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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-07-15 17:42:18 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-ButanediammoniumHMDB
TetramethyldiamineHMDB
1,4 DiaminobutaneHMDB
1,4 ButanediamineHMDB
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 NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC 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
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-07-15View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, experimental)Ahselim2022-07-15View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentus
Actinidia chinensis
Agaricus bisporus
Agave
Allium ampeloprasum
Allium ascalonicum
Allium cepa
Allium cepa L.
Allium fistulosum
Allium sativum
Allium schoenoprasum
Allium tuberosum
Aloysia triphylla
Amaranthus
Amelanchier alnifolia
Anacardium occidentale
Ananas comosus
Anas platyrhynchos
Anatidae
Anethum graveolens
Angelica keiskei
Anisodus belladonnaKNApSAcK Database
Annona cherimola
Annona muricata
Annona reticulata
Annona squamosa
Anser anser
Anthriscus cerefolium
Apium graveolens
Apium graveolens var. dulce
Apium graveolens var. rapaceum
Apium graveolens var. secalinum
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaea
Arctium lappa
Armoracia rusticana
Artemisia dracunculus
Artemisia vulgaris
Artocarpus altilis
Artocarpus heterophyllus
Asparagus officinalis
Attalea speciosa
Auricularia auricula-judae
Auricularia polytricha
Avena sativa L.FooDB
Averrhoa carambola
Basella alba
Benincasa hispida
Bergera koenegii-
Bertholletia excelsa
Beta vulgaris
Beta vulgaris ssp. cicla
Bison bison
Borago officinalis
Bos taurus
Bos taurus X Bison bison
Brassica alboglabra
Brassica juncea
Brassica napus
Brassica napus var. napus
Brassica oleracea
Brassica oleracea var. botrytis
Brassica oleracea var. capitata
Brassica oleracea var. gemmifera
Brassica oleracea var. gongylodes
Brassica oleracea var. italica
Brassica oleracea var. sabauda
Brassica oleracea var. viridis
Brassica rapaFooDB
Brassica rapa ssp. chinensis
Brassica rapa var. pekinensis
Brassica rapa var. rapa
Brassica ruvo
Brosimum alicastrum
Bubalus bubalis
Byrsonima crassifolia
Cajanus cajan
Canarium ovatum
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibarius
Capparis spinosa
Capra aegagrus hircus
Capsicum annuumKNApSAcK Database
Capsicum annuum L.
Capsicum annuum var. annuum
Capsicum chinense
Capsicum pubescens
Carica papaya L.
Carissa macrocarpa
Carthamus tinctorius
Carum carvi
Carya
Carya illinoinensis
Castanea
Castanea crenata
Castanea mollissima
Castanea sativa
Ceratonia siliqua
Cervidae
Cervus canadensis
Chamaemelum nobile
Chamerion angustifolium
Chenopodium album
Chenopodium quinoa
Chrysanthemum coronarium
Cicer arietinum
Cichorium endiviaFooDB
Cichorium intybus
Cinnamomum
Cinnamomum aromaticum
Cinnamomum verum
Cirsium
Citrullus lanatus
Citrus ×limon (L.) Burm. f. (pro sp.)
Citrus aurantiifolia
Citrus latifolia
Citrus limon
Citrus maxima
Citrus paradisiFooDB
Citrus reticulata
Citrus sinensisKNApSAcK Database
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nucifera
Coffea arabica L.FooDB
Coffea canephora
Colocasia esculenta
Columba
Columbidae
Corchorus olitorius
Coriandrum sativum L.
Corydalis yanhusuoKNApSAcK Database
Corylus
Corylus avellana
Crateva religiosa
Crocus sativus
Cucumis melo
Cucumis metuliferus
Cucumis sativus L.
