Record Information |
---|
Version | 2.0 |
---|
Created at | 2005-11-16 15:48:42 UTC |
---|
Updated at | 2020-11-24 22:14:04 UTC |
---|
NP-MRD ID | NP0000256 |
---|
Secondary Accession Numbers | None |
---|
Natural Product 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 | [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=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 |
---|
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 Mass | 332.4770 Da |
---|
Monoisotopic Mass | 332.23514 Da |
---|
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 |
---|
Experimental Spectra |
---|
|
| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
---|
1D NMR | 1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
---|
|
| Not Available | Chemical Shift Submissions |
---|
|
| Not Available | Species |
---|
Species of Origin | |
---|
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 | |
---|
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
|
---|
Molecular Framework | Aliphatic homopolycyclic compounds |
---|
External Descriptors | |
---|
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 | |
---|
General References | - Shibusawa H, Sano Y, Yamamoto T, Kambegawa A, Ohkawa T, Satoh N, Okinaga S, Arai K: A radioimmunoassay of serum 16alpha-hydroxypregnenolone with specific antiserum. Endocrinol Jpn. 1978 Apr;25(2):185-9. [PubMed:668632 ]
- Homoki J, Teller WM: Increased urinary excretion of total 16 alpha-hydroxypregnenolone in newborn infants with congenital adrenal hyperplasia due to 21-hydroxylase deficiency. Klin Wochenschr. 1982 Apr 15;60(8):407-10. [PubMed:6980322 ]
- Den K, Haruyama T, Hagiwara H, Fujii KT, Kambegawa A, Takami T, Yoshida T, Takagi S: Plasma levels of 16 alpha-hydroxypregnenolone, 16 alpha-hydroxyprogesterone and 16 alpha-hydroxydehydroepiandrosterone in the fetus and neonates. Endocrinol Jpn. 1979 Aug;26(4):439-47. doi: 10.1507/endocrj1954.26.439. [PubMed:159171 ]
- Janoski AH, Kelly WG: On the metabolism of 16-alpha-hydroxy-C21-steroids. II. Evidence for the presence of a glucuronide of 16-alpha-hydroxypregnenolone in human urine and its utility in estimating the rates of production of 16-alpha-hydroxyprogesterone and 16-alpha-hydroxypregnenolone. J Clin Endocrinol Metab. 1969 Oct;29(10):1291-300. doi: 10.1210/jcem-29-10-1291. [PubMed:5353659 ]
|
---|