Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-02-26 21:22:15 UTC |
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HMDB ID | HMDB0000503 |
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Secondary Accession Numbers | - HMDB00503
- HMDB0062796
- HMDB62796
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Metabolite Identification |
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Common Name | 7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid |
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Description | 7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid, also known as 3-dehydrochenodeoxycholic acid or (5beta,7alpha)-7-hydroxy-3-oxocholan-24-oate, is classified as a monohydroxy bile acids, alcohol or a monohydroxy bile acids, alcohol derivative. Monohydroxy bile acids, alcohols are bile acids, alcohols or any of their derivatives bearing a hydroxyl group. 7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid is considered to be practically insoluble (in water) and acidic. 7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid is a bile acid lipid molecule. Glycine- and taurine-conjugated 7alpha-hydroxy-3-oxo-5beta-cholan-24-oic acid has been identified in normal human serum (PMID: 1939467 ) and as a cholesterol metabolite in bile acids produced in HepG2 cells, a well-differentiated human hepatoblastoma cell line (PMID: 1655725 ). |
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Structure | |
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Synonyms | Value | Source |
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(5beta,7alpha)-7-Hydroxy-3-oxocholan-24-Oic acid | ChEBI | 3-Dehydrochenodeoxycholic acid | ChEBI | 3-Oxochenodeoxycholic acid | ChEBI | Dehydrochenodeoxycholic acid | ChEBI | (5b,7a)-7-Hydroxy-3-oxocholan-24-Oate | Generator | (5b,7a)-7-Hydroxy-3-oxocholan-24-Oic acid | Generator | (5beta,7alpha)-7-Hydroxy-3-oxocholan-24-Oate | Generator | (5Β,7α)-7-hydroxy-3-oxocholan-24-Oate | Generator | (5Β,7α)-7-hydroxy-3-oxocholan-24-Oic acid | Generator | 3-Dehydrochenodeoxycholate | Generator | 3-Oxochenodeoxycholate | Generator | Dehydrochenodeoxycholate | Generator | 7a-Hydroxy-3-oxo-5b-cholan-24-Oate | Generator | 7a-Hydroxy-3-oxo-5b-cholan-24-Oic acid | Generator | 7alpha-Hydroxy-3-oxo-5beta-cholan-24-Oate | Generator | 7Α-hydroxy-3-oxo-5β-cholan-24-Oate | Generator | 7Α-hydroxy-3-oxo-5β-cholan-24-Oic acid | Generator | 7Α-hydroxy-3-oxo-5β-cholanic acid | HMDB | 3-oxo-7Α-hydroxy-5β-cholanic acid | HMDB | 3-oxo-7Α-hydroxycholan-24-Oic acid | HMDB | 3-Keto-7α-hydroxy-5β-cholanic acid | HMDB | 7Α-hydroxy-3-oxo-5β-cholanoic acid | HMDB | 7a-Hydroxy-3-oxo-5b-cholanoic acid | HMDB | 7alpha-Hydroxy-3-oxo-5beta-cholanoic acid | HMDB | (4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R)-9-Hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate | HMDB |
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Chemical Formula | C24H38O4 |
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Average Molecular Weight | 390.564 |
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Monoisotopic Molecular Weight | 390.277009704 |
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IUPAC Name | (4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid |
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Traditional Name | (4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid |
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CAS Registry Number | 4185-00-6 |
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SMILES | [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O |
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InChI Identifier | InChI=1S/C24H38O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-15,17-20,22,26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,17-,18+,19+,20-,22+,23+,24-/m1/s1 |
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InChI Key | KNVADAPHVNKTEP-CIGXQKLNSA-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
- 3-oxosteroid
- Hydroxysteroid
- Oxosteroid
- 7-hydroxysteroid
- 3-oxo-5-beta-steroid
- Cyclic alcohol
- Secondary alcohol
- Ketone
- Cyclic ketone
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organooxygen compound
- Organic oxygen compound
- Alcohol
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- 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 | 88 - 90 °C | 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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Synthesis Reference | Riva, Sergio; Bovara, Roberto; Zetta, Lucia; Pasta, Piero; Ottolina, Gianluca; Carrea, Giacomo. Enzymic a/b inversion of C-3 hydroxyl of bile acids and study of the effects of organic solvents on reaction rates. Journal of Organic Chemistry (1988), 53(1), 88-92. |
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General References | - Axelson M, Mork B, Everson GT: Bile acid synthesis in cultured human hepatoblastoma cells. J Biol Chem. 1991 Sep 25;266(27):17770-7. [PubMed:1655725 ]
- Goto J, Saisho Y, Nambara T: Studies on steroids. CCLII. Separation and characterization of 3-oxobile acids in serum by high-performance liquid chromatography with fluorescence detection. J Chromatogr. 1991 Jul 5;567(2):343-9. [PubMed:1939467 ]
- 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 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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