Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-26 05:17:58 UTC |
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Update Date | 2016-11-09 01:21:12 UTC |
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Accession Number | CHEM034879 |
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Identification |
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Common Name | 5a-Androstane-3b,17b-diol |
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Class | Small Molecule |
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Description | An androstane-3,17-diol that is 5alpha-androstane substituted by beta-hydroxy groups at positions 3 and 17. It is a metabolite of dihydrotestosterone. |
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Contaminant Sources | |
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Contaminant Type | Not Available |
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Chemical Structure | |
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Synonyms | Value | Source |
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(3beta,5alpha,17beta)-Androstane-3,17-diol | ChEBI | 3beta,17beta-Dihydroxy-5alpha-androstane | ChEBI | 5-ALPHA-ANDROSTANE-3-BETA,17BETA-diol | ChEBI | 5alpha-Androstan-3beta,17beta-diol | ChEBI | (3b,5a,17b)-Androstane-3,17-diol | Generator | (3Β,5α,17β)-androstane-3,17-diol | Generator | 3b,17b-Dihydroxy-5a-androstane | Generator | 3Β,17β-dihydroxy-5α-androstane | Generator | 5-a-ANDROSTANE-3-b,17b-diol | Generator | 5-Α-androstane-3-β,17β-diol | Generator | 5a-Androstan-3b,17b-diol | Generator | 5Α-androstan-3β,17β-diol | Generator | 5a-Androstane-3b,17b-diol | Generator | 5Α-androstane-3β,17β-diol | Generator | 3b,17b-Androstanediol | HMDB | 3b-Androstanediol | HMDB | 3Β-androstanediol | HMDB | 5alpha-Androstane-3beta,17beta-diol | HMDB |
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Chemical Formula | C19H32O2 |
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Average Molecular Mass | 292.456 g/mol |
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Monoisotopic Mass | 292.240 g/mol |
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CAS Registry Number | 571-20-0 |
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IUPAC Name | (1S,2S,5S,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol |
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Traditional Name | (1S,2S,5S,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol |
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SMILES | [H][C@]1(O)CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C |
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InChI Identifier | InChI=1S/C19H32O2/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/h12-17,20-21H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,17-,18-,19-/m0/s1 |
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InChI Key | CBMYJHIOYJEBSB-YSZCXEEOSA-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
- 17-hydroxysteroid
- 3-beta-hydroxysteroid
- Hydroxysteroid
- 3-hydroxysteroid
- Cyclic alcohol
- Secondary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Not Available |
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Cellular Locations | Not Available |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Not Available |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-03gj-0290000000-f3f7878ea28711151686 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-05fr-2226900000-73765a85fad7c004bde8 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0feb-0910000000-95c33219e21fca1431b4 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-006t-9621000000-2bf4147f35ce4e2b858a | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0aos-9851000000-65b418ed0598e7d18552 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004l-0090000000-22d60c19836ea8b4c291 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-056r-0390000000-edb0fb77b27575b4b729 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00mk-2980000000-cd6eafa93f3164ed780a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0090000000-bc689c3cdfdf044c011e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-006x-0090000000-bfbc140857bbdb62bcff | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-06vm-1290000000-bced1e06a8686f3501af | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-002f-0090000000-36f4d97265b0d994d628 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-052b-3940000000-b87bad8b672cc5fb32b0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0aos-3900000000-0f8ce10c286f165d6e0f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0090000000-11452f48ce72555f1f28 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-0090000000-11452f48ce72555f1f28 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000l-0090000000-ac9e93370094e8aebfa1 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Not Available |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | Not Available |
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Uses/Sources | Not Available |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB03882 |
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HMDB ID | HMDB0000493 |
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FooDB ID | FDB022073 |
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Phenol Explorer ID | Not Available |
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KNApSAcK ID | Not Available |
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BiGG ID | Not Available |
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BioCyc ID | Not Available |
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METLIN ID | 5479 |
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PDB ID | Not Available |
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Wikipedia Link | 3β-Androstanediol |
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Chemspider ID | 211834 |
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ChEBI ID | 18329 |
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PubChem Compound ID | 242332 |
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Kegg Compound ID | C12525 |
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YMDB ID | Not Available |
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ECMDB ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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MSDS | Not Available |
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General References | 1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15958594 | 2. Merlani, M. I.; Amiranashvili, L. Sh.; Men'shova, N. I.; Kemertelidze, E. P. Synthesis of 5a-androstan-3b,17b-diol from tigogenin. Chemistry of Natural Compounds (2007), 43(1), 97-99. | 3. Stewart ME, Pochi PE, Strauss JS, Wotiz HH, Clark SJ: In-vitro metabolism of [3H]testosterone by scalp and back skin: conversion of testosterone into 5alpha-androstane-3beta, 17beta-diol. J Endocrinol. 1977 Mar;72(3):385-90. | 4. Guerini V, Sau D, Scaccianoce E, Rusmini P, Ciana P, Maggi A, Martini PG, Katzenellenbogen BS, Martini L, Motta M, Poletti A: The androgen derivative 5alpha-androstane-3beta,17beta-diol inhibits prostate cancer cell migration through activation of the estrogen receptor beta subtype. Cancer Res. 2005 Jun 15;65(12):5445-53. |
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