Record Information |
---|
Version | 4.0 |
---|
Status | Detected and Quantified |
---|
Creation Date | 2005-11-16 15:48:42 UTC |
---|
Update Date | 2020-02-26 21:22:03 UTC |
---|
HMDB ID | HMDB0000315 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | 16-a-Hydroxypregnenolone |
---|
Description | 16-alpha-hydroxypregnenolone, also known as (3beta,16alpha)-3,16-dihydroxypregn-5-en-20-one, is classified as a gluco/mineralocorticoid, a progestogin or aprogestogin derivative. Gluco/mineralocorticoids are steroids with a structure based on a hydroxylated prostane moiety. Thus, 16-alpha-hydroxypregnenolone is a steroid lipid molecule. 16-alpha-hydroxypregnenolone is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 16-alpha-hydroxypregnenolone can be found primarily in blood, urine and in human umbilical cord tissue. Within the cell, 16-alpha-hydroxypregnenolone is primarily located in the membrane, and in the nucleus bound to cytoplasmic glucocorticoid receptors. 16-alpha-hydroxypregnenolone exists in all vertebrates. 16-a-Hydroxypregnenolone is a normal urinary metabolite with increased total excretion in newborn infants with congenital adrenal hyperplasia due to 21-hydroxylase deficiency (PMID 6980322 ). |
---|
Structure | |
---|
Synonyms | Value | Source |
---|
(3beta,16alpha)-3,16-Dihydroxypregn-5-en-20-one | ChEBI | 16-alpha-Hydroxypregnenolone | ChEBI | (3b,16a)-3,16-Dihydroxypregn-5-en-20-one | Generator | (3Β,16α)-3,16-dihydroxypregn-5-en-20-one | Generator | 16-Α-hydroxypregnenolone | Generator | 16 alpha-Hydroxypregnenolone | HMDB | 16-a-Hydroxy-pregnenolone | HMDB | 16-alpha-Hydroxy-pregnenolone | HMDB | 16alpha-Hydroxypregnenolone | HMDB | 3b,16a-Dihydroxypreg-5-en-20-one | HMDB | 3b,16a-Dihydroxypregn-5-en-20-one | HMDB | 3b,16a-Dihydroxypregnen-5-en-20-one | HMDB | 5-Pregnene-3b,16a-diol-20-one | HMDB | Pregn-5-en-3b,16a-diol-20-one | HMDB | 3 alpha,16 alpha-Dihydroxypregn-5-en-20-one | HMDB | 3 beta,16 alpha-Dihydroxypregn-5-en-20-one | HMDB | 3 beta,16 beta-Dihydroxypregn-5-en-20-one | HMDB | 16a-Hydroxypregnenolone | HMDB | 16Α-hydroxypregnenolone | HMDB | 16-a-Hydroxypregnenolone | Generator |
|
---|
Chemical Formula | C21H32O3 |
---|
Average Molecular Weight | 332.477 |
---|
Monoisotopic Molecular Weight | 332.23514489 |
---|
IUPAC Name | 1-[(1S,2R,5S,10S,11S,13R,14R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one |
---|
Traditional Name | 1-[(1S,2R,5S,10S,11S,13R,14R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethanone |
---|
CAS Registry Number | 520-88-7 |
---|
SMILES | [H][C@@]12C[C@@H](O)[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C |
---|
InChI Identifier | InChI=1S/C21H32O3/c1-12(22)19-18(24)11-17-15-5-4-13-10-14(23)6-8-20(13,2)16(15)7-9-21(17,19)3/h4,14-19,23-24H,5-11H2,1-3H3/t14-,15+,16-,17-,18+,19-,20-,21-/m0/s1 |
---|
InChI Key | ZAKJZPQDUPCXSD-YRWKUUEZSA-N |
---|
Chemical Taxonomy |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Steroids and steroid derivatives |
---|
Sub Class | Pregnane steroids |
---|
Direct Parent | Gluco/mineralocorticoids, progestogins and derivatives |
---|
Alternative Parents | Not Available |
---|
Substituents | Not Available |
---|
Molecular Framework | Aliphatic homopolycyclic compounds |
---|
External Descriptors | Not Available |
---|
Ontology |
---|
|
Disposition | Route of exposure: Source: Biological location: |
---|
Process | Naturally occurring process: |
---|
Role | Biological role: Industrial application: |
---|
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 | splash10-010d-1094000000-48d07553e41a7f133af6 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-03di-2016900000-9dfed36ce29372d939de | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0159-0049000000-2ccfec5d85aa1a19cec3 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014j-0194000000-e0041edd20068fee3d7b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a6v-1391000000-a896ab547c468e369ce5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0019000000-2ab7fa56b70d72f5890d | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01q9-0029000000-8ccb6ff65b91e81bbea5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00ri-1093000000-56249f185b497261aed4 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
|
---|