Fri. Nov 22nd, 2024
Common Name

3a,7a-Dihydroxy-5b-cholestanoyl-CoA Description

First activated by a fatty acyl-CoA ligase activity, can then be converted to chenodeoxycholic acid by peroxisome rich fractions from rat and human liver (J Lipid Res. 1988 Aug;29(8):997-1004, PMID 3183523 ). Structure

Synonyms

Value Source 3-alpha,7-alpha-Dihydroxy-5-beta-cholestanoyl-CoAHMDB 3-alpha,7-alpha-Dihydroxy-5-beta-cholestanoyl-coenzyme AHMDB 3alpha,7alpha-Dihydroxy-5beta-cholestanoyl-CoAHMDB 3alpha,7alpha-Dihydroxy-5beta-cholestanoyl-coenzyme AHMDB DHCAHMDB

Chemical Formlia

C48H80N7O19P3S Average Molecliar Weight

1184.171 Monoisotopic Molecliar Weight

1183.444253639 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}slifanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid Traditional 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}slifanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid CAS Registry Number

2461-62-3 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

InChI Identifier

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

InChI Key

SBYLHTNKEWSLBA-CPRJDYHCSA-N Chemical Taxonomy Classification

Not classified Ontology Status

Expected but not Quantified Origin

  • Endogenous
  • Food
  • Biofunction

  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Lipid biosynthesis, Fatty acid transport
  • Membrane integrity/stability
  • Application

  • Nutrients
  • Stabilizers
  • Surfactants and Emlisifiers
  • Cellliar locations

  • Extracellliar
  • Membrane
  • Endoplasmic reticlium
  • Peroxisome
  • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.37 mg/mLALOGPS 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 Å2ChemAxon Rotatable Bond Count26ChemAxon Refractivity282.61 m3·mol-1ChemAxon Polarizability117.46 Å3ChemAxon Number of Rings7ChemAxon Bioavailability0ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-000i-1900112000-0c75e0a93454d43ab753View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-000i-0900314000-ee39276da14ef1ec86d2View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-000i-1900000010-5f6513051536bb79e578View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-00lr-2901332400-00267947c2aa67bae2f7View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-003r-3900111010-35ffb32be4339618cff9View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-057i-6900100000-125c30cd4205b3d5be3dView in MoNA

    Biological Properties Cellliar Locations

  • Extracellliar
  • Membrane
  • Endoplasmic reticlium
  • Peroxisome
  • Biofluid Locations

    Not Available Tissue Location

    Not Available Pathways

    Name SMPDB Link KEGG Link 27-Hydroxylase DeficiencySMP00720Not Available Bile Acid BiosynthesisSMP00035map00120 Cerebrotendinous Xanthomatosis (CTX)SMP00315Not Available Congenital Bile Acid Synthesis Defect Type IISMP00314Not Available Congenital Bile Acid Synthesis Defect Type IIISMP00318Not Available Familial Hypercholanemia (FHCA)SMP00317Not Available Zellweger SyndromeSMP00316Not Available

    Normal Concentrations Not Available Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    FDB022875 KNApSAcK ID

    Not Available Chemspider ID

    389367 KEGG Compound ID

    C04644 BioCyc ID

    Not Available BiGG ID

    44249 Wikipedia Link

    Not Available NuGOwiki Link

    HMDB02159 Metagene Link

    HMDB02159 METLIN ID

    6517 PubChem Compound

    440420 PDB ID

    Not Available ChEBI ID

    15494

    Product: Diiodohydroxyquinoline

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. 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 ]

    Enzymes

    General function:
    Involved in transferase activity, transferring acyl groups other than amino-acyl groups
    Specific function:
    Abolishes BNIP3-mediated apoptosis and mitochondrial damage.
    Gene Name:
    ACAA2
    Uniprot ID:
    P42765
    Molecular weight:
    41923.82
    Reactions
    Propionyl-CoA + Chenodeoxycholoyl-CoA → Coenzyme A + 3a,7a-Dihydroxy-5b-cholestanoyl-CoA details
    General function:
    Involved in transferase activity, transferring acyl groups other than amino-acyl groups
    Specific function:
    Not Available
    Gene Name:
    ACAA1
    Uniprot ID:
    P09110
    Molecular weight:
    34664.46
    Reactions
    Propionyl-CoA + Chenodeoxycholoyl-CoA → Coenzyme A + 3a,7a-Dihydroxy-5b-cholestanoyl-CoA details
    General function:
    Involved in transferase activity, transferring acyl groups other than amino-acyl groups
    Specific function:
    Not Available
    Gene Name:
    HADHB
    Uniprot ID:
    P55084
    Molecular weight:
    51293.955
    Reactions
    Propionyl-CoA + Chenodeoxycholoyl-CoA → Coenzyme A + 3a,7a-Dihydroxy-5b-cholestanoyl-CoA details
    General function:
    Involved in catalytic activity
    Specific function:
    Acyl-CoA synthetase involved in bile acid metabolism. Proposed to catalyze the first step in the conjugation of C24 bile acids (choloneates) to glycine and taurine before excretion into bile canaliculi by activating them to their CoA thioesters. Seems to activate secondary bile acids entering the liver from the enterohepatic circulation. In vitro, also activates 3-alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholestanate (THCA), the C27 precursor of cholic acid deriving from the de novo synthesis from cholesterol.
    Gene Name:
    SLC27A5
    Uniprot ID:
    Q9Y2P5
    Molecular weight:
    75384.375
    Reactions
    Adenosine triphosphate + 3a,7a-Dihydroxy-5b-cholestanate + Coenzyme A → Adenosine monophosphate + Pyrophosphate + 3a,7a-Dihydroxy-5b-cholestanoyl-CoA details
    General function:
    Involved in acyl-CoA dehydrogenase activity
    Specific function:
    Has very high activity toward isobutyryl-CoA. Is an isobutyryl-CoA dehydrogenase that functions in valine catabolism. Plays a role in transcriptional coactivation within the ARC complex.
    Gene Name:
    ACAD8
    Uniprot ID:
    Q9UKU7
    Molecular weight:
    45069.39

    PMID: 9464661

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