ECMDB: N-Acetylputrescine (ECMDB02064) (M2MDB000434)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (1)XML

Proteins (213)

Record Information

Version

2.0

Creation Date

2012-05-31 13:55:18 -0600

Update Date

2015-09-13 12:56:12 -0600

Secondary Accession Numbers

ECMDB02064

Identification

Name:

N-Acetylputrescine

Description

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. 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:

Acetylputrescine
Monoacetylputrescine
N-(4-Aminobutyl)acetamide

Chemical Formula:

C₆H₁₄N₂O

Weight:

Average: 130.1882
Monoisotopic: 130.11061308

InChI Key:

KLZGKIDSEJWEDW-UHFFFAOYSA-N

InChI:

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

CAS number:

18233-70-0

IUPAC Name:

N-(4-aminobutyl)acetamide

Traditional IUPAC Name:

acetylputrescine

SMILES:

CC(=O)NCCCCN

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 )

Physical Properties

State:

Solid

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Acetyl-CoA + Putrescine <> Coenzyme A + N-Acetylputrescine

SMPDB Pathways:

Not Available

KEGG Pathways:

Arginine and proline metabolism ec00330

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

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

References

References:

Abdel-Monem MM, Ohno K: Polyamine metabolism I: Synthesis of dansyl derivatives of N-(monoaminoalkyl)- and N-(polyaminoalkyl)acetamides and elucidation in urine of a cancer patient. J Pharm Sci. 1977 Aug;66(8):1089-94. Pubmed: 197226
Hiramatsu K, Kamei S, Sugimoto M, Kinoshita K, Iwasaki K, Kawakita M: An improved method of determining free and acetylated polyamines by HPLC involving an enzyme reactor and an electrochemical detector. J Biochem (Tokyo). 1994 Mar;115(3):584-9. Pubmed: 8056776
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 (Tokyo). 1995 Jan;117(1):107-12. Pubmed: 7775374
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
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. Pubmed: 9464484
Loser C, Folsch UR, Paprotny C, Creutzfeldt W: Polyamines in colorectal cancer. Evaluation of polyamine concentrations in the colon tissue, serum, and urine of 50 patients with colorectal cancer. Cancer. 1990 Feb 15;65(4):958-66. Pubmed: 2297664

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	17768
HMDB ID	HMDB02064
Pubchem Compound ID	122356
Kegg ID	C02714
ChemSpider ID	109095
Wikipedia ID	Not Available
BioCyc ID	CPD-569
EcoCyc ID	CPD-569

Enzymes

Protein Details

1. Spermidine N(1)-acetyltransferase

General function:: Involved in N-acetyltransferase activity
Specific function:: Regulates polyamine concentration by their degradation. Acts on spermidine, forming N(1)- and N(8)-acetylspermidine
Gene Name:: speG
Uniprot ID:: P0A951
Molecular weight:: 21887

Reactions

Acetyl-CoA + an alkane-alpha,omega-diamine = CoA + an N-acetyldiamine.

N-Acetylputrescine (ECMDB02064) (M2MDB000434)

Structure for #<Compound:0xa505648c>

Enzymes

Reactions