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> Main
CHEBI:71676 - esculeogenin A
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ChEBI Name
esculeogenin A
ChEBI ID
CHEBI:71676
Definition
A sapogenin that is spirosolane substituted by hydroxy groups at positions 3, 23 and 27 (the 3β,5α,22α,23
S
,25
S
stereoisomer).
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This entity has been manually annotated by the ChEBI Team.
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Formula
C27H45NO4
Net Charge
0
Average Mass
447.65050
Monoisotopic Mass
447.33486
InChI
InChI=1S/C27H45NO4/c1-
15-
24-
22(32-
27(15)
23(31)
10-
16(14-
29)
13-
28-
27)
12-
21-
19-
5-
4-
17-
11-
18(30)
6-
8-
25(17,2)
20(19)
7-
9-
26(21,24)
3/h15-
24,28-
31H,4-
14H2,1-
3H3/t15-
,16-
,17-
,18-
,19+,20-
,21-
,22-
,23-
,24-
,25-
,26-
,27-
/m0/s1
InChIKey
FBKQAVWTYDQPAB-HBDLFPIVSA-N
SMILES
[H]
[C@@]
12CC[C@]
3([H]
)
[C@]
([H]
)
(CC[C@@]
4(C)
[C@@]
3([H]
)
C[C@]
3([H]
)
O[C@@]
5(NC[C@@H]
(CO)
C[C@@H]
5O)
[C@@H]
(C)
[C@]
43[H]
)
[C@@]
1(C)
CC[C@H]
(O)
C2
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.
EC 2.3.1.26 (sterol O-acyltransferase) inhibitor
An EC 2.3.1.* (acyltransferase transferring other than amino-acyl group) inhibitor that interferes with the action of acyl-CoA:cholesterol acyltransferase (EC 2.3.1.26).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
esculeogenin A (
CHEBI:71676
)
has role
EC 2.3.1.26 (sterol
O
-acyltransferase) inhibitor (
CHEBI:64696
)
esculeogenin A (
CHEBI:71676
)
has role
metabolite (
CHEBI:25212
)
esculeogenin A (
CHEBI:71676
)
is a
3β-hydroxy steroid (
CHEBI:36836
)
esculeogenin A (
CHEBI:71676
)
is a
azaspiro compound (
CHEBI:35624
)
esculeogenin A (
CHEBI:71676
)
is a
oxaspiro compound (
CHEBI:37948
)
esculeogenin A (
CHEBI:71676
)
is a
sapogenin (
CHEBI:26606
)
IUPAC Name
(3β,5α,22α,23
S
,25
S
)-spirosolane-3,23,27-triol
Registry Number
Type
Source
9826338
Reaxys Registry Number
Reaxys
Citations
Types
Sources
17872457
PubMed citation
Europe PMC
18591823
PubMed citation
Europe PMC
20853874
PubMed citation
Europe PMC
21395308
PubMed citation
Europe PMC
22223387
PubMed citation
Europe PMC
22224814
PubMed citation
Europe PMC
Last Modified
24 April 2013