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CHEBI:167548 - ophiobolin C

ChEBI IDCHEBI:167548
ChEBI Nameophiobolin C
Stars
DefinitionA 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.
Last Modified24 February 2021
SubmitterKristian Axelsen
DownloadsMolfile
FormulaC25H38O3
Net Charge0
Average Mass386.576
Monoisotopic Mass386.28210
SMILES[H]C(=O)/C1=C/C[C@]2([H])[C@](C)(CC[C@]2([H])[C@@H](C)CCC=C(C)C)C[C@]2([H])[C@](C)(O)CC(=O)[C@]12[H]
InChIInChI=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
InChIKeyPLWMYIADTRHIMY-BNFAVABNSA-N
Species of MetaboliteComponentSourceComments
Aspergillus ustus (ncbitaxon:40382) - PubMed (24287995)
Mollisia sp. (ncbitaxon:1928189) - PubMed (15217290)
Cochliobolus heterostrophus (ncbitaxon:5016) - PubMed (8735840)
Roles Classification
Biological Roles:
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 .
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
chemokine receptor 5 antagonist  An antogonist that blocks chemokine receptor 5 (CCR5).
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
nematicide  A substance used to destroy pests of the phylum Nematoda (roundworms).
ChEBI Ontology
Outgoing Relation(s)
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  Source
3-hydroxy-5-oxo-ophiobola-7,19-dien-25-alChemIDplus
(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-carbaldehydeIUPAC
UniProt Name  Source
ophiobolin CUniProt
Registry NumbersSources
CAS:19022-51-6ChemIDplus
Citations