| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 23:06:02 UTC |
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| Update Date | 2020-05-11 20:56:18 UTC |
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| BMDB ID | BMDB0003759 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | 5a-Pregnane-3,20-dione |
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| Description | 5a-5a-5a-pregnane-3,20-dione, also known as 5a-5a-pregnane-3,20-dione or 5a-5a-pregnane-3,20-dione, belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. Thus, 5a-5a-pregnane-3,20-dione is considered to be a steroid lipid molecule. 5a-5a-5a-pregnane-3,20-dione exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 5a-5a-5a-pregnane-3,20-dione exists in all living organisms, ranging from bacteria to humans. 5a-5a-5a-pregnane-3,20-dione participates in a number of enzymatic reactions, within cattle. In particular, 5a-5a-5a-pregnane-3,20-dione can be biosynthesized from progesterone; which is catalyzed by the enzyme 3-oxo-5-beta-steroid 4-dehydrogenase. In addition, 5a-5a-5a-pregnane-3,20-dione can be biosynthesized from 3a-hydroxy-5b-pregnane-20-one; which is catalyzed by the enzyme aldo-keto reductase family 1 member C4. In cattle, 5a-5a-pregnane-3,20-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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| 3,20-Allopregnanedione | ChEBI | | 3,20-Dioxo-5alpha-pregnane | ChEBI | | 5-alpha-Dihydroprogesterone | ChEBI | | 5alpha-Dihydroprogesterone | ChEBI | | 3,20-Dioxo-5a-pregnane | Generator | | 3,20-Dioxo-5α-pregnane | Generator | | 5-a-Dihydroprogesterone | Generator | | 5-Α-dihydroprogesterone | Generator | | 5a-Dihydroprogesterone | Generator | | 5Α-dihydroprogesterone | Generator | | 5-alpha-Pregnane-3,20-dione | HMDB, MeSH | | 5a-Pregnan-3,20-dione | HMDB | | 5alpha-Pregnan-3,20-dione | HMDB | | 5alpha-Pregnane-3,20-dione | HMDB, MeSH | | 5b-Pregnane-3,20-dione | HMDB | | 5beta-Pregnane-3,20-dione | HMDB | | Allopregnan-3,20-dione | HMDB | | Pregnane-3,20-dione | HMDB | | 5 alpha Dihydroprogesterone | MeSH, HMDB | | 5 beta Pregnane 3,20 dione | MeSH, HMDB | | 5 beta-Pregnane-3,20-dione | MeSH, HMDB | | 5-beta-Dihydroprogesterone | MeSH, HMDB | | 5alpha-DHP | MeSH, HMDB | | 3,20-Allopregnanedione, (5beta,13alpha,17alpha)-isomer | MeSH, HMDB | | 5 alpha Pregnanedione | MeSH, HMDB | | 5alpha DHP | MeSH, HMDB | | 5alpha Pregnane 3,20 dione | MeSH, HMDB | | 5beta DHP | MeSH, HMDB | | 5beta-DHP | MeSH, HMDB | | 3,20 Allopregnanedione | MeSH, HMDB | | 3,20-Allopregnanedione, (5alpha)-isomer | MeSH, HMDB | | 5 alpha Pregnane 3,20 dione | MeSH, HMDB | | 5 alpha-Dihydroprogesterone | MeSH, HMDB | | 5 alpha-Pregnane-3,20-dione | MeSH, HMDB | | 5 beta Dihydroprogesterone | MeSH, HMDB | | 5-alpha-Pregnanedione | MeSH, HMDB |
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| Chemical Formula | C21H32O2 |
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| Average Molecular Weight | 316.4776 |
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| Monoisotopic Molecular Weight | 316.240230268 |
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| IUPAC Name | (1S,2S,7S,10R,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one |
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| Traditional Name | 5a-pregnane-3,20-dione |
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| CAS Registry Number | 566-65-4 |
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| SMILES | [H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C |
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| InChI Identifier | InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14,16-19H,4-12H2,1-3H3/t14-,16-,17+,18-,19-,20-,21+/m0/s1 |
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| InChI Key | XMRPGKVKISIQBV-BJMCWZGWSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. |
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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 | Pregnane steroids |
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| Direct Parent | Gluco/mineralocorticoids, progestogins and derivatives |
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| Alternative Parents | |
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| Substituents | - Progestogin-skeleton
- 20-oxosteroid
- 3-oxo-5-alpha-steroid
- Oxosteroid
- 3-oxosteroid
- Cyclic ketone
- Ketone
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | |
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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 | 200 °C | 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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