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> Main
CHEBI:66636 - 14-norpseurotin A
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ChEBI Ontology
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ChEBI Name
14-norpseurotin A
ChEBI ID
CHEBI:66636
Definition
An alkaloid that is the 14-nor derivative of pseurotin A. Isolated from
Aspergillus sydowii
, it exhibits antibacterial, antileishmanial and anticancer activities.
Stars
This entity has been manually annotated by the ChEBI Team.
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Formula
C21H23NO8
Net Charge
0
Average Mass
417.40920
Monoisotopic Mass
417.14237
InChI
InChI=1S/C21H23NO8/c1-
4-
8-
13(23)
14(24)
15-
11(2)
16(25)
20(30-
15)
18(27)
21(29-
3,22-
19(20)
28)
17(26)
12-
9-
6-
5-
7-
10-
12/h4-
10,13-
14,18,23-
24,27H,1-
3H3,(H,22,28)
/b8-
4-
/t13-
,14-
,18+,20+,21+/m0/s1
InChIKey
FCGCMRDADMTJIM-LFDIKFNASA-N
SMILES
CO[C@]1(NC(=O)[C@]2(OC([C@@H](O)[C@@H](O)\C=C/C)=C(C)C2=O)[C@H]1O)C(=O)c1ccccc1
Metabolite of Species
Details
Aspergillus sydowii
(NCBI:txid75750)
of strain PFW1-13 See:
PubMed
Roles Classification
Biological Role
(s):
antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
antileishmanial agent
An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus
Leishmania
.
Aspergillus metabolite
Any fungal metabolite produced during a metabolic reaction in the mould,
Aspergillus
.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via
alkaloid
)
Application
(s):
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
antileishmanial agent
An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus
Leishmania
.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
14-norpseurotin A (
CHEBI:66636
)
has functional parent
pseurotin A (
CHEBI:64535
)
14-norpseurotin A (
CHEBI:66636
)
has role
Aspergillus
metabolite (
CHEBI:76956
)
14-norpseurotin A (
CHEBI:66636
)
has role
antibacterial agent (
CHEBI:33282
)
14-norpseurotin A (
CHEBI:66636
)
has role
antileishmanial agent (
CHEBI:70868
)
14-norpseurotin A (
CHEBI:66636
)
has role
antineoplastic agent (
CHEBI:35610
)
14-norpseurotin A (
CHEBI:66636
)
is a
alkaloid (
CHEBI:22315
)
14-norpseurotin A (
CHEBI:66636
)
is a
azaspiro compound (
CHEBI:35624
)
14-norpseurotin A (
CHEBI:66636
)
is a
lactam (
CHEBI:24995
)
14-norpseurotin A (
CHEBI:66636
)
is a
oxaspiro compound (
CHEBI:37948
)
14-norpseurotin A (
CHEBI:66636
)
is a
secondary alcohol (
CHEBI:35681
)
IUPAC Name
(5
S
,8
S
,9
R
)-
8-
benzoyl-
2-
[(1
S
,2
S
,3
Z
)-
1,2-
dihydroxypent-
3-
en-
1-
yl]-
9-
hydroxy-
8-
methoxy-
3-
methyl-
1-
oxa-
7-
azaspiro[4.4]non-
2-
ene-
4,6-
dione
Manual Xref
Database
23329509
ChemSpider
View more database links
Registry Number
Type
Source
18842462
Reaxys Registry Number
Reaxys
Citations
Types
Sources
18505285
PubMed citation
Europe PMC
22474943
PubMed citation
Europe PMC
Last Modified
27 October 2016