Showing metabocard for 3a,7a-Dihydroxy-5b-cholestanoyl-CoA (BMDB0002159)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:51:53 UTC
Update Date2020-05-21 16:28:48 UTC
BMDB IDBMDB0002159
Secondary Accession Numbers
  • BMDB02159
Metabolite Identification
Common Name3a,7a-Dihydroxy-5b-cholestanoyl-CoA
Description3a,7a-Dihydroxy-5b-cholestanoyl-CoA 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. Based on a literature review very few articles have been published on 3a,7a-Dihydroxy-5b-cholestanoyl-CoA.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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 FormulaC48H80N7O19P3S
Average Molecular Weight1184.171
Monoisotopic Molecular Weight1183.444253639
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}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 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
CAS Registry Number2461-62-3
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 KeySBYLHTNKEWSLBA-CPRJDYHCSA-N
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 Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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 Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
  • Peroxisome
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24850079
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44263316
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Peroxisomal acyl-coenzyme A oxidase 1
General function:
Lipid transport and metabolism
Specific function:
Catalyzes the desaturation of acyl-CoAs to 2-trans-enoyl-CoAs.
Gene Name:
ACOX1
Uniprot ID:
Q3SZP5
Molecular weight:
74379.0
Reactions
3a,7a-Dihydroxy-5b-cholestanoyl-CoA + Water → 3a,7a-Dihydroxy-5b-cholest-24-enoyl-CoAdetails
Enzyme Details
2. AMACR protein
General function:
Not Available
Specific function:
Not Available
Gene Name:
AMACR
Uniprot ID:
Q148I9
Molecular weight:
42010.0
Reactions
3a,7a-Dihydroxy-5b-cholestanoyl-CoA → 3a,7a-Dihydroxy-5b-cholestanoyl-CoAdetails
Enzyme Details
3. Long-chain fatty acid transport protein 1
General function:
Not Available
Specific function:
Mediates the ATP-dependent import of long-chain fatty acids (LCFA) into the cell by mediating their translocation at the plasma membrane. Has also an acyl-CoA ligase activity for long-chain and very-long-chain fatty acids. May act directly as a bona fide transporter, or alternatively, in a cytoplasmic or membrane-associated multimeric protein complex to trap and draw fatty acids towards accumulation. Plays a pivotal role in regulating available LCFA substrates from exogenous sources in tissues undergoing high levels of beta-oxidation or triglyceride synthesis. May be involved in regulation of cholesterol metabolism.
Gene Name:
SLC27A1
Uniprot ID:
Q3ZKN0
Molecular weight:
71123.0
Reactions
3a,7a-Dihydroxycoprostanic acid + Adenosine triphosphate + Coenzyme A → 3a,7a-Dihydroxy-5b-cholestanoyl-CoA + Pyrophosphate + 3'-AMPdetails