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Record Information
Version3.6
Creation Date2006-05-22 14:17:31 UTC
Update Date2016-02-11 01:05:12 UTC
HMDB IDHMDB01993
Secondary Accession Numbers
  • HMDB01331
Metabolite Identification
Common Name7a-Hydroxy-cholestene-3-one
Description7a-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 ).
Structure
Thumb
Synonyms
ValueSource
7alpha-Hydroxy-4-cholesten-3-oneChEBI
Cholest-4-en-7alpha-ol-3-oneChEBI
7a-Hydroxy-4-cholesten-3-oneGenerator
7α-hydroxy-4-cholesten-3-oneGenerator
7 alpha-3Ox-CHMDB
7 alpha-Hydroxy-4-cholesten-3-oneHMDB
7-a-Hydroxy-4-cholesten-3-oneHMDB
7-a-Hydroxycholest-4-en-3-oneHMDB
7-alpha-Hydroxy-4-cholesten-3-oneHMDB
7-alpha-Hydroxycholest-4-en-3-oneHMDB
7-Hydroxycholest-4-en-3-oneHMDB
7a-Hydroxy-4-cholesten-3-one-12alphaHMDB
7alpha-Hydroxycholest-4-en-3-oneHMDB
HCOHMDB
Chemical FormulaC27H44O2
Average Molecular Weight400.6371
Monoisotopic Molecular Weight400.334130652
IUPAC Name(1S,2R,9R,10S,11S,14R,15R)-9-hydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Name7α-hydroxy-4-cholesten-3-one
CAS Registry Number3862-25-7
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 KeyInChIKey=IOIZWEJGGCZDOL-RQDYSCIWSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cholesterols and derivatives. These are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol-skeleton
  • 7-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected 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
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.000169 mg/mLALOGPS
logP5.46ALOGPS
logP6.37ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)17.14ChemAxon
pKa (Strongest Basic)-0.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity121.16 m3·mol-1ChemAxon
Polarizability50.6 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Liver
Pathways
NameSMPDB LinkKEGG Link
27-Hydroxylase DeficiencySMP00720Not Available
Bile Acid BiosynthesisSMP00035map00120
Cerebrotendinous Xanthomatosis (CTX)SMP00315Not Available
Congenital Bile Acid Synthesis Defect Type IISMP00314Not Available
Congenital Bile Acid Synthesis Defect Type IIISMP00318Not Available
Familial Hypercholanemia (FHCA)SMP00317Not Available
Zellweger SyndromeSMP00316Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified109.8 +/- 16.44 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.18 (0.102-0.28) uMAdult (>18 years old)BothIrritable bowel syndrome (IBS) details
BloodDetected and Quantified0.13 (0.09-0.17) uMAdult (>18 years old)BothDiverticular disease details
BloodDetected and Quantified0.15 uMAdult (>18 years old)BothIleocysoiplasty details
BloodDetected and Quantified0.132 uMAdult (>18 years old)BothMeckels diverticulum details
BloodDetected and Quantified0.127 uMAdult (>18 years old)BothAtrophic gastritis details
BloodDetected and Quantified0.12 uMAdult (>18 years old)BothCronh's ileitis details
BloodDetected and Quantified0.0999 uMAdult (>18 years old)BothChronic pancreatitis details
BloodDetected and Quantified0.16 (0.09-0.25) uMAdult (>18 years old)BothAlcohol abuse details
BloodDetected and Quantified0.033 +/- 0.011 uMAdult (>18 years old)BothGallstone disease details
Associated Disorders and Diseases
Disease References
Alcoholism
  1. 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. [8723414 ]
Crohn's disease
  1. 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. [8723414 ]
Gallbladder disease
  1. 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. [9615912 ]
Irritable bowel syndrome
  1. 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. [8723414 ]
Diverticular disease
  1. 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. [8723414 ]
Ileocystoplasty
  1. 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. [8723414 ]
Meckels diverticulum
  1. 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. [8723414 ]
Atrophic gastritis
  1. 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. [8723414 ]
Chronic pancreatitis
  1. 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. [8723414 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022786
KNApSAcK IDNot Available
Chemspider ID110306
KEGG Compound IDC05455
BioCyc IDNot Available
BiGG ID45848
Wikipedia LinkHCO
NuGOwiki LinkHMDB01993
Metagene LinkHMDB01993
METLIN ID6419
PubChem Compound123743
PDB IDNot Available
ChEBI ID17899
References
Synthesis ReferenceAlexander, 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. 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. [3919058 ]
  2. 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. [9425924 ]
  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. [2060639 ]
  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. [3865344 ]
  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. [3367085 ]
  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. [9952217 ]
  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. [8723414 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4-cholesten-3-one can also act as substrates.
Gene Name:
AKR1D1
Uniprot ID:
P51857
Molecular weight:
32889.38
Reactions
7a-Hydroxy-5b-cholestan-3-one + NADP → 7a-Hydroxy-cholestene-3-one + NADPH + Hydrogen Iondetails
General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids. HSD VII is active against four 7-alpha-hydroxylated sterols. Does not metabolize several different C(19/21) steroids as substrates. Involved in bile acid synthesis.
Gene Name:
HSD3B7
Uniprot ID:
Q9H2F3
Molecular weight:
21322.265
Reactions
Cholest-5-ene-3-beta,7-alpha-diol + NAD → 7a-Hydroxy-cholestene-3-one + NADHdetails
7a-Hydroxycholesterol + NAD → 7a-Hydroxy-cholestene-3-one + NADH + Hydrogen Iondetails
General function:
Involved in monooxygenase activity
Specific function:
Involved in bile acid synthesis and is responsible for the conversion of 7 alpha-hydroxy-4-cholesten-3-one into 7 alpha, 12 alpha-dihydroxy-4-cholesten-3-one. Responsible for the balance between formation of cholic acid and chenodeoxycholic acid. Has a rather broad substrate specificity including a number of 7-alpha-hydroxylated C27 steroids.
Gene Name:
CYP8B1
Uniprot ID:
Q9UNU6
Molecular weight:
58068.01
Reactions
7a-Hydroxy-cholestene-3-one + NADPH + Oxygen → 7a,12a-Dihydroxy-cholestene-3-one + NADP + Waterdetails
7a-Hydroxy-cholestene-3-one + Hydrogen Ion + Oxygen + NADPH → 7a,12a-Dihydroxy-cholestene-3-one + NADP + Waterdetails