(S)-3-hydroxyhexanoyl-CoA (CHEM041773)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:41:37 UTC
Update Date2016-11-09 01:22:32 UTC
Accession NumberCHEM041773
Identification
Common Name(S)-3-hydroxyhexanoyl-CoA
ClassSmall Molecule
Description(S)-Hydroxyhexanoyl-CoA, also known as (S)-3-hydroxycaproyl-coa, belongs to the class of organic compounds known as (s)-3-hydroxyacyl coas. These are organic compounds containing a (S)-3-hydroxyl acylated coenzyme A derivative. Thus, (S)-hydroxyhexanoyl-CoA is considered to be a fatty ester lipid molecule (S)-Hydroxyhexanoyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (S)-Hydroxyhexanoyl-CoA exists in all living species, ranging from bacteria to humans. In cattle, (S)-hydroxyhexanoyl-CoA is involved in the metabolic pathway called the mitochondrial Beta-oxidation OF short chain saturated fatty acids pathway.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(S)-3-Hydroxycaproyl-CoAChEBI
(S)-3-Hydroxycaproyl-coenzyme AChEBI
3-Hydroxyhexanoyl-coenzyme AChEBI
(S)-3-Hydroxyhexanoyl-CoAKegg
(S)-Hydroxyhexanoyl-CoAChEBI
Chemical FormulaC27H46N7O18P3S
Average Molecular Mass881.680 g/mol
Monoisotopic Mass881.183 g/mol
CAS Registry NumberNot Available
IUPAC Name4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-N-{2-[(2-{[(3S)-3-hydroxyhexanoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-3,3-dimethylbutanimidic acid
Traditional Name(S)-hydroxyhexanoyl-coa
SMILES[H][C@](O)(CCC)CC(=O)SCCN=C(O)CCN=C(O)[C@]([H])(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O
InChI IdentifierInChI=1S/C27H46N7O18P3S/c1-4-5-15(35)10-18(37)56-9-8-29-17(36)6-7-30-25(40)22(39)27(2,3)12-49-55(46,47)52-54(44,45)48-11-16-21(51-53(41,42)43)20(38)26(50-16)34-14-33-19-23(28)31-13-32-24(19)34/h13-16,20-22,26,35,38-39H,4-12H2,1-3H3,(H,29,36)(H,30,40)(H,44,45)(H,46,47)(H2,28,31,32)(H2,41,42,43)/t15-,16+,20+,21+,22-,26+/m0/s1
InChI KeyVAAHKRMGOFIORX-IKTBLOROSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as (s)-3-hydroxyacyl coas. These are organic compounds containing a (S)-3-hydroxyl acylated coenzyme A derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent(S)-3-hydroxyacyl 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 Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.71 g/LALOGPS
logP-0.28ALOGPS
logP-4.8ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)6.42ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area390.84 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity193.2 m³·mol⁻¹ChemAxon
Polarizability79.92 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1912000130-9d32f1a7db66966548f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0913000000-325a72f7e906068360b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1911000000-391d16b13e4ae8bf53deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-5911140350-4d35b969b1c6af839051Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3910110010-ec218967cee87cdd7488Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-4900100000-f4b7577fa42ccd3e2deeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0000000090-b8add5209e54d6b6e866Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pa-0500000290-e534ff3e17b57c33f0ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0029000000-3ad72154a1670e7077a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000090-22f1eaad51934a88d28cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00p0-7800102890-d08bf7452876ed8a38d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002o-9302601610-9537bb62a975804266fcSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0003942
FooDB IDFDB030163
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID10140154
ChEBI ID28276
PubChem Compound ID11966160
Kegg Compound IDC05268
YMDB IDYMDB16169
ECMDB IDECMDB03942
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Tamvakopoulos, Constantine S.; Anderson, Vernon E. Detection of acyl-coenzyme A thioester intermediates of fatty acid b-oxidation as the N-acylglycines by negative-ion chemical ionization gas chromatography mass spectrometry. Anal Biochem. 1992 Feb 1;200(2):381-7. Pubmed: 1632504
2. Dalluge JJ, Gort S, Hobson R, Selifonova O, Amore F, Gokarn R: Separation and identification of organic acid-coenzyme A thioesters using liquid chromatography/electrospray ionization-mass spectrometry. Anal Bioanal Chem. 2002 Nov;374(5):835-40. Epub 2002 Oct 8.
3. Klees AG, Linder D, Buckel W: 2-Hydroxyglutaryl-CoA dehydratase from Fusobacterium nucleatum (subsp. nucleatum): an iron-sulfur flavoprotein. Arch Microbiol. 1992;158(4):294-301.
4. Kim J, Hetzel M, Boiangiu CD, Buckel W: Dehydration of (R)-2-hydroxyacyl-CoA to enoyl-CoA in the fermentation of alpha-amino acids by anaerobic bacteria. FEMS Microbiol Rev. 2004 Oct;28(4):455-68.
5. Hofmeister AE, Buckel W: (R)-lactyl-CoA dehydratase from Clostridium propionicum. Stereochemistry of the dehydration of (R)-2-hydroxybutyryl-CoA to crotonyl-CoA. Eur J Biochem. 1992 Jun 1;206(2):547-52.
6. Kuchta RD, Hanson GR, Holmquist B, Abeles RH: Fe-S centers in lactyl-CoA dehydratase. Biochemistry. 1986 Nov 18;25(23):7301-7.
7. Kuchta RD, Abeles RH: Lactate reduction in Clostridium propionicum. Purification and properties of lactyl-CoA dehydratase. J Biol Chem. 1985 Oct 25;260(24):13181-9.
8. Sokatch JR: Alanine and aspartate formation during growth on valine-C14 by Pseudomonas aeruginosa. J Bacteriol. 1966 Jul;92(1):72-5.
9. Megraw RE, Reeves HC, Ajl SJ: Formation of lactyl-coenzyme A and pyruvyl-coenzyme A from lactic acid by Escherichia coli. J Bacteriol. 1965 Oct;90(4):984-8.