| Record Information |
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| Version | 4.0 |
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| Status | Detected but not Quantified |
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| Creation Date | 2009-07-13 12:02:10 UTC |
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| Update Date | 2020-02-26 21:37:36 UTC |
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| HMDB ID | HMDB0012453 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | 3beta-Hydroxy-5-cholestenoic acid |
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| Description | 3beta-Hydroxy-5-cholestenoic acid (CAS: 6561-58-6) belongs to the class of organic compounds known as monohydroxy bile acids, alcohols, and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group. 3beta-Hydroxy-5-cholestenoic acid is found in the primary bile acid biosynthesis pathway. 3beta-Hydroxy-5-cholestenoic acid is created from cholest-5-ene-3 beta,26-diol through the action of CYP27A (EC 1.14.13.15). 3beta-Hydroxy-5-cholestenoic acid is then converted into 3beta,7alpha-dihydroxy-5-cholestenoic acid by the action of CYP7B (EC 1.14.13.100). 3beta-Hydroxy-5-cholestenoic acid was identified as one of forty plasma metabolites that could be used to predict gut microbiome Shannon diversity (PMID: 31477923 ). Shannon diversity is a metric that summarizes both species abundance and evenness, and it has been suggested as a marker for microbiome health. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (25R)-3b-Hydroxycholest-5-en-26-Oate | Generator | | (25R)-3b-Hydroxycholest-5-en-26-Oic acid | Generator | | (25R)-3beta-Hydroxycholest-5-en-26-Oate | Generator | | (25R)-3Β-hydroxycholest-5-en-26-Oate | Generator | | (25R)-3Β-hydroxycholest-5-en-26-Oic acid | Generator | | 5-Cholesten-3-ol-25-carboxylic acid | MeSH | | (3beta)-3-Hydroxycholest-5-en-26-oic acid | HMDB | | (3beta,25R)-3-Hydroxycholest-5-en-26-oic acid | HMDB | | (3β)-3-Hydroxycholest-5-en-26-oic acid | HMDB | | (3β,25R)-3-Hydroxycholest-5-en-26-oic acid | HMDB | | 3beta-Hydroxy-5-cholestenoate | HMDB | | 3beta-Hydroxy-5-cholestenoic acid | HMDB | | 3beta-Hydroxycholest-5-en-26-oic acid | HMDB | | 3beta-Hydroxycholest-5-en-27-oic acid | HMDB | | 3β-Hydroxy-5-cholestenoate | HMDB | | 3β-Hydroxy-5-cholestenoic acid | HMDB | | 3β-Hydroxycholest-5-en-26-oic acid | HMDB | | 3β-Hydroxycholest-5-en-27-oic acid | HMDB |
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| Chemical Formula | C27H44O3 |
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| Average Molecular Weight | 416.646 |
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| Monoisotopic Molecular Weight | 416.329045277 |
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| IUPAC Name | (2R,6R)-6-[(1S,2R,5S,10S,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-2-methylheptanoic acid |
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| Traditional Name | (2R,6R)-6-[(1S,2R,5S,10S,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-2-methylheptanoic acid |
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| CAS Registry Number | 56845-87-5 |
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| SMILES | [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC[C@@H](C)C(O)=O |
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| InChI Identifier | InChI=1S/C27H44O3/c1-17(6-5-7-18(2)25(29)30)22-10-11-23-21-9-8-19-16-20(28)12-14-26(19,3)24(21)13-15-27(22,23)4/h8,17-18,20-24,28H,5-7,9-16H2,1-4H3,(H,29,30)/t17-,18-,20+,21+,22-,23+,24+,26+,27-/m1/s1 |
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| InChI Key | WVXOMPRLWLXFAP-KQOPCUSDSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group. |
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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 | Bile acids, alcohols and derivatives |
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| Direct Parent | Monohydroxy bile acids, alcohols and derivatives |
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| Alternative Parents | |
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| Substituents | - Monohydroxy bile acid, alcohol, or derivatives
- Steroid acid
- 3-hydroxy-delta-5-steroid
- 3-hydroxysteroid
- 3-beta-hydroxysteroid
- 3-beta-hydroxy-delta-5-steroid
- Hydroxysteroid
- Delta-5-steroid
- Medium-chain fatty acid
- Hydroxy fatty acid
- Fatty acyl
- Cyclic alcohol
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- 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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| Disposition | Route of exposure: Biological location: Source: |
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| Process | Naturally occurring process: |
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| Role | Industrial application: Biological role: |
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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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| General References | - Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- Wilmanski T, Rappaport N, Earls JC, Magis AT, Manor O, Lovejoy J, Omenn GS, Hood L, Gibbons SM, Price ND: Blood metabolome predicts gut microbiome alpha-diversity in humans. Nat Biotechnol. 2019 Oct;37(10):1217-1228. doi: 10.1038/s41587-019-0233-9. Epub 2019 Sep 2. [PubMed:31477923 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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