| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:32:13 UTC |
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| Update Date | 2020-05-11 20:21:05 UTC |
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| BMDB ID | BMDB0000527 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | 6a,12a-Dihydroxylithocholic acid |
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| Description | 6a,12a-Dihydroxylithocholic acid, also known as 3a,6a,12a-trihydroxy-5b-cholan-24-Oate, belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. Based on a literature review a significant number of articles have been published on 6a,12a-Dihydroxylithocholic acid. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 6a,12a-Dihydroxylithocholate | Generator | | 3a,6a,12a-Trihydroxy-5b-cholan-24-Oate | HMDB | | 3a,6a,12a-Trihydroxy-5b-cholan-24-Oic acid | HMDB | | 3a,6a,12a-Trihydroxycholate | HMDB | | 3a,6a,12a-Trihydroxycholic acid | HMDB | | (4R)-4-[(1S,2R,5R,8S,10R,11S,14R,15R,16S)-5,8,16-Trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate | HMDB | | 6a,12a-Dihydroxylithocholic acid | Generator |
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| Chemical Formula | C24H40O5 |
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| Average Molecular Weight | 408.5714 |
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| Monoisotopic Molecular Weight | 408.28757439 |
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| IUPAC Name | (4R)-4-[(1S,2R,5R,8S,10R,11S,14R,15R,16S)-5,8,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid |
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| Traditional Name | 3a,6a,12a-trihydroxycholate |
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| CAS Registry Number | 21066-18-2 |
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| SMILES | [H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])C[C@H](O)C2C[C@H](O)CC[C@]12C |
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| InChI Identifier | InChI=1S/C24H40O5/c1-13(4-7-22(28)29)16-5-6-17-15-11-20(26)19-10-14(25)8-9-23(19,2)18(15)12-21(27)24(16,17)3/h13-21,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14-,15+,16-,17+,18+,19?,20+,21+,23-,24-/m1/s1 |
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| InChI Key | GCAHOAMXTYBLNZ-YAZNBHORSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. |
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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 | Trihydroxy bile acids, alcohols and derivatives |
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| Alternative Parents | |
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| Substituents | - Trihydroxy bile acid, alcohol, or derivatives
- 3-hydroxysteroid
- 12-hydroxysteroid
- 3-alpha-hydroxysteroid
- 6-hydroxysteroid
- Hydroxysteroid
- Cyclic alcohol
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Polyol
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Alcohol
- Organooxygen compound
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Status | Expected but not Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | |
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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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| Spectra | |
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| Synthesis Reference | Iida, Takashi; Tamaru, Tamaaki; Chang, Frederic C.; Goto, Junichi; Nambara, Toshio. Potential bile acid metabolites. XVIII. Synthesis of stereoisomeric 3,6,12a-trihydroxy-5b-cholanoic acids. Journal of Lipid Research (1991), 32(4), 649-58. |
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