(S)-3-hydroxyhexacosanoyl-CoA (YMDB00959)

Identification

YMDB ID

YMDB00959

Name

(S)-3-hydroxyhexacosanoyl-CoA

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

(S)-3-hydroxyhexacosanoyl-CoA, also known as 3-hydroxycerotyl-coenzyme A, belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups. Thus, (S)-3-hydroxyhexacosanoyl-CoA is considered to be a fatty ester lipid molecule (S)-3-hydroxyhexacosanoyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (S)-3-hydroxyhexacosanoyl-CoA may be a unique S. cerevisiae (yeast) metabolite.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(S)-3-hydroxyhexacosanoyl-Coenzyme A
3-hydroxycerotyl-CoA
3-hydroxycerotyl-coenzyme A
beta-hydroxycerotyl-CoA
beta-hydroxycerotyl-coenzyme A
b-Hydroxycerotyl-CoA
Β-hydroxycerotyl-CoA
b-Hydroxycerotyl-coenzyme A
Β-hydroxycerotyl-coenzyme A

CAS number

Not Available

Weight

Average: 1162.208
Monoisotopic: 1161.496289209

InChI Key

GBMJOTOUUWGTIA-FUMULLQGSA-N

InChI

InChI=1S/C47H86N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-35(55)30-38(57)76-29-28-49-37(56)26-27-50-45(60)42(59)47(2,3)32-69-75(66,67)72-74(64,65)68-31-36-41(71-73(61,62)63)40(58)46(70-36)54-34-53-39-43(48)51-33-52-44(39)54/h33-36,40-42,46,55,58-59H,4-32H2,1-3H3,(H,49,56)(H,50,60)(H,64,65)(H,66,67)(H2,48,51,52)(H2,61,62,63)/t35-,36+,40+,41+,42-,46+/m0/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-{[(3S)-3-hydroxyhexacosanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

Traditional IUPAC Name

3-hydroxycerotyl-coa

Chemical Formula

C₄₇H₈₆N₇O₁₈P₃S

SMILES

CCCCCCCCCCCCCCCCCCCCCCC[C@H](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 hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexose phosphates

Alternative Parents

Substituents

Hexose phosphate
Monosaccharide phosphate
Monoalkyl phosphate
Organic phosphoric acid derivative
Alkyl phosphate
Oxane
Phosphoric acid ester
Hemiacetal
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Alcohol
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-hexopyranose 6-phosphate (CHEBI:48066 )
D-mannose 6-phosphate (CHEBI:48066 )

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	0.06 g/L	ALOGPS
logP	4.2	ALOGPS
logP	2.72	ChemAxon
logS	-4.3	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	44	ChemAxon
Refractivity	284.17 m³·mol⁻¹	ChemAxon
Polarizability	122.61 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

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

water + trans-hexacos-2-enoyl-CoA ↔ (S)-3-hydroxyhexacosanoyl-CoA

NAD + (S)-3-hydroxyhexacosanoyl-CoA ↔ NADH + hydron + 3-oxohexacosanoyl-CoA

NADPH + hydron + 3-oxohexacosanoyl-CoA ↔ NADP + (S)-3-hydroxyhexacosanoyl-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	splash10-000l-0900331100-1c21534cdeb29c87d08d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0079-0901522000-94695064d32e2ba8dcac	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0079-1900310000-d32819200e342cf66f54	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00o3-2903131310-350a01e002e90c53bf22	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-2901210010-43df746193d1f481f5f6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-7900000000-2cb625a570d900426ede	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
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	52976
HMDB ID	Not Available
Pubchem Compound ID	25271601
Kegg ID	Not Available
ChemSpider ID	Not Available
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. Peroxisomal hydratase-dehydrogenase-epimerase

General function:: Involved in oxidoreductase activity
Specific function:: Second trifunctional enzyme acting on the beta-oxidation pathway for fatty acids, possessing hydratase-dehydrogenase- epimerase activities. Converts trans-2-enoyl-CoA via D-3- hydroxyacyl-CoA to 3-ketoacyl-CoA
Gene Name:: FOX2
Uniprot ID:: Q02207
Molecular weight:: 98702.39844

Reactions

(3R)-3-hydroxyacyl-CoA → (2E)-2-enoyl-CoA + H(2)O.
(R)-3-hydroxyacyl-CoA + NAD(+) → 3-oxoacyl-CoA + NADH.

Protein Details

2. 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:0xaffb0388>

Enzymes

Reactions

Reactions