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CHEBI:156219 - ascochlorin

Default Structure
ChEBI IDCHEBI:156219
ChEBI Nameascochlorin
Stars
DefinitionA dihydroxybenzaldehyde that is 2,4-dihydroxybenzaldehyde which is substituted by a (1E,3E)-3-methyl-1-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-1,3-dien-5-yl group at position 3, chlorine at position 5, and a methyl group at position 6. A meroterpenoid produced by several fungi including Ascochyta viciae . It exhibits anticancer, antifungal and antiprotozoal activities.
Last Modified21 July 2020
SubmitterAdnan
DownloadsMolfile
FormulaC23H29ClO4
Net Charge0
Average Mass404.934
Monoisotopic Mass404.17544
SMILES[H]C(=O)c1c(C)c(Cl)c(O)c(C/C=C(C)/C=C/[C@@]2(C)[C@H](C)CCC(=O)[C@@H]2C)c1O
InChIInChI=1S/C23H29ClO4/c1-13(10-11-23(5)14(2)7-9-19(26)16(23)4)6-8-17-21(27)18(12-25)15(3)20(24)22(17)28/h6,10-12,14,16,27-28H,7-9H2,1-5H3/b11-10+,13-6+/t14-,16+,23+/m1/s1
InChIKeySETVRSKZJJWOPA-FLDGXQSCSA-N
Species of MetaboliteComponentSourceComments
Acremonium egyptiacum (ncbitaxon:749675) - DOI (10.1073/pnas.1819254116)
Ascochyta viciae (ncbitaxon:1677696) - PubMed (31028855)
Nigrosabulum globosum (ncbitaxon:95328) - PubMed (11374942)
Roles Classification
Biological Roles:
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
antiprotozoal drug  Any antimicrobial drug which is used to treat or prevent protozoal infections.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
angiogenesis inhibitor  An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
antiprotozoal drug  Any antimicrobial drug which is used to treat or prevent protozoal infections.
ChEBI Ontology
Outgoing Relation(s)
ascochlorin (CHEBI:156219) has role angiogenesis inhibitor (CHEBI:48422)
ascochlorin (CHEBI:156219) has role antifungal agent (CHEBI:35718)
ascochlorin (CHEBI:156219) has role antineoplastic agent (CHEBI:35610)
ascochlorin (CHEBI:156219) has role antiprotozoal drug (CHEBI:35820)
ascochlorin (CHEBI:156219) has role fungal metabolite (CHEBI:76946)
ascochlorin (CHEBI:156219) is a cyclohexanones (CHEBI:23482)
ascochlorin (CHEBI:156219) is a dihydroxybenzaldehyde (CHEBI:50196)
ascochlorin (CHEBI:156219) is a meroterpenoid (CHEBI:64419)
ascochlorin (CHEBI:156219) is a monochlorobenzenes (CHEBI:83403)
ascochlorin (CHEBI:156219) is a olefinic compound (CHEBI:78840)
ascochlorin (CHEBI:156219) is a resorcinols (CHEBI:33572)
ascochlorin (CHEBI:156219) is a sesquiterpenoid (CHEBI:26658)
ascochlorin (CHEBI:156219) is conjugate acid of ascochlorin(1−) (CHEBI:146157)
Incoming Relation(s)
ascochlorin(1−) (CHEBI:146157) is conjugate base of ascochlorin (CHEBI:156219)
IUPAC Name 
3-chloro-4,6-dihydroxy-2-methyl-5-{(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dien-1-yl}benzaldehyde
Synonyms  Source
antibiotic LL-Z1272 gammaChemIDplus
antibiotic LL-Z1272γChEBI
(−)-ascochlorinChEBI
ilicicolin DChemIDplus
LL-Z 1272 gammaChemIDplus
Manual XrefsDatabases
3H1PDBeChem
C00018754KNApSAcK
Registry NumbersSources
CAS:26166-39-2ChemIDplus
Citations