Identification

Name
Putrescine
Accession Number
DB01917  (EXPT02702)
Type
Small Molecule
Groups
Experimental
Description

Putrescine is a toxic diamine formed by putrefaction from the decarboxylation of arginine and ornithine. Putrescine is a solid. This compound belongs to the polyamines. These are compounds containing more than one amine group. Known drug targets of putrescine include putrescine-binding periplasmic protein, ornithine decarboxylase, and S-adenosylmethionine decarboxylase proenzyme.

Structure
Thumb
Synonyms
Not Available
External IDs
NSC-60545
Categories
UNII
V10TVZ52E4
CAS number
110-60-1
Weight
Average: 88.1515
Monoisotopic: 88.100048394
Chemical Formula
C4H12N2
InChI Key
KIDHWZJUCRJVML-UHFFFAOYSA-N
InChI
InChI=1S/C4H12N2/c5-3-1-2-4-6/h1-6H2
IUPAC Name
butane-1,4-diamine
SMILES
NCCCCN

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UOrnithine decarboxylaseNot AvailableHuman
US-adenosylmethionine decarboxylase proenzymeNot AvailableHuman
UPutrescine-binding periplasmic proteinNot AvailableEscherichia coli (strain K12)
UBeta-1 adrenergic receptorNot AvailableHuman
UBeta-2 adrenergic receptorNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Cystathionine Beta-Synthase DeficiencyDisease
Homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblG complementation typeDisease
S-Adenosylhomocysteine (SAH) Hydrolase DeficiencyDisease
Glycine N-methyltransferase DeficiencyDisease
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)Disease
Spermidine and Spermine BiosynthesisMetabolic
Methionine MetabolismMetabolic
Methionine Adenosyltransferase DeficiencyDisease
HypermethioninemiaDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Sang Yup Lee, Zhi Gang Qian, Xiaoxia Xia, Yong Jae Jeon, "MUTANT MICROORGANISMS HAVING A HIGH ABILITY TO PRODUCE PUTRESCINE AND METHOD FOR PRODUCING PUTRESCINE USING THE SAME." U.S. Patent US20100203599, issued August 12, 2010.

