(S)-3-Hydroxyoctadecanoyl-CoA (ECMDB21101) (M2MDB001510)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (3)Transporters (1)XML
Proteins (3)
Record Information
Version2.0
Creation Date2012-07-30 14:54:38 -0600
Update Date2015-06-03 17:20:38 -0600
Secondary Accession Numbers
  • ECMDB21101
Identification
Name:(S)-3-Hydroxyoctadecanoyl-CoA
Description(s)-3-hydroxyoctadecanoyl-coa belongs to the class of Acyl CoAs. These are organic compounds contaning a coenzyme A substructure linked to another moeity through an ester bond. (inferred from compound structure)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 3-Hydroxyoctadecanoyl-CoA
  • 3-Hydroxyoctadecanoyl-coenzyme A
  • b-Hydroxy stearyl-CoA
  • b-Hydroxystearoyl-CoA
  • beta-Hydroxy stearyl-CoA
  • beta-Hydroxystearoyl-CoA
  • β-Hydroxy stearyl-CoA
  • β-Hydroxystearoyl-CoA
Chemical Formula:C39H70N7O18P3S
Weight:Average: 1049.995
Monoisotopic: 1049.371088697
InChI Key:WZMAIEGYXCOYSH-UHFFFAOYSA-N
InChI:InChI=1S/C39H70N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-27(47)22-30(49)68-21-20-41-29(48)18-19-42-37(52)34(51)39(2,3)24-61-67(58,59)64-66(56,57)60-23-28-33(63-65(53,54)55)32(50)38(62-28)46-26-45-31-35(40)43-25-44-36(31)46/h25-28,32-34,38,47,50-51H,4-24H2,1-3H3,(H,41,48)(H,42,52)(H,56,57)(H,58,59)(H2,40,43,44)(H2,53,54,55)
CAS number:Not Available
IUPAC Name:{[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-3-{[2-({2-[(3-hydroxyoctadecanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name:[5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(3-hydroxy-3-{[2-({2-[(3-hydroxyoctadecanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid
SMILES:CCCCCCCCCCCCCCCC(O)CC(=O)SCCN=C(O)CCN=C(O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentLong-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 FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility1.66 g/LALOGPS
logP2.19ALOGPS
logP0.26ChemAxon
logS-2.8ALOGPS
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 Count36ChemAxon
Refractivity247.37 m³·mol⁻¹ChemAxon
Polarizability105.07 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
(S)-3-Hydroxyoctadecanoyl-CoA <> Water + Trans-Octadec-2-enoyl-CoA
3-Oxooctadecanoyl-CoA + Hydrogen ion + NADH <> (S)-3-Hydroxyoctadecanoyl-CoA + NAD
trans-Octadec-2-enoyl-CoA + Trans-Octadec-2-enoyl-CoA > (S)-3-Hydroxyoctadecanoyl-CoA + Water
(S)-3-Hydroxyoctadecanoyl-CoA + NAD > NADH + Hydrogen ion + 3-Oxooctadecanoyl-CoA + 3-Oxooctadecanoyl-CoA
(S)-3-Hydroxyoctadecanoyl-CoA > trans-Octadec-2-enoyl-CoA + Trans-Octadec-2-enoyl-CoA
SMPDB Pathways:
fatty acid oxidation (steareate)PW001024 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-5906510200-e27423e746c8a188623eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-1916320000-03020a5fa5850ac591ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-2903100000-ca873b27caba6e7216a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9650321500-62144c74f8beb42cc740View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-5920210100-6e6ca8f4f51c89fdbae3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-a794af09afbd829afccbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-8cc111a2d051da9f775aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-9100101220-525652784c717821868bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057u-9202401502-2f0d578b496e4c4171f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-9000000000-bb5d0296e5b17ed28334View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-9600100154-177624898c15b1e87fa0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0101390000-1c7948f2963c67ffff7eView in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB0012715
Pubchem Compound ID193824
Kegg IDNot Available
ChemSpider ID168203
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Fatty acid oxidation complex subunit alpha
General function:
Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:
Catalyzes the formation of an hydroxyacyl-CoA by addition of water on enoyl-CoA. Also exhibits 3-hydroxyacyl-CoA epimerase and 3-hydroxyacyl-CoA dehydrogenase activities. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
Gene Name:
fadB
Uniprot ID:
P21177
Molecular weight:
79593
Reactions
(S)-3-hydroxyacyl-CoA + NAD(+) = 3-oxoacyl-CoA + NADH.
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
(S)-3-hydroxybutanoyl-CoA = (R)-3-hydroxybutanoyl-CoA.
(3Z)-dodec-3-enoyl-CoA = (2E)-dodec-2-enoyl-CoA.
Protein Details
2. Probable enoyl-CoA hydratase paaF
General function:
Involved in catalytic activity
Specific function:
Could possibly oxidize fatty acids using specific components
Gene Name:
paaF
Uniprot ID:
P76082
Molecular weight:
27237
Reactions
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
Protein Details
3. Fatty acid oxidation complex subunit alpha_
General function:
Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:
Catalyzes the formation of an hydroxyacyl-CoA by addition of water on enoyl-CoA. Also exhibits 3-hydroxyacyl-CoA epimerase and 3-hydroxyacyl-CoA dehydrogenase activities. Strongly involved in the anaerobic degradation of long and medium-chain fatty acids in the presence of nitrate and weakly involved in the aerobic degradation of long-chain fatty acids
Gene Name:
fadJ
Uniprot ID:
P77399
Molecular weight:
77072
Reactions
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
(S)-3-hydroxyacyl-CoA + NAD(+) = 3-oxoacyl-CoA + NADH.
(S)-3-hydroxybutanoyl-CoA = (R)-3-hydroxybutanoyl-CoA.

Transporters

Protein Details
1. Fatty acid oxidation complex subunit alpha
General function:
Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:
Catalyzes the formation of an hydroxyacyl-CoA by addition of water on enoyl-CoA. Also exhibits 3-hydroxyacyl-CoA epimerase and 3-hydroxyacyl-CoA dehydrogenase activities. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
Gene Name:
fadB
Uniprot ID:
P21177
Molecular weight:
79593
Reactions
(S)-3-hydroxyacyl-CoA + NAD(+) = 3-oxoacyl-CoA + NADH.
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
(S)-3-hydroxybutanoyl-CoA = (R)-3-hydroxybutanoyl-CoA.
(3Z)-dodec-3-enoyl-CoA = (2E)-dodec-2-enoyl-CoA.