Record Information |
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Version | 2.0 |
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Created at | 2024-09-11 20:25:11 UTC |
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Updated at | 2024-09-11 20:25:11 UTC |
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NP-MRD ID | NP0339208 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 3a,7b,21-Trihydroxy-5b-cholanoic acid |
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Description | 3A,7b,21-Trihydroxy-5b-cholanoic acid, also known as 21-hydroxyisocholate or lagocholate, belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an nterohepatic circuit. 3A,7b,21-Trihydroxy-5b-cholanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are steroid acids found predominantly in bile of mammals. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. 3A,7b,21-Trihydroxy-5b-cholanoic acid is a bile acid. |
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Structure | C[C@]12CCC3C(C1CCC2[C@H](O)C(O)CCC(O)=O)[C@@H](O)CC1C[C@H](O)CC[C@]31C InChI=1S/C24H40O6/c1-23-9-7-14(25)11-13(23)12-19(27)21-15-3-4-17(24(15,2)10-8-16(21)23)22(30)18(26)5-6-20(28)29/h13-19,21-22,25-27,30H,3-12H2,1-2H3,(H,28,29)/t13?,14-,15?,16?,17?,18?,19+,21?,22+,23+,24+/m1/s1 |
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Synonyms | Value | Source |
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3a,7b,21-Trihydroxy-5b-cholanoate | Generator | 21-Hydroxyisocholate | HMDB | 21-Hydroxyisocholic acid | HMDB | 3a,7a,21-Trihydroxy-5b-cholanate | HMDB | 3a,7a,21-Trihydroxy-5b-cholanic acid | HMDB | 3a,7a,21-Trihydroxy-5b-cholanoate | HMDB | 3a,7a,21-Trihydroxy-5b-cholanoic acid | HMDB | Lagocholate | HMDB | Lagocholic acid | HMDB | (5S)-5-[(2S,5R,9S,15S)-5,9-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-4,5-dihydroxypentanoate | Generator |
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Chemical Formula | C24H40O6 |
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Average Mass | 424.5708 Da |
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Monoisotopic Mass | 424.28249 Da |
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IUPAC Name | (5S)-5-[(2S,5R,9S,15S)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-4,5-dihydroxypentanoic acid |
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Traditional Name | (5S)-5-[(2S,5R,9S,15S)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-4,5-dihydroxypentanoic acid |
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CAS Registry Number | Not Available |
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SMILES | C[C@]12CCC3C(C1CCC2[C@H](O)C(O)CCC(O)=O)[C@@H](O)CC1C[C@H](O)CC[C@]31C |
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InChI Identifier | InChI=1S/C24H40O6/c1-23-9-7-14(25)11-13(23)12-19(27)21-15-3-4-17(24(15,2)10-8-16(21)23)22(30)18(26)5-6-20(28)29/h13-19,21-22,25-27,30H,3-12H2,1-2H3,(H,28,29)/t13?,14-,15?,16?,17?,18?,19+,21?,22+,23+,24+/m1/s1 |
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InChI Key | JHBLUEHIRYMJOU-ZSFPCQDKSA-N |
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Experimental Spectra |
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| Not Available | 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 | Not Available |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. |
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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 | Androstane steroids |
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Direct Parent | Androgens and derivatives |
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Alternative Parents | |
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Substituents | - 20-hydroxysteroid
- Androgen-skeleton
- 3-hydroxysteroid
- 7-hydroxysteroid
- 7-alpha-hydroxysteroid
- 3-alpha-hydroxysteroid
- Hydroxysteroid
- Medium-chain hydroxy acid
- Medium-chain fatty acid
- Hydroxy fatty acid
- Fatty acyl
- Fatty acid
- Cyclic alcohol
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Alcohol
- Organic oxygen compound
- Carbonyl group
- Organic oxide
- Hydrocarbon derivative
- 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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Physical Properties |
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State | Not Available |
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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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