MiMeDB: Showing metabocard for 7beta-Hydroxycholesterol (MMDBc0000614)

Pharmaceutical

Xenobiotic

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:51:09 UTC

Update Date

2024-10-15 18:27:40 UTC

Metabolite ID

MMDBc0000614

Metabolite Identification

Common Name

7beta-Hydroxycholesterol

Description

7beta-Hydroxycholesterol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 7beta-hydroxycholesterol is considered to be a sterol lipid molecule. 7beta-Hydroxycholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 7beta-Hydroxycholesterol has been identified in atheromatous plaques and in plasma of atherosclerotic patients (PMID: 16604541 ). 7beta-Hydroxycholesterol induces apoptosis in Caco-2 cells and alters lysosomal membrane integrity. It exhibits a specific enhancement of oxidative stress and of endonuclease G expression (PMID: 17136497 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₂₇H₄₆O₂

Average Mass

402.6529

Monoisotopic Mass

402.349780716

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C27H46O2/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/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24+,25+,26+,27-/m1/s1

InChI Key

OYXZMSRRJOYLLO-KGZHIOMZSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	209.2
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	43.5
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	683.3
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	955.8
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	1087.0
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	570.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	3539.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	97.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	335.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	915.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	531.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	228.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	277.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-23	8.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	235.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	643.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	567.0
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	2089.1
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1855.1

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	7beta-Hydroxycholesterol_TMS_1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@H](O)CC1=C[C@@H]3O[Si](C)(C)C	standard non polar	2025-10-23	1709.71
Gas Chromatography	7beta-Hydroxycholesterol_TMS_2	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)CC1=C[C@@H]3O	standard non polar	2025-10-23	1479.53
Gas Chromatography	7beta-Hydroxycholesterol_TMS_3	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)CC1=C[C@@H]3O[Si](C)(C)C	standard non polar	2025-10-23	1412.62
Gas Chromatography	7beta-Hydroxycholesterol_TMS_1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@H](O)CC1=C[C@@H]3O[Si](C)(C)C	standard polar	2025-10-23	1655.43
Gas Chromatography	7beta-Hydroxycholesterol_TMS_2	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)CC1=C[C@@H]3O	standard polar	2025-10-23	758.189
Gas Chromatography	7beta-Hydroxycholesterol_TMS_3	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)CC1=C[C@@H]3O[Si](C)(C)C	standard polar	2025-10-23	2019.53

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Placenta

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

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	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Multiple sclerosis		Association	Human Cerebrospinal Fluid (CSF)	HMDB	15576852

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Actinobacteria	2	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria/Eubacteria	Bacteroidetes	2	Human feces; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.004	0.0017	uM	Adult (>18 years old)	Both	Multiple Sclerosis	HMDB	15576852
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.003	0.0006	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	15576852
Human Blood	Detected and Quantified	0.011	0.0027	uM	Adult (>18 years old)	Both	Normal	HMDB	12531208
Human Placenta	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	25037050

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Prunet C, Montange T, Vejux A, Laubriet A, Rohmer JF, Riedinger JM, Athias A, Lemaire-Ewing S, Neel D, Petit JM, Steinmetz E, Brenot R, Gambert P, Lizard G: Multiplexed flow cytometric analyses of pro- and anti-inflammatory cytokines in the culture media of oxysterol-treated human monocytic cells and in the sera of atherosclerotic patients. Cytometry A. 2006 May;69(5):359-73. doi: 10.1002/cyto.a.20272. [PubMed:16604541 ]
Roussi S, Gosse F, Aoude-Werner D, Zhang X, Marchioni E, Geoffroy P, Miesch M, Raul F: Mitochondrial perturbation, oxidative stress and lysosomal destabilization are involved in 7beta-hydroxysitosterol and 7beta-hydroxycholesterol triggered apoptosis in human colon cancer cells. Apoptosis. 2007 Jan;12(1):87-96. doi: 10.1007/s10495-006-0485-y. [PubMed:17136497 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for 7beta-Hydroxycholesterol (MMDBc0000614)

MOL for #<Metabolite:0x00007f2e2d1dc358>

3D MOL for #<Metabolite:0x00007f2e2d1dc358>

3D SDF for #<Metabolite:0x00007f2e2d1dc358>

3D-SDF for #<Metabolite:0x00007f2e2d1dc358>

PDB for #<Metabolite:0x00007f2e2d1dc358>

3D PDB for #<Metabolite:0x00007f2e2d1dc358>

SMILES for #<Metabolite:0x00007f2e2d1dc358>

INCHI for #<Metabolite:0x00007f2e2d1dc358>

Structure for #<Metabolite:0x00007f2e2d1dc358>

3D Structure for #<Metabolite:0x00007f2e2d1dc358>