Andrographolide, 98%

Name: Andrographolide
Brand: Chempure

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CAS Number

5508-58-7

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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
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
inchi key	BOJKULTULYSRAS-OTESTREVSA-N
molecular formula	C20H30O5
synonyms	Andrographolide 5508-58-7 CHEBI:65408 HMPL004 UNII-410105JHGR
Compound Description	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 anti-HIV agent and an antineoplastic agent. It is a gamma-lactone, a primary alcohol, a secondary alcohol, a labdane diterpenoid and a carbobicyclic compound. Andrographolide is a botanical product extracted from a herb that occurs naturally in China. The herb has an extensive history of use in TCM for the treatment of upper respiratory tract infections and other inflammatory and infectious diseases. Andrographolide has been reported in Andrographis paniculata, Cymbopogon schoenanthus, and Ginkgo biloba with data available. Andrographolide is a labdane diterpenoid that is produced by the Andrographis paniculata plant, which has a broad range of therapeutic applications including anti-inflammatory and anti-platelet aggregation activities and potential antineoplastic properties. Since andrographolide has multiple therapeutic activities there are several proposed mechanisms of action for this agent. The anti-inflammatory effects of this agent appear to be related to the inhibition of nitric oxide production by macrophages. This agent may activate the NO/cyclic GMP pathway and inhibit both the phospholipase C gamma 2 /protein kinase C and PI3K/AKT-MAPK signaling pathways in activated platelets to inhibit platelet aggregation. In activated platelets, these three signaling pathways are downstream of integrin activation mediated by collagen binding and influence the association of fibrinogen with its receptors. Additionally, andrographolide may exert its anti-cancer activity through the induction of cell cycle arrest at G0/G1 phase and the stimulation of lymphocyte proliferation and activation. These processes could result in decreased proliferation of and increased immunocytotoxicity against tumor cells. ANDROGRAPHOLIDE is a small molecule drug with a maximum clinical trial phase of III and has 4 investigational indications.

Computed Properties

Molecular Weight:	350.4 g/mol
XLogP3:	2.2
Hydrogen Bond Donor Count:	3
Hydrogen Bond Acceptor Count:	5
Rotatable Bond Count:	3
Exact Mass:	350.20932405 g/mol
Monoisotopic Mass:	350.20932405 g/mol
Topological Polar Surface Area:	87 Å²
Heavy Atom Count:	25
Formal Charge:	0
Complexity:	597
Isotope Atom Count:	0
Defined Atom Stereocenter Count:	6
Undefined Atom Stereocenter Count:	0
Defined Bond Stereocenter Count:	1
Undefined Bond Stereocenter Count:	0
Covalently-Bonded Unit Count:	1
Compound Is Canonicalized:	Yes

hazard signal	Warning
hazard classes and categories	Skin Irrit. 2 (100%) Eye Irrit. 2 (100%) STOT SE 3 (100%)
precautionary statement codes	P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501
hazard statements	H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

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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
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
inchi key	BOJKULTULYSRAS-OTESTREVSA-N
molecular formula	C20H30O5
synonyms	Andrographolide 5508-58-7 CHEBI:65408 HMPL004 UNII-410105JHGR
Compound Description	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 anti-HIV agent and an antineoplastic agent. It is a gamma-lactone, a primary alcohol, a secondary alcohol, a labdane diterpenoid and a carbobicyclic compound. Andrographolide is a botanical product extracted from a herb that occurs naturally in China. The herb has an extensive history of use in TCM for the treatment of upper respiratory tract infections and other inflammatory and infectious diseases. Andrographolide has been reported in Andrographis paniculata, Cymbopogon schoenanthus, and Ginkgo biloba with data available. Andrographolide is a labdane diterpenoid that is produced by the Andrographis paniculata plant, which has a broad range of therapeutic applications including anti-inflammatory and anti-platelet aggregation activities and potential antineoplastic properties. Since andrographolide has multiple therapeutic activities there are several proposed mechanisms of action for this agent. The anti-inflammatory effects of this agent appear to be related to the inhibition of nitric oxide production by macrophages. This agent may activate the NO/cyclic GMP pathway and inhibit both the phospholipase C gamma 2 /protein kinase C and PI3K/AKT-MAPK signaling pathways in activated platelets to inhibit platelet aggregation. In activated platelets, these three signaling pathways are downstream of integrin activation mediated by collagen binding and influence the association of fibrinogen with its receptors. Additionally, andrographolide may exert its anti-cancer activity through the induction of cell cycle arrest at G0/G1 phase and the stimulation of lymphocyte proliferation and activation. These processes could result in decreased proliferation of and increased immunocytotoxicity against tumor cells. ANDROGRAPHOLIDE is a small molecule drug with a maximum clinical trial phase of III and has 4 investigational indications.

Computed Properties

Molecular Weight:	350.4 g/mol
XLogP3:	2.2
Hydrogen Bond Donor Count:	3
Hydrogen Bond Acceptor Count:	5
Rotatable Bond Count:	3
Exact Mass:	350.20932405 g/mol
Monoisotopic Mass:	350.20932405 g/mol
Topological Polar Surface Area:	87 Å²
Heavy Atom Count:	25
Formal Charge:	0
Complexity:	597
Isotope Atom Count:	0
Defined Atom Stereocenter Count:	6
Undefined Atom Stereocenter Count:	0
Defined Bond Stereocenter Count:	1
Undefined Bond Stereocenter Count:	0
Covalently-Bonded Unit Count:	1
Compound Is Canonicalized:	Yes

hazard signal	Warning
hazard classes and categories	Skin Irrit. 2 (100%) Eye Irrit. 2 (100%) STOT SE 3 (100%)
precautionary statement codes	P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501
hazard statements	H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Product No: CI0758

Andrographolide, 98%

Product No: CI0758

About this item

NAME AND IDENTIFIERS

CHEMICAL AND PHYSICAL PROPERTIES

SAFETY AND HAZARDS

About this item

Documentation

Certificate of Analysis

Require a Sample Certificate of Analysis (COA) ?

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Product No: CI0758

About this item

NAME AND IDENTIFIERS

CHEMICAL AND PHYSICAL PROPERTIES

SAFETY AND HAZARDS

Require a Sample Certificate of Analysis (COA) ?