CHEBI:155905 - crinosterol

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ChEBI Name crinosterol
ChEBI ID CHEBI:155905
Definition A 3β-sterol that is campesterol in which position 22 has been dehydrogenated to introduce a double bond. It is a phytosterol found in marine algae, mussels, crinoids, mites and plants.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Mark Williams
Supplier Information No supplier information found for this compound.
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Epibrassicasterol (also called crinosterol) is a type of cholesterol most commonly found in marine invertebrates. Epibrassicasterol is a 28 carbon cholesterol with an alpha oriented methyl group at carbon 24. It is often mixed isomerically with the more common beta-isomer, brassicasterol. Epibrassicasterol can be used as a biomarker to identify the presence of marine life in an environment and can be dated based on the location of fossilized remains in various rock structures.
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Formula C28H46O
Net Charge 0
Average Mass 398.675
Monoisotopic Mass 398.35487
InChI InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-9,18-20,22-26,29H,10-17H2,1-6H3/b8-7+/t19-,20-,22+,23+,24-,25+,26+,27+,28-/m1/s1
InChIKey OILXMJHPFNGGTO-SDMVIZLASA-N
SMILES C[C@]12[C@](CC[C@@]1([C@@H](/C=C/[C@H](C(C)C)C)C)[H])([H])[C@]3([C@@]([C@@]4(C(=CC3)C[C@H](CC4)O)C)(CC2)[H])[H]
Metabolite of Species Details
Comatula (NCBI:txid1320698) See: PubMed
Brassica campestris (NCBI:txid145471) Found in seed (BTO:0001226). See: PubMed
Cosmoglyphus hughesi (NCBI:txid223505) See: PubMed
Cryptomonas sp. (NCBI:txid3031) See: DOI
Phaeocystis pouchetii (NCBI:txid33659) Found in Whole Organism (NCIT:C13413). of strain Phaeocystis pouchetii str. AJ01 See: MetaboLights Study
Brassica juncea (NCBI:txid3707) Found in seed (BTO:0001226). See: DOI
Isochrysis galbana (NCBI:txid37099) See: DOI
Aureoumbra lagunensis (NCBI:txid44058) See: PubMed
Mytilidae (NCBI:txid6547) See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
animal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.
marine metabolite
Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
algal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
Application(s): biomarker
A substance used as an indicator of a biological state.
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ChEBI Ontology
Outgoing crinosterol (CHEBI:155905) has functional parent campesterol (CHEBI:28623)
crinosterol (CHEBI:155905) has role algal metabolite (CHEBI:84735)
crinosterol (CHEBI:155905) has role animal metabolite (CHEBI:75767)
crinosterol (CHEBI:155905) has role biomarker (CHEBI:59163)
crinosterol (CHEBI:155905) has role marine metabolite (CHEBI:76507)
crinosterol (CHEBI:155905) has role plant metabolite (CHEBI:76924)
crinosterol (CHEBI:155905) is a 3β-hydroxy-Δ5-steroid (CHEBI:1722)
crinosterol (CHEBI:155905) is a 3β-sterol (CHEBI:35348)
crinosterol (CHEBI:155905) is a ergostanoid (CHEBI:50403)
crinosterol (CHEBI:155905) is a phytosterols (CHEBI:26125)
IUPAC Name
(22E,24S)-ergosta-5,22-dien-3β-ol
Synonyms Sources
(24S)-24-methyl-cholesta-5,22(E)-dien-3β-ol ChEBI
(E)-22-dehydrocampesterol ChEBI
22-dehydrocampesterol ChEBI
24-epibrassicasterol LIPID MAPS
campesta-5,22E-dien-3β-ol LIPID MAPS
pincasterol LIPID MAPS
trans-22-dehydrocampesterol ChEBI
Manual Xrefs Databases
CPD-8135 MetaCyc
Epibrassicasterol Wikipedia
FDB030745 FooDB
LMST01030114 LIPID MAPS
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Citations Waiting for Citations
Last Modified
17 January 2023