Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.


Record Information
Version2.0
Creation Date2012-05-31 13:55:51 -0600
Update Date2015-06-03 15:54:15 -0600
Secondary Accession Numbers
  • ECMDB02159
Identification
Name:3alpha,7alpha-Dihydroxy-5beta-cholestanoyl-CoA
DescriptionTrans-octadec-2-enoyl-CoA is a member of the chemical class known as Coenzyme A and Derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine.
Structure
Thumb
Synonyms:
  • 3-a,7-a-Dihydroxy-5-b-cholestanoyl-CoA
  • 3-a,7-a-Dihydroxy-5-b-cholestanoyl-coenzyme A
  • 3-alpha,7-alpha-Dihydroxy-5-beta-cholestanoyl-CoA
  • 3-alpha,7-alpha-Dihydroxy-5-beta-cholestanoyl-Coenzyme A
  • 3-α,7-α-Dihydroxy-5-β-cholestanoyl-CoA
  • 3-α,7-α-Dihydroxy-5-β-cholestanoyl-coenzyme A
  • 3a,7a-Dihydroxy-5b-cholestanoyl-CoA
  • 3a,7a-Dihydroxy-5b-cholestanoyl-coenzyme A
  • 3alpha,7alpha-Dihydroxy-5beta-cholestanoyl-CoA
  • 3alpha,7alpha-Dihydroxy-5beta-cholestanoyl-Coenzyme A
  • 3α,7α-Dihydroxy-5β-cholestanoyl-CoA
  • 3α,7α-Dihydroxy-5β-cholestanoyl-coenzyme A
  • DHCA
Chemical Formula:C48H80N7O19P3S
Weight:Average: 1184.171
Monoisotopic: 1183.444253639
InChI Key:SBYLHTNKEWSLBA-CPRJDYHCSA-N
InChI:InChI=1S/C48H80N7O19P3S/c1-26(30-10-11-31-36-32(13-16-48(30,31)6)47(5)15-12-29(56)20-28(47)21-33(36)57)8-7-9-27(2)45(62)78-19-18-50-35(58)14-17-51-43(61)40(60)46(3,4)23-71-77(68,69)74-76(66,67)70-22-34-39(73-75(63,64)65)38(59)44(72-34)55-25-54-37-41(49)52-24-53-42(37)55/h24-34,36,38-40,44,56-57,59-60H,7-23H2,1-6H3,(H,50,58)(H,51,61)(H,66,67)(H,68,69)(H2,49,52,53)(H2,63,64,65)/t26?,27?,28-,29+,30?,31?,32?,33+,34+,36?,38+,39+,40?,44+,47-,48+/m0/s1
CAS number:2461-62-3
IUPAC Name:{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-({6-[(2S,5R,7S,9R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2-methylheptanoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name:[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-{[({3-[(2-{[2-({6-[(2S,5R,7S,9R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2-methylheptanoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid
SMILES:[H][C@@]12C[C@H](O)CC[C@]1(C)C1CC[C@]3(C)C(CCC3C1[C@H](O)C2)C(C)CCCC(C)C(=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=C(N)N=CN=C12
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent2,3,4-saturated fatty acyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Steroidal glycoside
  • Dihydroxy bile acid, alcohol, or derivatives
  • Hydroxy bile acid, alcohol, or derivatives
  • Cholane-skeleton
  • Bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 7-hydroxysteroid
  • Steroid
  • Ribonucleoside 3'-phosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • Organic pyrophosphate
  • 6-aminopurine
  • Pentose monosaccharide
  • Monosaccharide phosphate
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Pyrimidine
  • Monosaccharide
  • N-acyl-amine
  • Phosphoric acid ester
  • Fatty amide
  • N-substituted imidazole
  • Imidolactam
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Azole
  • Tetrahydrofuran
  • Cyclic alcohol
  • Imidazole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Carbothioic s-ester
  • Carboxamide group
  • Thiocarboxylic acid ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Thiocarboxylic acid or derivatives
  • Oxacycle
  • Sulfenyl compound
  • Azacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Primary amine
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organopnictogen compound
  • Amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
State:Solid
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.37 g/LALOGPS
logP1.86ALOGPS
logP-1.6ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area404.09 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity282.61 m³·mol⁻¹ChemAxon
Polarizability117.46 ųChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1900112000-0c75e0a93454d43ab753View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900314000-ee39276da14ef1ec86d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000010-5f6513051536bb79e578View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00lr-2901332400-00267947c2aa67bae2f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-3900111010-35ffb32be4339618cff9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-125c30cd4205b3d5be3dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0900000000-eb50c2a058862834d250View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-0900102622-13f5492940fca24737d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0000119000-c789136e01e3fc6660eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-787baca3a444ef57d1b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2900301100-c831b98264288f5ecac5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0170-6605603900-a71bad576505bfdacb19View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Keseler, I. M., Collado-Vides, J., Gama-Castro, S., Ingraham, J., Paley, S., Paulsen, I. T., Peralta-Gil, M., Karp, P. D. (2005). "EcoCyc: a comprehensive database resource for Escherichia coli." Nucleic Acids Res 33:D334-D337. Pubmed: 15608210
  • Prydz K, Kase BF, Bjorkhem I, Pedersen JI: Subcellular localization of 3 alpha, 7 alpha-dihydroxy- and 3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholestanoyl-coenzyme A ligase(s) in rat liver. J Lipid Res. 1988 Aug;29(8):997-1004. Pubmed: 3183523
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID15494
HMDB IDHMDB02159
Pubchem Compound ID440420
Kegg IDC04644
ChemSpider ID389367
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

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
Uniprot ID:
P21151
Molecular weight:
40876
Reactions
Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA.
General function:
Involved in transferase 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. Strongly involved in the anaerobic degradation of long and medium-chain fatty acids in the presence of nitrate and weakly involved in the aerobic degradation of long- chain fatty acids
Gene Name:
fadI
Uniprot ID:
P76503
Molecular weight:
46530
Reactions
Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA.