decanoyl-CoA (YMDB00532)

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Identification

YMDB ID

YMDB00532

Name

decanoyl-CoA

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

decanoyl-CoA, also known as 10:0-CoA or capryl-CoA, 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. Based on a literature review a significant number of articles have been published on decanoyl-CoA.

Structure

MOL SDF PDB SMILES InChI

Synonyms

10:0-CoA
C10:0-CoA
Coenzyme A, S-decanoate
D5269_SIGMA
Decanoyl coenzyme a monohydrate
Decanoyl-CoA
Decanoyl-coenzyme a
hexadecanoyl-coa
Palmitoyl-CoA
s-decanoate
s-decanoate coenzyme a
s-decanoic acid
Capryl-CoA
Capryl-coenzyme A
coenzyme A, S-Decanoic acid

CAS number

1264-57-9

Weight

Average: 921.783
Monoisotopic: 921.250973563

InChI Key

CNKJPHSEFDPYDB-HSJNEKGZSA-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

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-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

decanoyl-coa

Chemical Formula

C₃₁H₅₄N₇O₁₇P₃S

SMILES

CCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](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

Description

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 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Ribonucleoside 3'-phosphate
Pentose phosphate
Pentose-5-phosphate
Beta amino acid or derivatives
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Monoalkyl phosphate
Aminopyrimidine
Imidolactam
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Monosaccharide
Pyrimidine
Alkyl phosphate
Fatty amide
Phosphoric acid ester
Tetrahydrofuran
Imidazole
Azole
Heteroaromatic compound
Carbothioic s-ester
Secondary alcohol
Thiocarboxylic acid ester
Carboxamide group
Secondary carboxylic acid amide
Amino acid or derivatives
Sulfenyl compound
Thiocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Organosulfur compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Primary amine
Organopnictogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

medium-chain fatty acyl-CoA (CHEBI:28493 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	2.94 g/L	ALOGPS
logP	0.87	ALOGPS
logP	-2.1	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.01	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	89.29 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

lipid particle
endoplasmic reticulum
peroxisome
cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Biosynthesis of unsaturated fatty acids	PW002403
Cholesterol biosynthesis and metabolism CE(10:0)	PW002545
Fatty acid elongation in mitochondria	PW002467
Fatty acid metabolism	PW002460
Sphingolipid metabolism	PW002479

KEGG Pathways

Biosynthesis of unsaturated fatty acids	ec01040
Fatty acid elongation in mitochondria	ec00062
Fatty acid metabolism	ec00071
Glycosylphosphatidylinositol(GPI)-anchor biosynthesis	ec00563
Sphingolipid metabolism	ec00600

SMPDB Reactions

decanoyl-CoA + Acetyl-CoA → 3-oxolauroyl-CoA + Coenzyme A

decanoyl-CoA + electron-transfer flavoprotein → (2E)-Decenoyl-CoA + Reduced electron-transfer flavoprotein

(2E)-Decenoyl-CoA + NADPH → decanoyl-CoA + NADP

KEGG Reactions

3-oxolauroyl-CoA + Coenzyme A → Acetyl-CoA + decanoyl-CoA

decanoyl-CoA + oxygen → Hydrogen peroxide + trans-dec-2-enoyl-CoA

malonyl-CoA + hydron + octanoyl-CoA + NADPH → decanoyl-CoA + Carbon dioxide + NADP + water + Coenzyme A

capric acid + Adenosine triphosphate + Coenzyme A ↔ Adenosine monophosphate + Pyrophosphate + decanoyl-CoA

decanoyl-CoA + malonyl-CoA + hydron + NADPH → Carbon dioxide + NADP + water + lauroyl-CoA + Coenzyme A

