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

Metabolite 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

Molecular Formula

C₂₇H₄₄O₂

Average Mass

400.6371

Monoisotopic Mass

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

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

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

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192197	3-oxo-5-beta-steroid 4-dehydrogenase	Enzyme	P51857	Homo_sapiens
MMDBp0193987	3 beta-hydroxysteroid dehydrogenase type 7	Unknown	Q9H2F3	Homo_sapiens
MMDBp0194026	7-alpha-hydroxycholest-4-en-3-one 12-alpha-hydroxylase	Unknown	Q9UNU6	Homo_sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Evidence Type	Host and Biospecimen	Data Source	Reference
Alcoholism	Association	Human Blood	HMDB	8723414
Atrophic gastritis	Association	Human Blood	HMDB	8723414
Chronic pancreatitis	Association	Human Blood	HMDB	8723414
Crohn's disease	Association	Human Blood	HMDB	8723414
Gallbladder disease	Association	Human Blood	HMDB	9615912
Irritable bowel syndrome	Association	Human Blood	HMDB	8723414
Meckels diverticulum	Association	Human Blood	HMDB	8723414

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

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
Human	Detected and Quantified	0.16		0.09	0.25	Adult (>18 years old)	Both	Alcohol abuse	HMDB	8723414
Human	Detected and Quantified	0.127				Adult (>18 years old)	Both	Atrophic gastritis	HMDB	8723414
Human	Detected and Quantified	0.0999				Adult (>18 years old)	Both	Chronic pancreatitis	HMDB	8723414
Human	Detected and Quantified	0.12				Adult (>18 years old)	Both	Cronh's ileitis	HMDB	8723414
Human	Detected and Quantified	0.13		0.09	0.17	Adult (>18 years old)	Both	Diverticular disease	HMDB	8723414
Human	Detected and Quantified	0.033	0.011			Adult (>18 years old)	Both	Gallstone disease	HMDB	9615912
Human	Detected and Quantified	0.15				Adult (>18 years old)	Both	Ileocysoiplasty	HMDB	8723414
Human	Detected and Quantified	0.18		0.102	0.28	Adult (>18 years old)	Both	Irritable bowel syndrome (IBS)	HMDB	8723414
Human	Detected and Quantified	0.132				Adult (>18 years old)	Both	Meckels diverticulum	HMDB	8723414
Human	Detected and Quantified	109.8	16.44			Adult (>18 years old)	Both	Normal	HMDB	16544968
Human Liver	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597

External Links

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:0x0000560be1c1e9c0>

3D MOL for #<Metabolite:0x0000560be1c1e9c0>

3D SDF for #<Metabolite:0x0000560be1c1e9c0>

3D-SDF for #<Metabolite:0x0000560be1c1e9c0>

PDB for #<Metabolite:0x0000560be1c1e9c0>

3D PDB for #<Metabolite:0x0000560be1c1e9c0>

SMILES for #<Metabolite:0x0000560be1c1e9c0>

INCHI for #<Metabolite:0x0000560be1c1e9c0>

Structure for #<Metabolite:0x0000560be1c1e9c0>

3D Structure for #<Metabolite:0x0000560be1c1e9c0>