3-hydroxyicosanoyl-CoA (YMDB00731)

Identification

YMDB ID

YMDB00731

Name

3-hydroxyicosanoyl-CoA

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

3-hydroxyicosanoyl-CoA, also known as 3-hydroxy-C20-CoA, belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms. Thus, 3-hydroxyicosanoyl-CoA is considered to be a fatty ester lipid molecule. 3-hydroxyicosanoyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI

Synonyms

3-hydroxy-C20-CoA
3-hydroxyeicosanoyl-CoA
3-hydroxyeicosanoyl-coenzyme A
3-hydroxyicosanoyl-coenzyme A

CAS number

Not Available

Weight

Average: 1078.049
Monoisotopic: 1077.402388825

InChI Key

KNSVYMFEJLUJST-MJMSVFGZSA-N

InChI

InChI=1S/C41H74N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-29(49)24-32(51)70-23-22-43-31(50)20-21-44-39(54)36(53)41(2,3)26-63-69(60,61)66-68(58,59)62-25-30-35(65-67(55,56)57)34(52)40(64-30)48-28-47-33-37(42)45-27-46-38(33)48/h27-30,34-36,40,49,52-53H,4-26H2,1-3H3,(H,43,50)(H,44,54)(H,58,59)(H,60,61)(H2,42,45,46)(H2,55,56,57)/t29?,30-,34-,35-,36+,40-/m1/s1

IUPAC Name

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

Traditional IUPAC Name

3-hydroxyeicosanoyl-coa

Chemical Formula

C₄₁H₇₄N₇O₁₈P₃S

SMILES

CCCCCCCCCCCCCCCCCC(O)CC(=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 long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

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

3-hydroxy fatty acyl-CoA (CHEBI:52324 )

Physical Properties

State

Not Available

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	0.99 g/L	ALOGPS
logP	2.72	ALOGPS
logP	0.052	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	4.95	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	383.86 Å²	ChemAxon
Rotatable Bond Count	38	ChemAxon
Refractivity	256.57 m³·mol⁻¹	ChemAxon
Polarizability	110.84 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

endoplasmic reticulum

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

NADPH + hydron + 3-oxoicosanoyl-CoA ↔ NADP + 3-hydroxyicosanoyl-CoA

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	splash10-000i-5906510200-d2ac6070fc964f6ca746	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1917220000-af2c96a0931bad1b7725	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1903100000-ab9263783a739bc837a9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a7i-9632231500-d64e5c579355e8f13fd8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0560-4911310100-6753d331abbd5cd1f247	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-8900100000-96ee8b08a2d765025324	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
Han, G., Gable, K., Kohlwein, S. D., Beaudoin, F., Napier, J. A., Dunn, T. M. (2002). "The Saccharomyces cerevisiae YBR159w gene encodes the 3-ketoreductase of the microsomal fatty acid elongase." J Biol Chem 277:35440-35449.12087109

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	52324
HMDB ID	Not Available
Pubchem Compound ID	25229587
Kegg ID	Not Available
ChemSpider ID	23106991
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. 3-ketoacyl-CoA reductase

General function:: Involved in oxidoreductase activity
Specific function:: Component of the microsomal membrane bound fatty acid elongation system, which produces the 26-carbon very long-chain fatty acids (VLCFA) from palmitate. Catalyzes the reduction of the 3-ketoacyl-CoA intermediate that is formed in each cycle of fatty acid elongation. VLCFAs serve as precursors for ceramide and sphingolipids
Gene Name:: IFA38
Uniprot ID:: P38286
Molecular weight:: 38707.80078

Reactions

3-hydroxyacyl-CoA + NADP(+) → 3-oxoacyl-CoA + NADPH.

Structure for #<Compound:0xa39564e4>

Enzymes

Reactions