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f79-1954000202-8d907a9f329604f17ece	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0019-0962100000-ed75a9f7f93a2ec0ff66	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0019-1931000000-325d65bba2be79776f67	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0kji-2911031304-cd2823d592b2c6993b1c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-2901110000-23abe6fff1dc8b31aad0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-7900100000-a458d99a8f9f4588efa1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000000009-9c6e246136b34450c460	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0901101444-7d82560a0eb08046a336	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0001900000-6a815c213e5111ab7135	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000000009-b80ec55ac3d3f5f28bff	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00fr-4300202419-e5dbe4788b92dec8f8ff	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ftr-5504602935-4a47c48ba0e88b3c9b65	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Jones, J. M., Nau, K., Geraghty, M. T., Erdmann, R., Gould, S. J. (1999). "Identification of peroxisomal acyl-CoA thioesterases in yeast and humans." J Biol Chem 274:9216-9223.10092594

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	28493
HMDB ID	HMDB06404
Pubchem Compound ID	25244140
Kegg ID	C00154
ChemSpider ID	24784920
FOODB ID	FDB030805
Wikipedia ID	Not Available
BioCyc ID	CPD-10267

Enzymes

Protein Details

1. Acyl-coenzyme A oxidase

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Acyl-CoA + O(2) = trans-2,3-dehydroacyl-CoA + H(2)O(2)
Gene Name:: POX1
Uniprot ID:: P13711
Molecular weight:: 84041.39844

Reactions

Acyl-CoA + O(2) → trans-2,3-dehydroacyl-CoA + H(2)O(2).

Protein Details

2. Long-chain-fatty-acid--CoA ligase 2

General function:: Involved in catalytic activity
Specific function:: Esterification, concomitant with transport, of endogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. Preferentially acts on C9:0-C13:0 fatty acids although C7:0-C17:0 fatty acids are tolerated
Gene Name:: FAA2
Uniprot ID:: P39518
Molecular weight:: 83437.10156

Reactions

ATP + a long-chain carboxylic acid + CoA → AMP + diphosphate + an acyl-CoA.

Protein Details

3. 3-ketoacyl-CoA thiolase, peroxisomal

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA
Gene Name:: POT1
Uniprot ID:: P27796
Molecular weight:: 44729.89844

Reactions

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

Protein Details

4. Fatty acid synthase subunit beta

General function:: Involved in transferase activity
Specific function:: Fatty acid synthetase catalyzes the formation of long- chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. The beta subunit contains domains for:[acyl-carrier-protein] acetyltransferase and malonyltransferase, S-acyl fatty acid synthase thioesterase, enoyl-[acyl-carrier-protein] reductase, and 3-hydroxypalmitoyl-[acyl-carrier-protein] dehydratase
Gene Name:: FAS1
Uniprot ID:: P07149
Molecular weight:: 228689.0

Reactions

Acetyl-CoA + n malonyl-CoA + 2n NADH + 2n NADPH → long-chain-acyl-CoA + n CoA + n CO(2) + 2n NAD(+) + 2n NADP(+).
Acetyl-CoA + [acyl-carrier-protein] → CoA + acetyl-[acyl-carrier-protein].
Malonyl-CoA + [acyl-carrier-protein] → CoA + malonyl-[acyl-carrier-protein].
(3R)-3-hydroxypalmitoyl-[acyl-carrier-protein] → hexadec-2-enoyl-[acyl-carrier-protein] + H(2)O.
Acyl-[acyl-carrier-protein] + NAD(+) → trans-2,3-dehydroacyl-[acyl-carrier-protein] + NADH.
Oleoyl-[acyl-carrier-protein] + H(2)O → [acyl-carrier-protein] + oleate.

Protein Details

5. Peroxisomal acyl-coenzyme A thioester hydrolase 1

General function:: Involved in acyl-CoA thioesterase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH
Gene Name:: TES1
Uniprot ID:: P41903
Molecular weight:: 40259.39844

Reactions

Palmitoyl-CoA + H(2)O → CoA + palmitate.

Structure for #<Compound:0xad679244>

Enzymes

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