| Record Information |
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| Version | 2.0 |
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| Created at | 2022-05-11 16:50:13 UTC |
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| Updated at | 2022-05-11 16:50:14 UTC |
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| NP-MRD ID | NP0087458 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 5-alpha-Dihydrotestosterone glucuronide |
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| Description | 5-Alpha-Dihydrotestosterone glucuronide, also known as stanolone glucuronate or 17b-hydroxy-5a-androstan-3-one glucuronide, belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton. Thus, 5-alpha-dihydrotestosterone glucuronide is considered to be a steroid conjugate lipid molecule. 5-alpha-Dihydrotestosterone glucuronide was first documented in 1978 (PMID: 263350). 5-Alpha-Dihydrotestosterone glucuronide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 12560362) (PMID: 3140586). |
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| Structure | [H][C@@]12CC[C@H](O[C@]3([H])O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C InChI=1S/C25H38O8/c1-24-9-7-13(26)11-12(24)3-4-14-15-5-6-17(25(15,2)10-8-16(14)24)32-23-20(29)18(27)19(28)21(33-23)22(30)31/h12,14-21,23,27-29H,3-11H2,1-2H3,(H,30,31)/t12-,14-,15-,16-,17-,18-,19-,20+,21-,23+,24-,25-/m0/s1 |
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| Synonyms | | Value | Source |
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| (5alpha,17beta)-3-Oxoandrostan-17-yl beta-D-glucopyranosiduronic acid | ChEBI | | 17beta-Hydroxy-5alpha-androstan-3-one glucuronide | ChEBI | | 5alpha-Dihydrotestosterone 17-(beta-D-glucuronide) | ChEBI | | 5alpha-Dihydrotestosterone 17-beta-glucuronide | ChEBI | | 5alpha-Dihydrotestosterone 17-O-(beta-D-glucuronic acid) | ChEBI | | 5alpha-Dihydrotestosterone glucuronide | ChEBI | | 5alpha-Dihydrotestosterone-17g | ChEBI | | Dihydrotestosterone 17-glucuronide | ChEBI | | Dihydrotestosterone glucuronide | ChEBI | | Stanolone 17-glucuronide | ChEBI | | Stanolone glucuronate | ChEBI | | (5a,17b)-3-Oxoandrostan-17-yl b-D-glucopyranosiduronate | Generator | | (5a,17b)-3-Oxoandrostan-17-yl b-D-glucopyranosiduronic acid | Generator | | (5alpha,17beta)-3-Oxoandrostan-17-yl beta-D-glucopyranosiduronate | Generator | | (5Α,17β)-3-oxoandrostan-17-yl β-D-glucopyranosiduronate | Generator | | (5Α,17β)-3-oxoandrostan-17-yl β-D-glucopyranosiduronic acid | Generator | | 17b-Hydroxy-5a-androstan-3-one glucuronide | Generator | | 17Β-hydroxy-5α-androstan-3-one glucuronide | Generator | | 5a-Dihydrotestosterone 17-(b-D-glucuronide) | Generator | | 5Α-dihydrotestosterone 17-(β-D-glucuronide) | Generator | | 5a-Dihydrotestosterone 17-b-glucuronide | Generator | | 5Α-dihydrotestosterone 17-β-glucuronide | Generator | | 5a-Dihydrotestosterone 17-O-(b-D-glucuronate) | Generator | | 5a-Dihydrotestosterone 17-O-(b-D-glucuronic acid) | Generator | | 5alpha-Dihydrotestosterone 17-O-(beta-D-glucuronate) | Generator | | 5Α-dihydrotestosterone 17-O-(β-D-glucuronate) | Generator | | 5Α-dihydrotestosterone 17-O-(β-D-glucuronic acid) | Generator | | 5a-Dihydrotestosterone glucuronide | Generator | | 5Α-dihydrotestosterone glucuronide | Generator | | 5a-Dihydrotestosterone-17g | Generator | | 5Α-dihydrotestosterone-17g | Generator | | Stanolone glucuronic acid | Generator | | 5-a-Dihydrotestosterone glucuronide | Generator | | 5-Α-dihydrotestosterone glucuronide | Generator | | Dihydrotestosterone diglucuronide | HMDB | | Dihydrotestosterone glucuronide, (5beta,17beta)-isomer | HMDB |
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| Chemical Formula | C25H38O8 |
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| Average Mass | 466.5644 Da |
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| Monoisotopic Mass | 466.25667 Da |
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| IUPAC Name | (2S,3S,4S,5R,6R)-6-{[(1S,2S,7S,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid |
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| Traditional Name | (2S,3S,4S,5R,6R)-6-{[(1S,2S,7S,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid |
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| CAS Registry Number | Not Available |
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| SMILES | [H][C@@]12CC[C@H](O[C@]3([H])O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=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/C25H38O8/c1-24-9-7-13(26)11-12(24)3-4-14-15-5-6-17(25(15,2)10-8-16(14)24)32-23-20(29)18(27)19(28)21(33-23)22(30)31/h12,14-21,23,27-29H,3-11H2,1-2H3,(H,30,31)/t12-,14-,15-,16-,17-,18-,19-,20+,21-,23+,24-,25-/m0/s1 |
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| InChI Key | CLQMBSSRTBUNDV-CPKOJWPQSA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid 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 | Steroidal glycosides |
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| Direct Parent | Steroid glucuronide conjugates |
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| Alternative Parents | |
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| Substituents | - Steroid-glucuronide-skeleton
- Androgen-skeleton
- Androstane-skeleton
- 3-oxosteroid
- 3-oxo-5-alpha-steroid
- Oxosteroid
- 1-o-glucuronide
- O-glucuronide
- Glucuronic acid or derivatives
- Hexose monosaccharide
- O-glycosyl compound
- Glycosyl compound
- Beta-hydroxy acid
- Hydroxy acid
- Oxane
- Monosaccharide
- Pyran
- Cyclic ketone
- Secondary alcohol
- Ketone
- Polyol
- Acetal
- Organoheterocyclic compound
- Carboxylic acid
- Carboxylic acid derivative
- Oxacycle
- Monocarboxylic acid or derivatives
- Organic oxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Organooxygen compound
- Aliphatic heteropolycyclic compound
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| Molecular Framework | Aliphatic heteropolycyclic compounds |
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| External Descriptors | |
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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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