Human Metabolome Database Version 3.5

Showing metabocard for 3a,7a,12a,24-Tetrahydroxy-5b-cholestanoyl-CoA (HMDB06890)

Record Information
Version 3.5
Creation Date 2008-08-14 12:05:41 -0600
Update Date 2013-07-24 11:56:53 -0600
HMDB ID HMDB06890
Secondary Accession Numbers None
Metabolite Identification
Common Name 3a,7a,12a,24-Tetrahydroxy-5b-cholestanoyl-CoA
Description 3a,7a,12a,24-Tetrahydroxy-5b-cholestanoyl-CoA is an intermediate in bile acid synthesis. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487 Link_out, 16037564 Link_out, 12576301 Link_out, 11907135 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (24R,25R)-3-alpha,7-alpha,12-alpha,24-tetrahydroxy-5-beta-cholestanoyl-CoA
  2. (24R,25R)-3-alpha,7-alpha,12-alpha,24-tetrahydroxy-5-beta-cholestanoyl-Coenzyme A
  3. 3a,7a,12a,24-Tetrahydroxy-5b-cholestanoyl-CoA
  4. 3a,7a,12a,24-Tetrahydroxy-5b-cholestanoyl-Coenzyme A
  5. 3a,7a,12a,24z-Tetrahydroxy-5b-cholestanoyl-CoA
  6. 3a,7a,12a,24z-Tetrahydroxy-5b-cholestanoyl-Coenzyme A
  7. 3alpha,7alpha,12alpha,24-Tetrahydroxy-5beta-cholestanoyl-CoA
  8. 3alpha,7alpha,12alpha,24-Tetrahydroxy-5beta-cholestanoyl-Coenzyme A
  9. 3alpha,7alpha,12alpha,24zeta-Tetrahydroxy-5beta-cholestanoyl-CoA
  10. 3alpha,7alpha,12alpha,24zeta-Tetrahydroxy-5beta-cholestanoyl-Coenzyme A
Chemical Formula C48H80N7O21P3S
Average Molecular Weight 1216.169
Monoisotopic Molecular Weight 1215.434082883
IUPAC Name {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({3-hydroxy-3-[(2-{[2-({3-hydroxy-2-methyl-6-[(5R,7S,9R,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]-2,2-dimethylpropoxy})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(3-hydroxy-3-[(2-{[2-({3-hydroxy-2-methyl-6-[(5R,7S,9R,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)carb
CAS Registry Number Not Available
SMILES [H][C@@]12C[C@H](O)CCC1(C)C1C[C@H](O)C3(C)C(CCC3C1[C@H](O)C2)C(C)CCC(O)C(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=C1N=CN=C2N
InChI Identifier InChI=1S/C48H80N7O21P3S/c1-24(28-8-9-29-36-30(19-34(59)48(28,29)6)47(5)13-11-27(56)17-26(47)18-32(36)58)7-10-31(57)25(2)45(64)80-16-15-50-35(60)12-14-51-43(63)40(62)46(3,4)21-73-79(70,71)76-78(68,69)72-20-33-39(75-77(65,66)67)38(61)44(74-33)55-23-54-37-41(49)52-22-53-42(37)55/h22-34,36,38-40,44,56-59,61-62H,7-21H2,1-6H3,(H,50,60)(H,51,63)(H,68,69)(H,70,71)(H2,49,52,53)(H2,65,66,67)/t24?,25?,26-,27+,28?,29?,30?,31?,32+,33+,34-,36?,38+,39+,40?,44+,47?,48?/m0/s1
InChI Key PXHZOQNODUPJKC-QVXJXFLKSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acid Esters
Sub Class Acyl CoAs
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1 Phosphoribosyl Imidazole
  • 12 Hydroxy Steroid
  • 24 Hydroxy Steroid
  • 3 Hydroxy Steroid
  • 7 Hydroxy Steroid
  • Aminopyrimidine
  • Bicyclohexane
  • Bile Acid, Alcohol, Or Derivative
  • Carboxamide Group
  • Carboxylic Thioester
  • Cholesterol
  • Coenzyme A
  • Cyclic Alcohol
  • Cyclohexane
  • Decaline
  • Glycosyl Compound
  • Hydroxy Bile Acid, Alcohol, Or Derivative
  • 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
  • Tetrahydroxy Bile Acid, Alcohol, Or Derivative
  • 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
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
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 1.18 g/L ALOGPS
LogP 0.65 ALOGPS
LogP -4.1 ChemAxon
LogS -3.01 ALOGPS
pKa (strongest acidic) 0.83 ChemAxon
pKa (strongest basic) 4.95 ChemAxon
Hydrogen Acceptor Count 21 ChemAxon
Hydrogen Donor Count 13 ChemAxon
Polar Surface Area 444.55 A2 ChemAxon
Rotatable Bond Count 26 ChemAxon
Refractivity 285.65 ChemAxon
Polarizability 119.66 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -4 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Bile Acid Biosynthesis SMP00035 map00120 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB024137
KNApSAcK ID Not Available
Chemspider ID 389556 Link_out
KEGG Compound ID C05450 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB06890 Link_out
Metagene Link HMDB06890 Link_out
METLIN ID Not Available
PubChem Compound 440677 Link_out
PDB ID Not Available
ChEBI ID 27458 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. Pubmed: 11316487 Link_out
  2. Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21. Pubmed: 16037564 Link_out
  3. Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. Pubmed: 12576301 Link_out
  4. Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. Pubmed: 11907135 Link_out

Enzymes
Name: Peroxisomal multifunctional enzyme type 2
Reactions:
3a,7a,12a,24-Tetrahydroxy-5b-cholestanoyl-CoA + NAD unknown 3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA + NADH + Hydrogen Ion details
3a,7a,12a,24-Tetrahydroxy-5b-cholestanoyl-CoA unknown 3a,7a,12a-Trihydroxy-5b-cholest-24-enoyl-CoA + Water details
Gene Name: HSD17B4
Uniprot ID: P51659 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Retinol dehydrogenase 13
Reactions: Not Available
Gene Name: RDH13
Uniprot ID: Q8NBN7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Isobutyryl-CoA dehydrogenase, mitochondrial
Reactions: Not Available
Gene Name: ACAD8
Uniprot ID: Q9UKU7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA