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> Main
CHEBI:30853 - glycyrrhetinic acid
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ChEBI Ontology
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ChEBI Name
glycyrrhetinic acid
ChEBI ID
CHEBI:30853
Definition
A pentacyclic triterpenoid that is olean-12-ene substituted by a hydroxy group at position 3, an oxo group at position 11 and a carboxy group at position 30.
Stars
This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs
CHEBI:24417, CHEBI:5507
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Wikipedia
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Read full article at Wikipedia
Formula
C30H46O4
Net Charge
0
Average Mass
470.68380
Monoisotopic Mass
470.33961
InChI
InChI=1S/C30H46O4/c1-
25(2)
21-
8-
11-
30(7)
23(28(21,5)
10-
9-
22(25)
32)
20(31)
16-
18-
19-
17-
27(4,24(33)
34)
13-
12-
26(19,3)
14-
15-
29(18,30)
6/h16,19,21-
23,32H,8-
15,17H2,1-
7H3,(H,33,34)
/t19-
,21-
,22-
,23+,26+,27-
,28-
,29+,30+/m0/s1
InChIKey
MPDGHEJMBKOTSU-YKLVYJNSSA-N
SMILES
[H]
[C@@]
12C[C@]
(C)
(CC[C@]
1(C)
CC[C@]
1(C)
C2=CC(=O)
[C@]
2([H]
)
[C@@]
3(C)
CC[C@H]
(O)
C(C)
(C)
[C@]
3([H]
)
CC[C@@]
12C)
C(O)
=O
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):
immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application
(s):
immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
glycyrrhetinic acid (
CHEBI:30853
)
has parent hydride
oleanane (
CHEBI:36481
)
glycyrrhetinic acid (
CHEBI:30853
)
has role
immunomodulator (
CHEBI:50846
)
glycyrrhetinic acid (
CHEBI:30853
)
has role
plant metabolite (
CHEBI:76924
)
glycyrrhetinic acid (
CHEBI:30853
)
is a
cyclic terpene ketone (
CHEBI:36130
)
glycyrrhetinic acid (
CHEBI:30853
)
is a
hydroxy monocarboxylic acid (
CHEBI:35868
)
glycyrrhetinic acid (
CHEBI:30853
)
is a
pentacyclic triterpenoid (
CHEBI:25872
)
glycyrrhetinic acid (
CHEBI:30853
)
is conjugate acid of
glycyrrhetinate (
CHEBI:17573
)
Incoming
3α-hydroxyglycyrrhetinic acid (
CHEBI:16317
)
has functional parent
glycyrrhetinic acid (
CHEBI:30853
)
3-oxoglycyrrhetinic acid (
CHEBI:16404
)
has functional parent
glycyrrhetinic acid (
CHEBI:30853
)
glycyrrhetic acid 3-
O
-glucuronide (
CHEBI:189708
)
has functional parent
glycyrrhetinic acid (
CHEBI:30853
)
glycyrrhetinate (
CHEBI:17573
)
is conjugate base of
glycyrrhetinic acid (
CHEBI:30853
)
IUPAC Name
3β-hydroxy-11-oxoolean-12-en-30-oic acid
Synonyms
Sources
18β-glycyrrhetic acid
ChemIDplus
Enoxolone
KEGG COMPOUND
Glycyrrhetinic acid
KEGG COMPOUND
Manual Xrefs
Databases
3178
DrugCentral
C00003521
KNApSAcK
C02283
KEGG COMPOUND
CBW
PDBeChem
D00156
KEGG DRUG
Glycyrrhetinic_acid
Wikipedia
View more database links
Registry Numbers
Types
Sources
1449-05-4
CAS Registry Number
KEGG COMPOUND
2229654
Beilstein Registry Number
Beilstein
2229654
Reaxys Registry Number
Reaxys
471-53-4
CAS Registry Number
KEGG COMPOUND
471-53-4
CAS Registry Number
ChemIDplus
Citations
Types
Sources
14411793
PubMed citation
Europe PMC
17166674
PubMed citation
Europe PMC
18771671
PubMed citation
Europe PMC
24386942
PubMed citation
Europe PMC
Last Modified
16 February 2022