US20100203599
General References
Not Available
External Links
Human Metabolome Database
HMDB01414
KEGG Compound
C02896
PubChem Compound
1045
PubChem Substance
46506728
ChemSpider
13837702
BindingDB
50009385
ChEBI
17148
ChEMBL
CHEMBL46257
IUPHAR
2388
Guide to Pharmacology
GtP Drug Page
HET
PUT
Wikipedia
Putrescine
PDB Entries
1a99 / 1f3t / 1i72 / 1i79 / 1i7b / 1i7c / 1i7m / 1jl0 / 1msv / 2o06
show 27 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)27.5 °CPhysProp
boiling point (°C)158.5 °CPhysProp
logP-0.70SANGSTER (1994)
pKa10.8 (at 20 °C)PERRIN,DD (1965)
Predicted Properties
PropertyValueSource
Water Solubility236.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.38 m3·mol-1ChemAxon
Polarizability11.07 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8896
Blood Brain Barrier+0.8645
Caco-2 permeable+0.8867
P-glycoprotein substrateNon-substrate0.56
P-glycoprotein inhibitor INon-inhibitor0.9692
P-glycoprotein inhibitor IINon-inhibitor0.8872
Renal organic cation transporterNon-inhibitor0.647
CYP450 2C9 substrateNon-substrate0.895
CYP450 2D6 substrateSubstrate0.5153
CYP450 3A4 substrateNon-substrate0.8448
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9497
CYP450 2C19 inhibitorNon-inhibitor0.9084
CYP450 3A4 inhibitorNon-inhibitor0.9111
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8704
Ames testNon AMES toxic0.908
CarcinogenicityNon-carcinogens0.5694
BiodegradationNot ready biodegradable0.529
Rat acute toxicity2.3026 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8553
hERG inhibition (predictor II)Non-inhibitor0.8449
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)GC-MSsplash10-00di-1910000000-5694141cafbe39951441
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-00di-1900000000-eeb4354250406805ebe6
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)GC-MSsplash10-00di-8910000000-af71049ab8358b0042ff
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-00di-8900000000-0ba23327cabd9b2815f5
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-00di-2900000000-234e1b62f4e830226779
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-00di-1900000000-e29f1004e27fcb9cfe7b
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-001i-9000000000-224d3a5d3fbe7e1c6bd4
GC-MS Spectrum - EI-BGC-MSsplash10-001i-9000000000-5759f91b24f2e27cc466
GC-MS Spectrum - CI-BGC-MSsplash10-00di-9000000000-226a78b715ff64ec7067
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-1910000000-5694141cafbe39951441
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-1900000000-eeb4354250406805ebe6
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-8910000000-af71049ab8358b0042ff
GC-MS Spectrum - GC-MSGC-MSsplash10-00di-8900000000-0ba23327cabd9b2815f5
GC-MS Spectrum - GC-MSGC-MSsplash10-00di-2900000000-234e1b62f4e830226779
GC-MS Spectrum - GC-MSGC-MSsplash10-00di-1900000000-e29f1004e27fcb9cfe7b
GC-MS Spectrum - GC-MSGC-MSsplash10-00di-8900000000-0ba23327cabd9b2815f5
GC-MS Spectrum - GC-MSGC-MSsplash10-00di-2900000000-234e1b62f4e830226779
GC-MS Spectrum - GC-MSGC-MSsplash10-00di-1900000000-e29f1004e27fcb9cfe7b
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-1900000000-6861f65288867dab7690
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-2900000000-7923303f8f970b8d2dd6
Mass Spectrum (Electron Ionization)MSsplash10-001i-9000000000-2b410aa72c9bb951a79d
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-00di-9000000000-f718a117761c1c7ea80d
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-00di-9000000000-47752c8c65e2d83e78fb
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-00du-9000000000-3603b20551e892ad6c5e
MS/MS Spectrum - EI-B (HITACHI RMU-6L) , PositiveLC-MS/MSsplash10-001i-9000000000-224d3a5d3fbe7e1c6bd4
MS/MS Spectrum - EI-B (HITACHI RMU-6M) , PositiveLC-MS/MSsplash10-001i-9000000000-5759f91b24f2e27cc466
MS/MS Spectrum - CI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-00di-9000000000-226a78b715ff64ec7067
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-00dr-9000000000-0b342438cba3ac71bccb
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-00di-9000000000-8add450cd915232f7353
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-00di-9000000000-7a496471bdf7e391fdc8
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-00di-9000000000-84da87b521647b4f42ab
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-001l-9000000000-3ca1e2cd5a7e125ac52e
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-000i-9000000000-830221d5ea74a91c32e1
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0079-9000000000-896934367d7bc245c8b3
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-05g0-9000000000-96d51f0aa46b0ab332d0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-9000000000-de02b50a4b8a279875e4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-9000000000-73c448854a91ad5a9644
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-9000000000-c600a93b8d737a254884
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-059f-9000000000-ce7ae61a17ef7cb9b2c2
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00dr-9000000000-0b342438cba3ac71bccb
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-9000000000-8add450cd915232f7353
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-9000000000-7a496471bdf7e391fdc8
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-9000000000-84da87b521647b4f42ab
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001l-9000000000-3ca1e2cd5a7e125ac52e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-9000000000-830221d5ea74a91c32e1
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound 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
Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Organopnictogen compound / Hydrocarbon derivative / Primary aliphatic amine / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
alkane-alpha,omega-diamine (CHEBI:17148) / Biogenic amines (C00134) / an aliphatic α,ω-diamine (PUTRESCINE)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein homodimerization activity
Specific Function
Key enzyme of polyamine biosynthesis that converts ornithine into putrescine, which is the precursor for the polyamines, spermidine and spermine.
Gene Name
ODC1
Uniprot ID
P11926
Uniprot Name
Ornithine decarboxylase
Molecular Weight
51147.73 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Putrescine binding
Specific Function
Essential for biosynthesis of the polyamines spermidine and spermine. Promotes maintenance and self-renewal of embryonic stem cells, by maintaining spermine levels (By similarity).
Gene Name
AMD1
Uniprot ID
P17707
Uniprot Name
S-adenosylmethionine decarboxylase proenzyme
Molecular Weight
38339.335 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Putrescine-importing atpase activity
Specific Function
Required for the activity of the bacterial periplasmic transport system of putrescine. Polyamine binding protein.
Gene Name
potF
Uniprot ID
P31133
Uniprot Name
Putrescine-binding periplasmic protein
Molecular Weight
40839.305 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Receptor signaling protein activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
Gene Name
ADRB1
Uniprot ID
P08588
Uniprot Name
Beta-1 adrenergic receptor
Molecular Weight
51322.1 Da
References
  1. Meana C, Bordallo J, Bordallo C, Suarez L, Cantabrana B, Sanchez M: Functional effects of polyamines via activation of human beta1- and beta2-adrenoceptors stably expressed in CHO cells. Pharmacol Rep. 2010 Jul-Aug;62(4):696-706. [PubMed:20885010]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein homodimerization activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
Gene Name
ADRB2
Uniprot ID
P07550
Uniprot Name
Beta-2 adrenergic receptor
Molecular Weight
46458.32 Da
References
  1. Meana C, Bordallo J, Bordallo C, Suarez L, Cantabrana B, Sanchez M: Functional effects of polyamines via activation of human beta1- and beta2-adrenoceptors stably expressed in CHO cells. Pharmacol Rep. 2010 Jul-Aug;62(4):696-706. [PubMed:20885010]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without...
Gene Name
SLC22A4
Uniprot ID
Q9H015
Uniprot Name
Solute carrier family 22 member 4
Molecular Weight
62154.48 Da
References
  1. Yabuuchi H, Tamai I, Nezu J, Sakamoto K, Oku A, Shimane M, Sai Y, Tsuji A: Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73. [PubMed:10215651]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:06