Record Information |
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Version | 1.0 |
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Creation date | 2015-05-07 18:56:43 UTC |
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Update date | 2019-11-26 03:21:40 UTC |
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Primary ID | FDB030278 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | 17-α-hydroxypregnenolone |
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Description | 17-α-hydroxypregnenolone, also known as (3beta)-3,17-dihydroxypregn-5-en-20-one or 5-pregnen-3b,17a-diol-20-one, belongs to gluco/mineralocorticoids, progestogins and derivatives class of compounds. Those are steroids with a structure based on a hydroxylated prostane moiety. Thus, 17-α-hydroxypregnenolone is considered to be a steroid lipid molecule. 17-α-hydroxypregnenolone is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 17-α-hydroxypregnenolone can be found in a number of food items such as strawberry guava, java plum, conch, and chives, which makes 17-α-hydroxypregnenolone a potential biomarker for the consumption of these food products. 17-α-hydroxypregnenolone can be found primarily in blood, as well as in human adrenal cortex and testes tissues. In humans, 17-α-hydroxypregnenolone is involved in a couple of metabolic pathways, which include androgen and estrogen metabolism and steroidogenesis. 17-α-hydroxypregnenolone is also involved in several metabolic disorders, some of which include aromatase deficiency, adrenal hyperplasia type 3 or congenital adrenal hyperplasia due to 21-hydroxylase deficiency, adrenal hyperplasia type 5 or congenital adrenal hyperplasia due to 17 alpha-hydroxylase deficiency, and apparent mineralocorticoid excess syndrome. |
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CAS Number | 387-79-1 |
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Structure | |
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Synonyms | Synonym | Source |
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(3beta)-3,17-Dihydroxypregn-5-en-20-one | ChEBI | 17-Hydroxypregnenolone | ChEBI | 5-Pregnen-3beta,17alpha-diol-20-one | ChEBI | (3b)-3,17-Dihydroxypregn-5-en-20-one | Generator | (3Β)-3,17-dihydroxypregn-5-en-20-one | Generator | 5-Pregnen-3b,17a-diol-20-one | Generator | 5-Pregnen-3β,17α-diol-20-one | Generator | 17-Hydroxy-D5-pregnenolone | HMDB | 17-OH-Pregnenolone | HMDB | 17a-Hydroxypregnolone | HMDB | 17alpha-Hydroxypregnanolone | HMDB | 17alpha-Hydroxypregnenolone | HMDB | 3b,17-Dihydroxy-5-pregnen-20-one | HMDB | 3b,17-Dihydroxy-pregn-5-en-20-one | HMDB | 3b,17a-Dihydroxypregn-5-en-20-one | HMDB | 17alpha Hydroxypregnenolone | HMDB | Hydroxypregnenolone | HMDB | 17 Hydroxypregnenolone | HMDB | 17 alpha Hydroxypregnenolone | HMDB | 17-Hydroxypregnenolone, (3alpha)-isomer | HMDB | 17-Hydroxypregnenolone, (3beta,13alpha)-isomer | HMDB | 17-alpha-Hydroxypregnenolone | HMDB | 17 alpha-Hydroxypregnenolone | HMDB | 17-Hydroxypregnenolone, (3beta,13alpha,17alpha)-isomer | HMDB | 17-Hydroxypregnenolone, (3beta,17alpha)-isomer | HMDB |
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Predicted Properties | |
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Chemical Formula | C21H32O3 |
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IUPAC name | 1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one |
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InChI Identifier | InChI=1S/C21H32O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h4,15-18,23-24H,5-12H2,1-3H3/t15-,16+,17-,18-,19-,20-,21-/m0/s1 |
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InChI Key | JERGUCIJOXJXHF-TVWVXWENSA-N |
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Isomeric SMILES | [H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C |
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Average Molecular Weight | 332.477 |
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Monoisotopic Molecular Weight | 332.23514489 |
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Classification |
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Description | Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. |
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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 | Pregnane steroids |
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Direct Parent | Gluco/mineralocorticoids, progestogins and derivatives |
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Alternative Parents | |
