CHEBI:15889 - sterol

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ChEBI Name sterol ChEBI ID CHEBI:15889 Definition Any 3-hydroxy steroid whose skeleton is closely related to cholestan-3-ol (additional carbon atoms may be present in the side chain). Stars This entity has been manually annotated by the ChEBI Team. Secondary ChEBI IDs CHEBI:13688, CHEBI:15114, CHEBI:9266, CHEBI:26771 Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Wikipedia License A sterol is any organic compound with a skeleton closely related to cholestan-3-ol. The simplest sterol is gonan-3-ol, which has a formula of C17H28O, and is derived from that of gonane by replacement of a hydrogen atom on C3 position by a hydroxyl group. It is therefore an alcohol of gonane. More generally, any compounds that contain the gonane structure, additional functional groups, and/or modified ring systems derived from gonane are called steroids. Therefore, sterols are a subgroup of the steroids. They occur naturally in most eukaryotes, including plants, animals, and fungi, and can also be produced by some bacteria (however likely with different functions). The most familiar type of animal sterol is cholesterol, which is vital to the structure of the cell membrane, and functions as a precursor to fat-soluble vitamins and steroid hormones. While technically alcohols, sterols are classified by biochemists as lipids (fats in the broader sense of the term). Some sources make a distinction between sterols and stanols. In this context, the difference between them is analogous to the difference between cholesterol and cholestanol, in that sterols have a double bond between C-5 and C-6, while stanols have not. Read full article at Wikipedia Formula C19H31OR Net Charge 0 Average Mass (excl. R groups) 275.450 Monoisotopic Mass (excl. R groups) 275.23749 SMILES C12C(C3C(C(CC3)*)(C)CC1)CCC4C2(CCC(C4)O)C Metabolite of Species Details Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed ChEBI Ontology Outgoing sterol (CHEBI:15889) is a 3-hydroxy steroid (CHEBI:36834) Incoming Δ5,Δ7-sterol (CHEBI:138131) is a sterol (CHEBI:15889) Δ7-sterol (CHEBI:138130) is a sterol (CHEBI:15889) 3α-sterol (CHEBI:35347) is a sterol (CHEBI:15889) 3β-hydroxy-16α,17α-epoxypregnenolone (CHEBI:145045) is a sterol (CHEBI:15889) 3β-sterol (CHEBI:35348) is a sterol (CHEBI:15889) 5-dehydroepisterol (CHEBI:20565) is a sterol (CHEBI:15889) 6α-hydroxycholestanol (CHEBI:132620) is a sterol (CHEBI:15889) 6-deoxotyphasterol (CHEBI:20717) is a sterol (CHEBI:15889) androstane sterol (CHEBI:131640) is a sterol (CHEBI:15889) cycloartane sterol (CHEBI:131638) is a sterol (CHEBI:15889) ergostane sterol (CHEBI:131642) is a sterol (CHEBI:15889) estrane sterol (CHEBI:131641) is a sterol (CHEBI:15889) lanostane sterol (CHEBI:131637) is a sterol (CHEBI:15889) oxysterol (CHEBI:53030) is a sterol (CHEBI:15889) phytosterols (CHEBI:26125) is a sterol (CHEBI:15889) pregnane sterol (CHEBI:131698) is a sterol (CHEBI:15889) stigmastane sterol (CHEBI:131703) is a sterol (CHEBI:15889) IUPAC Name sterols Synonyms Sources 3-hydroxysteroids ChEBI a sterol UniProt Sterol KEGG COMPOUND Manual Xrefs Databases C00370 KEGG COMPOUND LMST01 LIPID MAPS Sterol Wikipedia Sterols MetaCyc View more database links Last Modified 11 August 2017

General Comments 2017-05-15 The chemical structure shown (which is analogous to those used in KEGG and MetaCyc) is a generic structure devised to represent a common steroid skeleton. Derivatives with ring substituents at positions other than positions 3 and 16 as well as those containing double bonds, aromatic A-rings, expanded/contracted rings etc. are also included. 2017-08-11 Although this definition of sterols is rather restrictive, a less restrictive definition would cause difficulties, e.g. androst-16-en-3β-ol is normally not called a sterol and should not fall under the definition.