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Showing metabocard for 3a,7a,12a-Trihydroxy-5b-cholestanoyl-CoA (HMDB02178)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:40 -0600
Update Date 2013-02-08 17:11:30 -0700
HMDB ID HMDB02178
Secondary Accession Numbers None
Metabolite Identification
Common Name 3a,7a,12a-Trihydroxy-5b-cholestanoyl-CoA
Description 3a,7a,12a-Trihydroxy-5b-cholestanoyl-CoA is an intermediate in the Bile acid biosynthesis pathway (KEGG). C27-bile acyl-CoAs are converted to their (S)-stereoisomers by the enzyme Alpha-methylacyl-CoA racemase (OMIM 604489 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (25R)-3-alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholestan-26-oyl-CoA
  2. (25R)-3-alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholestan-26-oyl-Coenzyme A
  3. (25R)-3-alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholestanoyl-CoA
  4. (25R)-3-alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholestanoyl-Coenzyme A
  5. 25(S)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoA
  6. 25(S)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-Coenzyme A
  7. 25(S)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoyl-CoA
  8. 25(S)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoyl-Coenzyme A
  9. 25(S)-5beta-cholestane-3alpha,7alpha,12alpha-triol-26-oyl-CoA
  10. 25(S)-5beta-cholestane-3alpha,7alpha,12alpha-triol-26-oyl-Coenzyme A
  11. 25(S)-Trihydroxycoprostanoyl-CoA
  12. 25(S)-Trihydroxycoprostanoyl-Coenzyme A
  13. 3-alpha,7-alpha,12-alpha-Trihydroxy-5-beta- cholanoyl-CoA
  14. 3-alpha,7-alpha,12-alpha-Trihydroxy-5-beta- cholanoyl-Coenzyme A
  15. 3a,7a,12a-Trihydroxy-5b-cholestan-26-oyl-CoA
  16. 3a,7a,12a-Trihydroxy-5b-cholestan-26-oyl-Coenzyme A
  17. 3a,7a,12a-Trihydroxy-5b-cholestanoate
  18. 3a,7a,12a-Trihydroxy-5b-cholestanoic acid
  19. 3a,7a,12a-Trihydroxy-5b-cholestanoic acid coenzyme A ester
  20. 3a,7a,12a-Trihydroxy-5b-cholestanoyl CoA
  21. 3a,7a,12a-Trihydroxy-5b-cholestanoyl Coenzyme A
  22. 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoyl-CoA
  23. 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoyl-CoA(S)
  24. 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoyl-Coenzyme A
  25. 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoyl-Coenzyme A(S)
  26. S-(3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoyl)-coenzyme
  27. S-TrHCCoA
  28. S-TrHCCoenzyme A
Chemical Formula C48H80N7O20P3S
Average Molecular Weight 1200.17
Monoisotopic Molecular Weight 1199.439168261
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[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]heptanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name [(2R,3S,4R,5R)-5-(6-aminopurin-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[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]heptanoyl]s
CAS Registry Number 57458-60-3
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 Identifier InChI=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 Key MNYDLIUNNOCPHG-TUTZYBGQSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acid Esters
Sub Class Acyl CoAs
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • cholestanoyl-CoA(ChEBI)
Substituents
  • 1 Phosphoribosyl Imidazole
  • 12 Hydroxy Steroid
  • 3 Hydroxy Steroid
  • 7 Hydroxy Steroid
  • Aminopyrimidine
  • Bicyclohexane
  • Carboxamide Group
  • Carboxylic Thioester
  • Cholesterol
  • Cholesterol Skeleton
  • Coenzyme A
  • Cyclic Alcohol
  • Cyclohexane
  • Decaline
  • Glycosyl Compound
  • Imidazole
  • Imidazopyrimidine
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Polycyclic Triterpene
  • Purine
  • Purine Ribonucleoside 3',5' Bisphosphate
  • Pyrimidine
  • Saccharide
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Steroid
  • Terpene Glycoside
  • Thiocarboxylic Acid Ester
  • Triterpene
  • Triterpene Glycoside
Direct Parent Steroidal Acyl CoAs
Ontology
Status Expected and 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 Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
  • Peroxisome
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.87 g/L ALOGPS
LogP 1.21 ALOGPS
LogP -2.8 ChemAxon
LogS -3.14 ALOGPS
pKa (strongest acidic) 0.83 ChemAxon
pKa (strongest basic) 4.95 ChemAxon
Hydrogen Acceptor Count 20 ChemAxon
Hydrogen Donor Count 12 ChemAxon
Polar Surface Area 424.32 A2 ChemAxon
Rotatable Bond Count 26 ChemAxon
Refractivity 284.13 ChemAxon
Polarizability 118.88 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -4 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
  • Peroxisome
Biofluid Locations Not Available
Tissue Location
  • Liver
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022888
KNApSAcK ID Not Available
Chemspider ID 13085527 Link_out
KEGG Compound ID C05448 Link_out
BioCyc ID Not Available
BiGG ID 44498 Link_out
Wikipedia Link A Link_out
NuGOwiki Link HMDB02178 Link_out
Metagene Link HMDB02178 Link_out
METLIN ID 6529 Link_out
PubChem Compound 15942872 Link_out
PDB ID Not Available
ChEBI ID 15493 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not 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. Pubmed: 1839974 Link_out
  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. Pubmed: 15892178 Link_out
  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. Pubmed: 8694830 Link_out
Enzymes
Name: Bile acyl-CoA synthetase
Reactions:
  • (1) ATP + cholate + CoA = AMP + diphosphate + choloyl-CoA [RN:R02794]
  • (2) ATP + (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oate + CoA = AMP + diphosphate + (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoyl-CoA [RN:R04580]
Gene Name: SLC27A5
Uniprot ID: Q9Y2P5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Retinol dehydrogenase 13
Reactions:
    Gene Name: RDH13
    Uniprot ID: Q8NBN7 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Isobutyryl-CoA dehydrogenase, mitochondrial
    Reactions:
      Gene Name: ACAD8
      Uniprot ID: Q9UKU7 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA