hexacosanoyl-CoA (YMDB00537)

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Identification

YMDB ID

YMDB00537

Name

hexacosanoyl-CoA

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Hexacosanoyl-CoA, also known as C26:0-CoA or C26:0-coenzyme A, belongs to the class of organic compounds known as very long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a very long aliphatic chain of 22 carbon atoms or more. Thus, hexacosanoyl-CoA is considered to be a fatty ester. Based on a literature review a small amount of articles have been published on Hexacosanoyl-CoA.

Structure

MOL SDF PDB SMILES InChI

Synonyms

C26:0-CoA
C26:0-coenzyme A
cerotoyl-CoA
cerotoyl-coenzyme A
hexacosanoyl-CoA (N-C26:0CoA)
hexacosanoyl-coenzyme A
CoA(26:0)
Hexacosanoyl-CoA

CAS number

Not Available

Weight

Average: 1146.209
Monoisotopic: 1145.501374587

InChI Key

FHLYYFPJDVYWQH-CPIGOPAHSA-N

InChI

InChI=1S/C47H86N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-38(56)75-31-30-49-37(55)28-29-50-45(59)42(58)47(2,3)33-68-74(65,66)71-73(63,64)67-32-36-41(70-72(60,61)62)40(57)46(69-36)54-35-53-39-43(48)51-34-52-44(39)54/h34-36,40-42,46,57-58H,4-33H2,1-3H3,(H,49,55)(H,50,59)(H,63,64)(H,65,66)(H2,48,51,52)(H2,60,61,62)/t36-,40-,41-,42+,46-/m1/s1

IUPAC Name

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

cerotoyl-coa

Chemical Formula

C₄₇H₈₆N₇O₁₇P₃S

SMILES

CCCCCCCCCCCCCCCCCCCCCCCCCC(=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 very long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a very long aliphatic chain of 22 carbon atoms or more.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Very long-chain 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

very long-chain fatty acyl-CoA (CHEBI:52966 )

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	0.025 g/L	ALOGPS
logP	4.87	ALOGPS
logP	5.04	ChemAxon
logS	-4.7	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	44	ChemAxon
Refractivity	282.66 m³·mol⁻¹	ChemAxon
Polarizability	123.71 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

KEGG Pathways

Biosynthesis of unsaturated fatty acids

ec01040

SMPDB Reactions

(2E)-cerotenoyl-CoA + hydron + NADPH → hexacosanoyl-CoA + NADP

Phytosphingosine + hexacosanoyl-CoA → hydron + Coenzyme A + N-hexacosanoyl-C20-4-hydroxysphinganine

KEGG Reactions

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	splash10-002r-1901440100-be2cb6c2191090fe572c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f79-1901622000-b08e5e670a96cf61ebb9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f79-2900310000-1d404b474b20b8fee769	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0059-2902131300-bde43e887248b77390ea	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-2901110100-45ca204dcebfff70c1b5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-7900000000-2c0e52b0c82b1e816685	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-1085fa2af20a0dfa0644	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-3900000202-40c01c9de3627834fbae	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0000149000-6d6f39c024375a1b351f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-a9918ff61f2464cb8d15	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002f-4901402400-a3ab78dd365d8bf194d5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-6903400300-a03f951b6d8319e16c97	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
Mao, C., Xu, R., Bielawska, A., Szulc, Z. M., Obeid, L. M. (2000). "Cloning and characterization of a Saccharomyces cerevisiae alkaline ceramidase with specificity for dihydroceramide." J Biol Chem 275:31369-31378.10900202
Jiang, J. C., Kirchman, P. A., Zagulski, M., Hunt, J., Jazwinski, S. M. (1998). "Homologs of the yeast longevity gene LAG1 in Caenorhabditis elegans and human." Genome Res 8:1259-1272.9872981

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	52966
HMDB ID	HMDB0006459
Pubchem Compound ID	25246198
Kegg ID	Not Available
ChemSpider ID	23107092
FOODB ID	FDB023919
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. Alkaline ceramidase YDC1

General function:: Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amides
Specific function:: Catalyzes the conversion of dihydroceramide and also phytoceramide to dihydrosphingosine or phytosphingosine. Prefers dihydroceramide. Very low reverse hydrolysis activity, catalyzing synthesis of dihydroceramide from fatty acid and dihydrosphingosine. Is not responsible for the breakdown of unsaturated ceramide. May play a role in heat stress response
Gene Name:: YDC1
Uniprot ID:: Q02896
Molecular weight:: 37230.5

Reactions

Protein Details

2. 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

3. Sphingosine N-acyltransferase LAG1

General function:: Involved in protein binding
Specific function:: Component of the ceramide synthase complex required for C26-CoA-dependent ceramide synthesis. Redundant with LAC1. Facilitates ER-to-Golgi transport of GPI-anchored proteins. Involved in the aging process. Deletion of LAG1 results in a pronounced increase (approximately 50%) in mean and in maximum life span
Gene Name:: LAG1
Uniprot ID:: P38703
Molecular weight:: 48454.10156

Reactions

Acyl-CoA + sphingosine → CoA + N-acylsphingosine.

Protein Details

4. Alkaline ceramidase YPC1

General function:: Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amides
Specific function:: Hydrolyzes phytoceramide and also dihydroceramide into phytosphingosine or dihydrosphingosine. Prefers phytoceramide. Has also reverse hydrolysis activity, catalyzing synthesis of phytoceramide and dihydroceramide from palmitic acid and phytosphingosine or dihydrosphingosine. Is not responsible for the breakdown of unsaturated ceramide
Gene Name:: YPC1
Uniprot ID:: P38298
Molecular weight:: 36419.39844

Reactions

Protein Details

5. Sphingosine N-acyltransferase LAC1

General function:: Involved in identical protein binding
Specific function:: Component of the ceramide synthase complex required for C26-CoA-dependent ceramide synthesis. Redundant with LAG1. Facilitates ER-to-Golgi transport of GPI-anchored proteins
Gene Name:: LAC1
Uniprot ID:: P28496
Molecular weight:: 48991.60156

Reactions

Acyl-CoA + sphingosine → CoA + N-acylsphingosine.

Protein Details

6. Enoyl-[acyl-carrier protein] reductase [NADPH, B-specific], mitochondrial

General function:: Involved in zinc ion binding
Specific function:: Required for respiration and the maintenance of the mitochondrial compartment. May have a role in the mitochondrial synthesis of fatty acids
Gene Name:: ETR1
Uniprot ID:: P38071
Molecular weight:: 42066.5

Reactions

Acyl-[acyl-carrier-protein] + NADP(+) → trans-2,3-dehydroacyl-[acyl-carrier-protein] + NADPH.
Acyl-CoA + NADP(+) → trans-2,3-dehydroacyl-CoA + NADPH.

Transporters

Protein Details

1. Very long-chain fatty acid transport protein

General function:: Involved in catalytic activity
Specific function:: May be involved in long-chain fatty acids uptake, and thus may play a pivotal role in regulating their accessibility prior to metabolic utilization. May play an important role in uptake of these hydrophobic compounds under conditions where fatty acid synthesis is compromised
Gene Name:: FAT1
Uniprot ID:: P38225
Molecular weight:: 77140.29688

Reactions

Structure for #<Compound:0xaf7aa1c0>

Enzymes

Reactions

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Transporters

Reactions