stearoyl-CoA (PAMDB110390)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110390
Identification
Name: stearoyl-CoA
Description:An acyl-CoA(4-) arising from deprotonation of phosphate and diphosphate functions of stearoyl-CoA.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • Stearoyl-CoA (n-C18:0CoA)
  • stearyl-CoA
  • stearyl coenzyme A
Chemical Formula: C39H66N7O17P3S
Average Molecular Weight: 1030
Monoisotopic Molecular Weight: 1033.3761740791
InChI Key: SIARJEKBADXQJG-LFZQUHGESA-J
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)/p-4/t28-,32-,33-,34+,38-/m1/s1
CAS number: 362-66-3
IUPAC Name:3'-phosphonatoadenosine 5'-(3-{(3R)-3-hydroxy-2,2-dimethyl-4-[(3-{[2-(octadecanoylsulfanyl)ethyl]amino}-3-oxopropyl)amino]-4-oxobutyl} diphosphate)
Traditional IUPAC Name: [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-[(2-{[2-(octadecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
SMILES:CCCCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(C(O)C(C)(C)COP([O-])(=O)OP([O-])(=O)OCC1(C(OP(=O)([O-])[O-])C(O)C(O1)N3(C=NC2(C(N)=NC=NC=23))))=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities 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 Chemical entities
Super ClassOrganic compounds
Class Lipids and lipid-like molecules
Sub ClassFatty Acyls
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
  • Pentose phosphate
  • Pentose-5-phosphate
  • Ribonucleoside 3'-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • 6-aminopurine
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Fatty amide
  • Imidolactam
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Primary aromatic amine
  • Pyrimidine
  • Oxolane
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Thiocarboxylic acid ester
  • Carboxamide group
  • Carbothioic s-ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Alcohol
  • Organic nitrogen compound
  • Amine
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Primary amine
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-4
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.95 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
Polarizability104.58 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
stearoyl-CoA + Oxygen + Hydrogen ion → oleoyl-CoA + Water
stearoyl-CoA + Water → Hydrogen ion + Octadecanoate (N-C18:0) + coenzyme A
Pathways: Not Available
Spectra
Spectra: Not Available
References
References:
  • Castro-Chavez F: Microarrays, antiobesity and the liver. Ann Hepatol. 2004 Oct-Dec;3(4):137-45. [15657555 ]
  • Miyazaki M, Ntambi JM: Role of stearoyl-coenzyme A desaturase in lipid metabolism. Prostaglandins Leukot Essent Fatty Acids. 2003 Feb;68(2):113-21. [12538075 ]
  • Sonnino S, Chigorno V: Ganglioside molecular species containing C18- and C20-sphingosine in mammalian nervous tissues and neuronal cell cultures. Biochim Biophys Acta. 2000 Sep 18;1469(2):63-77. [10998569 ]
Synthesis Reference: Boiron F; Heape M A; Cassagne C Assay of stearoyl-CoA synthesis in microsomes from normal and Trembler mouse sciatic nerves. Neuroscience letters (1984), 48(1), 7-12.
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CAS362-66-3
ChEBI57394
HMDBHMDB01114
IAF12601451385
KEGGC00412
MetaboLightsMTBLC57394
PubChem25245778