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InChI=1S/CH4O/c1-2/h2H,1H3
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ChEBI
> Main
CHEBI:69108 - withalongolide C
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ChEBI Ontology
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ChEBI Name
withalongolide C
ChEBI ID
CHEBI:69108
Definition
A withanolide that is withaferin A substituted by a hydroxy group at position 11. Isolated from
Physalis longifolia
, it exhibits antineoplastic activity.
Stars
This entity has been manually annotated by the ChEBI Team.
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Formula
C28H38O7
Net Charge
0
Average Mass
486.59710
Monoisotopic Mass
486.26175
InChI
InChI=1S/C28H38O7/c1-
13-
9-
20(34-
25(33)
16(13)
12-
29)
14(2)
17-
5-
6-
18-
15-
10-
23-
28(35-
23)
22(32)
8-
7-
21(31)
27(28,4)
24(15)
19(30)
11-
26(17,18)
3/h7-
8,14-
15,17-
20,22-
24,29-
30,32H,5-
6,9-
12H2,1-
4H3/t14-
,15-
,17+,18-
,19-
,20+,22-
,23+,24+,26+,27+,28+/m0/s1
InChIKey
UPRPPTFVJBNIPP-VAPFTTHESA-N
SMILES
C[C@@H]
([C@H]
1CC[C@H]
2[C@@H]
3C[C@H]
4O[C@]
44[C@@H]
(O)
C=CC(=O)
[C@]
4(C)
[C@H]
3[C@@H]
(O)
C[C@]
12C)
[C@H]
1CC(C)
=C(CO)
C(=O)
O1
Metabolite of Species
Details
Physalis longifolia
(NCBI:txid161495)
Found in aerial part
(BTO:0001658)
. CH2Cl2-MeOH(1:1) extract of the air-dried aerial parts See:
PubMed
Roles Classification
Biological Role
(s):
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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
withalongolide C (
CHEBI:69108
)
has functional parent
withaferin A (
CHEBI:69120
)
withalongolide C (
CHEBI:69108
)
has role
antineoplastic agent (
CHEBI:35610
)
withalongolide C (
CHEBI:69108
)
has role
metabolite (
CHEBI:25212
)
withalongolide C (
CHEBI:69108
)
has role
plant metabolite (
CHEBI:76924
)
withalongolide C (
CHEBI:69108
)
is a
δ-lactone (
CHEBI:18946
)
withalongolide C (
CHEBI:69108
)
is a
11β-hydroxy steroid (
CHEBI:35346
)
withalongolide C (
CHEBI:69108
)
is a
27-hydroxy steroid (
CHEBI:37914
)
withalongolide C (
CHEBI:69108
)
is a
4-hydroxy steroid (
CHEBI:62846
)
withalongolide C (
CHEBI:69108
)
is a
enone (
CHEBI:51689
)
withalongolide C (
CHEBI:69108
)
is a
epoxy steroid (
CHEBI:145217
)
withalongolide C (
CHEBI:69108
)
is a
ergostanoid (
CHEBI:50403
)
withalongolide C (
CHEBI:69108
)
is a
primary alcohol (
CHEBI:15734
)
withalongolide C (
CHEBI:69108
)
is a
secondary alcohol (
CHEBI:35681
)
withalongolide C (
CHEBI:69108
)
is a
withanolide (
CHEBI:74716
)
IUPAC Name
(4β,5β,6β,11β,22
R
)-
4,11,27-
trihydroxy-
5,6:22,26-
diepoxyergosta-
2,24-
diene-
1,26-
dione
Synonym
Source
11β-hydroxywithaferin A
ChEBI
Registry Number
Type
Source
22217709
Reaxys Registry Number
Reaxys
Citation
Type
Source
22098611
PubMed citation
Europe PMC
Last Modified
29 October 2019