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CHEBI:156301 - auricin

ChEBI IDCHEBI:156301
ChEBI Nameauricin
Stars
DefinitionAn angucycline-like polyketide discovered in Streptomyces aureofaciens that is only stable at acidic pH.
Last Modified14 April 2021
SubmitterMartin Larralde
DownloadsMolfile
FormulaC28H31NO10
Net Charge0
Average Mass541.553
Monoisotopic Mass541.19480
SMILES[H][C@@]12CC(=O)O[C@]1([H])C1=C(C(=O)c3c(O)cccc3C1=O)[C@]1(O[C@H](C)CC(=O)[C@H]1OC1CCC(N(C)C)C(C)O1)O2
InChIInChI=1S/C28H31NO10/c1-12-10-17(31)27(37-20-9-8-15(29(3)4)13(2)35-20)28(38-12)23-22(26-18(39-28)11-19(32)36-26)24(33)14-6-5-7-16(30)21(14)25(23)34/h5-7,12-13,15,18,20,26-27,30H,8-11H2,1-4H3/t12-,13?,15?,18-,20?,26+,27-,28+/m1/s1
InChIKeyDIESPMSGQPRWLG-VLKAYIDRSA-N
Species of MetaboliteComponentSourceComments
Streptomyces lavendulae subsp. lavendulae (ncbitaxon:58340) - PubMed (23373695) The strain was formerly known as Streptomyces aureofaciens CCM 3239. See PMID:29496832. Strain: CCM 3239
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
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.
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
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.
ChEBI Ontology
Outgoing Relation(s)
auricin (CHEBI:156301) has role bacterial metabolite (CHEBI:76969)
auricin (CHEBI:156301) is a 1,4-benzoquinones (CHEBI:132124)
auricin (CHEBI:156301) is a angucycline antibiotic (CHEBI:70737)
auricin (CHEBI:156301) is a benzoisochromanequinone (CHEBI:48129)
auricin (CHEBI:156301) is a organic heteropentacyclic compound (CHEBI:38164)
auricin (CHEBI:156301) is a oxanes (CHEBI:46942)
auricin (CHEBI:156301) is a phenols (CHEBI:33853)
auricin (CHEBI:156301) is a polyketide (CHEBI:26188)
auricin (CHEBI:156301) is a tertiary amino compound (CHEBI:50996)
auricin (CHEBI:156301) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(2'S,3'R,3aR,6'R,11bR)-3'-{[5-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl]oxy}-7-hydroxy-6'-methyl-3a,5',6',11b-tetrahydrospiro[benzo[g]furo[3,2-c]isochromene-5,2'-pyran]-2,4',6,11(3H,3'H)-tetrone
Citations