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Showing metabocard for 7a-Hydroxy-cholestene-3-one (HMDB01993)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:31 -0600
Update Date 2013-02-08 17:11:10 -0700
HMDB ID HMDB01993
Secondary Accession Numbers
  • HMDB01331
Metabolite Identification
Common Name 7a-Hydroxy-cholestene-3-one
Description 7a-Hydroxy-cholestene-3-one is a metabolite in bile acid synthesis. It is derived from 7a-hydroxy-cholesterol and can be further metabolized to 7a,12a,-dihydroxy-cholest-4-en-3-one. Analysis of 7a-Hydroxycholestene-3-one (HCO) in serum may serve as a novel, simple, and sensitive method for the detection of bile acid malabsorption in patients with chronic diarrhea of unknown origin (PMID 9952217 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 7 alpha-3ox-C
  2. 7 alpha-Hydroxy-4-cholesten-3-one
  3. 7-a-Hydroxy-4-cholesten-3-one
  4. 7-a-Hydroxycholest-4-en-3-one
  5. 7-alpha-Hydroxy-4-cholesten-3-one
  6. 7-alpha-Hydroxycholest-4-en-3-one
  7. 7-Hydroxycholest-4-en-3-one
  8. 7a-Hydroxy-4-cholesten-3-one-12alpha
  9. 7alpha-Hydroxy-4-cholesten-3-one
  10. 7alpha-Hydroxycholest-4-en-3-one
  11. Cholest-4-en-7alpha-ol-3-one
  12. HCO
Chemical Formula C27H44O2
Average Molecular Weight 400.6371
Monoisotopic Molecular Weight 400.334130652
IUPAC Name (1S,2R,9R,10S,11S,14R,15R)-9-hydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
Traditional IUPAC Name cholest-4-en-7α-ol-3-one
CAS Registry Number 3862-25-7
SMILES [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)CC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
InChI Identifier InChI=1S/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h15,17-18,21-25,29H,6-14,16H2,1-5H3/t18-,21-,22+,23+,24-,25+,26+,27-/m1/s1
InChI Key IOIZWEJGGCZDOL-RQDYSCIWSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Cholesterols and Derivatives
Other Descriptors
  • 3-oxo steroid(ChEBI)
  • 7alpha-hydroxy steroid(ChEBI)
  • Aliphatic Homopolycyclic Compounds
  • C27 bile acids, alcohols, and derivatives(Lipidmaps)
  • Cholesterol and derivatives(KEGG)
  • cholestanoid(ChEBI)
Substituents
  • 3 Keto Steroid
  • 7 Hydroxy Steroid
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Decaline
  • Ketone
  • Secondary Alcohol
  • Sesterterpene
Direct Parent Cholesterols and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • 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 1.690E-04 g/L ALOGPS
LogP 5.46 ALOGPS
LogP 6.37 ChemAxon
LogS -6.37 ALOGPS
pKa (strongest acidic) 17.14 ChemAxon
pKa (strongest basic) -0.64 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 121.16 ChemAxon
Polarizability 50.6 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Liver
Pathways
Name SMPDB Link KEGG Link
Bile Acid Biosynthesis SMP00035 map00120 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and Quantified
Article_icon
109.8 +/- 16.44 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.18 (0.102-0.28) uM Adult (>18 years old) Both Irritable bowel syndrome Not Available
Blood Detected and Quantified
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0.13 (0.09-0.17) uM Adult (>18 years old) Both Diverticular disease Not Available
Blood Detected and Quantified
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0.15 uM Adult (>18 years old) Both Ileocysoiplasty Not Available
Blood Detected and Quantified
Article_icon
0.132 uM Adult (>18 years old) Both Meckels diverticulum Not Available
Blood Detected and Quantified
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0.127 uM Adult (>18 years old) Both Atrophic gastritis Not Available
Blood Detected and Quantified
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0.12 uM Adult (>18 years old) Both Cronh's ileitis Not Available
Blood Detected and Quantified
Article_icon
0.0999 uM Adult (>18 years old) Both Chronic pancreatitis Not Available
Blood Detected and Quantified
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0.16 (0.09-0.25) uM Adult (>18 years old) Both Alcohol abuse Not Available
Blood Detected and Quantified
Article_icon
