CHEBI:2448 - actinorhodin

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ChEBI Name actinorhodin
ChEBI ID CHEBI:2448
Definition A member of the class of benzoisochromanequinone that is produced by Streptomyces coelicolor A3(2) and exhibits antibiotic activity.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C32H26O14
Net Charge 0
Average Mass 634.54044
Monoisotopic Mass 634.132
InChI InChI=1S/C32H26O14/c1-9-21-15(3-11(45-9)5-19(35)36)29(41)23-17(33)7-13(27(39)25(23)31(21)43)14-8-18(34)24-26(28(14)40)32(44)22-10(2)46-12(6-20(37)38)4-16(22)30(24)42/h7-12,41-44H,3-6H2,1-2H3,(H,35,36)(H,37,38)/t9-,10-,11+,12+/m1/s1
InChIKey FXTIILIJTTYSLT-WYUUTHIRSA-N
SMILES C[C@H]1O[C@H](CC(O)=O)Cc2c(O)c3C(=O)C=C(C(=O)c3c(O)c12)C1=CC(=O)c2c(O)c3C[C@@H](CC(O)=O)O[C@H](C)c3c(O)c2C1=O
Metabolite of Species Details
Streptomyces coelicolor A3(2) (NCBI:100226) 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): bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via heterocyclic antibiotic )
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ChEBI Ontology
Outgoing actinorhodin (CHEBI:2448) has role antimicrobial agent (CHEBI:33281)
actinorhodin (CHEBI:2448) has role bacterial metabolite (CHEBI:76969)
actinorhodin (CHEBI:2448) is a p-quinones (CHEBI:25830)
actinorhodin (CHEBI:2448) is a benzoisochromanequinone (CHEBI:48129)
actinorhodin (CHEBI:2448) is a dicarboxylic acid (CHEBI:35692)
actinorhodin (CHEBI:2448) is a polyketide (CHEBI:26188)
actinorhodin (CHEBI:2448) is a polyphenol (CHEBI:26195)
actinorhodin (CHEBI:2448) is a ring assembly (CHEBI:36820)
actinorhodin (CHEBI:2448) is conjugate acid of actinorhodin(3−) (CHEBI:91020)
Incoming actinorhodin(3−) (CHEBI:91020) is conjugate base of actinorhodin (CHEBI:2448)
IUPAC Name
2,2'-[(1R,1'R,3S,3'S)-5,5',10,10'-tetrahydroxy-1,1'-dimethyl-6,6',9,9'-tetraoxo[3,3',4,4',6,6',9,9'-octahydro-1H,1'H-8,8'-binaphtho[2,3-c]pyran]-3,3'-diyl]diacetic acid
Synonyms Sources
Actinorhodin ChemIDplus
Actinorhodin KEGG COMPOUND
Actinorhodine KEGG COMPOUND
Database Links Databases
Actinorhodin Wikipedia
C06691 KEGG COMPOUND
CPD1A0-6123 MetaCyc
ZCT PDBeChem
View more database links
Registry Numbers Types Sources
1397-77-9 CAS Registry Number ChemIDplus
22788170 Reaxys Registry Number Reaxys
76401 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
15054568 PubMed citation Europe PMC
17579485 PubMed citation Europe PMC
24240146 PubMed citation Europe PMC
24963940 PubMed citation Europe PMC
Last Modified
06 June 2016