MiMeDB: Showing metabocard for 7a-Hydroxy-cholestene-3-one (MMDBc0047936)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-23 23:16:44 UTC

Update Date

2022-09-01 02:02:27 UTC

MiMeDB ID

MMDBc0047936

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 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₇H₄₄O₂

Average Molecular Weight

400.6371

Monoisotopic Molecular Weight

400.334130652

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

3862-25-7

SMILES

Not Available

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

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Feces
Liver
Urine

Tissue Locations

Liver

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

#<MetaboliteProteinLink:0x000055b76def0a18>

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Related Health Condition	Evidence Type	Measured in Matrix	Reference
Alcoholism	This associated disease is originally imported from HMDB metabolite HMDB0001993 concentration id 62776	Association	Human Blood	8723414	details
Atrophic gastritis	This associated disease is originally imported from HMDB metabolite HMDB0001993 concentration id 62773	Association	Human Blood	8723414	details
Chronic pancreatitis	This associated disease is originally imported from HMDB metabolite HMDB0001993 concentration id 62775	Association	Human Blood	8723414	details
Crohn's disease	This associated disease is originally imported from HMDB metabolite HMDB0001993 concentration id 62774	Association	Human Blood	8723414	details
Gallbladder disease	This associated disease is originally imported from HMDB metabolite HMDB0001993 concentration id 17586	Association	Human Blood	9615912	details
Irritable bowel syndrome	This associated disease is originally imported from HMDB metabolite HMDB0001993 concentration id 62769	Association	Human Blood	8723414	details
Meckels diverticulum	This associated disease is originally imported from HMDB metabolite HMDB0001993 concentration id 62772	Association	Human Blood	8723414	details

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
	Proteobacteria	1	Human Feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified								HMDB		details
Human	Detected and Quantified	0.16		0.09	0.25	Adult (>18 years old)	Both	Alcohol abuse	HMDB	8723414	details
Human	Detected and Quantified	0.127				Adult (>18 years old)	Both	Atrophic gastritis	HMDB	8723414	details
Human	Detected and Quantified	0.0999				Adult (>18 years old)	Both	Chronic pancreatitis	HMDB	8723414	details
Human	Detected and Quantified	0.12				Adult (>18 years old)	Both	Cronh's ileitis	HMDB	8723414	details
Human	Detected and Quantified	0.13		0.09	0.17	Adult (>18 years old)	Both	Diverticular disease	HMDB	8723414	details
Human	Detected and Quantified	0.033	0.011			Adult (>18 years old)	Both	Gallstone disease	HMDB	9615912	details
Human	Detected and Quantified	0.15				Adult (>18 years old)	Both	Ileocysoiplasty	HMDB	8723414	details
Human	Detected and Quantified	0.18		0.102	0.28	Adult (>18 years old)	Both	Irritable bowel syndrome (IBS)	HMDB	8723414	details
Human	Detected and Quantified	0.132				Adult (>18 years old)	Both	Meckels diverticulum	HMDB	8723414	details
Human	Detected and Quantified	109.8	16.44			Adult (>18 years old)	Both	Normal	HMDB	16544968	details
Human Liver	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597	details

External Links

Not Available

References

Synthesis Reference

Not Available

General References

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. doi: 10.1016/0014-5793(91)80688-y. [PubMed:2060639 ]
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 ]
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 ]
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. doi: 10.1172/JCI111719. [PubMed:3919058 ]
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. doi: 10.1097/00042737-199602000-00005. [PubMed:8723414 ]
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. doi: 10.1002/hep.510270117. [PubMed:9425924 ]
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. doi: 10.1023/a:1026681512303. [PubMed:9952217 ]

Showing metabocard for 7a-Hydroxy-cholestene-3-one (MMDBc0047936)

MOL for #<Metabolite:0x000055b76dc92aa0>

3D MOL for #<Metabolite:0x000055b76dc92aa0>

3D SDF for #<Metabolite:0x000055b76dc92aa0>

3D-SDF for #<Metabolite:0x000055b76dc92aa0>

PDB for #<Metabolite:0x000055b76dc92aa0>

3D PDB for #<Metabolite:0x000055b76dc92aa0>

SMILES for #<Metabolite:0x000055b76dc92aa0>

INCHI for #<Metabolite:0x000055b76dc92aa0>

Structure for #<Metabolite:0x000055b76dc92aa0>

3D Structure for #<Metabolite:0x000055b76dc92aa0>