You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NamePutrescine
Accession NumberDB01917  (EXPT02702)
TypeSmall Molecule
GroupsExperimental
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
SynonymsNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number110-60-1
WeightAverage: 88.1515
Monoisotopic: 88.100048394
Chemical FormulaC4H12N2
InChI KeyKIDHWZJUCRJVML-UHFFFAOYSA-N
InChI
InChI=1S/C4H12N2/c5-3-1-2-4-6/h1-6H2
IUPAC Name
butane-1,4-diamine
SMILES
NCCCCN
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassAmines
Sub ClassPrimary amines
Direct ParentMonoalkylamines
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Spermidine and Spermine BiosynthesisMetabolicSMP00445
HypermethioninemiaDiseaseSMP00341
Homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblG complementation typeDiseaseSMP00570
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)DiseaseSMP00340
Glycine N-methyltransferase DeficiencyDiseaseSMP00222
Cystathionine Beta-Synthase DeficiencyDiseaseSMP00177
Methionine Adenosyltransferase DeficiencyDiseaseSMP00221
Methionine MetabolismMetabolicSMP00033
S-Adenosylhomocysteine (SAH) Hydrolase DeficiencyDiseaseSMP00214
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.9071
CYP450 2D6 substrateNon-inhibitor0.9497
CYP450 2C19 substrateNon-inhibitor0.9084
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point27.5 °CPhysProp
boiling point158.5 °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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraGC-MSMS/MSLC-MSMS1D NMR2D NMR
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 ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Ornithine decarboxylase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Ornithine decarboxylase P11926 Details

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
  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
  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

2. S-adenosylmethionine decarboxylase proenzyme

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
S-adenosylmethionine decarboxylase proenzyme P17707 Details

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
  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

3. Putrescine-binding periplasmic protein

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
Putrescine-binding periplasmic protein P31133 Details

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
  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

Transporters

1. Solute carrier family 22 member 4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 4 Q9H015 Details

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

Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on October 24, 2014 14:06