0.033 +/- 0.011 uM Adult (>18 years old) Both Gallstone disease Not Available
Associated Disorders and Diseases
Disease References
Gallbladder disease
  • Hillebrant CG, Axelson M, Bjorkhem I, Wang FH, Nyberg B, Einarsson C: Effects of short-term treatment with pravastatin on the hepatic synthesis of cholesterol and bile acids in gallstone patients. Eur J Clin Invest. 1998 Apr;28(4):324-8. Pubmed: 9615912 Link_out
    Irritable bowel syndrome
    • Brydon WG, Nyhlin H, Eastwood MA, Merrick MV: Serum 7 alpha-hydroxy-4-cholesten-3-one and selenohomocholyltaurine (SeHCAT) whole body retention in the assessment of bile acid induced diarrhoea. Eur J Gastroenterol Hepatol. 1996 Feb;8(2):117-23. Pubmed: 8723414 Link_out
      Diverticular disease
      • Brydon WG, Nyhlin H, Eastwood MA, Merrick MV: Serum 7 alpha-hydroxy-4-cholesten-3-one and selenohomocholyltaurine (SeHCAT) whole body retention in the assessment of bile acid induced diarrhoea. Eur J Gastroenterol Hepatol. 1996 Feb;8(2):117-23. Pubmed: 8723414 Link_out
        Ileocystoplasty
        • Brydon WG, Nyhlin H, Eastwood MA, Merrick MV: Serum 7 alpha-hydroxy-4-cholesten-3-one and selenohomocholyltaurine (SeHCAT) whole body retention in the assessment of bile acid induced diarrhoea. Eur J Gastroenterol Hepatol. 1996 Feb;8(2):117-23. Pubmed: 8723414 Link_out
          Meckels diverticulum
          • Brydon WG, Nyhlin H, Eastwood MA, Merrick MV: Serum 7 alpha-hydroxy-4-cholesten-3-one and selenohomocholyltaurine (SeHCAT) whole body retention in the assessment of bile acid induced diarrhoea. Eur J Gastroenterol Hepatol. 1996 Feb;8(2):117-23. Pubmed: 8723414 Link_out
            Atrophic gastritis
            • Brydon WG, Nyhlin H, Eastwood MA, Merrick MV: Serum 7 alpha-hydroxy-4-cholesten-3-one and selenohomocholyltaurine (SeHCAT) whole body retention in the assessment of bile acid induced diarrhoea. Eur J Gastroenterol Hepatol. 1996 Feb;8(2):117-23. Pubmed: 8723414 Link_out
              Crohn's disease
              • Brydon WG, Nyhlin H, Eastwood MA, Merrick MV: Serum 7 alpha-hydroxy-4-cholesten-3-one and selenohomocholyltaurine (SeHCAT) whole body retention in the assessment of bile acid induced diarrhoea. Eur J Gastroenterol Hepatol. 1996 Feb;8(2):117-23. Pubmed: 8723414 Link_out
                Chronic pancreatitis
                • Brydon WG, Nyhlin H, Eastwood MA, Merrick MV: Serum 7 alpha-hydroxy-4-cholesten-3-one and selenohomocholyltaurine (SeHCAT) whole body retention in the assessment of bile acid induced diarrhoea. Eur J Gastroenterol Hepatol. 1996 Feb;8(2):117-23. Pubmed: 8723414 Link_out
                  Alcoholism
                  • Brydon WG, Nyhlin H, Eastwood MA, Merrick MV: Serum 7 alpha-hydroxy-4-cholesten-3-one and selenohomocholyltaurine (SeHCAT) whole body retention in the assessment of bile acid induced diarrhoea. Eur J Gastroenterol Hepatol. 1996 Feb;8(2):117-23. Pubmed: 8723414 Link_out
                    Associated OMIM IDs
                    DrugBank ID Not Available
                    Phenol Explorer Compound ID Not Available
                    Phenol Explorer Metabolite ID Not Available
                    FoodDB ID FDB022786
                    KNApSAcK ID Not Available
                    Chemspider ID 110306 Link_out
                    KEGG Compound ID C05455 Link_out
                    BioCyc ID Not Available
                    BiGG ID 45848 Link_out
                    Wikipedia Link HCO Link_out
                    NuGOwiki Link HMDB01993 Link_out
                    Metagene Link HMDB01993 Link_out
                    METLIN ID 6419 Link_out
                    PubChem Compound 123743 Link_out
                    PDB ID Not Available
                    ChEBI ID 17899 Link_out
                    References
                    Synthesis Reference Alexander, David L.; Fisher, Jed F. A convenient synthesis of 7a-hydroxycholest-4-en-3-one by the hydroxypropyl-b-cyclodextrin-facilitated cholesterol oxidase oxidation of 3b,7a-cholest-5-ene-3,7-diol. Steroids (1995), 60(3), 290-4.
