Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:31:30 UTC |
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Update Date | 2020-04-22 15:03:49 UTC |
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BMDB ID | BMDB0000490 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Etiocholanolone |
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Description | Etiocholanolone, also known as Etiocholanolone, 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, etiocholanolone is considered to be a steroid lipid molecule. Etiocholanolone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Etiocholanolone exists in all living organisms, ranging from bacteria to humans. Etiocholanolone can be biosynthesized from etiocholanedione through the action of the enzyme aldo-keto reductase family 1 member C4. In cattle, etiocholanolone is involved in the metabolic pathway called the androstenedione metabolism pathway. |
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Structure | |
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Synonyms | Value | Source |
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(3alpha,5beta)-3-Hydroxyandrostan-17-one | ChEBI | 3alpha-Etiocholanolone | ChEBI | 3alpha-Hydroxyetiocholan-17-one | ChEBI | 5-Isoandrosterone | ChEBI | 5beta-Androstan-3alpha-ol-17-one | ChEBI | 5beta-Androsterone | ChEBI | AETIOCHOLANOLONE | ChEBI | Etiocholan-3alpha-ol-17-one | ChEBI | 3alpha-Hydroxy-5beta-androstan-17-one | Kegg | (3a,5b)-3-Hydroxyandrostan-17-one | Generator | (3Α,5β)-3-hydroxyandrostan-17-one | Generator | 3a-Etiocholanolone | Generator | 3Α-etiocholanolone | Generator | 3a-Hydroxyetiocholan-17-one | Generator | 3Α-hydroxyetiocholan-17-one | Generator | 5b-Androstan-3a-ol-17-one | Generator | 5Β-androstan-3α-ol-17-one | Generator | 5b-Androsterone | Generator | 5Β-androsterone | Generator | Etiocholan-3a-ol-17-one | Generator | Etiocholan-3α-ol-17-one | Generator | 3a-Hydroxy-5b-androstan-17-one | Generator | 3Α-hydroxy-5β-androstan-17-one | Generator | 3a-Hydroxy-5b-androstane-17-one | HMDB | 5 beta Androsterone | HMDB | 5b-Androstane-3a-ol-17-one | HMDB | a-Etiocholanolone | HMDB | alpha-Etiocholanolone | HMDB | 3-alpha-Hydroxy-5-beta-androstan-17-one | HMDB | 5-beta-Androsterone | HMDB | 3 alpha Hydroxy 5 beta androstan 17 one | HMDB |
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Chemical Formula | C19H30O2 |
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Average Molecular Weight | 290.4403 |
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Monoisotopic Molecular Weight | 290.224580204 |
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IUPAC Name | (1S,2S,5R,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one |
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Traditional Name | (1S,2S,5R,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one |
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CAS Registry Number | 53-42-9 |
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SMILES | [H][C@@]12CCC(=O)[C@@]1(C)CC[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/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,18+,19+/m1/s1 |
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InChI Key | QGXBDMJGAMFCBF-BNSUEQOYSA-N |
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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
- 3-hydroxysteroid
- 3-alpha-hydroxysteroid
- Oxosteroid
- 17-oxosteroid
- Hydroxysteroid
- Cyclic alcohol
- Secondary alcohol
- Ketone
- Organic oxygen compound
- Organooxygen compound
- Hydrocarbon derivative
- Carbonyl group
- Organic oxide
- Alcohol
- 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
- Endoplasmic reticulum
- 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 | 152 - 154 °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 | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-052f-1890000000-943a0458e0d4232522f5 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-052f-1890000000-943a0458e0d4232522f5 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-03ea-0390000000-17f2f9f14aa5e282a19a | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0f7k-1139000000-2bff067a4137502d6ea7 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-052e-0090000000-976ebe75980115c6df37 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-052k-4920000000-cd0699d57cde00089d27 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-015c-6900000000-4cfdb3def9bc28b9a339 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive | splash10-052f-1890000000-7047f583d11b20a72f9b | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00dl-0090000000-42eb8c941695a061666d | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00dl-0290000000-1a37c17eb6ea7be9211c | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-06u7-2790000000-d6e7cebd4af538181f77 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0090000000-9e9f9de3b33af0311acd | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0090000000-5ba62f51f815ded16002 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0596-2190000000-513ad65531fff88b9f69 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0090000000-c8c452fd99c6bb4f3631 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0090000000-c8c452fd99c6bb4f3631 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000i-0090000000-00c0e7de4e528b98df5c | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0090000000-afb176951034ef62419f | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-052e-0930000000-1ed776267953f7acda8a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4j-2900000000-1ba60805778f2942bfd7 | View in MoNA |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental) | Not Available | View in JSpectraViewer |
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2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | Not Available | View in JSpectraViewer |
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Synthesis Reference | Pelli, Beatrice; Traldi, Pietro; Gargano, Michele; Ravasio, Nicoletta; Rossi, Michele. Easy determination of epimeric androsterones by collision spectroscopy: the molar ratio of 5b-androstan-3a-ol-17-one and 5b-androstan-3b-ol-17-one obtained by hydrogenation of 5b-androstane-3,17-dione on copper/alumina. Organic Mass Spectrometry (1987), 22(3), 183-5. |
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