Record Information |
---|
Version | 4.0 |
---|
Status | Expected but not Quantified |
---|
Creation Date | 2008-08-06 15:31:56 UTC |
---|
Update Date | 2020-02-26 21:26:44 UTC |
---|
HMDB ID | HMDB0006762 |
---|
Secondary Accession Numbers | - HMDB0000382
- HMDB00382
- HMDB06762
|
---|
Metabolite Identification |
---|
Common Name | 17alpha,21-Dihydroxypregnenolone |
---|
Description | 17alpha,21-Dihydroxypregnenolone is an intermediate in the human fetus at midpregnancy that is converted into cortisol (PMID: 4231965 ). It has also been found as an intermediate in alternative pathways in human adrenal steroidogenesis that take place under in vitro conditions. In normal adrenal slices from patients with hypernephroid kidney carcinomas these pathways bypass cholesterol, pregnenolone, and progesterone, and proceed to 21-hydroxypregnenolone (PMID: 6247575 ). 17alpha,21-Dihydroxypregnenolone is an intermediate in C21-Steroid hormone metabolism. 17alpha,21-Dihydroxypregnenolone is the 5th to last step in the synthesis of Cortol and is converted from 17alpha-Hydroxypregnenolone via the enzyme cytochrome P450 (EC 1.14.99.10). It is then converted to 11beta,17alpha,21-Trihydroxypregnenolone via the enzyme cytochrome P450 (EC 1.14.15.4). |
---|
Structure | |
---|
Synonyms | Value | Source |
---|
17a,21-Dihydroxypregnenolone | Generator | 17Α,21-dihydroxypregnenolone | Generator | 17alpha,21-Dihydroxypreg-nenolone | HMDB | 17, 21-Dihydroxypregnenolone | HMDB | 3Β,17α,21-trihydroxypregnenone | HMDB | 3beta,17alpha,21-Trihydroxypregnenone | HMDB | 17,21-Dihydroxypregnenolone | HMDB | 3Β,17,21-trihydroxy-pregn-5-en-20-one | HMDB | 3beta,17,21-Trihydroxy-pregn-5-en-20-one | HMDB | (3Β)-3,17,21-trihydroxypregn-5-en-20-one | HMDB | (3beta)-3,17,21-Trihydroxypregn-5-en-20-one | HMDB | 3Β,17α,21-trihydroxypregn-5-en-20-one | HMDB | 3beta,17alpha,21-Trihydroxypregn-5-en-20-one | HMDB | 17alpha,21-Dihydroxypregnenolone | HMDB |
|
---|
Chemical Formula | C21H32O4 |
---|
Average Molecular Weight | 348.4764 |
---|
Monoisotopic Molecular Weight | 348.230059512 |
---|
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]-2-hydroxyethan-1-one |
---|
Traditional 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]-2-hydroxyethanone |
---|
CAS Registry Number | 1167-48-2 |
---|
SMILES | [H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C |
---|
InChI Identifier | InChI=1S/C21H32O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h3,14-17,22-23,25H,4-12H2,1-2H3/t14-,15+,16-,17-,19-,20-,21-/m0/s1 |
---|
InChI Key | JNHJGXQUDOYJAK-IYRCEVNGSA-N |
---|
Chemical Taxonomy |
---|
Description | belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Steroids and steroid derivatives |
---|
Sub Class | Hydroxysteroids |
---|
Direct Parent | 21-hydroxysteroids |
---|
Alternative Parents | |
---|
Substituents | - Progestogin-skeleton
- 21-hydroxysteroid
- 20-oxosteroid
- Pregnane-skeleton
- 3-hydroxy-delta-5-steroid
- 3-hydroxysteroid
- Oxosteroid
- 3-beta-hydroxy-delta-5-steroid
- 3-beta-hydroxysteroid
- 17-hydroxysteroid
- Delta-5-steroid
- Cyclic alcohol
- Tertiary alcohol
- Alpha-hydroxy ketone
- Ketone
- Secondary alcohol
- Alcohol
- Hydrocarbon derivative
- Organooxygen compound
- Organic oxide
- Organic oxygen compound
- Primary alcohol
- Carbonyl group
- Aliphatic homopolycyclic compound
|
---|
Molecular Framework | Aliphatic homopolycyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Disposition | Route of exposure: Source: Biological location: |
---|
Process | Naturally occurring process: |
---|
Role | Industrial application: Biological role: |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Predicted Properties | |
---|
| Spectrum Type | Description | Splash Key | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-00lr-4189000000-38652a1384b510a4e849 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-0f6t-1111090000-ac64327581e7c755d285 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001j-0029000000-0868a1856a2a865dc2da | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01qa-0097000000-873e4eef53be76546e5f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00xr-0491000000-bf3679c3178ebe5ceb4e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0029000000-5f642a89fae11d677fda | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-05bs-3098000000-d61819020861e0a89cf5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-6091000000-8a9828ddf7d9d4a69ef6 | Spectrum |
|
---|
General References | - Pasqualini JR, Lowy J, Wiqvist N, Diczfalusy E: Biosynthesis of cortisol from 3 beta, 17 alpha,21-trihydroxypregn-5-en-20-one by the intact human foetus at midpregnancy. Biochim Biophys Acta. 1968 May 1;152(3):648-50. [PubMed:4231965 ]
- Kaufmann SH, Sinterhauf K, Lommer D: Alternative pathways in human corticosteroid biosynthesis. J Steroid Biochem. 1980 Jun;13(6):599-605. [PubMed:6247575 ]
|
---|