| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 23:25:35 UTC |
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| Update Date | 2020-04-22 15:18:27 UTC |
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| BMDB ID | BMDB0006755 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | 3a,21-Dihydroxy-5b-pregnane-11,20-dione |
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| Description | 3a,21-Dihydroxy-5b-pregnane-11,20-dione, also known as 3a,21-dihydroxy-5b-pregnane-11,20-dione, belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Thus, 3a,21-dihydroxy-5b-pregnane-11,20-dione is considered to be a steroid lipid molecule. 3a,21-Dihydroxy-5b-pregnane-11,20-dione is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3a,21-Dihydroxy-5b-pregnane-11,20-dione participates in a number of enzymatic reactions, within cattle. In particular, 3a,21-Dihydroxy-5b-pregnane-11,20-dione can be biosynthesized from tetrahydrocorticosterone through its interaction with the enzyme corticosteroid 11-beta-dehydrogenase isozyme 1. In addition, 3a,21-Dihydroxy-5b-pregnane-11,20-dione can be converted into 21-hydroxy-5b-pregnane-3,11,20-trione; which is catalyzed by the enzyme aldo-keto reductase family 1 member C4. In cattle, 3a,21-dihydroxy-5b-pregnane-11,20-dione is involved in the metabolic pathway called the steroidogenesis pathway. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 3alpha,21-Dihydroxy-5beta-pregnane-11,20-dione | HMDB | | 5beta-Pregnane-3alpha,21-diol-11,20-dione | HMDB |
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| Chemical Formula | C21H32O4 |
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| Average Molecular Weight | 348.4764 |
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| Monoisotopic Molecular Weight | 348.230059512 |
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| IUPAC Name | (1S,2S,5R,7R,10S,11S,15S)-5-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-17-one |
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| Traditional Name | (1S,2S,5R,7R,10S,11S,15S)-5-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-17-one |
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| CAS Registry Number | 566-03-0 |
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| SMILES | [H][C@@]12CCC(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C |
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| InChI Identifier | InChI=1S/C21H32O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h12-16,19,22-23H,3-11H2,1-2H3/t12-,13-,14+,15+,16?,19-,20+,21+/m1/s1 |
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| InChI Key | XWYBFXIUISNTQG-XPYNSANSSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. |
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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 | Hydroxysteroids |
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| Direct Parent | 21-hydroxysteroids |
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| Alternative Parents | |
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| Substituents | - Progestogin-skeleton
- 21-hydroxysteroid
- 20-oxosteroid
- Pregnane-skeleton
- 3-hydroxysteroid
- 11-oxosteroid
- Oxosteroid
- 3-alpha-hydroxysteroid
- Cyclic alcohol
- Alpha-hydroxy ketone
- Ketone
- Secondary alcohol
- Alcohol
- Hydrocarbon derivative
- Organooxygen compound
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- Primary alcohol
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | - C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030199 )
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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 | - Cell membrane
- Cytoplasm
- Membrane
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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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