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CHEBI:133462 - firefly sulfoluciferin

ChEBI IDCHEBI:133462
ChEBI Namefirefly sulfoluciferin
Stars
DefinitionA member of the class of benzothiazoles that is Photinus luciferin in which the phenolic hydroxy group has been replaced by a sulfo group. Enzymatic derivative of firefly luciferin produced by luciferin sulfotransferase (LST) from luciferin with 3'-phosphoadenosine-5'-phosphosulfate (PAPS) as co-substrate. Not a substrate for firefly luciferase. Likely the in-vivo storage form of luciferin.
Last Modified17 August 2023
Submittertfallon
DownloadsMolfile
FormulaC11H8N2O6S3
Net Charge0
Average Mass360.394
Monoisotopic Mass359.95445
SMILESO=C(O)[C@H]1CSC(c2nc3ccc(OS(=O)(=O)O)cc3s2)=N1
InChIInChI=1S/C11H8N2O6S3/c14-11(15)7-4-20-9(13-7)10-12-6-2-1-5(3-8(6)21-10)19-22(16,17)18/h1-3,7H,4H2,(H,14,15)(H,16,17,18)/t7-/m1/s1
InChIKeyLPKFAQWRYNJJRB-SSDOTTSWSA-N
Species of MetaboliteComponentSourceComments
Photinus pyralis (ncbitaxon:7054) - PubMed (27227579)
Pyractomena sp. (ncbitaxon:95015) - PubMed (27227579)
Photuris sp. (ncbitaxon:4171) - PubMed (27227579)
Ellychnia corrusca (ncbitaxon:94999) - PubMed (27227579)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
animal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.
ChEBI Ontology
Outgoing Relation(s)
firefly sulfoluciferin (CHEBI:133462) has functional parent Photinus luciferin (CHEBI:17165)
firefly sulfoluciferin (CHEBI:133462) has role animal metabolite (CHEBI:75767)
firefly sulfoluciferin (CHEBI:133462) is a 1,3-thiazolemonocarboxylic acid (CHEBI:48652)
firefly sulfoluciferin (CHEBI:133462) is a aryl sulfate (CHEBI:37919)
firefly sulfoluciferin (CHEBI:133462) is a benzothiazoles (CHEBI:37947)
firefly sulfoluciferin (CHEBI:133462) is a imidothioate (CHEBI:83991)
firefly sulfoluciferin (CHEBI:133462) is conjugate acid of firefly D-sulfoluciferin(2−) (CHEBI:143025)
Incoming Relation(s)
firefly D-sulfoluciferin(2−) (CHEBI:143025) is conjugate base of firefly sulfoluciferin (CHEBI:133462)
IUPAC Name 
(4S)-2-[6-(sulfooxy)-1,3-benzothiazol-2-yl]-4,5-dihydro-1,3-thiazole-4-carboxylic acid
Synonyms  Source
(6-sulfooxy-1,3-benzothiazol-2-yl)-4,5-dihydro-1,3-thiazole-4-carboxylic acidChEBI
Photinus luciferin O-sulfateChEBI
D-luciferin O-sulfateChEBI
Photinus luciferin sulfateChEBI
firefly luciferin sulfateChEBI
firefly luciferin O-sulfateChEBI
Registry NumbersSources
Reaxys:13866155Reaxys
Citations