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> Main
CHEBI:77692 - peloruside A
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ChEBI Ontology
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ChEBI Name
peloruside A
ChEBI ID
CHEBI:77692
Definition
A macrolide that is a novel secondary metabolite isolated from a New Zealand marine sponge,
Mycale hentscheli
.
Stars
This entity has been manually annotated by the ChEBI Team.
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Formula
C27H48O11
Net Charge
0
Average Mass
548.66340
Monoisotopic Mass
548.31966
InChI
InChI=1S/C27H48O11/c1-
8-
16(14-
28)
9-
15(2)
19-
10-
17(34-
5)
13-
22(29)
26(3,4)
27(33)
24(31)
21(36-
7)
12-
18(38-
27)
11-
20(35-
6)
23(30)
25(32)
37-
19/h9,16-
24,28-
31,33H,8,10-
14H2,1-
7H3/b15-
9-
/t16-
,17-
,18+,19+,20-
,21-
,22+,23+,24-
,27+/m0/s1
InChIKey
NETARJWZTMGMRM-JRTPPQMASA-N
SMILES
CC[C@H]
(CO)
\C=C(\C)
[C@H]
1C[C@@H]
(C[C@@H]
(O)
C(C)
(C)
[C@]
2(O)
O[C@@H]
(C[C@H]
(OC)
[C@@H]
2O)
C[C@H]
(OC)
[C@@H]
(O)
C(=O)
O1)
OC
Roles Classification
Biological Role
(s):
marine metabolite
Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
antimitotic
Any compound that inhibits cell division (mitosis).
microtubule-stabilising agent
Any substance that interacts with tubulin to promote polymerisation of microtubules.
Application
(s):
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
peloruside A (
CHEBI:77692
)
has role
antimitotic (
CHEBI:64911
)
peloruside A (
CHEBI:77692
)
has role
antineoplastic agent (
CHEBI:35610
)
peloruside A (
CHEBI:77692
)
has role
marine metabolite (
CHEBI:76507
)
peloruside A (
CHEBI:77692
)
has role
microtubule-stabilising agent (
CHEBI:61950
)
peloruside A (
CHEBI:77692
)
is a
cyclic hemiketal (
CHEBI:59780
)
peloruside A (
CHEBI:77692
)
is a
ether (
CHEBI:25698
)
peloruside A (
CHEBI:77692
)
is a
macrolide (
CHEBI:25106
)
peloruside A (
CHEBI:77692
)
is a
organic heterobicyclic compound (
CHEBI:27171
)
peloruside A (
CHEBI:77692
)
is a
primary alcohol (
CHEBI:15734
)
peloruside A (
CHEBI:77692
)
is a
secondary alcohol (
CHEBI:35681
)
IUPAC Name
(1
S
,3
S
,4
R
,7
R
,9
R
,11
R
,13
S
,14
S
,15
S
)-
4,11,13,14-
tetrahydroxy-
7-
[(2
Z
,4
S
)-
4-
(hydroxymethyl)hex-
2-
en-
2-
yl]-
3,9,15-
trimethoxy-
12,12-
dimethyl-
6,17-
dioxabicyclo[11.3.1]heptadecan-
5-
one
Synonym
Source
(−)-peloruside A
ChEBI
Registry Number
Type
Source
14282578
Reaxys Registry Number
Reaxys
Citations
Types
Sources
12067973
PubMed citation
Europe PMC
20107863
PubMed citation
Europe PMC
20862516
PubMed citation
Europe PMC
21926482
PubMed citation
Europe PMC
22180309
PubMed citation
Europe PMC
22326528
PubMed citation
Europe PMC
22584948
PubMed citation
Europe PMC
22594877
PubMed citation
Europe PMC
24056987
PubMed citation
Europe PMC
24060965
PubMed citation
Europe PMC
24156744
PubMed citation
Europe PMC
24245693
PubMed citation
Europe PMC
24470331
PubMed citation
Europe PMC
Last Modified
30 September 2015