ChemFOnt: Showing chemical card for N-Acetylputrescine (CFc000001385)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:00 UTC

Chemfont ID

CFc000001385

Molecule Identification

Common Name

N-Acetylputrescine

Definition

N-Acetylputrescine is a polyamine commonly occurring excreted in normal human urine (PMID 7775374 ). N-Acetylputrescine is the most abundant of all polyamines both in normal individuals and in patients with leukemia (PMID 9464484 ). N-Acetylputrescine is the N-acetylated form of the naturally occurring polyamine called putrescine. The N-acetylation is mediated by the enzyme diamine N-acetyltransferase. 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 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. N-Acetylputrescine can be found in Corynebacterium as well (PMID:25919117 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Acetylputrescine	HMDB
Monoacetylputrescine	HMDB
N-(4-Aminobutyl)acetamide	HMDB
N-Acetylputrescine monohydrochloride	HMDB

Chemical Formula

C₆H₁₄N₂O

Average Molecular Weight

130.1882

Monoisotopic Molecular Weight

130.11061308

IUPAC Name

N-(4-aminobutyl)acetamide

Traditional Name

acetylputrescine

CAS Registry Number

18233-70-0

SMILES

CC(=O)NCCCCN

InChI Identifier

InChI=1S/C6H14N2O/c1-6(9)8-5-3-2-4-7/h2-5,7H2,1H3,(H,8,9)

InChI Key

KLZGKIDSEJWEDW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboximidic acids and derivatives

Sub Class

Carboximidic acids

Direct Parent

Carboximidic acids

Alternative Parents

Substituents

Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-substituted putrescine (CHEBI:17768 )
N-monoacetylalkane-alpha,omega-diamine (CHEBI:17768 )
an aliphatic <i>N</i>-acetyl-diamine (CPD-569 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)
Saliva (PMID: 22308371)

Organ

Placenta (HMDB: HMDB0002064)

Excreta

Biofluid or Excreta

Urine (PMID: 3757213)
Feces (PMID: 27275383)

Cellular substructure

Cytoplasm (HMDB: HMDB0002064)

Source

Endogenous

Endogenous (HMDB: HMDB0002064)

Microbe

Microbe (HMDB: HMDB0002064)
Corynebacterium glutamicum (HMDB: HMDB0002064)

Exogenous

Exogenous (HMDB: HMDB0002064)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Leukemia (MarkerDB: MDB00000373)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	141 g/L	ALOGPS
logP	-0.84	ALOGPS
logP	-1	ChemAxon
logS	0.04	ALOGPS
pKa (Strongest Acidic)	16.48	ChemAxon
pKa (Strongest Basic)	9.9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	55.12 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	36.82 m³·mol⁻¹	ChemAxon
Polarizability	15.28 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon