trans-oct-2-enoyl-CoA (PAMDB120324)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120324
Identification
Name: trans-oct-2-enoyl-CoA
Description:A trans-2,3-didehydroacyl-CoA(4−) arising from deprotonation of the phosphate and diphosphate OH groups of trans-oct-2-enoyl-CoA; major species at pH 7.3.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (2E)-octenoyl-CoA
  • (2E)-octenoyl-CoA(4−)
  • (2E)-octenoyl-coenzyme A(4−)
  • trans-2,3-didehydroacyl-CoA (C8)(4−)
  • trans-2-octenoyl-coenzyme A(4−)
  • trans-oct-2-enoyl-coenzyme A(4−)
Chemical Formula: C29H44N7O17P3S
Average Molecular Weight: 887.685
Monoisotopic Molecular Weight: 891.20404
InChI Key: CPSDNAXXKWVYIY-NTLMCJQISA-J
InChI:InChI=1S/C29H48N7O17P3S/c1-4-5-6-7-8-9-20(38)57-13-12-31-19(37)10-11-32-27(41)24(40)29(2,3)15-50-56(47,48)53-55(45,46)49-14-18-23(52-54(42,43)44)22(39)28(51-18)36-17-35-21-25(30)33-16-34-26(21)36/h8-9,16-18,22-24,28,39-40H,4-7,10-15H2,1-3H3,(H,31,37)(H,32,41)(H,45,46)(H,47,48)(H2,30,33,34)(H2,42,43,44)/p-4/b9-8+/t18-,22-,23-,24+,28-/m1/s1
CAS number: 10018-94-7
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-[(2E)-oct-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-[(2E)-oct-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
SMILES:CCCCCC=CC(=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 medium-chain 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a medium-chain 2-enoyl chain of 5 to 12 carbon atoms.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Lipids and lipid-like molecules
Sub ClassFatty Acyls
Direct Parent Medium-chain 2-enoyl 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
LogP-1.281Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.13 mg/mLALOGPS
logP0.55ALOGPS
logP-3.8ChemAxon
logS-2.5ALOGPS
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 Count25ChemAxon
Refractivity200.93 m3·mol-1ChemAxon
Polarizability81.26 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
trans-oct-2-enoyl-CoA + Water → (S)-3-hydroxyoctanoyl-CoA
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1912000120-6a4c400b3152685ddc42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0933000000-6bfba9e629e0c41c1c83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1911000000-7bd78cc2705414ac12aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00gl-3911030340-0a6b8d53ed19f026db3fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ai-3910010010-8cc155429b1ae945edc0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900000000-8852cd72aadbe50cd70bView in MoNA
References
References:
  • Tajima G, Sakura N, Yofune H, Nishimura Y, Ono H, Hasegawa Y, Hata I, Kimura M, Yamaguchi S, Shigematsu Y, Kobayashi M: Enzymatic diagnosis of medium-chain acyl-CoA dehydrogenase deficiency by detecting 2-octenoyl-CoA production using high-performance liquid chromatography: a practical confirmatory test for tandem mass spectrometry newborn screening in Japan. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Sep 5;823(2):122-30. [16046200 ]
  • Cummings JG, Lau SM, Powell PJ, Thorpe C: Reductive half-reaction in medium-chain acyl-CoA dehydrogenase: modulation of internal equilibrium by carboxymethylation of a specific methionine residue. Biochemistry. 1992 Sep 15;31(36):8523-9. [1390638 ]
  • Kumar NR, Srivastava DK: Reductive half-reaction of medium-chain fatty acyl-CoA dehydrogenase utilizing octanoyl-CoA/octenoyl-CoA as a physiological substrate/product pair: similarity in the microscopic pathways of octanoyl-CoA oxidation and octenoyl-CoA binding. Biochemistry. 1994 Jul 26;33(29):8833-41. [8038175 ]
Synthesis Reference: Reiser, S. E.; Gruys, K. J.; Mitsky, T. A. Characterization and cloning of an (R)-specific trans-2,3-enoylacyl-CoA hydratase from Rhodospirillum rubrum and use of this enzyme for PHA production in Escherichia coli. Applied Microbiology and Biotechnology (2000), 53(2), 209-218.
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
HMDBHMDB03949
BIGG45482
CHEBI62242
PUBCHEM46173358
LIGAND-CPDC05276