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Human Metabolome Database Version 2.5

 

Showing metabocard for 3a,7a,12a-Trihydroxy-5b-cholestan-26-al (HMDB03533)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2006-08-13 00:14:06
Update Date 2009-05-05 20:59:48
Accession Number HMDB03533
Secondary Accession Numbers HMDB06263
Common Name 3a,7a,12a-Trihydroxy-5b-cholestan-26-al
Description 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestan-26-al is an intermediate in bile acid biosynthesis. 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, 16037564, 12576301, 11907135) 3a,7a,12a-trihydroxy-5b-cholestane-27-al is an enzymatically generated intermediate in the oxidation process of 5b-cholestane-3a,7a,12a,27-tetrol into 3a,7a,12a-trihydroxy-5b-cholestanoic acid in liver mitochondria. Mitochondrial sterol 27-hydroxylase (EC 1.14.13.60) appears to perform multiple monooxygenations in this conversion. (PMID: 8496170)
Synonyms
  1. 3,7,12-Trihydroxycholestan-26-al
  2. 3-alpha-7-alpha-12-alpha-trihydroxy-5-beta-cholestan-26-al
  3. 3alpha,7-alpha,12alpha-Trihydroxy-5beta-cholestan-26-al
  4. (6R)-2-methyl-6-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]heptanal
Chemical IUPAC Name (6R)-2-methyl-6-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]heptanal
Chemical Formula C27H46O4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Cholesterols and derivatives
Class
  • Steroids and Steroid Derivatives
Sub Class
  • Trihydroxy steroids
Family
  • Mammalian Metabolite
Species
  • aldehyde
  • secondary alcohol
Biofunction
  • Hormones
  • Membrane component
Application
—
Source
  • Endogenous
Average Molecular Weight 434.652
Monoisotopic Molecular Weight 434.339600
Isomeric SMILES CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C)C=O
Canonical SMILES CC(CCCC(C)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C)C=O
KEGG Compound ID C01301 Link Image
BioCyc ID ALPHA-N-DIACETYLNEURAMINYL-23-BETA-D-ETC Link Image
BiGG ID 37315 Link Image
Wikipedia Link Not Available
NuGOwiki Link HMDB03533 Link Image
Metagene Link HMDB03533 Link Image
METLIN ID Not Available
PubChem Compound 439479 Link Image
PubChem Substance 3883228 Link Image
ChEBI ID 16466 Link Image
CAS Registry Number 3836-01-9
InChI Identifier InChI=1/C27H46O4/c1-16(15-28)6-5-7-17(2)20-8-9-21-25-22(14-24(31)27(20,21)4)26(3)11-10-19(29)12-18(26)13-23(25)30/h15-25,29-31H,5-14H2,1-4H3/t16?,17-,18+,19-,20-,21+,22+,23?,24+,25+,26+,27-/m1/s1
Synthesis Reference Dayal B; Tint G S; Batta A K; Shefer S; Salen G Synthesis of biological precursors of cholic acid II. Steroids (1981), 37(2), 205-11.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.013200001 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity 4.265 Source: PhysProp
Predicted LogP/Hydrophobicity 3.92 [Predicted by ALOGPS]; 5.9 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Mitochondria
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Bile Acid Biosynthesis SMP00035 Link Image map00120 Link Image
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 Link Image]
  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 Link Image]
  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 Link Image]
  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 Link Image]
  5. Holmberg-Betsholtz I, Lund E, Bjorkhem I, Wikvall K: Sterol 27-hydroxylase in bile acid biosynthesis. Mechanism of oxidation of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,27-tetrol into 3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholestanoic acid. J Biol Chem. 1993 May 25;268(15):11079-85. [PubMed Link Image]