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ChEBI
> Main
CHEBI:167548 - ophiobolin C
Main
ChEBI Ontology
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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
Download
Molfile
XML
SDF
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Molfile
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
(7
E
)-3-hydroxy-5-oxoophiobola-7,19-dien-25-al
Synonyms
Sources
(1
R
,3
S
,4
R
,7
S
,8
E
,11
S
,12
R
)-
4-
hydroxy-
1,4-
dimethyl-
12-
[(2
S
)-
6-
methylhept-
5-
en-
2-
yl]-
6-
oxotricyclo[9.3.0.0
3,7
]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
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