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> Main
CHEBI:73058 - madecassic acid
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ChEBI Name
madecassic acid
ChEBI ID
CHEBI:73058
Definition
A pentacyclic triterpenoid that is ursane substituted by a carboxy group at position 28 and hydroxy groups at positions 2, 3, 6 and 23 (the 2α,3β,6β stereoisomer).
Stars
This entity has been manually annotated by the ChEBI Team.
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Formula
C30H48O6
Net Charge
0
Average Mass
504.69850
Monoisotopic Mass
504.34509
InChI
InChI=1S/C30H48O6/c1-
16-
9-
10-
30(25(35)
36)
12-
11-
28(5)
18(22(30)
17(16)
2)
7-
8-
21-
26(3)
13-
20(33)
24(34)
27(4,15-
31)
23(26)
19(32)
14-
29(21,28)
6/h7,16-
17,19-
24,31-
34H,8-
15H2,1-
6H3,(H,35,36)
/t16-
,17+,19-
,20-
,21-
,22+,23-
,24+,26-
,27+,28-
,29-
,30+/m1/s1
InChIKey
PRAUVHZJPXOEIF-AOLYGAPISA-N
SMILES
[H]
[C@]
12CC=C3[C@]
4([H]
)
[C@@H]
(C)
[C@H]
(C)
CC[C@@]
4(CC[C@@]
3(C)
[C@]
1(C)
C[C@@H]
(O)
[C@@]
1([H]
)
[C@]
(C)
(CO)
[C@@H]
(O)
[C@H]
(O)
C[C@]
21C)
C(O)
=O
Metabolite of Species
Details
Centella asiatica
(NCBI:txid48106)
See:
PubMed
Roles Classification
Chemical Role
(s):
antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
madecassic acid (
CHEBI:73058
)
has parent hydride
ursane (
CHEBI:35711
)
madecassic acid (
CHEBI:73058
)
has role
antioxidant (
CHEBI:22586
)
madecassic acid (
CHEBI:73058
)
has role
plant metabolite (
CHEBI:76924
)
madecassic acid (
CHEBI:73058
)
is a
monocarboxylic acid (
CHEBI:25384
)
madecassic acid (
CHEBI:73058
)
is a
pentacyclic triterpenoid (
CHEBI:25872
)
madecassic acid (
CHEBI:73058
)
is a
tetrol (
CHEBI:33573
)
Incoming
madecassoside (
CHEBI:66651
)
has functional parent
madecassic acid (
CHEBI:73058
)
IUPAC Name
(2α,3β,6β)-2,3,6,23-tetrahydroxyurs-12-en-28-oic acid
Synonyms
Sources
6β-hydroxyasiatic acid
ChemIDplus
brahmic acid
ChemIDplus
Manual Xrefs
Databases
CN101991578
Patent
FR2963553
Patent
HMDB0036670
HMDB
TW200938215
Patent
View more database links
Registry Numbers
Types
Sources
18449-41-7
CAS Registry Number
ChemIDplus
3041357
Reaxys Registry Number
Reaxys
Citations
Types
Sources
22816768
PubMed citation
Europe PMC
22966846
PubMed citation
Europe PMC
23346217
PubMed citation
Europe PMC
Last Modified
14 April 2015