EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:156219 - ascochlorin

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
Nigrosabulum globosum (ncbitaxon:95328) - PubMed (11374942)
Ascochyta viciae (ncbitaxon:1677696) - PubMed (31028855)
Acremonium egyptiacum (ncbitaxon:749675) - DOI (10.1073/pnas.1819254116)
Roles Classification
Biological Roles:
antiprotozoal drug  Any antimicrobial drug which is used to treat or prevent protozoal infections.
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.
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.
antiprotozoal drug  Any antimicrobial drug which is used to treat or prevent protozoal infections.
angiogenesis inhibitor  An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
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
LL-Z 1272 gammaChemIDplus
ilicicolin DChemIDplus
antibiotic LL-Z1272 gammaChemIDplus
(−)-ascochlorinChEBI
antibiotic LL-Z1272γChEBI
Manual XrefsDatabases
C00018754KNApSAcK
3H1PDBeChem
Registry NumbersSources
CAS:26166-39-2ChemIDplus
Citations