Acrylyl-CoA (PAMDB000455)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000455
Identification
Name: Acrylyl-CoA
Description:Acrylyl-CoA is involved in alternative pathways of propionate metabolism.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • Acryloyl coenzyme A
  • Acryloyl-CoA
  • Acryloyl-Coenzyme A
  • Acrylyl coenzyme A
  • Acrylyl-CoA
  • Acrylyl-Coenzyme A
  • CoA S-2-propenoate
  • CoA S-2-propenoic acid
  • CoA S-acrylate
  • CoA S-acrylic acid
  • Coenzyme A S-2-propenoate
  • Coenzyme A S-2-propenoic acid
  • Coenzyme A S-acrylate
  • Coenzyme A S-acrylic acid
  • Propenoyl-coa
  • Thioacrylate S-ester with coenzyme A
  • Thioacrylic acid S-ester with coenzyme A
Chemical Formula: C24H38N7O17P3S
Average Molecular Weight: 821.582
Monoisotopic Molecular Weight: 821.125773051
InChI Key: POODSGUMUCVRTR-UXYNFSPESA-N
InChI:InChI=1S/C24H38N7O17P3S/c1-4-15(33)52-8-7-26-14(32)5-6-27-22(36)19(35)24(2,3)10-45-51(42,43)48-50(40,41)44-9-13-18(47-49(37,38)39)17(34)23(46-13)31-12-30-16-20(25)28-11-29-21(16)31/h4,11-13,17-19,23,34-35H,1,5-10H2,2-3H3,(H,26,32)(H,27,36)(H,40,41)(H,42,43)(H2,25,28,29)(H2,37,38,39)/t13-,17-,18-,19?,23-/m1/s1
CAS number: 5776-58-9
IUPAC Name:{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({3-hydroxy-2,2-dimethyl-3-[(2-{[2-(prop-2-enoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
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-(prop-2-enoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
SMILES:CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12)C(O)C(=O)NCCC(=O)NCCSC(=O)C=C
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent Acyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside 3',5'-bisphosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Beta amino acid or derivatives
  • 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
  • N-acyl-amine
  • Monosaccharide
  • Fatty amide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Thiocarboxylic acid ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thioether
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-4
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility4.22 mg/mLALOGPS
logP-0.49ALOGPS
logP-6ChemAxon
logS-2.3ALOGPS
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 Count21ChemAxon
Refractivity176.86 m3·mol-1ChemAxon
Polarizability71.4 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Propionyl-CoA + NADP <> Acrylyl-CoA + NADPH + Hydrogen ion
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1901000210-a4d30f2a70c854ec2d82View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1912000000-803501d303e8cc732cc1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2901000000-4d83b3d16e1c6d64ab2eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0kji-9830230550-6f9418c26a029c54b1b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-5910100000-b4ef2aba16bbad4960fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900000000-a50282352f056780b347View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • OMMBID: http://genetics.accessmedicine.com/server-java/Arknoid/amed/mmbid/co_chapters/ch094/ch094_p03.html: http://genetics.accessmedicine.com/server-java/Arknoid/amed/mmbid/co_chapters/ch094/ch094_p03.html
Synthesis Reference: Symes, Kenneth Charles; Collier, Simon Andrew; Armitage, Yvonne Christine; Mistry, Rajesh; Baranyai, Robert. Biocatalytic manufacturing of (meth)acrylic esters. PCT Int. Appl. (2007), 40pp. CODEN: PIXXD2 WO 2007039415 A1 20070412 CAN 146:40
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID15513
HMDB IDHMDB02307
Pubchem Compound ID439340
Kegg IDC00894
ChemSpider ID388468
Wikipedia IDNot Available
BioCyc IDACRYLYL-COA
EcoCyc IDACRYLYL-COA