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CHEBI:61702 - dinoflagellate luciferin

Default Structure
ChEBI IDCHEBI:61702
ChEBI Namedinoflagellate luciferin
Stars
DefinitionA member of the class of bilenes that is 1,2,3,21-tetrahydro-5,7-ethanobilene-a-19(16H),52-dione which is substituted at positions 2, 8, 13 and 18 by methyl groups and at positions 1, 3, 12 and 17 by carboxy, 2-carboxyethyl, ethyl and vinyl groups, respectively (the 1S,2S,3S diastereoisomer).
Last Modified27 March 2015
SubmitterGareth Owen
DownloadsMolfile
FormulaC33H40N4O6
Net Charge0
Average Mass588.705
Monoisotopic Mass588.29478
SMILES[H][C@]1(C(=O)O)N/C(=C2/CC(=O)c3c2nc(Cc2nc(CC4NC(=O)C(C)=C4C=C)c(C)c2CC)c3C)[C@@H](CCC(=O)O)[C@@H]1C
InChIInChI=1S/C33H40N4O6/c1-7-18-14(3)22(12-25-19(8-2)16(5)32(41)36-25)34-24(18)13-23-17(6)28-26(38)11-21(31(28)35-23)30-20(9-10-27(39)40)15(4)29(37-30)33(42)43/h8,15,20,25,29,34-35,37H,2,7,9-13H2,1,3-6H3,(H,36,41)(H,39,40)(H,42,43)/b30-21-/t15-,20-,25?,29-/m0/s1
InChIKeyQUHVVVWAQMRCSJ-IXXPHHLHSA-N
Roles Classification
Chemical Roles:
luciferin  A low-molecular-mass compound present in bioluminescent organisms that emits light when oxidized in presence of enzyme luciferase.
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
luciferin  A low-molecular-mass compound present in bioluminescent organisms that emits light when oxidized in presence of enzyme luciferase.
ChEBI Ontology
Outgoing Relation(s)
dinoflagellate luciferin (CHEBI:61702) has role luciferin (CHEBI:25078)
dinoflagellate luciferin (CHEBI:61702) is a amino dicarboxylic acid (CHEBI:36164)
dinoflagellate luciferin (CHEBI:61702) is a bilenes (CHEBI:36736)
dinoflagellate luciferin (CHEBI:61702) is a non-proteinogenic L-α-amino acid (CHEBI:83822)
dinoflagellate luciferin (CHEBI:61702) is a oxo dicarboxylic acid (CHEBI:36145)
dinoflagellate luciferin (CHEBI:61702) is conjugate acid of dinoflagellate luciferin(1−) (CHEBI:61796)
Incoming Relation(s)
dinoflagellate luciferin(1−) (CHEBI:61796) is conjugate base of dinoflagellate luciferin (CHEBI:61702)
IUPAC Name 
(1S,2S,3S)-1-carboxy-3-(2-carboxyethyl)-12-ethyl-2,8,13,18-tetramethyl-17-vinyl-1,2,3,21-tetrahydro-5,7-ethanobilene-a-19(16H),52-dione
Synonym  Source
(3S,4S,5Z)-4-(2-carboxyethyl)-5-[2-({5-[(3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)methyl]-3-ethyl-4-methyl-1H-pyrrol-2-yl}methyl)-3-methyl-4-oxo-4,5-dihydrocyclopenta[b]pyrrol-6(1H)-ylidene]-3-methyl-L-prolineIUPAC