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Substituents | - Progestogin-skeleton
- 20-oxosteroid
- 3-hydroxy-delta-5-steroid
- 3-hydroxysteroid
- 17-hydroxysteroid
- 3-beta-hydroxysteroid
- 3-beta-hydroxy-delta-5-steroid
- Oxosteroid
- Hydroxysteroid
- Delta-5-steroid
- Alpha-hydroxy ketone
- Tertiary alcohol
- Cyclic alcohol
- Secondary alcohol
- Ketone
- Organic oxygen compound
- Organooxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Alcohol
- Organic oxide
- 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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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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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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GC-MS | 17alpha-Hydroxypregnenolone, 1 MEOX; 2 TMS, GC-MS Spectrum | splash10-054x-4900000000-df86d10979d808f20e67 | Spectrum | GC-MS | 17alpha-Hydroxypregnenolone, 1 MEOX; 2 TMS, GC-MS Spectrum | splash10-0a73-3910000000-7a0eea991ac4d2fac97e | Spectrum | GC-MS | 17alpha-Hydroxypregnenolone, non-derivatized, GC-MS Spectrum | splash10-0f89-2891000000-3605ad7dd57f97382115 | Spectrum | GC-MS | 17alpha-Hydroxypregnenolone, non-derivatized, GC-MS Spectrum | splash10-0ff0-3792000000-974e157d4c25e376b004 | Spectrum | GC-MS | 17alpha-Hydroxypregnenolone, non-derivatized, GC-MS Spectrum | splash10-054x-4900000000-df86d10979d808f20e67 | Spectrum | GC-MS | 17alpha-Hydroxypregnenolone, non-derivatized, GC-MS Spectrum | splash10-0a73-3910000000-7a0eea991ac4d2fac97e | Spectrum | Predicted GC-MS | 17alpha-Hydroxypregnenolone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-000f-3295000000-48ed11374901b134a70d | Spectrum | Predicted GC-MS | 17alpha-Hydroxypregnenolone, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-03di-0111900000-e55e71b4d8c63cde89c2 | Spectrum | Predicted GC-MS | 17alpha-Hydroxypregnenolone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 17alpha-Hydroxypregnenolone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 17alpha-Hydroxypregnenolone, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 17alpha-Hydroxypregnenolone, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 17alpha-Hydroxypregnenolone, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 17alpha-Hydroxypregnenolone, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 17alpha-Hydroxypregnenolone, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 17alpha-Hydroxypregnenolone, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 17alpha-Hydroxypregnenolone, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 17alpha-Hydroxypregnenolone, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 17alpha-Hydroxypregnenolone, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 17alpha-Hydroxypregnenolone, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 17alpha-Hydroxypregnenolone, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-001i-0039000000-28c103ca6cdf072557bf | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0a4i-0900000000-ae3004bb674d9632cd0c | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-014i-0900000000-a2f467560b451d5c9b0e | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive | splash10-0f89-2891000000-82e62584fff36943bcba | 2012-08-31 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0159-0029000000-131b75950fb7123106d9 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-015i-0094000000-2a48017855d3965d5626 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0g29-2690000000-3d1b2b0525a2f6da149c | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0009000000-4c286aa6d88850e66ba9 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-008i-0098000000-77ce542de402b225ac27 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0avr-0092000000-e39f57cc01b46a017728 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0009000000-08a5ce4022cbdbf8bfa1 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0029000000-8619dcbabe228085742a | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000i-0091000000-4088584830d78ccb6fb2 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00lr-0029000000-275368791dddb24379f9 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014m-0910000000-b08f322c49579d81e79a | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0002-1940000000-1f423724847a658c9f85 | 2021-09-24 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | Not Available |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | Not Available |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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