| Record Information |
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| Version | 1.0 |
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| Creation date | 2015-10-09 22:30:57 UTC |
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| Update date | 2017-01-19 02:36:26 UTC |
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| FoodComEx ID | PC000494 |
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| FoodDB Record | FDB011602 |
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| Chemical Information |
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| Name | Allocholic acid |
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| Description | Isolated from many animal sources. Bile acid in sturgeon (Acipenser sturio)
A bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. ; Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. ; Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487, 16037564, 12576301, 11907135). |
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| CAS Number | 2464-18-8 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| 3,7,12-Trihydroxy-(3alpha,5alpha,7alpha,12alpha)-cholan-24-Oate | HMDB | | 3,7,12-Trihydroxy-(3alpha,5alpha,7alpha,12alpha)-cholan-24-Oic acid | HMDB | | 3a,7a,12a-trihydroxy-(5a)-cholan-24-oate | biospider | | 3a,7a,12a-trihydroxy-(5a)-cholan-24-oic acid | biospider | | 3a,7a,12a-trihydroxy-5a-cholan-24-oate | biospider | | 3a,7a,12a-trihydroxy-5a-cholan-24-oic acid | biospider | | 3alpha,7alpha,12alpha-Trihydroxy-5alpha-cholan-24-oic acid | biospider | | 5a-Allocholate | biospider | | 5a-Allocholic acid | biospider | | 5a-Cholate | biospider | | 5a-Cholic acid | biospider | | Allocholate | biospider | | Allocholic acid | db_source |
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| Chemical Formula | C24H40O5 |
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| IUPAC name | 4-{5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanoic acid |
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| InChI Identifier | InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29) |
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| InChI Key | BHQCQFFYRZLCQQ-UHFFFAOYSA-N |
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| Isomeric SMILES | CC(CCC(O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C |
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| Average Molecular Weight | 408.5714 |
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| Monoisotopic Molecular Weight | 408.28757439 |
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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
- 7-hydroxysteroid
- Hydroxysteroid
- Cyclic alcohol
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Polyol
- Monocarboxylic acid or derivatives
- Organic oxide
- Alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Carbonyl group
- 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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| Physico-Chemical Properties - Experimental |
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| Property | Value | Reference |
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| Experimental logP | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Melting Point | Mp 250-251° | DFC |
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| Foods of Origin |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Production Data |
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| Production Method | commercial |
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| Production Method Reference | Not Available |
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| Production Method Reference File | Not Available |
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| Quantity Available | Production upon request, up to 10 mg |
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| Delivery Time | Not Available |
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| Storage Form | solid |
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| Storage Conditions | -80°C |
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| Stability | Not Available |
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| Purity | Not Available |
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| Spectra |
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| Spectral Data Upon Request | Not Available |
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| Provider Information |
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| Commercial Vendors |
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| Toronto Research Chemicals | A545000 |
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