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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-10-09 21:01:49 UTC |
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HMDB ID | HMDB0001496 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 7alpha-Hydroxycholesterol |
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Description | 7alpha-Hydroxycholesterol is an oxysterol and can serve as a biomarker for lipid peroxidation (PMID: 17386651 ). Products of cholesterol oxidation accumulate within atherosclerotic plaque and have been proposed to contribute to inflammatory signalling in the diseased artery (PMID: 17364953 ). 7alpha-Hydroxycholesterol is a cholesterol oxide that has been described as a biomarker of oxidative stress in subjects with impaired glucose tolerance and diabetes (PMID: 16634125 ). 7alpha-Hydroxycholesterol has been identified in the human placenta (PMID: 32033212 ). |
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Structure | |
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Synonyms | Value | Source |
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7alpha-Hydroxy-cholesterol | ChEBI | Cholest-5-ene-3beta,7alpha-diol | ChEBI | 7a-Hydroxy-cholesterol | Generator | 7Α-hydroxy-cholesterol | Generator | Cholest-5-ene-3b,7a-diol | Generator | Cholest-5-ene-3β,7α-diol | Generator | 7a-Hydroxycholesterol | Generator | 7Α-hydroxycholesterol | Generator | 7 alpha-Hydroxycholesterol | MeSH | Cholest-5-en-3 beta,7 alpha-diol | MeSH | (3beta,7alpha)-Cholest-5-ene-3,7-diol | HMDB | (3β,7α)-Cholest-5-ene-3,7-diol | HMDB | 7alpha-Hydroxycholest-5-en-3beta-ol | HMDB | 7alpha-Hydroxycholesterol | HMDB | 7alphaOHChol | HMDB | 7α-Hydroxycholest-5-en-3β-ol | HMDB | 7αOHChol | HMDB |
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Chemical Formula | C27H46O2 |
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Average Molecular Weight | 402.663 |
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Monoisotopic Molecular Weight | 402.349780721 |
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IUPAC Name | (1S,2R,5S,9S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,9-diol |
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Traditional Name | (1S,2R,5S,9S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,9-diol |
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CAS Registry Number | 566-26-7 |
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SMILES | [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C |
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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 |
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InChI Key | OYXZMSRRJOYLLO-RVOWOUOISA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Cholestane steroids |
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Direct Parent | Cholesterols and derivatives |
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Alternative Parents | |
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Substituents | - Cholesterol
- Cholesterol-skeleton
- 3-hydroxy-delta-5-steroid
- 3-hydroxysteroid
- Hydroxysteroid
- 3-beta-hydroxy-delta-5-steroid
- 3-beta-hydroxysteroid
- 7-hydroxysteroid
- Delta-5-steroid
- Cyclic alcohol
- Secondary alcohol
- Alcohol
- Organooxygen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Not Available |
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Biological Properties |
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Cellular Locations | - Extracellular
- Membrane (predicted from logP)
- Endoplasmic reticulum
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Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Feces
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 0.18 +/- 0.047 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.335 +/- 0.068 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.012 +/- 0.002 uM | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.004 +/- 0.0016 uM | Adult (>18 years old) | Not Specified | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 0.054 +/- 0.019 uM | Adult (>18 years old) | Both | Cirrhosis | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.005 +/- 0.0021 uM | Adult (>18 years old) | Not Specified | Multiple Sclerosis | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details |
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Associated Disorders and Diseases |
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Disease References | Cirrhosis |
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- Hahn C, Reichel C, von Bergmann K: Serum concentration of 7 alpha-hydroxycholesterol as an indicator of bile acid synthesis in humans. J Lipid Res. 1995 Sep;36(9):2059-66. [PubMed:8558093 ]
| Multiple sclerosis |
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- Leoni V, Lutjohann D, Masterman T: Levels of 7-oxocholesterol in cerebrospinal fluid are more than one thousand times lower than reported in multiple sclerosis. J Lipid Res. 2005 Feb;46(2):191-5. Epub 2004 Dec 1. [PubMed:15576852 ]
| Colorectal cancer |
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- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022655 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 96891 |
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KEGG Compound ID | C03594 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | 7α-Hydroxycholesterol |
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METLIN ID | Not Available |
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PubChem Compound | 107722 |
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PDB ID | Not Available |
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ChEBI ID | 17500 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | MDB00000333 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Kitano S, Yoshida Y, Kawano K, Hibi N, Niki E: Oxidative status of human low density lipoprotein isolated by anion-exchange high-performance liquid chromatography--assessment by total hydroxyoctadecadienoic acid, 7-hydroxycholesterol, and 8-iso-prostaglandin F(2alpha). Anal Chim Acta. 2007 Feb 28;585(1):86-93. Epub 2006 Dec 23. [PubMed:17386651 ]
- Erridge C, Webb DJ, Spickett CM: 25-Hydroxycholesterol, 7beta-hydroxycholesterol and 7-ketocholesterol upregulate interleukin-8 expression independently of Toll-like receptor 1, 2, 4 or 6 signalling in human macrophages. Free Radic Res. 2007 Mar;41(3):260-6. [PubMed:17364953 ]
- Ferderbar S, Pereira EC, Apolinario E, Bertolami MC, Faludi A, Monte O, Calliari LE, Sales JE, Gagliardi AR, Xavier HT, Abdalla DS: Cholesterol oxides as biomarkers of oxidative stress in type 1 and type 2 diabetes mellitus. Diabetes Metab Res Rev. 2007 Jan;23(1):35-42. [PubMed:16634125 ]
- 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 ]
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