                    Material Safety Data Sheet (MSDS) Not Available
                    General References
                    1. Lin RC, Fillenwarth MJ, Du X: Cytotoxic effect of 7alpha-hydroxy-4-cholesten-3-one on HepG2 cells: hypothetical role of acetaldehyde-modified delta4-3-ketosteroid-5beta-reductase (the 37-kd-liver protein) in the pathogenesis of alcoholic liver injury in the rat. Hepatology. 1998 Jan;27(1):100-7. Pubmed: 9425924 Link_out
                    2. Skrede S, Bjorkhem I, Buchmann MS, Hopen G, Fausa O: A novel pathway for biosynthesis of cholestanol with 7 alpha-hydroxylated C27-steroids as intermediates, and its importance for the accumulation of cholestanol in cerebrotendinous xanthomatosis. J Clin Invest. 1985 Feb;75(2):448-55. Pubmed: 3919058 Link_out
                    3. Axelson M, Bjorkhem I, Reihner E, Einarsson K: The plasma level of 7 alpha-hydroxy-4-cholesten-3-one reflects the activity of hepatic cholesterol 7 alpha-hydroxylase in man. FEBS Lett. 1991 Jun 24;284(2):216-8. Pubmed: 2060639 Link_out
                    4. Skrede S, Bjorkhem I: A novel route for the biosynthesis of cholestanol, and its significance for the pathogenesis of cerebrotendinous xanthomatosis. Scand J Clin Lab Invest Suppl. 1985;177:15-21. Pubmed: 3865344 Link_out
                    5. Skrede S, Buchmann MS, Bjorkhem I: Hepatic 7 alpha-dehydroxylation of bile acid intermediates, and its significance for the pathogenesis of cerebrotendinous xanthomatosis. J Lipid Res. 1988 Feb;29(2):157-64. Pubmed: 3367085 Link_out
                    6. Sauter GH, Munzing W, von Ritter C, Paumgartner G: Bile acid malabsorption as a cause of chronic diarrhea: diagnostic value of 7alpha-hydroxy-4-cholesten-3-one in serum. Dig Dis Sci. 1999 Jan;44(1):14-9. Pubmed: 9952217 Link_out
                    7. Brydon WG, Nyhlin H, Eastwood MA, Merrick MV: Serum 7 alpha-hydroxy-4-cholesten-3-one and selenohomocholyltaurine (SeHCAT) whole body retention in the assessment of bile acid induced diarrhoea. Eur J Gastroenterol Hepatol. 1996 Feb;8(2):117-23. Pubmed: 8723414 Link_out
                    Enzymes
                    Name: 3-oxo-5-beta-steroid 4-dehydrogenase
                    Reactions:
                    • (1) 5beta-cholestan-3-one + NADP+ = cholest-4-en-3-one + NADPH + H+ [RN:R02609]
                    • (2) 17,21-dihydroxy-5beta-pregnane-3,11,20-trione + NADP+ = cortisone + NADPH + H+ [RN:R02893]
                    Gene Name: AKR1D1
                    Uniprot ID: P51857 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA