNApSAcK IDC00001428
Chemspider ID13837702
KEGG Compound IDC02896
BioCyc IDPUTRESCINE
BiGG IDNot Available
Wikipedia LinkPutrescine
METLIN IDNot Available
PubChem Compound1045
PDB IDNot Available
ChEBI ID17148
Good Scents IDrw1148651
References
General References
  1. 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 ]
  2. 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 ]
  3. 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. doi: 10.1038/nature07762. [PubMed:19212411 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. Harik SI, Sutton CH: Putrescine as a biochemical marker of malignant brain tumors. Cancer Res. 1979 Dec;39(12):5010-5. [PubMed:227593 ]
  9. 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 ]
  10. Goldman SS, Volkow ND, Brodie J, Flamm ES: Putrescine metabolism in human brain tumors. J Neurooncol. 1986;4(1):23-9. [PubMed:3746382 ]
  11. 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 ]
  12. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
  13. 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 ]
  14. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
  15. Wendisch VF: Microbial Production of Amino Acid-Related Compounds. Adv Biochem Eng Biotechnol. 2017;159:255-269. doi: 10.1007/10_2016_34. [PubMed:27872963 ]