Record Information |
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Version | 2.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2021-10-07 20:41:49 UTC |
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NP-MRD ID | NP0001016 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Deoxycholic acid glycine conjugate |
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Description | Deoxycholic acid glycine conjugate, or or Deoxyglycocholic acid or Deoxygcholylglycine is a bile salt formed in the liver by conjugation of deoxycholate with glycine. It usually exists as the sodium salt. Deoxygcholylglycine is a secondary bile acid produced by the action of enzymes existing in the microbial flora of the colonic environment. In hepatocytes, both primary and secondary bile acids undergo amino acid conjugation at the C-24 carboxylic acid on the side chain, and almost all bile acids in the bile duct therefore exist in a glycine conjugated form (PMID: 16949895 ). As a bile acid Deoxyglycocholic acid acts as a detergent to solubilize fats for absorption and is itself absorbed. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, and depends 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 ). Deoxyglycocholic acid is used as a cholagogue and choleretic. |
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Structure | [H][C@]12CCC3C4CC[C@H]([C@H](C)CCC(=O)NCC(O)=O)[C@@]4(C)[C@@H](O)CC3[C@@]1(C)CC[C@@H](O)C2 InChI=1S/C26H43NO5/c1-15(4-9-23(30)27-14-24(31)32)19-7-8-20-18-6-5-16-12-17(28)10-11-25(16,2)21(18)13-22(29)26(19,20)3/h15-22,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16-,17-,18?,19-,20?,21?,22+,25+,26-/m1/s1 |
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Synonyms | Value | Source |
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Deoxycholate glycine conjugate | Generator | Deoxycholic acid glycine conjugic acid | Generator | Deoxycholylglycine | HMDB | Deoxyglycocholate | HMDB | Deoxyglycocholic acid | HMDB | Glycodeoxycholate | HMDB | Glycodeoxycholic acid | HMDB | Glycodesoxycholate | HMDB | Glycodesoxycholic acid | HMDB | Glycyldeoxycholate | HMDB | Glycyldeoxycholic acid | HMDB | N-(3a,12a-Dihydroxy-5b-cholan-24-oyl)-glycine | HMDB | N-(Carboxymethyl)-3a,12a-dihydroxy-5b-cholan-24-amide | HMDB | Deoxycholate, glycine | HMDB | Acid, glycodeoxycholic | HMDB | Glycine deoxycholate | HMDB |
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Chemical Formula | C26H43NO5 |
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Average Mass | 449.6233 Da |
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Monoisotopic Mass | 449.31412 Da |
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IUPAC Name | 2-[(4R)-4-[(2S,5R,7R,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid |
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Traditional Name | [(4R)-4-[(2S,5R,7R,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid |
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CAS Registry Number | 360-65-6 |
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SMILES | [H][C@]12CCC3C4CC[C@H]([C@H](C)CCC(=O)NCC(O)=O)[C@@]4(C)[C@@H](O)CC3[C@@]1(C)CC[C@@H](O)C2 |
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InChI Identifier | InChI=1S/C26H43NO5/c1-15(4-9-23(30)27-14-24(31)32)19-7-8-20-18-6-5-16-12-17(28)10-11-25(16,2)21(18)13-22(29)26(19,20)3/h15-22,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16-,17-,18?,19-,20?,21?,22+,25+,26-/m1/s1 |
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InChI Key | WVULKSPCQVQLCU-ZMBDPXIHSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Species Where Detected | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as glycinated bile acids and derivatives. Glycinated bile acids and derivatives are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton. |
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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 | Glycinated bile acids and derivatives |
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Alternative Parents | |
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Substituents | - Glycinated bile acid
- Dihydroxy bile acid, alcohol, or derivatives
- Hydroxy bile acid, alcohol, or derivatives
- 3-hydroxysteroid
- 12-hydroxysteroid
- Hydroxysteroid
- 3-alpha-hydroxysteroid
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- Alpha-amino acid or derivatives
- Fatty amide
- Fatty acyl
- N-acyl-amine
- Cyclic alcohol
- Carboxamide group
- Secondary alcohol
- Secondary carboxylic acid amide
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Organic nitrogen compound
- Organopnictogen compound
- Carbonyl group
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen 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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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 | 0.0027 mg/mL | Not Available | LogP | 2.25 | Roda, A., Minutello, A., Angellotti, M. A., & Fini, A. (1990). Bile acid structure-activity relationship: evaluation of bile acid lipophilicity using 1-octanol/water partition coefficient and reverse phase HPLC. Journal of lipid research, 31(8), 1433-1443. |
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Predicted Properties | |
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