Madecassic acid - Moligand™, ≥98% , CAS No.18449-41-7

CAS: 18449-41-7 Cat. No.: M759137 Molecular Weight: 504.71

GRADE & PURITY Moligand™, ≥98%

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

Specifications

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Triterpenoid compound extracted from Centella asiatica with multiple biological activites. Non-competive cytochrome P450 (CYP) inhibitor (K i values are 34.1 and 49.7µM for CYP2C9 and CYP2D6 respectively). Inhibits LPS-induced NFκB activity.

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 528774720
• Canonical Smiles: CC1CCC2(CCC3(C(=CCC4C3(CC(C5C4(CC(C(C5(C)CO)O)O)C)O)C)C2C1C)C)C(=O)O
• 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
• InChIKey: PRAUVHZJPXOEIF-AOLYGAPISA-N
• 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
• Isomeric 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
• Molecular Weight: 504.71
• Reaxy-Rn: 2713234
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2713234&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Triterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Triterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Triterpenoids
• Alternative Parents: 7-alpha-hydroxysteroids 12-beta-hydroxysteroids Secondary alcohols Cyclic alcohols and derivatives Polyols Monocarboxylic acids and derivatives Carboxylic acids Primary alcohols Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Triterpenoid - 12-hydroxysteroid - Hydroxysteroid - 12-beta-hydroxysteroid - 7-hydroxysteroid - 7-alpha-hydroxysteroid - Steroid - Cyclic alcohol - Secondary alcohol - Polyol - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Primary alcohol - Organooxygen compound - Organic oxide - Organic oxygen compound - Alcohol - Carbonyl group - Hydrocarbon derivative - Aliphatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
• External Descriptors: monocarboxylic acid - tetrol - pentacyclic triterpenoid

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Molecular Weight: 504.700 g/mol
• XLogP3: 4.400
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 504.345 Da
• Monoisotopic Mass: 504.345 Da
• Topological Polar Surface Area: 118.000 Ų
• Heavy Atom Count: 36
• Formal Charge: 0
• Complexity: 963.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 13
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1