CHEBI:156219 - ascochlorin

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ChEBI Name ascochlorin
ChEBI ID CHEBI:156219
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C23H29ClO4
Net Charge 0
Average Mass 404.930
Monoisotopic Mass 404.17544
InChI InChI=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
InChIKey SETVRSKZJJWOPA-FLDGXQSCSA-N
SMILES C1(=C(C(=C(C(=C1Cl)C)C([H])=O)O)C/C=C(/C=C/[C@@]2([C@H](C(=O)CC[C@H]2C)C)C)\C)O
Metabolite of Species Details
Ascochyta viciae (NCBI:txid1677696) See: PubMed
Acremonium egyptiacum (NCBI:txid749675) See: DOI
Nigrosabulum globosum (NCBI:txid95328) See: PubMed
Roles Classification
Biological Role(s): 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.
(via meroterpenoid )
Application(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 Sources
(−)-ascochlorin ChEBI
antibiotic LL-Z1272 gamma ChemIDplus
antibiotic LL-Z1272γ ChEBI
ilicicolin D ChemIDplus
LL-Z 1272 gamma ChemIDplus
Manual Xrefs Databases
3H1 PDBeChem
C00018754 KNApSAcK
View more database links
Registry Number Type Source
26166-39-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11029223 PubMed citation Europe PMC
11374942 PubMed citation Europe PMC
19253369 PubMed citation Europe PMC
20025846 PubMed citation Europe PMC
20558137 PubMed citation Europe PMC
21947785 PubMed citation Europe PMC
22109717 PubMed citation Europe PMC
25624051 PubMed citation Europe PMC
28427561 PubMed citation Europe PMC
28569433 PubMed citation Europe PMC
28833404 PubMed citation Europe PMC
30900461 PubMed citation Europe PMC
30952781 PubMed citation Europe PMC
31028855 PubMed citation Europe PMC
Last Modified
21 July 2020