CHEBI:90127 - scytonemin

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ChEBI Name scytonemin
ChEBI ID CHEBI:90127
Definition A ring assembly obtained by 1,1'-coupling of two molecules of (3E)-3-[(4-hydroxyphenyl)methylidene]cyclopenta[b]indol-2(3H)-one. A UV-screening molecule produced by many strains of cyanobacteria.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C36H20N2O4
Net Charge 0
Average Mass 544.556
Monoisotopic Mass 544.142
InChI InChI=1S/C36H20N2O4/c39-21-13-9-19(10-14-21)17-25-33-29(23-5-1-3-7-27(23)37-33)31(35(25)41)32-30-24-6-2-4-8-28(24)38-34(30)26(36(32)42)18-20-11-15-22(40)16-12-20/h1-18,39-40H/b25-17+,26-18+
InChIKey CGZKSPLDUIRCIO-RPCRKUJJSA-N
SMILES C1(C2=C3C(=NC4=C3C=CC=C4)\C(\C2=O)=C/C5=CC=C(C=C5)O)=C6C(=NC7=C6C=CC=C7)\C(\C1=O)=C/C8=CC=C(C=C8)O
Metabolite of Species Details
Scytonema sp. (NCBI:txid1542952) of strain R77DM See: PubMed
Lyngbya (NCBI:txid28073) of strain CU2555 See: PubMed
Roles Classification
Chemical Role(s): ultraviolet filter
A photochemical role realized in the absorption of ultraviolet light, for example to protect skin cells from damage.
Biological Role(s): biological pigment
An endogenous molecular entity that results in a colour of an organism as the consequence of the selective absorption of light.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
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ChEBI Ontology
Outgoing scytonemin (CHEBI:90127) has role bacterial metabolite (CHEBI:76969)
scytonemin (CHEBI:90127) has role biological pigment (CHEBI:26130)
scytonemin (CHEBI:90127) has role ultraviolet filter (CHEBI:73335)
scytonemin (CHEBI:90127) is a enone (CHEBI:51689)
scytonemin (CHEBI:90127) is a organic heterotricyclic compound (CHEBI:26979)
scytonemin (CHEBI:90127) is a organonitrogen heterocyclic compound (CHEBI:38101)
scytonemin (CHEBI:90127) is a polyphenol (CHEBI:26195)
scytonemin (CHEBI:90127) is a ring assembly (CHEBI:36820)
IUPAC Name
(3E,3'E)-3,3'-bis[(4-hydroxyphenyl)methylidene][1,1'-bicyclopenta[b]indole]-2,2'(3H,3'H)-dione
Manual Xrefs Databases
C00045068 KNApSAcK
Scytonemin Wikipedia
View more database links
Registry Numbers Types Sources
152075-98-4 CAS Registry Number ChemIDplus
22043325 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
21501195 PubMed citation Europe PMC
22688245 PubMed citation Europe PMC
24111939 PubMed citation Europe PMC
25056905 PubMed citation Europe PMC
25226055 PubMed citation Europe PMC
25368346 PubMed citation Europe PMC
26013282 PubMed citation Europe PMC
26452010 PubMed citation Europe PMC
8405307 PubMed citation Europe PMC
Last Modified
28 October 2015