Cucurbita
Cucurbita maxima
Cucurbita moschata
Cuminum cyminum
Curcuma longa
Cydonia oblonga
Cymbopogon citratus
Cynara cardunculus
Cynara scolymus
Datura metelKNApSAcK Database
Datura stramoniumKNApSAcK Database
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dimocarpus longan
Dioscorea
Dioscorea pentaphylla
Diospyros
Diospyros kaki
Diospyros virginiana
Dromaius novaehollandiae
Durio zibethinus
Dysphania ambrosioides
Elaeis
Eleocharis dulcis
Elettaria cardamomum
Empetrum nigrum
Equus caballus
Eragrostis tef
Eriobotrya japonica
Eruca vesicaria subsp. Sativa
Erythoxylum coca-
Eugenia javanica
Eugenia uniflora
Eutrema japonicum
Fagopyrum esculentum
Fagopyrum tataricum
Fagus
Feijoa sellowiana
Ficus carica
Flammulina velutipes
Foeniculum vulgare
Fragaria x ananassa
Gallus gallus
Garcinia mangostana
Gaylussacia baccata
Ginkgo biloba
Glycine maxKNApSAcK Database
Glycine sojaKNApSAcK Database
Gossypium
Grifola frondosa
Hedysarum alpinum
Helianthus annuus L.
Helianthus tuberosus
Hibiscus sabbariffa
Hippophae rhamnoides
Hordeum vulgareKNApSAcK Database
Hyssopus officinalis L.
Illicium verum
Ipomoea aquatica
Ipomoea batatas
Juglans
Juglans ailanthifolia
Juglans cinerea
Juglans nigra L.
Juglans regia
Lablab purpureus
Lactuca sativaFooDB
Lagenaria siceraria
Lagopus muta
Lathyrus sativus
Laurus nobilis L.
Lens culinarisFooDB
Lentinus edodes
Lepidium sativum
Leporidae
Lepus timidus
Levisticum officinale
Linum usitatissimum
Litchi chinensis
Luffa aegyptiaca
Lupinus
Lupinus albus
Lyallia kerguelensisKNApSAcK Database
Macadamia
Macadamia tetraphylla
Malpighia emarginata
Malus
Malus pumilaFooDB
Mammea americana
Mangifera indica
Manihot esculenta
Manilkara zapota
Maranta arundinacea
Matricaria recutita
Matteuccia struthiopteris
Medicago sativa
Melanitta fusca
Meleagris gallopavo
Melissa officinalis L.
Mentha
Mentha aquatica
Mentha arvensis
Mentha spicata
Mentha x piperita
Mespilus germanica
Metroxylon sagu
Momordica charantia
Morchellaceae
Morella rubra
Moringa oleifera
Morus
Morus nigra
Murraya paniculataKNApSAcK Database
Musa acuminata
Musa x paradisiaca
Myrica
Myristica fragrans
Nelumbo
Nelumbo nucifera
Nephelium lappaceum
Nicotiana tabacumKNApSAcK Database
Numida meleagris
Nuphar lutea
Ocimum basilicum
Odocoileus
Oenothera biennis
Olea europaea
Opuntia
Opuntia cochenillifera
Opuntia macrorhiza
Origanum majorana
Origanum onites
Origanum vulgare
Origanum X majoricum
Oryctolagus
Oryza rufipogon
Oryza sativa
Ovis aries
Pachyrhizus erosus
Panax ginsengKNApSAcK Database
Pangium edule
Panicum miliaceum
Passiflora edulis
Pastinaca sativa
Pediomelum esculentum
Perideridia oregana
Persea americana
Petasites japonicus
Petroselinum crispum
Phaseolus coccineus
Phaseolus lunatus
Phaseolus vulgaris
Phasianidae
Phasianus colchicus
Phoenix dactylifera
Photinia melanocarpa
Phyllostachys edulis
Physalis
Physalis philadelphica var. immaculata
Phytolacca americana
Pimenta dioica
Pimpinella anisum
Pinus
Pinus edulis
Piper nigrum L.
Pistacia vera
Pisum sativumFooDB
Pleurotus ostreatus
Polygonum alpinum
Portulaca oleracea
Pouteria sapota
Prunus armeniaca
Prunus aviumKNApSAcK Database
Prunus avium L.
