(S)-3-hydroxydecanoyl-CoA (YMDB00464)

Identification
YMDB IDYMDB00464
Name(S)-3-hydroxydecanoyl-CoA
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description(S)-3-hydroxydecanoyl-CoA, also known as 3-OH 10:0-CoA or 3-hydroxydecanoyl-coenzyme A, belongs to the class of organic compounds known as (s)-3-hydroxyacyl coas. These are organic compounds containing a (S)-3-hydroxyl acylated coenzyme A derivative. Based on a literature review a small amount of articles have been published on (S)-3-hydroxydecanoyl-CoA.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (S)-3-Hydroxydecanoyl-CoA
  • (S)-3-Hydroxydecanoyl-Coenzyme A
  • (S)-Hydroxydecanoyl-CoA
  • 3-Hydroxydecanoyl-CoA
  • 3-Hydroxydecanoyl-Coenzyme A
  • 3-OH 10:0-CoA
  • 3-OH C10:0-CoA
  • 3S-hydroxy-decanoyl-CoA
  • 3S-hydroxy-decanoyl-Coenzyme A
  • b-Hydroxydecanoyl coenzyme A
  • beta-Hydroxydecanoyl coenzyme A
  • beta-hydroxydecanoyl-CoA
  • coenzyme A S-3-hydroxydecanoate
  • DL-b-Hydroxydecanoyl coenzyme A
  • DL-beta-Hydroxydecanoyl coenzyme A
  • S-(3-hydroxydecanoate
  • S-(3-hydroxydecanoate) CoA
  • S-(3-hydroxydecanoate) Coenzyme A
  • S-(3-hydroxydecanoic acid
  • S-(3-Hydroxydecanoyl)coenzyme A
  • Β-hydroxydecanoyl coenzyme A
  • b-Hydroxydecanoyl-CoA
  • Β-hydroxydecanoyl-CoA
  • coenzyme A S-3-Hydroxydecanoic acid
  • 3-Hydroxydecanoyl-coenzyme A, (R)-isomer
CAS number6245-70-1
WeightAverage: 937.783
Monoisotopic: 937.245888185
InChI KeyHIVSMYZAMUNFKZ-PNPVFPMQSA-N
InChIInChI=1S/C31H54N7O18P3S/c1-4-5-6-7-8-9-19(39)14-22(41)60-13-12-33-21(40)10-11-34-29(44)26(43)31(2,3)16-53-59(50,51)56-58(48,49)52-15-20-25(55-57(45,46)47)24(42)30(54-20)38-18-37-23-27(32)35-17-36-28(23)38/h17-20,24-26,30,39,42-43H,4-16H2,1-3H3,(H,33,40)(H,34,44)(H,48,49)(H,50,51)(H2,32,35,36)(H2,45,46,47)/t19-,20+,24+,25+,26-,30+/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-hydroxydecanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name(S)-3-hydroxydecanoyl-coa
Chemical FormulaC31H54N7O18P3S
SMILESCCCCCCC[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 (s)-3-hydroxyacyl coas. These are organic compounds containing a (S)-3-hydroxyl acylated coenzyme A derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent(S)-3-hydroxyacyl 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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogP-1.219PhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.25 g/LALOGPS
logP0.31ALOGPS
logP-3.3ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area383.86 ŲChemAxon
Rotatable Bond Count28ChemAxon
Refractivity210.56 m³·mol⁻¹ChemAxon
Polarizability88.82 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • lipid particle
  • endoplasmic reticulum
  • peroxisome
Organoleptic PropertiesNot Available
SMPDB Pathways
Fatty acid elongation in mitochondriaPW002467 ThumbThumb?image type=greyscaleThumb?image type=simple
Fatty acid metabolismPW002460 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Fatty acid elongation in mitochondriaec00062 Map00062
Fatty acid metabolismec00071 Map00071
SMPDB Reactions
(S)-3-hydroxydecanoyl-CoA ↔ (2E)-Decenoyl-CoA + water
(S)-3-hydroxydecanoyl-CoA + NAD ↔ 3-oxodecanoyl-CoA + hydron + NADH
KEGG Reactions
(S)-3-hydroxydecanoyl-CoA ↔ water + trans-dec-2-enoyl-CoA
NADH + 3-oxodecanoyl-CoA + hydron ↔ (S)-3-hydroxydecanoyl-CoA + NAD
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1955100204-d6525c792d0660eed578JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-1962200000-a6554b2032895e40ea2fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2931000000-994000eb5c23a4a22111JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-017i-2901021304-e79be825caf02b5a8633JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2900210001-793115062cfccb42901dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-7900000000-3c7fb40503eb64a75147JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000009-6ce5bb10296fb5962d7fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0170-3200101229-19c5c4b5d884bb6971bcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00p3-3403501934-b1b23288f3869f2596e0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0000000009-72e71f0413c0c2a433c3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1600100197-d4e309ba205f695a9bcbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0001900000-ddc361c28129c2b8128eJSpectraViewer
MSMass Spectrum (Electron Ionization)Not AvailableJSpectraViewer
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
Synthesis Reference:Qi, Q.; Steinbuchel, A.; Rehm, B. H. A. In vitro synthesis of poly(3-hydroxydecanoate): purification and enzymatic characterization of type II polyhydroxyalkanoate synthases PhaC1 and PhaC2 from Pseudomonas aeruginosa. Applied Microbiology and Biotech
External Links:
ResourceLink
CHEBI ID28325
HMDB IDHMDB03938
Pubchem Compound ID16061159
Kegg IDC05264
ChemSpider ID10140152
FOODB IDFDB030162
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. 3-hydroxyisobutyryl-CoA hydrolase, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes 3-hydroxyisobutyryl-CoA (HIBYL-CoA), a saline catabolite. Has high activity toward isobutyryl-CoA. Could be an isobutyryl-CoA dehydrogenase that functions in valine catabolism. Also hydrolyzes 3-hydroxypropanoyl-CoA. Has an indirect role in endocytic membrane trafficking. May have a function in protein biosynthesis in mitochondrial small ribosomal subunit
Gene Name:
EHD3
Uniprot ID:
P28817
Molecular weight:
56287.89844
Reactions
3-hydroxy-2-methylpropanoyl-CoA + H(2)O → CoA + 3-hydroxy-2-methylpropanoate.
Protein Details
2. 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
3. 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.