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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-08-13 09:18:02 UTC |
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Update Date | 2019-07-23 05:46:00 UTC |
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HMDB ID | HMDB0004026 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 21-Hydroxypregnenolone |
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Description | 21-hydroxypregnenolone is an essential intermediate in corticosterone synthesis. The hydrolysis of 21-hydroxypregnenolone of fetal origin by steryl-sulfatase (SOS, EC 3.1.6.2), may be important in the biosynthesis of deoxycorticosterone, which is present in the plasma of pregnant women in high concentration. 21-hydroxypregnenolone has been identified in follicular fluid from follicles of women. Pregnenolone is transformed to 21-hydroxypregnenolone by human adrenal microsomal preparations, suggesting the involvement of alternative paths via 17a,21-dihydroxypregnenolone in human. (PMID 974176 , 3347051 , 3495701 , 7382480 , 6247575 ). |
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Structure | |
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Synonyms | Value | Source |
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(3beta)-3,21-Dihydroxypregn-5-en-20-one | ChEBI | (3b)-3,21-Dihydroxypregn-5-en-20-one | Generator | (3Β)-3,21-dihydroxypregn-5-en-20-one | Generator | (3b)-3,21-Dihydroxy-pregn-5-en-20-one | HMDB | 3b,21-Dihydroxy-5-pregnen-20-one | HMDB | 3b,21-Dihydroxy-pregn-5-en-20-one | HMDB | 5-Pregnen-3.beta.,21-diol-20-one | HMDB | 5-Pregnen-3b,21-diol-20-one | HMDB | 5-Pregnen-3beta,21-diol-20-one | HMDB | Oprea1_642453 | HMDB | Pregn-5-ene-3b,21-diol-20-one | HMDB |
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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 | 2-hydroxy-1-[(1S,2R,5S,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]ethan-1-one |
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Traditional Name | 21-hydroxypregnenolone |
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CAS Registry Number | 1164-98-3 |
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SMILES | [H][C@@]12CC[C@H](C(=O)CO)[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/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h3,14-18,22-23H,4-12H2,1-2H3/t14-,15-,16-,17-,18+,20-,21-/m0/s1 |
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InChI Key | MOIQRAOBRXUWGN-WPWXJNKXSA-N |
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Chemical Taxonomy |
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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. |
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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 | Hydroxysteroids |
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Direct Parent | 21-hydroxysteroids |
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Alternative Parents | |
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Substituents | - 21-hydroxysteroid
- Progestogin-skeleton
- Pregnane-skeleton
- 20-oxosteroid
- 3-hydroxy-delta-5-steroid
- 3-hydroxysteroid
- 3-beta-hydroxysteroid
- 3-beta-hydroxy-delta-5-steroid
- Oxosteroid
- Delta-5-steroid
- Alpha-hydroxy ketone
- Cyclic alcohol
- Secondary alcohol
- Ketone
- Organic oxygen compound
- Organooxygen compound
- Primary alcohol
- 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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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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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS) | splash10-004u-4910000000-a498e59adb4a11849d3e | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-004u-4910000000-a498e59adb4a11849d3e | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0fk9-0196000000-9576ba4a3e3fe81eccd0 | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-03dj-1014900000-72c174690c4421659ce6 | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0159-0039000000-34e73b29188e789dcd9c | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-015a-0196000000-bd55e2f11df2c7f294d3 | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4j-2391000000-3937d95bf8b6f55a8382 | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0009000000-9d13365707b48184b4b3 | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-06si-2069000000-284db8a88c06364a507e | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-3091000000-fbd05f20ca5983385f71 | JSpectraViewer | MoNA |
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Biological Properties |
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Cellular Locations | - Extracellular
- Membrane (predicted from logP)
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | | Not Available | Not Available | Normal | | details | Urine | Detected and Quantified | 2.9 +/- 0.8 umol/mmol creatinine | Newborn (0-30 days old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 0.04 +/- 0.02 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB023281 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 216208 |
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KEGG Compound ID | C05485 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | 21-Hydroxypregnenolone |
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METLIN ID | 7002 |
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PubChem Compound | 247020 |
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PDB ID | Not Available |
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ChEBI ID | 28043 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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References |
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Synthesis Reference | Daniewski, Andrzej Robert; Wojciechowska, Wanda. Preparation of 5-pregnene-3b, 21-diol-20-one. Pol. (1987), 4 pp. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Shackleton CH, Homoki J, Taylor NF: A paradox: elevated 21-hydroxypregnenolone production in newborns with 21-hydroxylase deficiency. Steroids. 1987 Apr-May;49(4-5):295-311. [PubMed:3502660 ]
- Iudaev NA, Afinogenova SA: [Pathways of corticosteroid biosynthesis in human adrenals (Itsenko-Cushing disease)]. Biokhimiia. 1976 Sep;41(9):1619-27. [PubMed:974176 ]
- Guerami A, Varner MW, Shackleton CH, MacDonald PC, Casey ML: Origin of deoxycorticosterone and deoxycorticosterone sulfate in human pregnancy: absence of steroid 21-sulfatase activity in sulfatase-deficient placenta. J Steroid Biochem. 1988 Jan;29(1):57-62. [PubMed:3347051 ]
- Dehennin L, Nahoul K, Scholler R: Steroid 21-hydroxylation by human preovulatory follicles from stimulated cycles: a mass spectrometrical study of deoxycorticosterone, 21-hydroxypregnenolone and 11-deoxycortisol in follicular fluid. J Steroid Biochem. 1987 Mar;26(3):337-43. [PubMed:3495701 ]
- Kaufmann SH, Sinterhauf K, Lommer D: 21-Hydroxylation of pregnenolone by microsomal preparations of rat and human adrenals. J Steroid Biochem. 1980 Jan;13(1):101-3. [PubMed:7382480 ]
- Kaufmann SH, Sinterhauf K, Lommer D: Alternative pathways in human corticosteroid biosynthesis. J Steroid Biochem. 1980 Jun;13(6):599-605. [PubMed:6247575 ]
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