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Andrographolide

CAT: 0013-GTR19162039-01Size: 1 gDry Ice: NoHazardous: No
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CAT#:0013-GTR19162039-01Size:1 g
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Description
Andrographolide (Andrographis) is an irreversible antagonist of NF-κB and prevents in vitro T cell activation; displays antiviral, antiinflammatory, antiapoptotic, and antihyperglycemic properties. (In Vitro) :Andrographolide (AP) concentration-dependently suppresses receptor activator of nuclear factor kappa B ligand (RANKL) -mediated osteoclast differentiation and bone resorption in vitro and reduces the expression of osteoclast-specific markers. Andrographolide attenuates inflammation by inhibition of TNFα-induced NF-κB activation through covalent modification of reduced Cys62 of p50, without affecting IκBα degradation or p50/p65 nuclear translocation. Andrographolide also inhibits the ERK/MAPK signalling pathway without affecting p38 or JNK signalling. Andrographolide inhibits osteoclast differentiation of RAW 264.7 cells in a concentration-dependent manner. Andrographolide suppresses osteoclast formation in a concentration-dependent manner without any obvious cytotoxic effects, in both BMMs and RAW 264.7 cells. Andrographolide treatment substantially reduces the area of bone resorption. Only approximately 30% of the bone resorption observed in the control group is achieved after treatment with 2.5 μM Andrographolide. Osteoclastic bone resorption is almost completely inhibited after treatment with 10 μM Andrographolide. (In Vivo) :Treatment with Andrographolide (5 or 30 mg/kg) reduces the extent of bone loss induced by LPS. Moreover, Andrographolide slightly increases the BMD and cortex thickness compared to LPS treatment. Histological examination confirms the protective effects of Andrographolide on LPS-induced bone loss. LPS injection leads to inflammatory bone erosion and increased numbers of TRAP-positive osteoclasts.
CAS Number
5508-58-7
Purity
>98% (HPLC)
Solubility
Ethanol: 8 mg/mL (22.82 mM) ; DMSO: 70 mg/mL (199.74 mM)
Smiles
O=C1OCC (O) /C1=C\CC2C (CCC3C (C) (CO) C (O) CCC23C) =C
Molecular Formula
C20H30O5
Molecular Weight
350.44
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.
Other Product Names
3-[2-[decahydro-6-hydroxy-5- (hydroxymethyl) -5,8a- dimethyl-2-methylene-1- napthalenyl]ethylidene]dihydro- 4-hydroxy-2 (3H) -furanone

Chemical Information

Andrographolide

Andrographolide is a labdane diterpenoid isolated from the leaves and roots of Andrographis paniculata that exhibits anti-HIV, anti-inflammatory and antineoplastic properties. It has a role as a metabolite, an anti-inflammatory drug, an antineoplastic agent and an anti-HIV agent. It is a primary alcohol, a secondary alcohol, a labdane diterpenoid, a carbobicyclic compound and a gamma-lactone.

CAS Number5508-58-7
PubChem CID5318517
IUPAC Name(3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one
Molecular FormulaC20H30O5
Molecular Weight350.4
XLogP2.2
Topological Polar Surface Area87
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Heavy Atom Count25
Formal Charge0
Complexity597
SMILES
C[C@@]12CC[C@H]([C@@]([C@H]1CCC(=C)[C@H]2C/C=C/3\[C@@H](COC3=O)O)(C)CO)O
InChI
InChI=1S/C20H30O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5,14-17,21-23H,1,4,6-11H2,2-3H3/b13-5+/t14-,15-,16+,17-,19+,20+/m1/s1
InChIKey
BOJKULTULYSRAS-OTESTREVSA-N
Chemical Structure
2D Structure
2D structure of Andrographolide
CAS: 5508-58-7
CID: 5318517
Formula: C20H30O5
MW: 350.4
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight350.4
XLogP32.2
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Exact Mass350.20932405
Monoisotopic Mass350.20932405
Topological Polar Surface Area87 Ų
Heavy Atom Count25
Formal Charge0
Complexity597
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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