| Record Information |
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| Version | 1.0 |
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| Creation date | 2015-10-09 22:31:14 UTC |
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| Update date | 2017-01-19 02:36:27 UTC |
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| FoodComEx ID | PC000537 |
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| FoodDB Record | FDB022072 |
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| Chemical Information |
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| Name | Etiocholanolone |
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| Description | Etiocholanolone is the 5-beta-reduced isomer of androsterone. Etiocholanolone is a major metabolite of testosterone and androstenedione in many mammalian species including humans. It is excreted in the urine and is androgenically inactive. Classified a ketosteroid, it causes fever (it is a pyrogen), immunostimulation and leukocytosis. The pyrogenic effect of Etiocholanolone has been shown to be due to the release of interleukin-1 (IL-1) from the leukocytes that are mobilized in response to its production or injection. Etiocholanolone has anticonvulsant activity and may be an endogenous modulator of seizure susceptibility. Significantly increased values of etiocholanolone (along with testoterone and androsterone) an be detected in the urine of men with androgenic alopecia (male pattern baldness). [HMDB] |
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| CAS Number | 53-42-9 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| (3a,5b)-3-Hydroxyandrostan-17-one | Generator | | (3alpha,5beta)-3-Hydroxyandrostan-17-one | ChEBI | | (3α,5β)-3-hydroxyandrostan-17-one | Generator | | 3a-Etiocholanolone | hmdb | | 3a-Hydroxy-5b-androstan-17-one | Generator | | 3a-Hydroxy-5b-androstane-17-one | hmdb | | 3a-Hydroxyetiocholan-17-one | Generator | | 3alpha-Etiocholanolone | ChEBI | | 3alpha-Hydroxy-5beta-androstan-17-one | hmdb | | 3alpha-Hydroxyetiocholan-17-one | hmdb | | 3α-etiocholanolone | Generator | | 3α-hydroxy-5β-androstan-17-one | Generator | | 3α-hydroxyetiocholan-17-one | Generator | | 5 beta Androsterone | hmdb | | 5-Isoandrosterone | hmdb | | 5b-Androstan-3a-ol-17-one | hmdb | | 5b-Androstane-3a-ol-17-one | hmdb | | 5b-Androsterone | hmdb | | 5beta-Androstan-3alpha-ol-17-one | ChEBI | | 5beta-Androsterone | ChEBI | | 5β-androstan-3α-ol-17-one | Generator | | 5β-androsterone | Generator | | a-Etiocholanolone | hmdb | | Aetiocholanolone | hmdb | | alpha-Etiocholanolone | hmdb | | Etiocholan-3a-ol-17-one | Generator | | Etiocholan-3alpha-ol-17-one | ChEBI | | Etiocholan-3α-ol-17-one | Generator |
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| Chemical Formula | C19H30O2 |
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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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| 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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| Isomeric 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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| Average Molecular Weight | 290.4403 |
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| Monoisotopic Molecular Weight | 290.224580204 |
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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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| Physico-Chemical Properties - Experimental |
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| Property | Value | Reference |
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| Experimental logP | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Melting Point | Not Available | |
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| Foods of Origin |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Production Data |
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| Production Method | commercial |
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| Production Method Reference | Not Available |
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| Production Method Reference File | Not Available |
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| Quantity Available | Production upon request, up to 20 mg |
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| Delivery Time | Not Available |
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| Storage Form | solid |
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| Storage Conditions | -80°C |
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| Stability | Not Available |
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| Purity | Not Available |
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| Spectra |
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| Spectral Data Upon Request | Not Available |
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| Provider Information |
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| Commercial Vendors |
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| Toronto Research Chemicals | A637630 |
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