Human Metabolome Database: Showing metabocard for 5-Acetamidovalerate (HMDB0012175)

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

Record Information

Version

4.0

Status

Expected but not Quantified

Creation Date

2009-04-06 16:20:29 UTC

Update Date

2020-02-26 21:37:03 UTC

HMDB ID

HMDB0012175

Secondary Accession Numbers

HMDB12175

Metabolite Identification

Common Name

5-Acetamidovalerate

Description

5-Acetamidovalerate is involved in the lysine degradation III pathway. It can be generated from the enzymatic reduction of 5-aminopentanoate or enzymatic oxidation of 2-keto-6-acetamidocaproate. Experiment using DL-{4,5-3H}lysine showed 5-acetamidovalerate as the major product. If radiolabeled N6-acetyl-L-lysine was used with added α-ketoglutarate, and pyridoxal phosphate, radiolabeled 2-keto-6-acetamidocaproate was produced. α-Ketoglutarate was preferred over pyruvate, and there was little or no dependence on pyridoxal phosphate. If thiamine pyrophosphate and NAD were added to a similar reaction, virtually all of the label was in 5-acetamidovalerate. If labeled 5-acetamidovalerate was used, labeled 5-aminovalerate (5-aminopentanoate) was identified. In addition, whole cell cultures of R. leguminicola incubated with labeled 5-acetamidovalerate accumulated radiolabeled glutarate. Whole cell cultures incubated with radiolabeled glutarate produced a mixture of tricarboxylic acid cycle acids and other carboxylic acids.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-Acetamidovaleric acid	Generator
5-Acetamidopentanoate	HMDB
5-Acetamidopentanoic acid	HMDB

Chemical Formula

C₇H₁₃NO₃

Average Molecular Weight

159.183

Monoisotopic Molecular Weight

159.089543287

IUPAC Name

5-acetamidopentanoic acid

Traditional Name

5-acetamidopentanoic acid

CAS Registry Number

Not Available

SMILES

CC(=O)NCCCCC(O)=O

InChI Identifier

InChI=1S/C7H13NO3/c1-6(9)8-5-3-2-4-7(10)11/h2-5H2,1H3,(H,8,9)(H,10,11)

InChI Key

TZZSWAXSIGWXOS-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Straight chain fatty acids

Alternative Parents

Substituents

Straight chain fatty acid
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

acetamides (CHEBI:2024 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Biofluid and excreta:

Urine

Cell and elements:

Extracellular

Subcellular:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physical Properties

State

Solid

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
Water Solubility	9.38 g/L	ALOGPS
logP	-0.07	ALOGPS
logP	-0.36	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	4.59	ChemAxon
pKa (Strongest Basic)	-0.63	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	39.5 m³·mol⁻¹	ChemAxon
Polarizability	16.88 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	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-a0c945a55189dc0b5f84	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00r6-9300000000-db46ea751d90a55021d9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gvo-0900000000-81e251b1e76b54d2d776	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-4900000000-98a16f866bc20ccf222b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-6b007ccfdfff6745a5ca	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-1900000000-aecd97b33c6bf04fdca4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-6900000000-9bd2790a6596e2944e71	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-603ec01906bf2465cedd	Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028829

KNApSAcK ID

Not Available

Chemspider ID

388937

KEGG Compound ID

C03087

BioCyc ID

5-ACETAMIDOVALERATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439903

PDB ID

Not Available

ChEBI ID

2024

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 5-Acetamidovalerate (HMDB0012175)

Structure for HMDB0012175 (5-Acetamidovalerate)