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Madecassic acid

CAT: 0127-BUP10594-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0127-BUP10594-01Size:5 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
18449-41-7
Synonyms
6-Deoxy-L-Galactose, L-Fucose, Brahmic acid, L-fucopyranose
Purity
=98%
Smiles
CC1CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(CO)C5C(O)CC34C)C2C1C)C(O)=O

Chemical Information

Madecassic Acid

Madecassic acid is 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 2alpha,3beta,6beta stereoisomer). It has a role as an antioxidant, an antibacterial agent, a hypoglycemic agent, an antineoplastic agent, an apoptosis inducer and a plant metabolite. It is a monocarboxylic acid, a pentacyclic triterpenoid and a tetrol. It is a conjugate acid of a madecassate. It derives from a hydride of an ursane.

CAS Number18449-41-7
PubChem CID73412
IUPAC Name(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-carboxylic acid
Molecular FormulaC30H48O6
Molecular Weight504.7
XLogP4.4
Topological Polar Surface Area118
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Heavy Atom Count36
Formal Charge0
Complexity963
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
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
Chemical Structure
2D Structure
2D structure of Madecassic Acid
CAS: 18449-41-7
CID: 73412
Formula: C30H48O6
MW: 504.7
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight504.7
XLogP34.4
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Exact Mass504.34508925
Monoisotopic Mass504.34508925
Topological Polar Surface Area118 Ų
Heavy Atom Count36
Formal Charge0
Complexity963
Isotope Atom Count0
Defined Atom Stereocenter Count13
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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CatalogName
SM5056-10mMMadecassic acid

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