Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2019-01-11 19:14:19 UTC |
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HMDB ID | HMDB0000315 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 16-a-Hydroxypregnenolone |
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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 ). |
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Structure | |
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Synonyms | Value | Source |
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(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 | MeSH | 3 beta,16 alpha-Dihydroxypregn-5-en-20-one | MeSH | 3 beta,16 beta-Dihydroxypregn-5-en-20-one | MeSH |
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Chemical Formula | C21H32O3 |
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Average Molecular Weight | 332.477 |
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Monoisotopic Molecular Weight | 332.23514489 |
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IUPAC Name | 1-[(1S,2R,5S,10S,11S,13R,14R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]ethan-1-one |
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Traditional Name | 16α-hydroxypregnenolone |
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CAS Registry Number | 520-88-7 |
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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 |
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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 |
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InChI Key | ZAKJZPQDUPCXSD-YRWKUUEZSA-N |
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Chemical Taxonomy |
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Description | This compound 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
- 3-beta-hydroxysteroid
- 16-hydroxysteroid
- 16-alpha-hydroxysteroid
- 3-beta-hydroxy-delta-5-steroid
- Oxosteroid
- Hydroxysteroid
- Delta-5-steroid
- Cyclic alcohol
- Secondary alcohol
- Ketone
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxygen compound
- Carbonyl group
- 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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Physical Properties |
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State | Solid |
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Experimental 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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Predicted Properties | |
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