Madecassoside

CAT: 0931-T2813-01Size: 10 mgDry Ice: NoHazardous: No

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CAT#:0931-T2813-01Size:10 mg

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CAS Number

34540-22-2

Target

Antioxidant, Apoptosis, Caspase, p38 MAPK, Autophagy, Nrf2, Endogenous Metabolite

Related Pathways

Autophagy, Proteases/Proteasome, MAPK, Immunology/Inflammation, Apoptosis, Oxidation-Reduction, Metabolism

Purity

0.9985

Bioactivity

Madecassoside (Asiaticoside A) is a pentacyclic triterpene extracted from Centella asitica (L.) with anti-inflammatory, anti-oxidative and anti-aging activities.

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[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O

Molecular Formula

C48H78O20

Molecular Weight

975.12

Shipping Conditions

Ice Packs

Storage Temperature

-20°C

Chemical Information

Madecassoside

Madecassoside is a triterpenoid saponin that is a trisaccharide derivative of madecassic acid. Isolated from Centella asiatica, it exhibits anti-inflammatory, antioxidant and antirheumatic activities. It has a role as an antioxidant, an antirheumatic drug, an anti-inflammatory agent, a vulnerary and a plant metabolite. It is a pentacyclic triterpenoid, a carboxylic ester, a triterpenoid saponin and a trisaccharide derivative. It is functionally related to a madecassic acid. It derives from a hydride of an ursane.

CAS Number	34540-22-2
PubChem CID	24825675
IUPAC Name	[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (1S,2R,4aS,6aR,6aS,6bR,8R,8aR,9R,10R,11R,12aR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylate
Molecular Formula	C48H78O20
Molecular Weight	975.1
XLogP	-1.2
Topological Polar Surface Area	335
Hydrogen Bond Donor Count	13
Hydrogen Bond Acceptor Count	20
Rotatable Bond Count	10
Heavy Atom Count	68
Formal Charge	0
Complexity	1860

SMILES

C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(C[C@H]([C@@H]5[C@@]4(C[C@H]([C@@H]([C@@]5(C)CO)O)O)C)O)C)[C@@H]2[C@H]1C)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O)O)O)O)O)O)O

InChI

InChI=1S/C48H78O20/c1-19-10-11-48(13-12-46(6)22(28(48)20(19)2)8-9-27-44(4)14-24(52)39(61)45(5,18-50)38(44)23(51)15-47(27,46)7)43(62)68-42-35(59)32(56)30(54)26(66-42)17-63-40-36(60)33(57)37(25(16-49)65-40)67-41-34(58)31(55)29(53)21(3)64-41/h8,19-21,23-42,49-61H,9-18H2,1-7H3/t19-,20+,21+,23-,24-,25-,26-,27-,28+,29+,30-,31-,32+,33-,34-,35-,36-,37-,38-,39+,40-,41+,42+,44-,45+,46-,47-,48+/m1/s1

InChIKey

BNMGUJRJUUDLHW-HCZMHFOYSA-N

Chemical Structure

2D Structure

CAS: 34540-22-2

CID: 24825675

Formula: C48H78O20

MW: 975.1

Interactive 3D Structure

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View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	975.1
XLogP3	-1.2
Hydrogen Bond Donor Count	13
Hydrogen Bond Acceptor Count	20
Rotatable Bond Count	10
Exact Mass	974.50864487
Monoisotopic Mass	974.50864487
Topological Polar Surface Area	335 Å²
Heavy Atom Count	68
Formal Charge	0
Complexity	1860
Isotope Atom Count	0
Defined Atom Stereocenter Count	28
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

Alternative Products

Catalog	Name
454118-01	Madecassoside

Madecassoside

Chemical Information

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