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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-02-26 21:22:18 UTC |
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HMDB ID | HMDB0000546 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Epietiocholanolone |
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Description | Epietiocholanolone, also known as 5b-epiandrosterone or M1A, 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, epietiocholanolone is considered to be a steroid lipid molecule. Epietiocholanolone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. |
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Structure | |
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Synonyms | Value | Source |
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3b-Etiocholanolone | HMDB | 3b-Hydroxy-17-oxo-5b-androstane | HMDB | 3b-Hydroxy-5b-androstan-17-one | HMDB | 3b-Hydroxy-5b-androstane-17-one | HMDB | 3b-Hydroxyetiocholan-17-one | HMDB | 5b-Androstan-3b-ol-17-one | HMDB | 5b-Androstane-3b-ol-17-one | HMDB | 5b-Epiandrosterone | HMDB | b-Etiocholanolone | HMDB | beta-Etiocholanolone | HMDB | Epi-5b-androsterone | HMDB | Epiaetiocholanolone | HMDB | Etiocholan-3b-ol-17-one | HMDB | M1A | HMDB | Methyl-1-alpha | 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,5S,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,5S,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 | 571-31-3 |
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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-XRJZGPCZSA-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-beta-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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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: Industrial application: |
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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 | 154 - 155 °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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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-03ea-0390000000-17f2f9f14aa5e282a19a | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-001i-2169000000-bf71d6f9c1a2a4af0d20 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0a4i-0690000000-3a0cb488894ffd730532 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0a5a-3910000000-0fea9c2b9985a4b5c4fc | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0uxu-6691000000-500e59c2f0eb04cba0d8 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-0gx3-0953000000-85e6abfd3e71f7e303f9 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-0a4j-0920100000-b9aa287b6300cd9902b6 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00dl-0090000000-fb385ad40b5d4ae1a6d9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00dm-0290000000-6287ec557af150ef07fe | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000t-3690000000-da6f3211b1e397dcf1ae | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0090000000-03f14a475acfab5558d6 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0090000000-5e4902f7af7820145954 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-06xx-2090000000-97cca29f0df7b3cc3714 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Female | Normal | | details | Blood | Detected and Quantified | 0.000017 (0.000011-0.000067) uM | Adult (>18 years old) | Male | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Schizophrenia | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Female | Schizophrenia | | details |
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Associated Disorders and Diseases |
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Disease References | Schizophrenia |
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- Bicikova M, Hill M, Ripova D, Mohr P, Hampl R: Determination of steroid metabolome as a possible tool for laboratory diagnosis of schizophrenia. J Steroid Biochem Mol Biol. 2013 Jan;133:77-83. doi: 10.1016/j.jsbmb.2012.08.009. Epub 2012 Aug 24. [PubMed:22944140 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022109 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 216866 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Epietiocholanolone |
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METLIN ID | 5531 |
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PubChem Compound | 247732 |
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PDB ID | Not Available |
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ChEBI ID | 542034 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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Synthesis Reference | Fajkos, J.; Sanda, V. Steroids. LXVI. 16-Bromo derivatives in the 5b-androstane series. Collection of Czechoslovak Chemical Communications (1962), 27 355-61. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Huck JH, Struys EA, Verhoeven NM, Jakobs C, van der Knaap MS: Profiling of pentose phosphate pathway intermediates in blood spots by tandem mass spectrometry: application to transaldolase deficiency. Clin Chem. 2003 Aug;49(8):1375-80. [PubMed:12881455 ]
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