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Identification
YMDB IDYMDB00132
NamePutrescine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionPutrescine, also known as 1,4-butanediamine or 1,4-diaminobutane, belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group. Putrescine is a very strong basic compound (based on its pKa). Putrescine exists in all living species, ranging from bacteria to humans. Putrescine is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 1,4-Butanediamine
  • 1,4-Butylenediamine
  • 1,4-Diaminobutane
  • 1,4-Tetramethylenediamine
  • Butylenediamine
  • Putrescin
  • Tetramethyldiamine
  • Tetramethylenediamine
  • Butane-1,4-diamine
  • H2N(CH2)4nh2
  • Putrescina
  • Putreszin
  • Tetramethylendiamin
  • 1,4-Butanediammonium
  • 1,4 Diaminobutane
  • 1,4 Butanediamine
CAS number110-60-1
WeightAverage: 88.1515
Monoisotopic: 88.100048394
InChI KeyKIDHWZJUCRJVML-UHFFFAOYSA-N
InChIInChI=1S/C4H12N2/c5-3-1-2-4-6/h1-6H2
IUPAC Namebutane-1,4-diamine
Traditional IUPAC Nameputrescine
Chemical FormulaC4H12N2
SMILES[H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H]
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
Charge0
Melting point27.5 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogP-0.70 [SANGSTER (1994)]PhysProp
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Glutathione metabolismPW002395 ThumbThumb?image type=greyscaleThumb?image type=simple
beta-Alanine metabolismPW002381 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Arginine and proline metabolismec00330 Map00330
Glutathione metabolismec00480 Map00480
beta-Alanine metabolismec00410 Map00410
SMPDB Reactions
Ornithine + hydronCarbon dioxide + Putrescine
Putrescine + S-Adenosylmethioninaminehydron + 5'-Methylthioadenosine + Spermidine
KEGG Reactions
Ornithine + hydronPutrescine + Carbon dioxide
Putrescine + S-AdenosylmethioninamineSpermidine + hydron + 5'-Methylthioadenosine
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
74 ± 4 µM YEB media with 0.5 mM glucoseaerobicBaker's yeastExperimentally Determined
Not Available
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00di-1910000000-5694141cafbe39951441JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00di-1900000000-eeb4354250406805ebe6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00di-8910000000-af71049ab8358b0042ffJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00di-8900000000-0ba23327cabd9b2815f5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-2900000000-234e1b62f4e830226779JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-00di-1900000000-e29f1004e27fcb9cfe7bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-224d3a5d3fbe7e1c6bd4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-5759f91b24f2e27cc466JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-00di-9000000000-226a78b715ff64ec7067JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1910000000-5694141cafbe39951441JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-eeb4354250406805ebe6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-8910000000-af71049ab8358b0042ffJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-8900000000-0ba23327cabd9b2815f5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-2900000000-234e1b62f4e830226779JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-1900000000-e29f1004e27fcb9cfe7bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-8900000000-0ba23327cabd9b2815f5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-2900000000-234e1b62f4e830226779JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-1900000000-e29f1004e27fcb9cfe7bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-6861f65288867dab7690JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-2900000000-7923303f8f970b8d2dd6JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-4d1729dd236ab6f44cd9JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-9000000000-f718a117761c1c7ea80dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-47752c8c65e2d83e78fbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00du-9000000000-3603b20551e892ad6c5eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-001i-9000000000-224d3a5d3fbe7e1c6bd4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-001i-9000000000-5759f91b24f2e27cc466JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - CI-B (HITACHI M-80) , Positivesplash10-00di-9000000000-226a78b715ff64ec7067JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00dr-9000000000-0b342438cba3ac71bccbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-9000000000-8add450cd915232f7353JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-9000000000-7a496471bdf7e391fdc8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00di-9000000000-84da87b521647b4f42abJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-001l-9000000000-3ca1e2cd5a7e125ac52eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-9000000000-830221d5ea74a91c32e1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dr-9000000000-0b342438cba3ac71bccbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9000000000-8add450cd915232f7353JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9000000000-7a496471bdf7e391fdc8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9000000000-84da87b521647b4f42abJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001l-9000000000-3ca1e2cd5a7e125ac52eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-9000000000-830221d5ea74a91c32e1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-9000000000-896934367d7bc245c8b3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05g0-9000000000-96d51f0aa46b0ab332d0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-de02b50a4b8a279875e4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-73c448854a91ad5a9644JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-c600a93b8d737a254884JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059f-9000000000-ce7ae61a17ef7cb9b2c2JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-2b410aa72c9bb951a79dJSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Pirkov, I., Norbeck, J., Gustafsson, L., Albers, E. (2008). "A complete inventory of all enzymes in the eukaryotic methionine salvage pathway." FEBS J 275:4111-4120.18625006
  • Tomitori, H., Kashiwagi, K., Asakawa, T., Kakinuma, Y., Michael, A. J., Igarashi, K. (2001). "Multiple polyamine transport systems on the vacuolar membrane in yeast." Biochem J 353:681-688.11171066
Synthesis Reference:Dudley, H. W.; Thorpe, W. V. Synthesis of N-methylputrescine and of putrescine. Biochemical Journal (1925), 19 845-9.
External Links:
ResourceLink
CHEBI ID17148
HMDB IDHMDB01414
Pubchem Compound ID1045
Kegg IDC00134
ChemSpider ID13837702
FOODB IDFDB001494
WikipediaPutrescine
BioCyc IDPUTRESCINE

