MiMeDB: Showing metabocard for N-Acetylcadaverine (MMDBc0000821)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 22:03:46 UTC

Update Date

2024-04-30 19:33:46 UTC

Metabolite ID

MMDBc0000821

Metabolite Identification

Common Name

N-Acetylcadaverine

Description

N-Acetylcadaverine is the acetylated form of the polyamine cadaverine. Cadaverine is produced by the breakdown of amino acids in living and dead organisms and is toxic in large doses. Cadaverine is largely responsible for the foul odor of putrefying flesh, but also contributes to the odor of such processes as bad breath and bacterial vaginosis. Cadaverine is also found in semen. Polyamines (and their acetylated forms) are known to be closely related with cell growth, cell proliferation, and synthesis of proteins and nucleic acids. Their concentrations are adjusted either by regulating the activity levels of the biosynthetic and catabolic reactions or by controlling the net direction of polyamine acetylation-deacetylation. In Alzheimer's disease (AD), the neurotoxic amyloid β-peptide is known to up-regulate polyamine metabolism by increasing ornithine decarboxylase activity and polyamine uptake by initiating free radical damage. Because of these findings, polyamines have been considered to play an important role in response to neurodegenerative conditions. Altered levels of polyamines have been found in tissue, hair and body fluids of patients with neuromuscular diseases and neurodegenerative conditions. (PMID: 17723614 ). N-Acetylcadaverine has been found to be a metabolite of several bacteria species (https://www.sciencedirect.com/science/article/pii/S209580991730423X).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Synonyms

Value	Source
Monoacetyl cadaverine	ChEBI
Monoacetylcadaverine	ChEBI
Acetylcadaverine	HMDB
N-(5-Aminopentyl)acetamide	HMDB

Molecular Formula

C₇H₁₆N₂O

Average Mass

144.2147

Monoisotopic Mass

144.126263144

IUPAC Name

N-(5-aminopentyl)acetamide

Traditional Name

N-acetylcadaverine

CAS Registry Number

Not Available

SMILES

CC(=O)NCCCCCN

InChI Identifier

InChI=1S/C7H16N2O/c1-7(10)9-6-4-2-3-5-8/h2-6,8H2,1H3,(H,9,10)

InChI Key

RMOIHHAKNOFHOE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acetamides. These are organic compounds with the general formula RNHC(=O)CH3, where R= organyl group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Acetamides

Alternative Parents

Substituents

Acetamide
Secondary carboxylic acid amide
Amino acid or derivatives
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	23.7 g/L	ALOGPS
logP	-0.4	ALOGPS
logP	-0.58	ChemAxon
logS	-0.78	ALOGPS
pKa (Strongest Acidic)	16.53	ChemAxon
pKa (Strongest Basic)	10.21	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	5	ChemAxon
Refractivity	41.42 m³·mol⁻¹	ChemAxon
Polarizability	17.36 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-9000000000-06147dfcd9c450f9f418	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ufs-3900000000-9d16b7430dbb509b83ed	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-9800000000-e75e37d1af196e17b6ea	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05nf-9000000000-4ae88c31526f55eef559	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-2900000000-20b0aeef985ef2a34ffe	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-5900000000-e747329b2881eb734d0e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-ca12c55eb237562ff8e1	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004s-2900000000-8d912fec58d282ee38f2	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9200000000-d196f42d15b308ed06ec	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-c75b850b1f4d70c9dc3e	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-3900000000-d74b7ce74028d6624d60	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-9981f655f72c6898948d	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-6887861a6c20fdd3a3dc	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0016570	Water	Acetic acid	Acetylpolyamine amidohydrolase	Hydrolysis of bond	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Leukemia		Association	Human Urine	HMDB	9464484

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	6	Human stool; Human feces; Human mucosa; Human ; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Bacteroidetes	1	Human stool; Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Proteobacteria	3	Human

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	0.16		0.04	0.87	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	3757213
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	9464484
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Leukemia	HMDB	9464484
Human Urine	Detected and Quantified	0.279	0.17			umol/mmol creatinine	Adult (>18 years old)	Both		HMDB	9464484
Human Urine	Detected and Quantified	0.46	0.232			umol/mmol creatinine	Adult (>18 years old)	Both	Leukemia	HMDB	9464484
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Colorectal Cancer	HMDB	27275383
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected and Quantified	0.460	0.232			umol/mmol creatinine	Adult (>18 years old)	Both	Leukemia	HMDB	9464484
Human Urine	Detected and Quantified	0.16		0.04	0.87	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	3757213
Human Urine	Detected and Quantified	0.279	0.17			umol/mmol creatinine	Adult (>18 years old)	Both		HMDB	9464484
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	9464484
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0002284

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022947

KNApSAcK ID

Not Available

Chemspider ID

164295

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

189087

PDB ID

Not Available

ChEBI ID

88824

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Abdel-Monem MM, Ohno K: Polyamine metabolism II: N-(Monoaminoalkyl)- and N-(polyaminoalkyl)acetamides in human urine. J Pharm Sci. 1977 Aug;66(8):1195-7. doi: 10.1002/jps.2600660837. [PubMed:894508 ]
Lee SH, Kim SO, Lee HD, Chung BC: Estrogens and polyamines in breast cancer: their profiles and values in disease staging. Cancer Lett. 1998 Nov 13;133(1):47-56. doi: 10.1016/s0304-3835(98)00189-x. [PubMed:9929159 ]
Paik MJ, Lee S, Cho KH, Kim KR: Urinary polyamines and N-acetylated polyamines in four patients with Alzheimer's disease as their N-ethoxycarbonyl-N-pentafluoropropionyl derivatives by gas chromatography-mass spectrometry in selected ion monitoring mode. Anal Chim Acta. 2006 Aug 18;576(1):55-60. doi: 10.1016/j.aca.2006.01.070. Epub 2006 Feb 24. [PubMed:17723614 ]

Showing metabocard for N-Acetylcadaverine (MMDBc0000821)

MOL for #<Metabolite:0x00007fd12c16d1b8>

3D MOL for #<Metabolite:0x00007fd12c16d1b8>

3D SDF for #<Metabolite:0x00007fd12c16d1b8>

3D-SDF for #<Metabolite:0x00007fd12c16d1b8>

PDB for #<Metabolite:0x00007fd12c16d1b8>

3D PDB for #<Metabolite:0x00007fd12c16d1b8>

SMILES for #<Metabolite:0x00007fd12c16d1b8>

INCHI for #<Metabolite:0x00007fd12c16d1b8>

Structure for #<Metabolite:0x00007fd12c16d1b8>

3D Structure for #<Metabolite:0x00007fd12c16d1b8>