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> Main
CHEBI:67583 - breynceanothanolic acid
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ChEBI Name
breynceanothanolic acid
ChEBI ID
CHEBI:67583
Definition
A triterpenoid of the nor-ceanothane-type isolated from the roots of
Breynia fruticosa
and has been shown to exhibit cytotoxicity against human cancer cell lines.
Stars
This entity has been manually annotated by the ChEBI Team.
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Formula
C29H40O5
Net Charge
0
Average Mass
468.62490
Monoisotopic Mass
468.28757
InChI
InChI=1S/C29H40O5/c1-
16(2)
18-
7-
9-
25(21(30)
31)
12-
13-
26-
19(20(18)
25)
8-
10-
28(33-
22(26)
32)
24(26,6)
11-
14-
27-
23(4,5)
15-
17(3)
29(27,28)
34-
27/h17-
20H,1,7-
15H2,2-
6H3,(H,30,31)
/t17-
,18-
,19+,20+,24-
,25-
,26+,27+,28+,29-
/m0/s1
InChIKey
SNCMVKNGLNUISS-GCWSBASFSA-N
SMILES
C[C@H]
1CC(C)
(C)
[C@]
23CC[C@]
4(C)
[C@]
5(CC[C@@H]
6[C@H]
7[C@@H]
(CC[C@@]
7(CC[C@@]
46C(=O)
O5)
C(O)
=O)
C(C)
=C)
[C@]
12O3
Metabolite of Species
Details
Breynia fruticosa
(NCBI:txid296042)
Found in root
(BTO:0001188)
. 90% Methanolic extract of air-dried, crushed roots See:
PubMed
Roles Classification
Chemical Role
(s):
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Br
o
nsted base).
(via
oxoacid
)
Biological Role
(s):
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application
(s):
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
breynceanothanolic acid (
CHEBI:67583
)
has role
antineoplastic agent (
CHEBI:35610
)
breynceanothanolic acid (
CHEBI:67583
)
has role
plant metabolite (
CHEBI:76924
)
breynceanothanolic acid (
CHEBI:67583
)
is a
epoxide (
CHEBI:32955
)
breynceanothanolic acid (
CHEBI:67583
)
is a
monocarboxylic acid (
CHEBI:25384
)
breynceanothanolic acid (
CHEBI:67583
)
is a
organic heteroheptacyclic compound (
CHEBI:52157
)
breynceanothanolic acid (
CHEBI:67583
)
is a
terpene lactone (
CHEBI:37668
)
breynceanothanolic acid (
CHEBI:67583
)
is a
triterpenoid (
CHEBI:36615
)
IUPAC Name
(1
S
,3a
R
,5a
S
,5b
S
,7a
S
,10
R
,10a
R
,10b
R
,12a
R
,12b
S
)-
1,3,3,5a-
tetramethyl-
15-
oxo-
10-
(prop-
1-
en-
2-
yl)dodecahydro-
1
H
,4
H
-
3a,12b-
epoxy-
12a,5b-
(epoxymethano)dicyclopenta[
a,i
]phenanthrene-
7a(8
H
)-
carboxylic acid
Synonym
Source
5α,10α-
epoxy-
9α,27α-
lactone-
25(10→2α)abeo-
A(1)-
norlup-
20(29)-
en-
28-
oic acid
ChEBI
Registry Number
Type
Source
21553370
Reaxys Registry Number
Reaxys
Citation
Type
Source
21428418
PubMed citation
Europe PMC
Last Modified
09 January 2014