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Record Information

Version

2.0

Creation Date

2012-07-30 14:55:07 -0600

Update Date

2015-09-13 15:15:31 -0600

Secondary Accession Numbers

ECMDB21254

Identification

Name:

N8-Acetylspermidine

Description

N8-Acetylspermidine is a polyamine. The polyamines, found in virtually all living organisms, are a ubiquitous group of compounds that appear to play a vital role in many cellular processes involving nucleic acids including cell growth and differentiation. The polyamines, found in virtually all living organisms, are a ubiquitous group of compounds that appear to play a vital role in many cellular processes involving nucleic acids including cell growth and differentiation. Acetylation on the terminal nitrogen adjacent to the 4-carbon chain produces N8-acetylspermidine. This reaction is catalyzed by spermidine N8-acetyltransferase and does not result in the conversion of spermidine to putrescine but, instead, the product undergoes deacetylation.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

N-[4-(3-Aminopropylamino)butyl]acetamide
N-[4-[(3-Aminopropyl)amino]butyl]-Acetamide
N-{4-[(3-Aminopropyl)amino]butyl}acetamide
N8-Acetylspermidine
N8-monoacetylspermidine

Chemical Formula:

C₉H₂₁N₃O

Weight:

Average: 187.2825
Monoisotopic: 187.168462309

InChI Key:

FONIWJIDLJEJTL-UHFFFAOYSA-N

InChI:

InChI=1S/C9H21N3O/c1-9(13)12-8-3-2-6-11-7-4-5-10/h11H,2-8,10H2,1H3,(H,12,13)

CAS number:

13431-24-8

IUPAC Name:

N-{4-[(3-aminopropyl)amino]butyl}acetamide

Traditional IUPAC Name:

N8-acetylspermidine

SMILES:

CC(=O)NCCCCNCCCN

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
Secondary amine
Secondary aliphatic amine
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

acetylspermidine (CHEBI:27911 )

Physical Properties

State:

Solid

Charge:

Melting point:

202-203 °C

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	4.4 g/L	ALOGPS
logP	-0.48	ALOGPS
logP	-1.3	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	16.53	ChemAxon
pKa (Strongest Basic)	10.29	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	67.15 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	54.41 m³·mol⁻¹	ChemAxon
Polarizability	23.1 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 + Spermidine > Coenzyme A + Hydrogen ion + N8-Acetylspermidine

SMPDB Pathways:

S-adenosyl-L-methionine biosynthesis

PW000837

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-9200000000-7350029bbf7fca576698	View in MoNA
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 - LC-ESI-QQ , positive	splash10-000i-0900000000-d04fb233b228bfc46b79	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-01w0-0900000000-e68fd1aa92642ae4208d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03k9-7900000000-287b3decd26c7daeb830	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0089-9100000000-e42a1f8955afadd5f50d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0089-9000000000-b18801afe8921946e40f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-03k9-4900000000-fc04b14a414610552acd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-009j-1900000000-ec737abcda867c6557b2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004j-6900000000-c57d66a60207b42d5604	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9100000000-5e4ff8c1235fb203f05f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-1900000000-ed4e22e75d7e4ab076e2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052o-5900000000-f486a2117b1dd060f58e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-dd7c2661d7b6091c7766	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-b573184691a2508c0c96	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052r-6900000000-9ecb44c4262e0df34ea4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-078ef81a1628477a273f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-3aacf768b87a62171bf0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0229-9600000000-8855f267bbadb8cff170	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-9100000000-286ce82869d4963e80f9	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Abdel-Monem MM, Merdink JL, Theologides A: Urinary excretion of monoacetyl polyamines in patients with non-Hodgkin's lymphoma. Cancer Res. 1982 May;42(5):2097-8. Pubmed: 7066912
Hrushesky WJ, Merdink J, Abdel-Monem MM: Circadian rhythmicity of polyamine urinary excretion. Cancer Res. 1983 Aug;43(8):3944-7. Pubmed: 6861156
Inoue H, Fukunaga K, Munemura S, Tsuruta Y: Simultaneous determination of free and N-acetylated polyamines in urine by semimicro high-performance liquid chromatography using 4-(5,6-dimethoxy-2-phthalimidinyl)-2-methoxyphenylsulfonyl chloride as a fluorescent labeling reagent. Anal Biochem. 2005 Apr 15;339(2):191-7. Pubmed: 15797558
Mudumba S, Menezes A, Fries D, Blankenship J: Differentiation of PC12 cells induced by N8-acetylspermidine and by N8-acetylspermidine deacetylase inhibition. Biochem Pharmacol. 2002 Jun 1;63(11):2011-8. Pubmed: 12093478
Seiler N, Graham A, Bartholeyns J: Enhanced urinary excretion of N1-acetylspermidine and the presence of tumors. Cancer Res. 1981 Apr;41(4):1572-3. Pubmed: 6897929

Synthesis Reference:

Tabor, Herbert; Tabor, Celia W.; De Meis, Leopold. Chemical synthesis of N-acetyl-1,4-diaminobutane, N1-acetylspermidine, and N8-acetylspermidine. Methods Enzymol. (1971), 17(Pt. B), 829-33.

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	27911
HMDB ID	HMDB02189
Pubchem Compound ID	123689
Kegg ID	C01029
ChemSpider ID	110264
Wikipedia ID	Not Available
BioCyc ID	CPD-3462
EcoCyc ID	CPD-3462
Ligand Expo	Q9C

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.

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N8-Acetylspermidine (M2MDB001662)

Structure for #<Compound:0xa6a17394>

Enzymes

Reactions