| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 23:07:16 UTC |
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| Update Date | 2020-05-05 18:38:12 UTC |
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| BMDB ID | BMDB0004026 |
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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, also known as 21-hydroxypregnenolone, 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. Thus, 21-hydroxypregnenolone is considered to be a steroid lipid molecule. 21-Hydroxypregnenolone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 21-Hydroxypregnenolone participates in a number of enzymatic reactions, within cattle. In particular, 21-Hydroxypregnenolone can be converted into deoxycorticosterone through the action of the enzyme 3-beta-HSD 1. In addition, 21-Hydroxypregnenolone can be biosynthesized from pregnenolone through its interaction with the enzyme steroid 21-hydroxylase. In cattle, 21-hydroxypregnenolone is involved in the metabolic pathway called the steroidogenesis pathway. |
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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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| Status | Detected but not Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | - Cell membrane
- Cytoplasm
- Membrane
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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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