Stearoyl-CoA (PAMDB001690)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB001690
Identification
Name: Stearoyl-CoA
Description:Stearoyl-CoA is derived from stearic acid, which is a saturated fatty acid consisting of 18 carbons. Stearoyl-CoA is a long-chain acyl CoA ester that acts as an intermediate metabolite in the biosynthesis of monounsaturated fatty acids. Stearoyl-CoA is converted into oleoyl-CoA and then used as a major substrate for the synthesis of various kinds of lipids including phospholipids, triglycerides, cholesteryl esters and wax esters. There is growing recognition that acyl-CoA esters could act as signaling molecules in cellular metabolism. (HMDB)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 3'-Phosphoadenosine 5'-(3-{(3R)-3-hydroxy-2,2-dimethyl-4-[(3-{[2-(octadecanoylsulfanyl)ethyl]amino}-3-oxopropyl)amino]-4-oxobutyl} dihydrogen diphosphate)
  • 3'-Phosphoadenosine 5'-(3-{(3R)-3-hydroxy-2,2-dimethyl-4-[(3-{[2-(octadecanoylsulfanyl)ethyl]amino}-3-oxopropyl)amino]-4-oxobutyl} dihydrogen diphosphoric acid)
  • 3'-Phosphoadenosine 5'-(3-{(3R)-3-hydroxy-2,2-dimethyl-4-[(3-{[2-(octadecanoylsulphanyl)ethyl]amino}-3-oxopropyl)amino]-4-oxobutyl} dihydrogen diphosphate)
  • 3'-Phosphoadenosine 5'-(3-{(3R)-3-hydroxy-2,2-dimethyl-4-[(3-{[2-(octadecanoylsulphanyl)ethyl]amino}-3-oxopropyl)amino]-4-oxobutyl} dihydrogen diphosphoric acid)
  • C18:0-CoA
  • C18:0-coenzyme A
  • Octadecanoyl-coa
  • Octadecanoyl-coenzyme A
  • S-Octadecanoate
  • S-Octadecanoate CoA
  • S-Octadecanoate Coenzyme A
  • S-Octadecanoic acid
  • S-Octadecanoic acid CoA
  • S-Octadecanoic acid Coenzyme A
  • S-Stearate CoA
  • S-Stearate Coenzyme A
  • S-Stearic acid CoA
  • S-Stearic acid Coenzyme A
  • S-Stearoyl-CoA
  • S-Stearoylcoenzyme A
  • Stearoyl coenzyme A
  • Stearoyl coenzyme A ester
  • Stearoyl-CoA
  • Stearoyl-CoA (N-C18:0CoA)
  • Stearoyl-coenzyme A
  • Stearyl coenzyme A
  • Stearyl-coa
  • Stearyl-Coenzyme A
Chemical Formula: C39H70N7O17P3S
Average Molecular Weight: 1033.996
Monoisotopic Molecular Weight: 1033.376174075
InChI Key: SIARJEKBADXQJG-KBEKLFCESA-N
InChI:InChI=1S/C39H70N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h26-28,32-34,38,49-50H,4-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/t28-,32-,33-,34?,38-/m1/s1
CAS number: 362-66-3
IUPAC Name:{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-[(2-{[2-(octadecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name: stearoyl-coa
SMILES:CCCCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(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
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as 2,3,4-saturated fatty acyl coas. These are acyl-CoAs carrying a 2,3,4-saturated fatty acyl chain.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent 2,3,4-saturated fatty acyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside 3',5'-bisphosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Thiocarboxylic acid ester
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfenyl compound
  • Thioether
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-4
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.947 mg/mLALOGPS
logP2.86ALOGPS
logP0.39ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area363.63 Å2ChemAxon
Rotatable Bond Count36ChemAxon
Refractivity245.85 m3·mol-1ChemAxon
Polarizability105.93 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Adenosine triphosphate + Coenzyme A + Hydrogen ion + Octadecanoate (N-C18:0) > Adenosine monophosphate + Hydrogen ion + Pyrophosphate + Stearoyl-CoA
FAD + Stearoyl-CoA <> FADH2 + Trans-Octadec-2-enoyl-CoA
Water + Stearoyl-CoA > Coenzyme A + Hydrogen ion + Octadecanoate (N-C18:0)
3-Oxohexadecanoyl-CoA + Coenzyme A > Acetyl-CoA + Stearoyl-CoA + Stearoyl-CoA
3-Oxooctadecanoyl-CoA + Coenzyme A + 3-Oxooctadecanoyl-CoA > Acetyl-CoA + Stearoyl-CoA + Stearoyl-CoA
Stearic acid + Adenosine triphosphate + Coenzyme A > Adenosine monophosphate + Stearoyl-CoA + Stearoyl-CoA
LPA(18:1(9Z)/0:0) + Stearoyl-CoA + Stearoyl-CoA > DG(19:1(9Z)/18:1(9Z)/0:0) + Coenzyme A
LPA(18:1(9Z)/0:0) + Stearoyl-CoA + Stearoyl-CoA > Coenzyme A + DG(18:1(9Z)/18:1(9Z)/0:0) + DG(18:1(9Z)/18:1(9Z)/0:0)
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-4902020200-5a1b761dbd3ae47645dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0913030000-5a17204843fadcac3bedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900010100-b6c7caf375fb95a63c12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00lr-9651431400-0641aa40dcbe88da74e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-4920210000-da4b1e3bca98f2ef639cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-7900000000-3a6248882b3973700845View in MoNA
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID15541
HMDB IDHMDB01114
Pubchem Compound ID439229
Kegg IDC00412
ChemSpider ID84957
Wikipedia IDStearoyl-CoA
BioCyc IDSTEAROYL-COA
EcoCyc IDSTEAROYL-COA

Enzymes

Protein Details
• 3-ketoacyl-CoA thiolase
General function:
Involved in acetyl-CoA C-acyltransferase activity
Specific function:
Catalyzes the final step of fatty acid oxidation in which acetyl-CoA is released and the CoA ester of a fatty acid two carbons shorter is formed. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
Gene Name:
fadA
Locus Tag:
PA3013
Molecular weight:
41.6 kDa
Reactions
Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA.
Protein Details
• Long-chain-fatty-acid--CoA ligase
General function:
Involved in catalytic activity
Specific function:
Catalyzes the esterification, concomitant with transport, of exogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids
Gene Name:
fadD
Locus Tag:
PA3299
Molecular weight:
61.7 kDa
Reactions
ATP + a long-chain fatty acid + CoA = AMP + diphosphate + an acyl-CoA.
Protein Details
• Acyl-coenzyme A dehydrogenase
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Catalyzes the dehydrogenation of acyl-CoA
Gene Name:
fadE
Locus Tag:
PA2815
Molecular weight:
88.8 kDa
Reactions
An acyl-CoA + FAD = a dehydrogenated acyl-CoA + FADH(2).
Protein Details
• Acyl-CoA thioesterase 2
General function:
Involved in acyl-CoA hydrolase activity
Specific function:
Can hydrolyze a broad range of acyl-CoA thioesters. Its physiological function is not known
Gene Name:
tesB
Locus Tag:
PA3942
Molecular weight:
32.9 kDa