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ChEBI
> Main
CHEBI:66326 - 20-hydroxytubocapsanolide A
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ChEBI Name
20-hydroxytubocapsanolide A
ChEBI ID
CHEBI:66326
Definition
A withanolide that is the 20-hydroxy derivative of tubocapsanolide A. Isolated from
Tubocapsicum anomalum
, it exhibits cytotoxic activity.
Stars
This entity has been manually annotated by the ChEBI Team.
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Formula
C28H36O7
Net Charge
0
Average Mass
484.58120
Monoisotopic Mass
484.24610
InChI
InChI=1S/C28H36O7/c1-
13-
10-
20(33-
23(31)
14(13)
2)
26(5,32)
28-
22(35-
28)
12-
17-
15-
11-
21-
27(34-
21)
19(30)
7-
6-
18(29)
25(27,4)
16(15)
8-
9-
24(17,28)
3/h6-
7,15-
17,19-
22,30,32H,8-
12H2,1-
5H3/t15-
,16+,17+,19+,20-
,21-
,22-
,24+,25+,26+,27-
,28-
/m1/s1
InChIKey
ONOYEGAYNUISOH-QTRSZHGFSA-N
SMILES
CC1=C(C)
C(=O)
O[C@H]
(C1)
[C@]
(C)
(O)
[C@@]
12O[C@@H]
1C[C@H]
1[C@@H]
3C[C@H]
4O[C@]
44[C@@H]
(O)
C=CC(=O)
[C@]
4(C)
[C@H]
3CC[C@]
21C
Metabolite of Species
Details
Tubocapsicum anomalum
(NCBI:txid180580)
See:
PubMed
Roles Classification
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.
(via
withanolide
)
Application
(s):
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
20-hydroxytubocapsanolide A (
CHEBI:66326
)
has functional parent
tubocapsanolide A (
CHEBI:66325
)
20-hydroxytubocapsanolide A (
CHEBI:66326
)
has role
antineoplastic agent (
CHEBI:35610
)
20-hydroxytubocapsanolide A (
CHEBI:66326
)
is a
δ-lactone (
CHEBI:18946
)
20-hydroxytubocapsanolide A (
CHEBI:66326
)
is a
20-hydroxy steroid (
CHEBI:36854
)
20-hydroxytubocapsanolide A (
CHEBI:66326
)
is a
4-hydroxy steroid (
CHEBI:62846
)
20-hydroxytubocapsanolide A (
CHEBI:66326
)
is a
enone (
CHEBI:51689
)
20-hydroxytubocapsanolide A (
CHEBI:66326
)
is a
epoxy steroid (
CHEBI:145217
)
20-hydroxytubocapsanolide A (
CHEBI:66326
)
is a
ergostanoid (
CHEBI:50403
)
20-hydroxytubocapsanolide A (
CHEBI:66326
)
is a
secondary alcohol (
CHEBI:35681
)
20-hydroxytubocapsanolide A (
CHEBI:66326
)
is a
tertiary alcohol (
CHEBI:26878
)
20-hydroxytubocapsanolide A (
CHEBI:66326
)
is a
withanolide (
CHEBI:74716
)
IUPAC Name
(4β,5β,6β,16α,17α)-
17-
{(1
S
)-
1-
[(2
R
)-
4,5-
dimethyl-
6-
oxo-
3,6-
dihydro-
2
H
-
pyran-
2-
yl]-
1-
hydroxyethyl}-
4-
hydroxy-
5,6:16,17-
diepoxyandrost-
2-
en-
1-
one
Synonym
Source
5β,6β:16α,17α-diepoxy-4β,20-dihydroxy-1-oxo-witha-2,24-dienolide
ChEBI
Registry Number
Type
Source
11130281
Reaxys Registry Number
Reaxys
Citation
Type
Source
17417907
PubMed citation
Europe PMC
Last Modified
29 October 2019