Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2007-05-22 21:03:43 UTC |
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Update Date | 2021-09-14 15:40:13 UTC |
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HMDB ID | HMDB0006278 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 5a-Dihydrotestosterone sulfate |
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Description | 5a-Dihydrotestosterone sulfate is a sulfate derivative of 5a-Dihydrotestosterone produced through phase II metabolism. 5a-dihydrotestosterone (DHT) is a steroid similar to testosterone and androstenedione, that belongs to a class called androgens. DHT is a C19 steroid and possesses androgenic activity. Androgen production takes place mainly in the Leydig cells of the testes. Androgens circulate in the blood bound to proteins, especially sex hormone binding globulin (SHBG) and albumin. A trace amount of these steroids circulate in the unbound form in the blood and are referred to as the free fractions. DHT has at least three times the binding affinity for SHBG than testosterone. About 70% of DHT is derived from peripheral conversion of testosterone in males, while most of the DHT is derived from androstenedione in females. |
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Structure | [H][C@@]12CC[C@H](OS(O)(=O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C InChI=1S/C19H30O5S/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(24-25(21,22)23)19(15,2)10-8-16(14)18/h12,14-17H,3-11H2,1-2H3,(H,21,22,23)/t12-,14-,15-,16-,17-,18-,19-/m0/s1 |
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Synonyms | Value | Source |
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(5alpha,17beta)-3-Oxoandrostan-17-yl hydrogen sulfate | ChEBI | 5alpha-Dihydrotestosterone 17-sulfate | ChEBI | DHT-Sulfate | ChEBI | DHT-Sulphate | ChEBI | Dihydrotestosterone sulfate | ChEBI | Dihydrotestosterone sulphate | ChEBI | (5a,17b)-3-Oxoandrostan-17-yl hydrogen sulfate | Generator | (5a,17b)-3-Oxoandrostan-17-yl hydrogen sulfuric acid | Generator | (5a,17b)-3-Oxoandrostan-17-yl hydrogen sulphate | Generator | (5a,17b)-3-Oxoandrostan-17-yl hydrogen sulphuric acid | Generator | (5alpha,17beta)-3-Oxoandrostan-17-yl hydrogen sulfuric acid | Generator | (5alpha,17beta)-3-Oxoandrostan-17-yl hydrogen sulphate | Generator | (5alpha,17beta)-3-Oxoandrostan-17-yl hydrogen sulphuric acid | Generator | (5Α,17β)-3-oxoandrostan-17-yl hydrogen sulfate | Generator | (5Α,17β)-3-oxoandrostan-17-yl hydrogen sulfuric acid | Generator | (5Α,17β)-3-oxoandrostan-17-yl hydrogen sulphate | Generator | (5Α,17β)-3-oxoandrostan-17-yl hydrogen sulphuric acid | Generator | 5a-Dihydrotestosterone 17-sulfate | Generator | 5a-Dihydrotestosterone 17-sulfuric acid | Generator | 5a-Dihydrotestosterone 17-sulphate | Generator | 5a-Dihydrotestosterone 17-sulphuric acid | Generator | 5alpha-Dihydrotestosterone 17-sulfuric acid | Generator | 5alpha-Dihydrotestosterone 17-sulphate | Generator | 5alpha-Dihydrotestosterone 17-sulphuric acid | Generator | 5Α-dihydrotestosterone 17-sulfate | Generator | 5Α-dihydrotestosterone 17-sulfuric acid | Generator | 5Α-dihydrotestosterone 17-sulphate | Generator | 5Α-dihydrotestosterone 17-sulphuric acid | Generator | DHT-Sulfuric acid | Generator | DHT-Sulphuric acid | Generator | Dihydrotestosterone sulfuric acid | Generator | Dihydrotestosterone sulphuric acid | Generator | 5a-Dihydrotestosterone sulfuric acid | Generator | 5a-Dihydrotestosterone sulphate | Generator | 5a-Dihydrotestosterone sulphuric acid | Generator | 5alpha-Dihydrotestosterone sulfate | HMDB | 5alpha-Dihydrotestosterone sulphate | HMDB |
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Chemical Formula | C19H30O5S |
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Average Molecular Weight | 370.504 |
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Monoisotopic Molecular Weight | 370.18139476 |
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IUPAC Name | [(1S,2S,7S,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]oxidanesulfonic acid |
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Traditional Name | 5α-dihydrotestosterone sulfate |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@]12CC[C@H](OS(O)(=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/C19H30O5S/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(24-25(21,22)23)19(15,2)10-8-16(14)18/h12,14-17H,3-11H2,1-2H3,(H,21,22,23)/t12-,14-,15-,16-,17-,18-,19-/m0/s1 |
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InChI Key | KYVPWJSGFKNNLD-ABEVXSGRSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached 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 | Sulfated steroids |
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Direct Parent | Sulfated steroids |
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Alternative Parents | |
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Substituents | - Sulfated steroid skeleton
- Androgen-skeleton
- Androstane-skeleton
- 3-oxosteroid
- Oxosteroid
- 3-oxo-5-alpha-steroid
- Sulfuric acid ester
- Sulfuric acid monoester
- Sulfate-ester
- Alkyl sulfate
- Organic sulfuric acid or derivatives
- Cyclic ketone
- Ketone
- Organooxygen compound
- Carbonyl group