Prunus cerasus
Prunus domestica
Prunus dulcis
Prunus persica
Prunus persica var. nucipersica
Prunus persica var. persica
Prunus tomentosa
Prunus virginiana
Psidium cattleianum
Psidium guajava
Psophocarpus tetragonolobus
Punica granatum
Pyrus communis
Pyrus pyrifolia
Quercus
Raphanus sativusFooDB
Raphanus sativus var. longipinnatus
Raphanus sativus var. sativus
Rheum rhabarbarum
Ribes aureum
Ribes glandulosum
Ribes nigrum
Ribes rubrum
Ribes uva-crispa
Rosa
Rubus arcticus
Rubus chamaemorus
Rubus idaeus
Rubus occidentalis
Rubus spectabilis
Rumex
Rumex acetosa
Rumex articus
Sagittaria latifolia
Salix pulchra
Salvia elegans
Salvia hispanica
Salvia officinalis
Salvia rosmarinus
Sambucus nigra
Sambucus nigra L.
Santalum albumKNApSAcK Database
Satureja hortensis L.
Satureja montana
Scorzonera hispanica
Secale cereale
Sechium edule
Sesamum indicumFooDB
Sesbania bispinosa
Sinapis alba
Sisymbrium
Solanum lycopersicumFooDB
Solanum lycopersicum L.KNApSAcK Database
Solanum lycopersicum var. cerasiforme
Solanum lycopersicum var. lycopersicum
Solanum melongena
Solanum quitoense
Solanum tuberosum
Sorbus aucuparia
Sorghum bicolor
Spinacia oleracea
Struthio camelus
Sus scrofa
Sus scrofa domestica
Syzygium aromaticum
Syzygium cumini
Syzygium jambos
Tamarindus indica
Taraxacum officinale
Tetragonia tetragonioides
Thelesperma
Thymus pulegioides
Thymus vulgaris
Tilia cordata
Tilia L.
Tragopogon porrifolius
Trigonella foenum-graecum
Triticum
Triticum aestivumKNApSAcK Database
Triticum durum
Triticum spelta
Triticum turanicum
Typha angustifolia
Vaccinium
Vaccinium angustifolium
Vaccinium angustifolium X Vaccinium corymbosum
Vaccinium arboreum
Vaccinium corymbosum
Vaccinium deliciosum
Vaccinium elliottii
Vaccinium macrocarpon
Vaccinium myrtilloides
Vaccinium myrtillus
Vaccinium ovalifolium
Vaccinium ovatum
Vaccinium oxycoccos
Vaccinium parvifolium
Vaccinium reticulatum
Vaccinium stamineum
Vaccinium uliginosum
Vaccinium vitis-idaea
Valerianella locusta
Vanilla
Verbena officinalis
Viburnum edule
Vicia faba
Vigna aconitifolia
Vigna angularis
Vigna mungo
Vigna radiataFooDB
Vigna umbellata
Vigna unguiculata
Vigna unguiculata ssp. cylindrica
Vigna unguiculata ssp. unguiculata
Vigna unguiculata var. sesquipedalis
Vitis
Vitis aestivalis
Vitis labrusca
Vitis rotundifolia
Vitis vinifera L.
Xanthosoma sagittifolium
Zea mays L.FooDB
Zingiber officinale
Zizania
Zizania aquatica
Ziziphus zizyphus
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 Parents
Substituents
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.
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
HMDB IDHMDB0001414
DrugBank IDDB01917
Phenol Explorer Compound IDNot Available
FoodDB IDFDB006243
KNApSAcK IDC00001428
Chemspider ID13837702
KEGG Compound IDC02896
BioCyc IDPUTRESCINE
BiGG ID33980
Wikipedia LinkPutrescine
METLIN ID3226
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 ]
  16. Maiocchi S, Ku J, Hawtrey T, De Silvestro I, Malle E, Rees M, Thomas SR, Morris JC: Polyamine-Conjugated Nitroxides Are Efficacious Inhibitors of Oxidative Reactions Catalyzed by Endothelial-Localized Myeloperoxidase. Chem Res Toxicol. 2021 Jun 21;34(6):1681-1692. doi: 10.1021/acs.chemrestox.1c00094. Epub 2021 Jun 4. [PubMed:34085520 ]