| Record Information |
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| Version | 3.6 |
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| Creation Date | 2006-08-13 09:18:02 UTC |
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| Update Date | 2017-09-21 20:53:26 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 | This compound 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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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | - Cell signaling
- Fuel and energy storage
- Fuel or energy source
- Hormones, Membrane component
- Membrane integrity/stability
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| Application | - Nutrients
- Stabilizers
- Surfactants and Emulsifiers
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| Cellular locations | - Extracellular
- Membrane (predicted from logP)
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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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| Spectra | |
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| General References | - Kaufmann SH, Sinterhauf K, Lommer D: Alternative pathways in human corticosteroid biosynthesis. J Steroid Biochem. 1980 Jun;13(6):599-605. [PubMed:6247575 ]
- Iudaev NA, Afinogenova SA: [Pathways of corticosteroid biosynthesis in human adrenals (Itsenko-Cushing disease)]. Biokhimiia. 1976 Sep;41(9):1619-27. [PubMed:974176 ]
- 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 ]
- 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 ]
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