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular 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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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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5a-Dihydrotestosterone sulfate,1TMS,isomer #1 | C[C@]12CCC(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@H]12 | 3088.1 | Semi standard non polar | 33892256 | 5a-Dihydrotestosterone sulfate,1TMS,isomer #1 | C[C@]12CCC(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@H]12 | 3069.4 | Standard non polar | 33892256 | 5a-Dihydrotestosterone sulfate,1TMS,isomer #1 | C[C@]12CCC(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@H]12 | 3744.1 | Standard polar | 33892256 | 5a-Dihydrotestosterone sulfate,1TMS,isomer #2 | C[C@]12CC=C(O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O)CC[C@@H]12 | 3112.9 | Semi standard non polar | 33892256 | 5a-Dihydrotestosterone sulfate,1TMS,isomer #2 | C[C@]12CC=C(O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O)CC[C@@H]12 | 2989.9 | Standard non polar | 33892256 | 5a-Dihydrotestosterone sulfate,1TMS,isomer #2 | C[C@]12CC=C(O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O)CC[C@@H]12 | 3847.5 | Standard polar | 33892256 | 5a-Dihydrotestosterone sulfate,1TMS,isomer #3 | C[C@]12CC[C@H]3[C@@H](CC[C@H]4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O | 3107.0 | Semi standard non polar | 33892256 | 5a-Dihydrotestosterone sulfate,1TMS,isomer #3 | C[C@]12CC[C@H]3[C@@H](CC[C@H]4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O | 3007.0 | Standard non polar | 33892256 | 5a-Dihydrotestosterone sulfate,1TMS,isomer #3 | C[C@]12CC[C@H]3[C@@H](CC[C@H]4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O | 3839.7 | Standard polar | 33892256 | 5a-Dihydrotestosterone sulfate,2TMS,isomer #1 | C[C@]12CC[C@H]3[C@@H](CC[C@H]4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O[Si](C)(C)C | 3108.3 | Semi standard non polar | 33892256 | 5a-Dihydrotestosterone sulfate,2TMS,isomer #1 | C[C@]12CC[C@H]3[C@@H](CC[C@H]4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O[Si](C)(C)C | 3208.4 | Standard non polar | 33892256 | 5a-Dihydrotestosterone sulfate,2TMS,isomer #1 | C[C@]12CC[C@H]3[C@@H](CC[C@H]4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O[Si](C)(C)C | 3794.7 | Standard polar | 33892256 | 5a-Dihydrotestosterone sulfate,2TMS,isomer #2 | C[C@]12CC=C(O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@H]12 | 3115.4 | Semi standard non polar | 33892256 | 5a-Dihydrotestosterone sulfate,2TMS,isomer #2 | C[C@]12CC=C(O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@H]12 | 3192.5 | Standard non polar | 33892256 | 5a-Dihydrotestosterone sulfate,2TMS,isomer #2 | C[C@]12CC=C(O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@H]12 | 3796.6 | Standard polar | 33892256 | 5a-Dihydrotestosterone sulfate,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C | 3308.3 | Semi standard non polar | 33892256 | 5a-Dihydrotestosterone sulfate,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C | 3377.8 | Standard non polar | 33892256 | 5a-Dihydrotestosterone sulfate,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C | 3864.4 | Standard polar | 33892256 | 5a-Dihydrotestosterone sulfate,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O)CC[C@@H]32)C1 | 3396.2 | Semi standard non polar | 33892256 | 5a-Dihydrotestosterone sulfate,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O)CC[C@@H]32)C1 | 3285.8 | Standard non polar | 33892256 | 5a-Dihydrotestosterone sulfate,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O)CC[C@@H]32)C1 | 3987.1 | Standard polar | 33892256 | 5a-Dihydrotestosterone sulfate,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1 | 3375.5 | Semi standard non polar | 33892256 | 5a-Dihydrotestosterone sulfate,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1 | 3311.7 | Standard non polar | 33892256 | 5a-Dihydrotestosterone sulfate,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1 | 3980.2 | Standard polar | 33892256 | 5a-Dihydrotestosterone sulfate,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@@H]32)C1 | 3589.0 | Semi standard non polar | 33892256 | 5a-Dihydrotestosterone sulfate,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@@H]32)C1 | 3749.7 | Standard non polar | 33892256 | 5a-Dihydrotestosterone sulfate,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@@H]32)C1 | 3954.5 | Standard polar | 33892256 | 5a-Dihydrotestosterone sulfate,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1 | 3559.9 | Semi standard non polar | 33892256 | 5a-Dihydrotestosterone sulfate,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1 | 3774.4 | Standard non polar | 33892256 | 5a-Dihydrotestosterone sulfate,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1 | 3951.8 | Standard polar | 33892256 |
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- Purvis K, Saksena SK, Cekan Z, Diczfalusy E, Giner J: Endocrine effects of vasectomy. Clin Endocrinol (Oxf). 1976 May;5(3):263-72. [PubMed:133774 ]
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- Sanchez-Guijo A, Oji V, Hartmann MF, Traupe H, Wudy SA: Simultaneous quantification of cholesterol sulfate, androgen sulfates, and progestagen sulfates in human serum by LC-MS/MS. J Lipid Res. 2015 Sep;56(9):1843-51. doi: 10.1194/jlr.D061499. Epub 2015 Aug 2. [PubMed:26239050 ]
- Xu H, Zheng X, Qian Y, Guan J, Yi H, Zou J, Wang Y, Meng L, Zhao A, Yin S, Jia W: Metabolomics Profiling for Obstructive Sleep Apnea and Simple Snorers. Sci Rep. 2016 Aug 2;6:30958. doi: 10.1038/srep30958. [PubMed:27480913 ]
- Dehennin L, Jondet M, Scholler R: Androgen and 19-norsteroid profiles in human preovulatory follicles from stimulated cycles: an isotope dilution-mass spectrometric study. J Steroid Biochem. 1987 Mar;26(3):399-405. [PubMed:3586654 ]
- Gibb W, Jeffery J: 5 -dihydrotestosterone sulphate and cortisone reductase. Biochim Biophys Acta. 1972 Dec 8;280(4):646-51. [PubMed:4648789 ]
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