Putrescine

Identification

Generic Name
Putrescine
DrugBank Accession Number
DB01917
Background

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.

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 88.1515
Monoisotopic: 88.100048394
Chemical Formula
C4H12N2
Synonyms
  • putrescina
External IDs
  • NSC-60545

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UBeta-1 adrenergic receptorNot AvailableHumans
UBeta-2 adrenergic receptorNot AvailableHumans
UOrnithine decarboxylaseNot AvailableHumans
US-adenosylmethionine decarboxylase proenzymeNot AvailableHumans
UPutrescine-binding periplasmic proteinNot AvailableEscherichia coli (strain K12)
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

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

Pathways
PathwayCategory
Cystathionine beta-Synthase DeficiencyDisease
Methionine MetabolismMetabolic
Methionine Adenosyltransferase DeficiencyDisease
Spermidine and Spermine BiosynthesisMetabolic
S-Adenosylhomocysteine (SAH) Hydrolase DeficiencyDisease
Glycine N-Methyltransferase DeficiencyDisease
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)Disease
HypermethioninemiaDisease
Homocystinuria-Megaloblastic Anemia Due to Defect in Cobalamin Metabolism, cblG Complementation TypeDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aliphatic acyclic compound / Hydrocarbon derivative / Organopnictogen compound / Primary aliphatic amine
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
alkane-alpha,omega-diamine (CHEBI:17148) / Biogenic amines (C00134) / an aliphatic α,ω-diamine (PUTRESCINE)
Affected organisms
Not Available

Chemical Identifiers

UNII
V10TVZ52E4
CAS number
110-60-1
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

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
Human Metabolome Database
HMDB0001414
KEGG Compound
C02896
PubChem Compound
1045
PubChem Substance
46506728
ChemSpider
13837702
BindingDB
50009385
ChEBI
17148
ChEMBL
CHEMBL46257
ZINC
ZINC000005828633
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
PUT
Wikipedia
Putrescine
PDB Entries
1a99 / 1f3t / 1i72 / 1i79 / 1i7b / 1i7c / 1i7m / 1jl0 / 1msv / 2o06
show 64 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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-MSsplash10-001i-9000000000-4d1729dd236ab6f44cd9
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
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9000000000-727621ddd7c56bd1076f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-9000000000-8ef86f0a1302153f4437
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ab9-9000000000-460396a215c9e08b65bf
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-9000000000-d25d93ad1c49442b4f9a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-d925efef7214ef949e51
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-06e7014cb29cd7375319
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-113.2333956
predicted
DarkChem Lite v0.1.0
[M-H]-113.2338956
predicted
DarkChem Lite v0.1.0
[M-H]-113.3238956
predicted
DarkChem Lite v0.1.0
[M-H]-118.99655
predicted
DeepCCS 1.0 (2019)
[M+H]+114.0996956
predicted
DarkChem Lite v0.1.0
[M+H]+114.0273956
predicted
DarkChem Lite v0.1.0
[M+H]+114.1102956
predicted
DarkChem Lite v0.1.0
[M+H]+120.90199
predicted
DeepCCS 1.0 (2019)
[M+Na]+113.5540956
predicted
DarkChem Lite v0.1.0
[M+Na]+113.7682956
predicted
DarkChem Lite v0.1.0
[M+Na]+113.7104956
predicted
DarkChem Lite v0.1.0
[M+Na]+128.92271
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Kind
Protein
Organism
Humans
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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
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. [Article]
  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. [Article]

Transporters

Kind
Protein
Organism
Humans
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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52