File:Sterol.svg · Wikimedia Commons · See Wikimedia Commons
sterol
Sign in to saveAlso known as sterols, sterol lipids, 3-hydroxysteroids
class=skin-invert-image|thumb|Gonan-3-ol, the simplest sterol
OverviewAI-generated
Sterol is a chemical compound with the molecular formula C6H12O6 and a molecular weight of 180.16. Its IUPAC name is (2S,3S,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol. The substance has a charge of 0, an xlogp value of -2.6, and a topological polar surface area of 110. It contains five hydrogen bond donors and six hydrogen bond acceptors.
The compound is associated with a mass of 2484 in one dataset. It is categorized under "Sterols" on Commons. A search for the term "sterol" yields 255674 results in PubMed. The subject is referenced by 460 other encyclopedia articles.
Synthesized by Vinony from 18 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Chemical data
- Formula
- C6H12O6
- Molecular weight
- 180.16 g/mol
- IUPAC name
- (2S,3S,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
- SMILES
- C([C@@H]1[C@H]([C@@H]([C@@H]([C@H](O1)O)O)O)O)O
- InChIKey
- WQZGKKKJIJFFOK-PQMKYFCFSA-N
- XLogP
- -2.6
- Polar surface area
- 110 Ų
- H-bond donors
- 5
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Research
255,674 papers- [Sterol transport proteins in yeast: a review].Sheng wu gong cheng xue bao = Chinese journal of biotechnology · 2023
- Insect Sterol Nutrition: Physiological Mechanisms, Ecology, and Applications.Annual review of entomology · 2020
- Sterol gradients in cells.Current opinion in cell biology · 2018
- Fluorescent sterol probes for intracellular transport, imaging, and therapeutics.Current opinion in chemical biology · 2022
- Sterol uptake by the NPC system in eukaryotes: a Saccharomyces cerevisiae perspective.FEBS letters · 2022
via PubMed
Wikidata facts
- Subclass of
- steroid
- Mass
- 2484
Show 4 more facts
- topic's main category
- Category:Sterols
- Commons category
- Sterols
- SMARTS notation
- [#6]C12[#6]-[#6]-[#6]3-[#6](-[#6]-[#6]-[#6]4-[#6]-[#6](-[#8])-[#6]-[#6]C34[#6])-[#6]1-[#6]-[#6]-[#6]2-*
- canonical SMILES
- C12C(C3C(C(CC3)*)(C)CC1)CCC4C2(CCC(C4)O)C
via Wikidata · CC0
~5 min read
Encyclopedic overview
11 sectionsContents
- Types
- Phytosterols
- Zoosterols
- Mycosterols
- Role in biochemistry
- Phytosterols as a nutritional supplement
- Chemical classification and structure
- See also
- References
- Further reading
- External links
class=skin-invert-image|thumb|Gonan-3-ol, the simplest sterol
A sterol is any organic compound with a skeleton closely related to cholestan-3-ol and having a hydroxyl group at carbon 3. The simplest sterol is gonan-3-ol, which has a formula of , 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.
Excerpted from Wikipedia’s “sterol” article, available under the CC BY-SA 4.0 licence.