CHEBI:138742 - cholesteryl hemisuccinate

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ChEBI Name cholesteryl hemisuccinate
ChEBI ID CHEBI:138742
Definition A dicarboxylic acid monoester resulting from the formal condensation of the hydroxy group of cholesterol with one of the carboxy groups of succinic acid. A detergent that is often used to replace cholesterol in protein crystallography, biochemical studies of proteins, and pharmacology.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Ceri
Supplier Information
Download Molfile XML SDF
Formula C31H50O4
Net Charge 0
Average Mass 486.727
Monoisotopic Mass 486.37091
InChI InChI=1S/C31H50O4/c1-20(2)7-6-8-21(3)25-11-12-26-24-10-9-22-19-23(35-29(34)14-13-28(32)33)15-17-30(22,4)27(24)16-18-31(25,26)5/h9,20-21,23-27H,6-8,10-19H2,1-5H3,(H,32,33)/t21-,23+,24+,25-,26+,27+,30+,31-/m1/s1
InChIKey WLNARFZDISHUGS-MIXBDBMTSA-N
SMILES C1[C@@]2([C@]3(CC[C@]4([C@]([C@@]3(CC=C2C[C@H](C1)OC(=O)CCC(O)=O)[H])(CC[C@@]4([C@H](C)CCCC(C)C)[H])[H])C)[H])C
Roles Classification
Chemical Role(s): detergent
A surfactant (or a mixture containing one or more surfactants) having cleaning properties in dilute solutions.
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Application(s): detergent
A surfactant (or a mixture containing one or more surfactants) having cleaning properties in dilute solutions.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cholesteryl hemisuccinate (CHEBI:138742) has functional parent cholesterol (CHEBI:16113)
cholesteryl hemisuccinate (CHEBI:138742) has role detergent (CHEBI:27780)
cholesteryl hemisuccinate (CHEBI:138742) is a cholestane ester (CHEBI:131696)
cholesteryl hemisuccinate (CHEBI:138742) is a dicarboxylic acid monoester (CHEBI:36244)
cholesteryl hemisuccinate (CHEBI:138742) is a hemisuccinate (CHEBI:138979)
IUPAC Name
4-[(3β)-cholest-5-en-3-yloxy]-4-oxobutanoic acid
Synonyms Sources
3β-hydroxy-5-cholestene 3-hemisuccinate SUBMITTER
4-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4-oxobutanoic acid SUBMITTER
cholest-5-en-3β-yl hydrogen succinate ChemIDplus
cholesteryl succinate ChemIDplus
Manual Xref Database
Y01 PDBeChem
View more database links
Registry Numbers Types Sources
1510-21-0 CAS Registry Number ChemIDplus
3181155 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
18302031 PubMed citation Europe PMC
24526383 PubMed citation Europe PMC
25450348 PubMed citation Europe PMC
9067481 PubMed citation Europe PMC
9858729 PubMed citation Europe PMC
Last Modified
05 December 2017