CHEBI:167548 - ophiobolin C

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ChEBI Name ophiobolin C
ChEBI ID CHEBI:167548
Definition A sesterterpenoid that is ophiobolane with a hydroxy group at position 3, oxo group at positions 5, formyl group at position 7, and double bonds at positions 7-8 and 19-20.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
Supplier Information
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Formula C25H38O3
Net Charge 0
Average Mass 386.576
Monoisotopic Mass 386.28210
InChI InChI=1S/C25H38O3/c1-16(2)7-6-8-17(3)19-11-12-24(4)13-21-23(22(27)14-25(21,5)28)18(15-26)9-10-20(19)24/h7,9,15,17,19-21,23,28H,6,8,10-14H2,1-5H3/b18-9-/t17-,19+,20-,21-,23+,24+,25+/m0/s1
InChIKey PLWMYIADTRHIMY-BNFAVABNSA-N
SMILES [H]C(=O)C1=C/C[C@@]2([H])[C@]([H])(CC[C@]2(C)C[C@@]2([H])[C@]\1([H])C(=O)C[C@@]2(C)O)[C@@H](C)CCC=C(C)C
Metabolite of Species Details
Mollisia sp. (NCBI:txid1928189) See: PubMed
Aspergillus ustus (NCBI:txid40382) See: PubMed
Cochliobolus heterostrophus (NCBI:txid5016) See: PubMed
Roles Classification
Biological Role(s): apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Aspergillus metabolite
Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
chemokine receptor 5 antagonist
An antogonist that blocks chemokine receptor 5 (CCR5).
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
nematicide
A substance used to destroy pests of the phylum Nematoda (roundworms).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ophiobolin C (CHEBI:167548) has parent hydride ophiobolane (CHEBI:36552)
ophiobolin C (CHEBI:167548) has role Aspergillus metabolite (CHEBI:76956)
ophiobolin C (CHEBI:167548) has role antineoplastic agent (CHEBI:35610)
ophiobolin C (CHEBI:167548) has role apoptosis inducer (CHEBI:68495)
ophiobolin C (CHEBI:167548) has role chemokine receptor 5 antagonist (CHEBI:63673)
ophiobolin C (CHEBI:167548) has role fungal metabolite (CHEBI:76946)
ophiobolin C (CHEBI:167548) has role nematicide (CHEBI:25491)
ophiobolin C (CHEBI:167548) is a carbotricyclic compound (CHEBI:38032)
ophiobolin C (CHEBI:167548) is a cyclic ketone (CHEBI:3992)
ophiobolin C (CHEBI:167548) is a enal (CHEBI:51688)
ophiobolin C (CHEBI:167548) is a olefinic compound (CHEBI:78840)
ophiobolin C (CHEBI:167548) is a sesterterpenoid (CHEBI:26660)
ophiobolin C (CHEBI:167548) is a tertiary alcohol (CHEBI:26878)
IUPAC Name
(7E)-3-hydroxy-5-oxoophiobola-7,19-dien-25-al
Synonyms Sources
(1R,3S,4R,7S,8E,11S,12R)-4-hydroxy-1,4-dimethyl-12-[(2S)-6-methylhept-5-en-2-yl]-6-oxotricyclo[9.3.0.03,7]tetradec-8-ene-8-carbaldehyde IUPAC
3-hydroxy-5-oxo-ophiobola-7,19-dien-25-al ChemIDplus
ophiobolin C UniProt
Registry Number Type Source
19022-51-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
15217290 PubMed citation Europe PMC
24287995 PubMed citation Europe PMC
27116000 PubMed citation SUBMITTER
8735840 PubMed citation Europe PMC
Last Modified
24 February 2021