P. aeruginosa Metabolome Database: S-Acetyldihydrolipoamide (PAMDB000411)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000411

Identification

Name:

S-Acetyldihydrolipoamide

Description:

S-acetyldihydrolipoamide is a member of the chemical class known as N-acyl Amines. These are compounds containing a fatty acid moiety linked to an amine group through an ester linkage. In Pseudomonas aeruginosa the dihydrolipoyl transacetylase component (E2) of the pyruvate dehydrogenase complex catalyzes the reaction of acetyl coenzyme A (acetyl-CoA) with dihydrolipoamide, producing coenzyme A and S-acetyldihydrolipoamide. [PMID: 3101735]

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

6-acetylsulfanyl-8-sulfanyl-octanamide
6-Acetylsulphanyl-8-sulphanyl-octanamide
6-S-Acetyldihydrolipoamide
S-Acetyldihydrolipoamide
S-[6-amino-6-oxo-1-(2-sulfanylethyl)hexyl] ethanethioate
S-[6-amino-6-oxo-1-(2-sulfanylethyl)hexyl] ethanethioic acid
S-[6-amino-6-oxo-1-(2-Sulphanylethyl)hexyl] ethanethioate
S-[6-amino-6-oxo-1-(2-Sulphanylethyl)hexyl] ethanethioic acid

Chemical Formula:

C₁₀H₁₉NO₂S₂

Average Molecular Weight:

249.393

Monoisotopic Molecular Weight:

249.085720237

InChI Key:

ARGXEXVCHMNAQU-UHFFFAOYSA-N

InChI:

InChI=1S/C10H19NO2S2/c1-8(12)15-9(6-7-14)4-2-3-5-10(11)13/h9,14H,2-7H2,1H3,(H2,11,13)

CAS number:

Not Available

IUPAC Name:

6-(acetylsulfanyl)-8-sulfanyloctanamide

Traditional IUPAC Name:

S(6)-acetyldihydrolipoamide

SMILES:

CC(=O)SC(CCS)CCCCC(N)=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as fatty amides. These are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty amides

Direct Parent

Fatty amides

Alternative Parents

Substituents

Fatty amide
Thiocarboxylic acid ester
Primary carboxylic acid amide
Carboxamide group
Sulfenyl compound
Thioether
Thiocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid amide
Alkylthiol
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

a small molecule (S-ACETYLDIHYDROLIPOAMIDE )

Physical Properties

State:

Not Available

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source
LogP:	1.914	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.0355 mg/mL	ALOGPS
logP	2.46	ALOGPS
logP	1.24	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	10.19	ChemAxon
pKa (Strongest Basic)	-0.58	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	60.16 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	67.23 m³·mol^-1	ChemAxon
Polarizability	27.66 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 + Dihydrolipoamide Coenzyme A + S-Acetyldihydrolipoamide
Hydrogen ion + Pyruvic acid + Lipoamide S-Acetyldihydrolipoamide + Carbon dioxide
Acetyl-CoA + Dihydrolipoamide + Dihydrolipoamide <> Coenzyme A + S-Acetyldihydrolipoamide

Pathways:

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0pc0-0390000000-f4f7a106ce708d65c83c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-5590000000-4df718aaa87a6fbbd795	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03k9-4900000000-d4adb6f2a43bf9e5b1b9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4j-2290000000-229a9fb285c737cc2c9f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4l-6590000000-6678ae77fcef8223dec9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-5de0a80883e527f54fbb	View in MoNA

References

References:

Butterworth PJ, Tsai CS, Eley MH, Roche TE, Reed LJ: A kinetic study of dihydrolipoyl transacetylase from bovine kidney. J Biol Chem. 1975 Mar 10;250(5):1921-5. Pubmed: 1089667
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
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
O'Connor TP, Roche TE, Paukstelis JV: 13C nuclear magnetic resonance study of the pyruvate dehydrogenase-catalyzed acetylation of dihydrolipoamide. J Biol Chem. 1982 Mar 25;257(6):3110-2. Pubmed: 6801041
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Yang, Y. S., Frey, P. A. (1986). "Dihydrolipoyl transacetylase of Escherichia coli. Formation of 8-S-acetyldihydrolipoamide." Biochemistry 25:8173-8178. Pubmed: 3101735

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	16807
HMDB ID	HMDB01526
Pubchem Compound ID	1076
Kegg ID	C01136
ChemSpider ID	1046
Wikipedia ID	Not Available
BioCyc ID	S-ACETYLDIHYDROLIPOAMIDE
EcoCyc ID	S-ACETYLDIHYDROLIPOAMIDE

S-Acetyldihydrolipoamide (PAMDB000411)

Structure for S-Acetyldihydrolipoamide (PAMDB000411)