Human Metabolome Database Version 3.5

Showing metabocard for 3a,7a-Dihydroxy-5b-cholestan-26-al (HMDB06894)

Record Information
Version 3.5
Creation Date 2008-08-14 12:14:34 -0600
Update Date 2013-05-29 13:45:26 -0600
HMDB ID HMDB06894
Secondary Accession Numbers None
Metabolite Identification
Common Name 3a,7a-Dihydroxy-5b-cholestan-26-al
Description 3alpha,7alpha-Dihydroxy-5beta-cholestan-26-al is an intermediate involved in bile acid biosynthesis, specifically in the synthesis of chenodeoxyglycocholate and lithocholate. 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. 3alpha,7alpha-dihydroxy-5beta-cholestan-27-al
  2. 5beta-cholestan-27-al-3alpha,7alpha-diol
  3. 5beta-cholestane-3alpha,7alpha-diol-27-al
Chemical Formula C27H46O3
Average Molecular Weight 418.6523
Monoisotopic Molecular Weight 418.344695338
IUPAC Name 6-[(2S,5R,9R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptanal
Traditional IUPAC Name 6-[(2S,5R,9R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptanal
CAS Registry Number Not Available
SMILES CC(CCCC(C)C1CCC2C3[C@H](O)CC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C)C=O
InChI Identifier InChI=1S/C27H46O3/c1-17(16-28)6-5-7-18(2)21-8-9-22-25-23(11-13-27(21,22)4)26(3)12-10-20(29)14-19(26)15-24(25)30/h16-25,29-30H,5-15H2,1-4H3/t17?,18?,19?,20-,21?,22?,23?,24-,25?,26+,27-/m1/s1
InChI Key YWGOKHMOJTZGBN-SBOSHUFNSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Cholesterols and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
Substituents
  • 3 Hydroxy Steroid
  • 7 Hydroxy Steroid
  • Aldehyde
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Decaline
  • Secondary Alcohol
  • Sesterterpene
Direct Parent Cholesterols and Derivatives
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
  • Membrane
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 6.970E-04 g/L ALOGPS
LogP 4.91 ALOGPS
LogP 4.99 ChemAxon
LogS -5.78 ALOGPS
pKa (strongest acidic) 16.07 ChemAxon
pKa (strongest basic) -0.54 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 57.53 A2 ChemAxon
Rotatable Bond Count 6 ChemAxon
Refractivity 122.12 ChemAxon
Polarizability 51.14 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 FDB024141
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID C05445 Link_out
BioCyc ID Not Available
BiGG ID 45826 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB06894 Link_out
Metagene Link HMDB06894 Link_out
METLIN ID Not Available
PubChem Compound 53477906 Link_out
PDB ID Not Available
ChEBI ID 27428 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: 4-trimethylaminobutyraldehyde dehydrogenase
Reactions:
3a,7a-Dihydroxy-5b-cholestan-26-al + NAD + Water unknown 3a,7a-Dihydroxy-5b-cholestanate + NADH + Hydrogen Ion details
Gene Name: ALDH9A1
Uniprot ID: P49189 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-aminoadipic semialdehyde dehydrogenase
Reactions:
3a,7a-Dihydroxy-5b-cholestan-26-al + NAD + Water unknown 3a,7a-Dihydroxy-5b-cholestanate + NADH + Hydrogen Ion details
Gene Name: ALDH7A1
Uniprot ID: P49419 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase family 1 member A3
Reactions: Not Available
Gene Name: ALDH1A3
Uniprot ID: P47895 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase, mitochondrial
Reactions:
3a,7a-Dihydroxy-5b-cholestan-26-al + NAD + Water unknown 3a,7a-Dihydroxy-5b-cholestanate + NADH + Hydrogen Ion details
Gene Name: ALDH2
Uniprot ID: P05091 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fatty aldehyde dehydrogenase
Reactions:
3a,7a-Dihydroxy-5b-cholestan-26-al + NAD + Water unknown 3a,7a-Dihydroxy-5b-cholestanate + NADH + Hydrogen Ion details
Gene Name: ALDH3A2
Uniprot ID: P51648 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase X, mitochondrial
Reactions:
3a,7a-Dihydroxy-5b-cholestan-26-al + NAD + Water unknown 3a,7a-Dihydroxy-5b-cholestanate + NADH + Hydrogen Ion details
Gene Name: ALDH1B1
Uniprot ID: P30837 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alcohol dehydrogenase class-3
Reactions: Not Available
Gene Name: ADH5
Uniprot ID: P11766 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alcohol dehydrogenase 1B
Reactions: Not Available
Gene Name: ADH1B
Uniprot ID: P00325 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alcohol dehydrogenase class 4 mu/sigma chain
Reactions: Not Available
Gene Name: ADH7
Uniprot ID: P40394 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alcohol dehydrogenase 1A
Reactions: Not Available
Gene Name: ADH1A
Uniprot ID: P07327 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alcohol dehydrogenase 6
Reactions: Not Available
Gene Name: ADH6
Uniprot ID: P28332 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alcohol dehydrogenase 1C
Reactions: Not Available
Gene Name: ADH1C
Uniprot ID: P00326 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sterol 26-hydroxylase, mitochondrial
Reactions:
3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane unknown 3a,7a-Dihydroxy-5b-cholestan-26-al details
3a,7a-Dihydroxy-5b-cholestan-26-al + NADPH + Oxygen + Hydrogen Ion unknown 3a,7a-Dihydroxy-5b-cholestanate + NADP + Water details
Gene Name: CYP27A1
Uniprot ID: Q02318 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA