3a,7a,12a-Trihydroxy-5b-cholestanoyl-CoA (CHEM035356)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:41:16 UTC
Update Date2016-11-09 01:21:18 UTC
Accession NumberCHEM035356
Identification
Common Name3a,7a,12a-Trihydroxy-5b-cholestanoyl-CoA
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,7,12-Trihydroxy-5beta-cholestanoyl-CoAChEBI
3,7,12-Trihydroxycholestan-26-oyl-CoAChEBI
3,7,12-Trihydroxycoprostanoyl-CoAChEBI
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestan-26-oyl-coenzyme AChEBI
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoyl-CoAChEBI
3alpha,7alpha,12alpha-Trihydroxycoprostanoyl-CoAChEBI
S-(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholestane-26-thioateChEBI
S-(3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoyl)-coenzyme AChEBI
THCA-CoAChEBI
Trihydroxycoprostanoyl-CoAChEBI
3,7,12-Trihydroxy-5b-cholestanoyl-CoAGenerator
3,7,12-Trihydroxy-5β-cholestanoyl-CoAGenerator
3a,7a,12a-Trihydroxy-5b-cholestan-26-oyl-coenzyme AGenerator
3Α,7α,12α-trihydroxy-5β-cholestan-26-oyl-coenzyme AGenerator
3Α,7α,12α-trihydroxy-5β-cholestanoyl-CoAGenerator
3a,7a,12a-Trihydroxycoprostanoyl-CoAGenerator
3Α,7α,12α-trihydroxycoprostanoyl-CoAGenerator
S-(3a,5b,7a,12a)-3,7,12-Trihydroxycholestane-26-thioateGenerator
S-(3a,5b,7a,12a)-3,7,12-Trihydroxycholestane-26-thioic acidGenerator
S-(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholestane-26-thioic acidGenerator
S-(3Α,5β,7α,12α)-3,7,12-trihydroxycholestane-26-thioateGenerator
S-(3Α,5β,7α,12α)-3,7,12-trihydroxycholestane-26-thioic acidGenerator
S-(3a,7a,12a-Trihydroxy-5b-cholestanoyl)-coenzyme AGenerator
S-(3Α,7α,12α-trihydroxy-5β-cholestanoyl)-coenzyme AGenerator
(25R)-3-alpha,7-alpha,12-alpha-Trihydroxy-5-beta-cholestan-26-oyl-CoAHMDB
(25R)-3-alpha,7-alpha,12-alpha-Trihydroxy-5-beta-cholestan-26-oyl-coenzyme AHMDB
(25R)-3-alpha,7-alpha,12-alpha-Trihydroxy-5-beta-cholestanoyl-CoAHMDB
(25R)-3-alpha,7-alpha,12-alpha-Trihydroxy-5-beta-cholestanoyl-coenzyme AHMDB
25(S)-3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestan-26-oyl-CoAHMDB
25(S)-3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestan-26-oyl-coenzyme AHMDB
25(S)-3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoyl-CoAHMDB
25(S)-3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoyl-coenzyme AHMDB
25(S)-5beta-Cholestane-3alpha,7alpha,12alpha-triol-26-oyl-CoAHMDB
25(S)-5beta-Cholestane-3alpha,7alpha,12alpha-triol-26-oyl-coenzyme AHMDB
25(S)-Trihydroxycoprostanoyl-CoAHMDB
25(S)-Trihydroxycoprostanoyl-coenzyme AHMDB
3-alpha,7-alpha,12-alpha-Trihydroxy-5-beta- cholanoyl-CoAHMDB
3-alpha,7-alpha,12-alpha-Trihydroxy-5-beta- cholanoyl-coenzyme AHMDB
3a,7a,12a-Trihydroxy-5b-cholestan-26-oyl-CoAHMDB
3a,7a,12a-Trihydroxy-5b-cholestanoateHMDB
3a,7a,12a-Trihydroxy-5b-cholestanoic acidHMDB
3a,7a,12a-Trihydroxy-5b-cholestanoic acid coenzyme A esterHMDB
3a,7a,12a-Trihydroxy-5b-cholestanoyl CoAHMDB
3a,7a,12a-Trihydroxy-5b-cholestanoyl coenzyme AHMDB
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoyl-CoA(S)HMDB
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoyl-coenzyme AHMDB
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoyl-coenzyme A(S)HMDB
S-(3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoyl)-coenzymeHMDB
S-TrHCCoAHMDB
S-TRHCcoenzyme AHMDB
3alpha,7alpha,12alpha-Trihydroxy-5 beta-cholestan-26-oyl-coenzyme AHMDB
3Α,7α,12α-trihydroxy-5β-cholestan-26-oyl-CoAHMDB
3a,7a,12a-Trihydroxy-5b-cholestanoyl-CoAGenerator
Chemical FormulaC48H80N7O20P3S
Average Molecular Mass1200.170 g/mol
Monoisotopic Mass1199.439 g/mol
CAS Registry Number57458-60-3
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-({2-[(2-{[(6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional Nametrihydroxycoprostanoyl-coa
SMILES[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)C(=O)SCCNC(=O)CCNC(=O)[C@H](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 IdentifierInChI=1S/C48H80N7O20P3S/c1-25(29-10-11-30-36-31(20-34(58)48(29,30)6)47(5)14-12-28(56)18-27(47)19-32(36)57)8-7-9-26(2)45(63)79-17-16-50-35(59)13-15-51-43(62)40(61)46(3,4)22-72-78(69,70)75-77(67,68)71-21-33-39(74-76(64,65)66)38(60)44(73-33)55-24-54-37-41(49)52-23-53-42(37)55/h23-34,36,38-40,44,56-58,60-61H,7-22H2,1-6H3,(H,50,59)(H,51,62)(H,67,68)(H,69,70)(H2,49,52,53)(H2,64,65,66)/t25-,26?,27+,28-,29-,30+,31+,32-,33-,34+,36+,38-,39-,40+,44-,47+,48-/m1/s1