Enzymes

General function:
Amino acid transport and metabolism
Specific function:
Involved in the production of beta-alanine, a precursor of pantothenic acid. Multicopy suppressor of fenpropimorph resistance
Gene Name:
FMS1
Uniprot ID:
P50264
Molecular weight:
57805.10156
Reactions
Spermine + O(2) + H(2)O → spermidine + 3-aminopropanal + H(2)O(2).
Spermidine + O(2) + H(2)O → putrescine + 3-aminopropanal + H(2)O(2).
N(1)-acetylspermine + O(2) + H(2)O → spermidine + 3-acetamidopropanal + H(2)O(2).
N(1)-acetylspermidine + O(2) + H(2)O → putrescine + 3-acetamidopropanal + H(2)O(2).
N(8)-acetylspermidine + O(2) + H(2)O → 4-acetamidobutanal + trimethylenediamine + H(2)O(2).
General function:
Involved in catalytic activity
Specific function:
S-adenosylmethioninamine + putrescine = 5'-S- methyl-5'-thioadenosine + spermidine
Gene Name:
SPE3
Uniprot ID:
Q12074
Molecular weight:
33323.80078
Reactions
S-adenosylmethioninamine + putrescine → 5'-S-methyl-5'-thioadenosine + spermidine.
General function:
Involved in catalytic activity
Specific function:
L-ornithine = putrescine + CO(2)
Gene Name:
SPE1
Uniprot ID:
P08432
Molecular weight:
52284.80078
Reactions
L-ornithine → putrescine + CO(2).

Transporters

General function:
Involved in transmembrane transport
Specific function:
Cell membrane polyamine/proton antiporter, involved in the detoxification of excess polyamines in the cytoplasm. Recognizes spermidine, spermine and the antimalarial drug quinidine, but not quinine, chloroquine and mefloquine
Gene Name:
TPO4
Uniprot ID:
Q12256
Molecular weight:
73222.20313
General function:
Involved in transport
Specific function:
Required for polyamine transport. Transports putrescine effectively and spermidine less effectively
Gene Name:
TPO5
Uniprot ID:
P36029
Molecular weight:
69242.0
General function:
Involved in transmembrane transport
Specific function:
Cell membrane polyamine/proton antiporter, involved in the detoxification of excess polyamines in the cytoplasm. Catalyzes polyamine uptake at alkaline pH and excretion at acidic pH. Recognizes spermidine, spermine and putrescine, the polyamine analogs methylglyoxal bis(guanylhydrazone) (MGBG) and paraquat, the antimalarial drug quinidine, and cycloheximide. Confers resistance to the non-steroidal anti-inflammatory drug indomethacin
Gene Name:
TPO1
Uniprot ID:
Q07824
Molecular weight:
64271.60156