firefly sulfoluciferin (CHEBI:133462)

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ChEBI Name	firefly sulfoluciferin

ChEBI ID	CHEBI:133462

Definition	A member of the class of benzothiazoles that is Photinus luciferin in which the phenolic hydroxy group has been replaced by a sulfo group.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.

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	tfallon

Supplier Information

Download	Molfile XML SDF

Formula

C11H8N2O6S3

Net Charge

Average Mass

360.390

Monoisotopic Mass

359.95445

InChI

InChI=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

InChIKey

LPKFAQWRYNJJRB-SSDOTTSWSA-N

SMILES

C=12C(=CC(=CC1)OS(O)(=O)=O)SC(=N2)C3=N[C@H](CS3)C(=O)O

Metabolite of Species	Details
Photuris sp. (NCBI:txid4171)	See: PubMed
Photinus pyralis (NCBI:txid7054)	See: PubMed
Ellychnia corrusca (NCBI:txid94999)	See: PubMed
Pyractomena sp. (NCBI:txid95015)	See: PubMed

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):	animal metabolite Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.

ChEBI Ontology
Outgoing	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	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	Sources
(6-sulfooxy-1,3-benzothiazol-2-yl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid	ChEBI
D-luciferin O-sulfate	ChEBI
D-luciferin sulfate	ChEBI
firefly luciferin O-sulfate	ChEBI
firefly luciferin sulfate	ChEBI
Photinus luciferin O-sulfate	ChEBI
Photinus luciferin sulfate	ChEBI
Photinus sulfoluciferin	ChEBI

Registry Number	Type	Source
13866155	Reaxys Registry Number	Reaxys

Last Modified

17 August 2023