InChI KeyMNYDLIUNNOCPHG-TUTZYBGQSA-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
  • Steroidal glycoside
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside 3',5'-bisphosphate
  • Trihydroxy bile acid, alcohol, or derivatives
  • Hydroxy bile acid, alcohol, or derivatives
  • Cholane-skeleton
  • Bile acid, alcohol, or derivatives
  • 7-hydroxysteroid
  • 12-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • Steroid
  • Pentose-5-phosphate
  • Ribonucleoside 3'-phosphate
  • Pentose phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • 6-aminopurine
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Pyrimidine
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Fatty amide
  • Phosphoric acid ester
  • Imidolactam
  • Tetrahydrofuran
  • Imidazole
  • Cyclic alcohol
  • Azole
  • Heteroaromatic compound
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carbothioic s-ester
  • Amino acid or derivatives
  • Thiocarboxylic acid ester
  • Sulfenyl compound
  • Organoheterocyclic compound
  • Thiocarboxylic acid or derivatives
  • Polyol
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Amine
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary amine
  • Organopnictogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • 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 Solubility0.87 g/LALOGPS
logP1.21ALOGPS
logP-2.8ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area424.32 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity284.13 m³·mol⁻¹ChemAxon
Polarizability118.88 ųChemAxon
Number of Rings7ChemAxon
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, Positivesplash10-01p9-1900012000-306bbd9daf9f3318488fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900225000-5921e3d880e90914438aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900011000-2ed71fabf2f55178e416Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900431400-f45d721b96129ae4c7d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3900121010-72e4566fdab381ea4026Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900100000-e150ebc7a1e6891987bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0690000000-9511f86a77e29df0eab8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0hh9-0930101412-831129ba600b9e4cdde6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0000119000-703112fba47fc9c4cae0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-ff1027fae88dfc628fbbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-2900401100-77c6c146b20b0be5989cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0171-6705703900-142e3b567367b3ed6035Spectrum
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
1D NMR1H 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 IDHMDB0002178
FooDB IDFDB022888
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID44498
BioCyc IDNot Available
METLIN ID6529
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID13085527
ChEBI ID15493
PubChem Compound ID15942872
Kegg Compound IDC05448
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Wanders RJ, Casteels M, Mannaerts GP, van Roermund CW, Schutgens RB, Kozich V, Zeman J, Hyanek J: Accumulation and impaired in vivo metabolism of di- and trihydroxycholestanoic acid in two patients. Clin Chim Acta. 1991 Oct 31;202(3):123-32.
2. Gan-Schreier H, Okun JG, Kohlmueller D, Langhans CD, Peters V, Ten Brink HJ, Verhoeven NM, Jakobs C, Voelkl A, Hoffmann GF: Measurement of bile acid CoA esters by high-performance liquid chromatography-electrospray ionisation tandem mass spectrometry (HPLC-ESI-MS/MS). J Mass Spectrom. 2005 Jul;40(7):882-9.
3. Pedersen JI, Veggan T, Bjorkhem I: Substrate stereospecificity in oxidation of (25S)-3 alpha, 7 alpha, 12 alpha-trihydroxy-5 beta-cholestanoyl-CoA by peroxisomal trihydroxy-5 beta-cholestanoyl-CoA oxidase. Biochem Biophys Res Commun. 1996 Jul 5;224(1):37-42.
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=12966071
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=1351423
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=3183523
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=8301225
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=8694830