P. aeruginosa Metabolome Database: Decanoyl-CoA (N-C10:0CoA) (PAMDB000670)

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

PAMDB000670

Identification

Name:

Decanoyl-CoA (N-C10:0CoA)

Description:

Decanoyl-CoA is an intermediate in fatty acid elongationand its formation is from acetyl-CoA. It is also involved in fatty acid metabolism. (KEGG)

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

Decanoyl coenzyme a monohydrate
Decanoyl coenzyme a monohydric acid
Decanoyl-CoA
Decanoyl-coenzyme a
S-Decanoate
S-Decanoate coenzyme a
S-Decanoic acid
S-Decanoic acid coenzyme a

Chemical Formula:

C₃₁H₅₄N₇O₁₇P₃S

Average Molecular Weight:

921.783

Monoisotopic Molecular Weight:

921.250973563

InChI Key:

CNKJPHSEFDPYDB-BOJFXZHGSA-N

InChI:

InChI=1S/C31H54N7O17P3S/c1-4-5-6-7-8-9-10-11-22(40)59-15-14-33-21(39)12-13-34-29(43)26(42)31(2,3)17-52-58(49,50)55-57(47,48)51-16-20-25(54-56(44,45)46)24(41)30(53-20)38-19-37-23-27(32)35-18-36-28(23)38/h18-20,24-26,30,41-42H,4-17H2,1-3H3,(H,33,39)(H,34,43)(H,47,48)(H,49,50)(H2,32,35,36)(H2,44,45,46)/t20-,24-,25-,26?,30-/m1/s1

CAS number:

1264-57-9

IUPAC Name:

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-(decanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid

Traditional IUPAC Name:

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-{[({3-[(2-{[2-(decanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid

SMILES:

CCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as 2,3,4-saturated fatty acyl coas. These are acyl-CoAs carrying a 2,3,4-saturated fatty acyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

2,3,4-saturated fatty acyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside diphosphate
Purine ribonucleoside 3',5'-bisphosphate
N-glycosyl compound
Glycosyl compound
Beta amino acid or derivatives
Organic pyrophosphate
Monosaccharide phosphate
6-aminopurine
Purine
Imidazopyrimidine
Monoalkyl phosphate
Aminopyrimidine
Imidolactam
Alkyl phosphate
Pyrimidine
Primary aromatic amine
Phosphoric acid ester
Organic phosphoric acid derivative
Organic phosphate
N-substituted imidazole
N-acyl-amine
Monosaccharide
Fatty amide
Saccharide
Heteroaromatic compound
Oxolane
Imidazole
Azole
Thiocarboxylic acid ester
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Oxacycle
Azacycle
Organoheterocyclic compound
Sulfenyl compound
Thioether
Thiocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid amide
Hydrocarbon derivative
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Fatty acyl CoAs (C05274 )

Physical Properties

State:

Solid

Charge:

-4

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	2.94 mg/mL	ALOGPS
logP	0.87	ALOGPS
logP	-3.2	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	4.95	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	363.63 Å²	ChemAxon
Rotatable Bond Count	28	ChemAxon
Refractivity	209.04 m³·mol^-1	ChemAxon
Polarizability	87.87 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	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:

Pathways:

Fatty acid metabolism pae00071

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1911101102-21a54e6ddc3bc3f0fa2f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0940200000-cde77193a5a7de49b086	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1910102000-ef500961059789acea18	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zpi-2912030303-cea2a707bb4d954482d6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fai-2901010000-90a07e7716a613da0fbb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900000000-a26ec16b7584e4b6f0cd	View in MoNA

References

References:

Gregersen N, Kolvraa S, Mortensen PB: Acyl-CoA: glycine N-acyltransferase: in vitro studies on the glycine conjugation of straight- and branched-chained acyl-CoA esters in human liver. Biochem Med Metab Biol. 1986 Apr;35(2):210-8. Pubmed: 3707752
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

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	28493
HMDB ID	HMDB06404
Pubchem Compound ID	164800
Kegg ID	C05274
ChemSpider ID	389510
Wikipedia ID	Not Available
BioCyc ID	CPD-10267
EcoCyc ID	CPD-10267

Enzymes

Protein Details

• 3-ketoacyl-CoA thiolase

General function:: Involved in acetyl-CoA C-acyltransferase activity
Specific function:: Catalyzes the final step of fatty acid oxidation in which acetyl-CoA is released and the CoA ester of a fatty acid two carbons shorter is formed. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
Gene Name:: fadA
Locus Tag:: PA3013
Molecular weight:: 41.6 kDa

Reactions

Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA.

Protein Details

• Long-chain-fatty-acid--CoA ligase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the esterification, concomitant with transport, of exogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids
Gene Name:: fadD
Locus Tag:: PA3299
Molecular weight:: 61.7 kDa

Reactions

ATP + a long-chain fatty acid + CoA = AMP + diphosphate + an acyl-CoA.

Protein Details

• Acyl-coenzyme A dehydrogenase

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Catalyzes the dehydrogenation of acyl-CoA
Gene Name:: fadE
Locus Tag:: PA2815
Molecular weight:: 88.8 kDa

Reactions

An acyl-CoA + FAD = a dehydrogenated acyl-CoA + FADH(2).

Protein Details

• Acyl-CoA thioesterase 2

General function:: Involved in acyl-CoA hydrolase activity
Specific function:: Can hydrolyze a broad range of acyl-CoA thioesters. Its physiological function is not known
Gene Name:: tesB
Locus Tag:: PA3942
Molecular weight:: 32.9 kDa

Decanoyl-CoA (N-C10:0CoA) (PAMDB000670)

Structure for Decanoyl-CoA (N-C10:0CoA) (PAMDB000670)

Enzymes

Reactions

Reactions

Reactions