CHEBI:74092 - biotin sulfone

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name biotin sulfone
ChEBI ID CHEBI:74092
Definition A member of the class of biotins that is biotin sulfoxide with a sulfone group replacing the sulfoxide.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ZINC000008551918
Download Molfile XML SDF
Formula C10H16N2O5S
Net Charge 0
Average Mass 276.30900
Monoisotopic Mass 276.07799
InChI InChI=1S/C10H16N2O5S/c13-8(14)4-2-1-3-7-9-6(5-18(7,16)17)11-10(15)12-9/h6-7,9H,1-5H2,(H,13,14)(H2,11,12,15)/t6-,7-,9-/m0/s1
InChIKey QPFQYMONYBAUCY-ZKWXMUAHSA-N
SMILES [H][C@]12CS(=O)(=O)[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=O)N2
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing biotin sulfone (CHEBI:74092) has functional parent biotin sulfoxide (CHEBI:62193)
biotin sulfone (CHEBI:74092) has role metabolite (CHEBI:25212)
biotin sulfone (CHEBI:74092) is a biotins (CHEBI:51570)
biotin sulfone (CHEBI:74092) is a sulfone (CHEBI:35850)
IUPAC Name
5-[(3aS,4S,6aR)-5,5-dioxido-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid
Synonyms Sources
5,5-Dioxide Biotin HMDB
[3aS-(3aa,4b,6aa)]-5,5-dioxide-hexahydro-2-oxo-1H-Thieno[3,4-D]imidazole-4-pentanoic acid HMDB
Manual Xref Database
HMDB0004818 HMDB
View more database links
Registry Numbers Types Sources
33724 Reaxys Registry Number Reaxys
40720-05-6 CAS Registry Number ChemIDplus
Citations
Collot M, Sendid B, Fievez A, Savaux C, Standaert-Vitse A, Tabouret M, Drucbert AS, Danzé PM, Poulain D, Mallet JM (2008)
Biotin sulfone as a new tool for synthetic oligosaccharide immobilization: application to multiple analysis profiling and surface plasmonic analysis of anti-Candida albicans antibody reactivity against alpha and beta (1-->2) oligomannosides.
Journal of medicinal chemistry 51, 6201-6210 [PubMed:18788729]
[show Abstract]
Zempleni J, McCormick DB, Mock DM (1997)
Identification of biotin sulfone, bisnorbiotin methyl ketone, and tetranorbiotin-l-sulfoxide in human urine.
The American journal of clinical nutrition 65, 508-511 [PubMed:9022537]
[show Abstract]
PELLEGRINO G (1957)
[Effects of biotin sulfone on disposition toward experimental reflex epilepsy].
Bollettino della Societa italiana di biologia sperimentale 33, 1191-1192 [PubMed:13510484]
RAVEL JM, SHIVE W (1955)
A study of biotin sulfone inhibition of Lactobacillus arabinosus.
Archives of biochemistry and biophysics 54, 341-348 [PubMed:14350781]
RUBIN SH, SCHEINER J (1949)
Antibiotin effect of homologs of biotin and biotin sulfone.
Archives of biochemistry 23, 400-410 [PubMed:18141516]
AXELROD AE, DeWOODY J, HOFMANN K (1946)
The differential effect of biotin sulfone and gamma-(3,4-ureylenecyclohexyl) butyric acid upon the microbiological activity of biotin and oxybiotin.
The Journal of biological chemistry 163, 771 [PubMed:20985652]
Last Modified
23 October 2015