| Record Information |
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| Version | 2.0 |
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| Created at | 2022-05-11 16:40:26 UTC |
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| Updated at | 2022-05-11 16:40:27 UTC |
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| NP-MRD ID | NP0087112 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 19-Hydroxyandrost-4-ene-3,17-dione |
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| Description | 19-Hydroxyandrost-4-ene-3,17-dione, also known as 19-HAED, 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. Thus, 19-hydroxyandrost-4-ene-3,17-dione is considered to be a steroid lipid molecule. 19-Hydroxyandrost-4-ene-3,17-dione is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, 19-hydroxyandrost-4-ene-3,17-dione participates in a number of enzymatic reactions. In particular, 19-hydroxyandrost-4-ene-3,17-dione can be biosynthesized from androstenedione; which is catalyzed by the enzyme cytochrome P450 19A1. In addition, 19-hydroxyandrost-4-ene-3,17-dione can be converted into 19-oxoandrost-4-ene-3,17-dione through the action of the enzyme cytochrome P450 19A1. In humans, 19-hydroxyandrost-4-ene-3,17-dione is involved in androstenedione metabolism. Outside of the human body, 19-Hydroxyandrost-4-ene-3,17-dione has been detected, but not quantified in, several different foods, such as kales, cottonseeds, common sages, wheats, and canada blueberries. This could make 19-hydroxyandrost-4-ene-3,17-dione a potential biomarker for the consumption of these foods. 19-Hydroxyandrost-4-ene-3,17-dione was first documented in 1987 (PMID: 3113917). 19-Hydroxyandrost-4-ene-3,17-dione is a substrate for Corticotropin-lipotropin and Cytochrome P450 19A1 (PMID: 2339447). |
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| Structure | [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12CO InChI=1S/C19H26O3/c1-18-8-7-16-14(15(18)4-5-17(18)22)3-2-12-10-13(21)6-9-19(12,16)11-20/h10,14-16,20H,2-9,11H2,1H3/t14-,15-,16-,18-,19+/m0/s1 |
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| Synonyms | | Value | Source |
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| 19-Hydroxyandrostenedione | ChEBI | | 19-Hydroxy-4-androstene-3,17-dione | HMDB | | 19-Hydroxy-4-androstene-3,17-dione, 18O-labeled | HMDB | | 19-HAED | HMDB |
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| Chemical Formula | C19H26O3 |
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| Average Mass | 302.4079 Da |
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| Monoisotopic Mass | 302.18819 Da |
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| IUPAC Name | (1S,2S,10R,11S,15S)-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,14-dione |
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| Traditional Name | 19-haed |
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| CAS Registry Number | Not Available |
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| SMILES | [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12CO |
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| InChI Identifier | InChI=1S/C19H26O3/c1-18-8-7-16-14(15(18)4-5-17(18)22)3-2-12-10-13(21)6-9-19(12,16)11-20/h10,14-16,20H,2-9,11H2,1H3/t14-,15-,16-,18-,19+/m0/s1 |
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| InChI Key | XGUHPTGEXRHMQQ-BGJMDTOESA-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 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 | - Androgen-skeleton
- 19-hydroxysteroid
- 3-oxo-delta-4-steroid
- 3-oxosteroid
- Oxosteroid
- 17-oxosteroid
- Hydroxysteroid
- Delta-4-steroid
- Cyclohexenone
- Cyclic ketone
- Ketone
- Primary alcohol
- Organic oxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Alcohol
- Organooxygen compound
- Organic oxide
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic 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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