Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2021-09-24 08:08:06 UTC |
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Update Date | 2021-09-24 08:08:06 UTC |
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HMDB ID | HMDB0304221 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | 5-beta-pregnan-3,20 dione |
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Description | (5beta)-pregnane-3,20-dione, also known as 3,20-pregnanedione or 5beta-dihydroprogesterone, belongs to gluco/mineralocorticoids, progestogins and derivatives class of compounds. Those are steroids with a structure based on a hydroxylated prostane moiety. Thus, (5beta)-pregnane-3,20-dione is considered to be a steroid lipid molecule (5beta)-pregnane-3,20-dione is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). (5beta)-pregnane-3,20-dione can be found in a number of food items such as opium poppy, walnut, rowal, and italian sweet red pepper, which makes (5beta)-pregnane-3,20-dione a potential biomarker for the consumption of these food products. |
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Structure | [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(C)=O 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-/m1/s1 |
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Synonyms | Value | Source |
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3,20-Pregnanedione | ChEBI | 5beta-Dihydroprogesterone | ChEBI | 5beta-Pregnan-3,20-dione | ChEBI | 5b-Dihydroprogesterone | Generator | 5Β-dihydroprogesterone | Generator | 5b-Pregnan-3,20-dione | Generator | 5Β-pregnan-3,20-dione | Generator | (5b)-PREGNANE-3,20-dione | Generator | (5Β)-pregnane-3,20-dione | Generator | (5BETA)-PREGNANE-3,20-dione | ChEBI |
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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,7R,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 | (5β)-pregnane-3,20-dione |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(C)=O |
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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-/m1/s1 |
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InChI Key | XMRPGKVKISIQBV-XWOJZHJZSA-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-beta-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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Not Available | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular 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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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 IndicesDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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5-beta-pregnan-3,20 dione,1TMS,isomer #1 | CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C | 2796.2 | Semi standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,1TMS,isomer #1 | CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C | 2729.1 | Standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,1TMS,isomer #1 | CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C | 3108.6 | Standard polar | 33892256 | 5-beta-pregnan-3,20 dione,1TMS,isomer #2 | CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C | 2781.6 | Semi standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,1TMS,isomer #2 | CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C | 2657.1 | Standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,1TMS,isomer #2 | CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C | 3124.2 | Standard polar | 33892256 | 5-beta-pregnan-3,20 dione,1TMS,isomer #3 | CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C | 2764.7 | Semi standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,1TMS,isomer #3 | CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C | 2674.8 | Standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,1TMS,isomer #3 | CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C | 3122.0 | Standard polar | 33892256 | 5-beta-pregnan-3,20 dione,1TMS,isomer #4 | C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C | 2782.9 | Semi standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,1TMS,isomer #4 | C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C | 2733.5 | Standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,1TMS,isomer #4 | C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C | 3215.6 | Standard polar | 33892256 | 5-beta-pregnan-3,20 dione,2TMS,isomer #1 | CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@@H]4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C | 2823.8 | Semi standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,2TMS,isomer #1 | CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@@H]4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C | 2766.4 | Standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,2TMS,isomer #1 | CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@@H]4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C | 3149.9 | Standard polar | 33892256 | 5-beta-pregnan-3,20 dione,2TMS,isomer #2 | CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@@H]4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C | 2831.2 | Semi standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,2TMS,isomer #2 | CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@@H]4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C | 2790.0 | Standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,2TMS,isomer #2 | CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@@H]4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C | 3148.7 | Standard polar | 33892256 | 5-beta-pregnan-3,20 dione,2TMS,isomer #3 | C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C | 2794.2 | Semi standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,2TMS,isomer #3 | C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C | 2757.4 | Standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,2TMS,isomer #3 | C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C | 3243.6 | Standard polar | 33892256 | 5-beta-pregnan-3,20 dione,2TMS,isomer #4 | C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C | 2776.7 | Semi standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,2TMS,isomer #4 | C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C | 2781.7 | Standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,2TMS,isomer #4 | C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C | 3241.1 | Standard polar | 33892256 | 5-beta-pregnan-3,20 dione,1TBDMS,isomer #1 | CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C | 3039.3 | Semi standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,1TBDMS,isomer #1 | CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C | 2980.0 | Standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,1TBDMS,isomer #1 | CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C | 3265.1 | Standard polar | 33892256 | 5-beta-pregnan-3,20 dione,1TBDMS,isomer #2 | CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C | 3020.9 | Semi standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,1TBDMS,isomer #2 | CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C | 2854.7 | Standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,1TBDMS,isomer #2 | CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C | 3268.1 | Standard polar | 33892256 | 5-beta-pregnan-3,20 dione,1TBDMS,isomer #3 | CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C | 2994.9 | Semi standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,1TBDMS,isomer #3 | CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C | 2886.4 | Standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,1TBDMS,isomer #3 | CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C | 3267.2 | Standard polar | 33892256 | 5-beta-pregnan-3,20 dione,1TBDMS,isomer #4 | C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C | 3040.0 | Semi standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,1TBDMS,isomer #4 | C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C | 2996.7 | Standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,1TBDMS,isomer #4 | C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C | 3354.2 | Standard polar | 33892256 | 5-beta-pregnan-3,20 dione,2TBDMS,isomer #1 | CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@@H]4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C | 3305.5 | Semi standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,2TBDMS,isomer #1 | CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@@H]4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C | 3131.9 | Standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,2TBDMS,isomer #1 | CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@@H]4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C | 3382.1 | Standard polar | 33892256 | 5-beta-pregnan-3,20 dione,2TBDMS,isomer #2 | CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@@H]4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C | 3306.9 | Semi standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,2TBDMS,isomer #2 | CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@@H]4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C | 3197.3 | Standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,2TBDMS,isomer #2 | CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@@H]4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C | 3384.6 | Standard polar | 33892256 | 5-beta-pregnan-3,20 dione,2TBDMS,isomer #3 | C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C | 3301.1 | Semi standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,2TBDMS,isomer #3 | C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C | 3123.7 | Standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,2TBDMS,isomer #3 | C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C | 3448.0 | Standard polar | 33892256 | 5-beta-pregnan-3,20 dione,2TBDMS,isomer #4 | C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C | 3265.9 | Semi standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,2TBDMS,isomer #4 | C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C | 3187.1 | Standard non polar | 33892256 | 5-beta-pregnan-3,20 dione,2TBDMS,isomer #4 | C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C | 3449.6 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - 5-beta-pregnan-3,20 dione GC-MS (Non-derivatized) | splash10-0kkc-7920000000-b2f5e9cd5c5f21cf2c3e | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-beta-pregnan-3,20 dione 10V, Positive-QTOF | splash10-014i-0259000000-c2d751219b7bd83c50f5 | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-beta-pregnan-3,20 dione 20V, Positive-QTOF | splash10-05ot-0492000000-6952daff63896df17039 | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-beta-pregnan-3,20 dione 40V, Positive-QTOF | splash10-052f-2390000000-3a3d590dd4e3e70e717b | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-beta-pregnan-3,20 dione 10V, Negative-QTOF | splash10-014i-0019000000-154e3b1bd00054948dbc | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-beta-pregnan-3,20 dione 20V, Negative-QTOF | splash10-014i-0049000000-d7397d0cc04aa171ef93 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-beta-pregnan-3,20 dione 40V, Negative-QTOF | splash10-006t-2090000000-fef94b1e76f86c22183c | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-beta-pregnan-3,20 dione 10V, Positive-QTOF | splash10-014j-0069000000-9a5dc6a8c96deb8fb292 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-beta-pregnan-3,20 dione 20V, Positive-QTOF | splash10-009t-1491000000-c085f98672eb15cc3dbb | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-beta-pregnan-3,20 dione 40V, Positive-QTOF | splash10-0006-9710000000-1235b6cf9eb7965603a2 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-beta-pregnan-3,20 dione 10V, Negative-QTOF | splash10-014i-0009000000-be6e06313d0abca8e664 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-beta-pregnan-3,20 dione 20V, Negative-QTOF | splash10-014i-0029000000-9ca213f70ddd56044add | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-beta-pregnan-3,20 dione 40V, Negative-QTOF | splash10-000j-0091000000-20393648742744408be0 | 2021-10-21 | Wishart Lab | View Spectrum |
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