Livestock Metabolome Database: Showing metabocard for N-Acetylputrescine (LMDB00377)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:48:29 UTC

Update Date

2016-09-23 18:45:17 UTC

Lmdb

LMDB00377

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Acetylputrescine

Description

N-Acetylputrescine is a polyamine commonly occurring excreted in normal animal 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.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00di-2900000000-5ce6ea5fec8a535152b1	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00di-9700000000-99b6d1613ba71642630c	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00di-9700000000-f5b3a7431b349387eaf4	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0fl9-3900000000-4e71aaf5516b6c95b4c8	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-00dr-5900000000-7f05a246fd26bf66b402	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-2900000000-5ce6ea5fec8a535152b1	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9700000000-99b6d1613ba71642630c	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9700000000-f5b3a7431b349387eaf4	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0fl9-3900000000-4e71aaf5516b6c95b4c8	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00dr-5900000000-7f05a246fd26bf66b402	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0fl9-3900000000-4e71aaf5516b6c95b4c8	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00dr-5900000000-7f05a246fd26bf66b402	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9000000000-8aea84b2256cb4c80b28	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03k9-3900000000-059ca8ad6ad85938c0f9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9000000000-9dc7efc6c0f52e2a1622	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00di-9100000000-cf5d10d7ed6eaebc6417	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-001i-0900000000-409c4453575d652233d4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0229-9700000000-128ded2b5a97118c2d5d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00di-9000000000-170cecf2246d1432d9b1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-00di-9000000000-4921ba95eaa0b725f1e9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-00dl-9000000000-6822cd785ae4293a429c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-03k9-4900000000-bee7a2928577d361331e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-0900000000-409c4453575d652233d4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0229-9700000000-128ded2b5a97118c2d5d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-9000000000-170cecf2246d1432d9b1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-9000000000-4921ba95eaa0b725f1e9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00dl-9000000000-6822cd785ae4293a429c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03k9-4900000000-bee7a2928577d361331e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-014i-3900000000-4c6930587dbe03729b9c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-01q9-0900000000-9782f79bcff20398ee5e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00dl-9000000000-005452a2f31ffdc3b2f5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-000i-9000000000-2615125feb868f3112f3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q0-9600000000-b7657fac110a60062e9b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0079-9000000000-9489cb75eca41b783e8e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0abc-9000000000-4d6f44ed73fd53b37795	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-5900000000-f9c8118634ba3d7bb53c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9200000000-7baa5995e911a5894fd3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-2afae62bc17432205556	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Milk

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23438684	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0002064

FooDB ID

FDB022827

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

1445791

BioCyc ID

CPD-569

METLIN ID

3252

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Hiramatsu K, Sugimoto M, Kamei S, Hoshino M, Kinoshita K, Iwasaki K, Kawakita M: Determination of amounts of polyamines excreted in urine: demonstration of N1,N8-diacetylspermidine and N1,N12-diacetylspermine as components commonly occurring in normal human urine. J Biochem. 1995 Jan;117(1):107-12. [7775374 ]
Lee SH, Suh JW, Chung BC, Kim SO: Polyamine profiles in the urine of patients with leukemia. Cancer Lett. 1998 Jan 9;122(1-2):1-8. [9464484 ]

Showing metabocard for N-Acetylputrescine (LMDB00377)

Structure for LMDB00377 (N-Acetylputrescine)