Record Information |
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Version | 5.0 |
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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 | 2022-03-07 02:49:03 UTC |
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HMDB ID | HMDB0000541 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 7b-Hydroxy-3-oxo-5b-cholanoic acid |
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Description | 7b-Hydroxy-3-oxo-5b-cholanoic acid was one of the bile acids present in significant proportions during early gestation, identified in amniotic fluid. (PMID 2373959 ). A bile acid. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending only on the 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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Structure | [H][C@@]12CC[C@H]([C@H](C)CCC(=O)OC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C(=O)CC2CC(=O)CC[C@]12C InChI=1S/C25H38O4/c1-15(5-8-22(28)29-4)18-6-7-19-23-20(10-12-25(18,19)3)24(2)11-9-17(26)13-16(24)14-21(23)27/h15-16,18-20,23H,5-14H2,1-4H3/t15-,16?,18-,19+,20+,23+,24+,25-/m1/s1 |
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Synonyms | Value | Source |
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7b-Hydroxy-3-oxo-5b-cholanoate | Generator | (5b,7b)-7-Hydroxy-3-oxo-cholan-24-Oate | HMDB | (5b,7b)-7-Hydroxy-3-oxo-cholan-24-Oic acid | HMDB | 7b-Hydroxy-3-oxo-5b-cholan-24-Oate | HMDB | 7b-Hydroxy-3-oxo-5b-cholan-24-Oic acid | HMDB | Methyl (4R)-4-[(1S,2S,10R,11S,14R,15R)-2,15-dimethyl-5,9-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid | HMDB | Methyl 3,7-dioxocholan-24-Oic acid | HMDB |
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Chemical Formula | C25H38O4 |
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Average Molecular Weight | 402.5668 |
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Monoisotopic Molecular Weight | 402.277009704 |
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IUPAC Name | methyl (4R)-4-[(1S,2S,10R,11S,14R,15R)-2,15-dimethyl-5,9-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate |
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Traditional Name | 7b-hydroxy-3-oxo-5b-cholanoate |
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CAS Registry Number | 77060-26-5 |
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SMILES | [H][C@@]12CC[C@H]([C@H](C)CCC(=O)OC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C(=O)CC2CC(=O)CC[C@]12C |
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InChI Identifier | InChI=1S/C25H38O4/c1-15(5-8-22(28)29-4)18-6-7-19-23-20(10-12-25(18,19)3)24(2)11-9-17(26)13-16(24)14-21(23)27/h15-16,18-20,23H,5-14H2,1-4H3/t15-,16?,18-,19+,20+,23+,24+,25-/m1/s1 |
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InChI Key | UZRRNRRCPZZPNY-ZECRIGHZSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as bile acids, alcohols and derivatives. These are organic compounds containing an alcohol or acid derivative of cholic acid. |
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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 | Bile acids, alcohols and derivatives |
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Alternative Parents | |
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Substituents | - Bile acid, alcohol, or derivatives
- 3-oxosteroid
- 7-oxosteroid
- Oxosteroid
- Fatty acid methyl ester
- Fatty acid ester
- Fatty acyl
- Methyl ester
- Carboxylic acid ester
- Cyclic ketone
- Ketone
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Organic oxygen compound
- Carbonyl group
- Organic oxide
- 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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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 171 - 173 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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7b-Hydroxy-3-oxo-5b-cholanoic acid,1TMS,isomer #1 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C)CC4CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C | 3265.7 | Semi standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,1TMS,isomer #1 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C)CC4CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C | 3268.5 | Standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,1TMS,isomer #1 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C)CC4CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C | 3726.6 | Standard polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,1TMS,isomer #2 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)=CC4CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C | 3194.6 | Semi standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,1TMS,isomer #2 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)=CC4CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C | 3222.1 | Standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,1TMS,isomer #2 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)=CC4CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C | 3708.1 | Standard polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,1TMS,isomer #3 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(=O)CC4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C | 3294.1 | Semi standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,1TMS,isomer #3 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(=O)CC4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C | 3247.7 | Standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,1TMS,isomer #3 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(=O)CC4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C | 3702.4 | Standard polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,1TMS,isomer #4 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(=O)CC4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3306.7 | Semi standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,1TMS,isomer #4 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(=O)CC4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3279.3 | Standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,1TMS,isomer #4 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(=O)CC4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3695.8 | Standard polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,2TMS,isomer #1 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C | 3252.1 | Semi standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,2TMS,isomer #1 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C | 3287.1 | Standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,2TMS,isomer #1 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C | 3733.3 | Standard polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,2TMS,isomer #2 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C)CC4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3267.5 | Semi standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,2TMS,isomer #2 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C)CC4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3301.6 | Standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,2TMS,isomer #2 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C)CC4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3729.6 | Standard polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,2TMS,isomer #3 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)=CC4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C | 3206.3 | Semi standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,2TMS,isomer #3 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)=CC4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C | 3219.2 | Standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,2TMS,isomer #3 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)=CC4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C | 3734.3 | Standard polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,2TMS,isomer #4 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)=CC4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3222.6 | Semi standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,2TMS,isomer #4 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)=CC4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3270.3 | Standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,2TMS,isomer #4 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)=CC4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3736.5 | Standard polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,1TBDMS,isomer #1 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)CC4CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C | 3483.3 | Semi standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,1TBDMS,isomer #1 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)CC4CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C | 3527.8 | Standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,1TBDMS,isomer #1 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)CC4CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C | 3837.1 | Standard polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,1TBDMS,isomer #2 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)=CC4CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C | 3430.8 | Semi standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,1TBDMS,isomer #2 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)=CC4CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C | 3389.8 | Standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,1TBDMS,isomer #2 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)=CC4CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C | 3819.6 | Standard polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,1TBDMS,isomer #3 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(=O)CC4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C | 3551.6 | Semi standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,1TBDMS,isomer #3 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(=O)CC4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C | 3450.2 | Standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,1TBDMS,isomer #3 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(=O)CC4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C | 3816.6 | Standard polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,1TBDMS,isomer #4 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(=O)CC4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3552.0 | Semi standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,1TBDMS,isomer #4 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(=O)CC4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3496.6 | Standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,1TBDMS,isomer #4 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(=O)CC4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3811.1 | Standard polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,2TBDMS,isomer #1 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)CC4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C | 3662.8 | Semi standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,2TBDMS,isomer #1 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)CC4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C | 3635.3 | Standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,2TBDMS,isomer #1 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)CC4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C | 3915.3 | Standard polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,2TBDMS,isomer #2 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)CC4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3692.9 | Semi standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,2TBDMS,isomer #2 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)CC4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3694.2 | Standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,2TBDMS,isomer #2 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)CC4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3913.5 | Standard polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,2TBDMS,isomer #3 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)=CC4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C | 3626.9 | Semi standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,2TBDMS,isomer #3 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)=CC4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C | 3500.9 | Standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,2TBDMS,isomer #3 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)=CC4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C | 3909.6 | Standard polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,2TBDMS,isomer #4 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)=CC4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3643.9 | Semi standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,2TBDMS,isomer #4 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)=CC4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3562.1 | Standard non polar | 33892256 | 7b-Hydroxy-3-oxo-5b-cholanoic acid,2TBDMS,isomer #4 | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)=CC4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3915.0 | Standard polar | 33892256 |
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