Andrograpanin - Moligand™, ≥98% , CAS No.82209-74-3

CAS: 82209-74-3 Cat. No.: A334598 Molecular Weight: 318.45

GRADE & PURITY Moligand™, ≥98%

Synonyms

3-[2-[(1R,4aS,5R,8aS)-Decahydro-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethyl]-2(5H)-furanone, ent-19-Hydroxy-8(17),13-labdadien-16,15-olide | 3,14-Dideoxyandrographolide | 3-[2-[(1R,4aS,5R,8aS)-Decahydro-5-(hydroxymethyl)-5,8a-dimethyl

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Andrograpanin is a bioactive compound from Andrographis paniculata. Andrograpanin has anti-inflammatory and anti-infectious properties. 

In vitro：

Andrograpanin boosts the movement of leukocytes towards higher concentrations of the chemokine SDF-1α in Jurkat, THP-1, and PBL cells, demonstrating its ability to enhance chemotaxis. Additionally, it exhibits anti-inflammatory effects by inhibiting the p38 MAPKs signaling pathways in macrophage cells stimulated with lipopolysaccharide

Specifications

Synonyms

3-[2-[(1R, 4aS, 5R, 8aS)-Decahydro-5-(hydroxymethyl)-5, 8a-dimethyl-2-methylene-1-naphthalenyl]ethyl]-2(5H)-furanone, ent-19-Hydroxy-8(17), 13-labdadien-16, 15-olide | 3, 14-Dideoxyandrographolide | 3-[2-[(1R, 4aS, 5R, 8aS)-Decahydro-5-(hydroxymethyl)-5, 8a-dimethyl

Specifications & Purity

Moligand™, ≥98%

Storage

Protected from light, Store at -20°C

Shipped In

Ice chest + Ice pads

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

Grade

Moligand™

Action Type

INHIBITOR

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC1(CCCC2(C1CCC(=C)C2CCC3=CCOC3=O)C)CO
• IUPAC Name: 4-[2-[(1R,4aS,5R,8aS)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-2H-furan-5-one
• InChIKey: WKKBRRFSRMDTJB-JYBIWHBTSA-N
• INCHI: 1S/C20H30O3/c1-14-5-8-17-19(2,13-21)10-4-11-20(17,3)16(14)7-6-15-9-12-23-18(15)22/h9,16-17,21H,1,4-8,10-13H2,2-3H3/t16-,17-,19+,20+/m1/s1
• Isomeric SMILES: C[C@]1(CCC[C@@]2([C@@H]1CCC(=C)[C@H]2CCC3=CCOC3=O)C)CO
• Molecular Weight: 318.45
• Reaxy-Rn: 47860113
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=47860113&ln=

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Terpene lactones
• Intermediate Tree Nodes: Not available
• Direct Parent: Diterpene lactones
• Alternative Parents: Colensane and clerodane diterpenoids Butenolides Enoate esters Lactones Oxacyclic compounds Monocarboxylic acids and derivatives Primary alcohols Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Diterpene lactone - Diterpenoid - Clerodane diterpenoid - 2-furanone - Dihydrofuran - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Carboxylic acid ester - Lactone - Monocarboxylic acid or derivatives - Oxacycle - Carboxylic acid derivative - Organoheterocyclic compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Alcohol - Carbonyl group - Organic oxygen compound - Primary alcohol - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.
• External Descriptors: Not available

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

Associated Targets(Human)

HL-60 (67320 Activities)

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Associated Targets(non-human)

Micrococcus luteus (7463 Activities)

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Staphylococcus aureus (210822 Activities)

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Escherichia coli (133304 Activities)

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Aspergillus niger (16508 Activities)

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Bacillus subtilis (32866 Activities)

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Candida albicans (78123 Activities)

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RAW264.7 (28094 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO: 55 mg/ml (172.71 mM)
• Sensitivity: Light sensitive
• Molecular Weight: 318.400 g/mol
• XLogP3: 4.200
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 318.219 Da
• Monoisotopic Mass: 318.219 Da
• Topological Polar Surface Area: 46.500 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 535.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• 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