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Andrographolide - 98%, high purity , CAS No.5508-58-7, Agonist of TAS2R46;Agonist of TAS2R50;Agonist of TAS2R8

In stock
Item Number
A101649
Grouped product items
SKU Size
Availability
Price Qty
A101649-100mg
100mg
4
$58.90
A101649-500mg
500mg
Available within 4-8 weeks(?)
Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!
$117.90
A101649-1g
1g
≥10
$212.90
A101649-5g
5g
5
$955.90
A101649-25g
25g
5
$4,301.90
A101649-100g
100g
2
$15,483.90
A101649-500g
500g
Available within 4-8 weeks(?)
Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!
$69,677.90

Inhibits NFκB; blocks androgen receptor (AR) expression

Basic Description

Synonyms ANDROGRAPHOLIDE [MI] | DTXCID1025980 | Q-100624 | DTXSID3045980 | (S,E)-4-Hydroxy-3-(2-((1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethylidene)dihydrofuran-2 | BRD-K89282837-001-01-0 | NSC-115849 | Q475
Specifications & Purity Moligand™, ≥98%
Biochemical and Physiological Mechanisms Inhibitor of NF-κB signaling; also attenuates concanavaline-induced IFNγproduction in murine T cells (IC50= 1.7μM). Blocks androgen receptor (AR) expression in AR-expressing C4-2 cells. Activates Nrf2 in BEAS-2B cells in response to cigarette smoke extrac
Shipped In Normal
Grade Moligand™
Action Type AGONIST
Mechanism of action Agonist of TAS2R46;Agonist of TAS2R50;Agonist of TAS2R8
Product Description

Andrographolide, a bioactive diterpene lactone, is the main constituent of Andrographis paniculata, a plant used in traditional medicines. It is known to have different biological activities such as anti-inflammatory, anti-malarial, anti-cancer and hepatoprotective activity. It also shows potent anti-viral effect against dengue virus

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
Superclass Organoheterocyclic compounds
Class Lactones
Subclass Gamma butyrolactones
Intermediate Tree Nodes Not available
Direct Parent Gamma butyrolactones
Alternative Parents Tetrahydrofurans  Enoate esters  Secondary alcohols  Cyclic alcohols and derivatives  Oxacyclic compounds  Monocarboxylic acids and derivatives  Primary alcohols  Organic oxides  Hydrocarbon derivatives  Carbonyl compounds  
Molecular Framework Aliphatic heteropolycyclic compounds
Substituents Gamma butyrolactone - Cyclic alcohol - Tetrahydrofuran - Enoate ester - Alpha,beta-unsaturated carboxylic ester - Carboxylic acid ester - Secondary alcohol - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Oxacycle - Primary alcohol - Organooxygen compound - Organic oxide - Organic oxygen compound - Alcohol - Carbonyl group - Hydrocarbon derivative - Aliphatic heteropolycyclic compound
Description This compound belongs to the class of organic compounds known as gamma butyrolactones. These are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
External Descriptors secondary alcohol - primary alcohol - gamma-lactone - carbobicyclic compound - labdane diterpenoid

Associated Targets(Human)

TAS2R8 Tchem Taste receptor type 2 member 8 (0 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
TAS2R46 Tchem Taste receptor type 2 member 46 (0 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
TAS2R50 Tchem Taste receptor type 2 member 50 (0 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
MGAM Tclin Maltase-glucoamylase (654 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ACHE Tclin Acetylcholinesterase (18204 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
NR1H4 Tclin Bile acid receptor FXR (6228 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
STAT3 Tchem Signal transducer and activator of transcription 3 (3313 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
NFKB1 Tclin Nuclear factor NF-kappa-B p105 subunit (1459 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
NOS3 Tchem Nitric-oxide synthase, endothelial (1452 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
GBA3 Tbio Beta-glucosidase cytosolic (63 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
AKT1 Tchem Serine/threonine-protein kinase AKT (9192 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
NFKBIA Tchem NF-kappaB inhibitor alpha (187 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
5637 (630 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
A2058 (690 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
A498 (42825 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ACHN (49357 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Caco-2 (12174 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Calu-3 (339 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CCRF-CEM (65223 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
DU-145 (51482 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HCT-8 (3484 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HL-60 (67320 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HT-29 (80576 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
K562 (73714 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
KM12 (47707 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
M14 (47487 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
MCF7 (126967 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
MDA-MB-361 (612 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
MDA-MB-468 (9477 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
PC-3 (62116 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SGC-7901 (2773 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SH-SY5Y (11521 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SK-MEL-2 (46422 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SK-MEL-28 (48833 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SK-MEL-5 (47095 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SK-OV-3 (52876 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SN12C (47755 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
THP-1 (11052 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
U-251 (51189 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
U-937 (7138 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
786-0 (47912 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
A549 (127892 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
NCI/ADR-RES (33767 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
T47D (39041 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Col2 (437 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
EKVX (44102 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
NCI-H322M (45589 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HCT-116 (91556 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HEK293 (82097 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HepG2 (196354 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
NCI-H460 (60772 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HUVEC (11049 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
KB (17409 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Associated Targets(non-human)

pol Human immunodeficiency virus type 1 reverse transcriptase (18245 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Hk2 Hexokinase type II (49 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Rhizopus arrhizus (810 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Pseudomonas aeruginosa (123386 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Pseudomonas fluorescens (1630 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Micrococcus luteus (7463 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Staphylococcus aureus (210822 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Escherichia coli (133304 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Haemophilus influenzae (8812 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Aspergillus niger (16508 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Bacillus subtilis (32866 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Aspergillus fumigatus (16427 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Candida albicans (78123 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Mus musculus (284745 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Hepatitis B virus (7925 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Human immunodeficiency virus 1 (70413 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Influenza A virus (11224 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Dengue virus (413 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Human immunodeficiency virus (3636 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
B16 (5829 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
J774.A1 (2436 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
P388 (20296 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
PC-12 (7051 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
RAW264.7 (28094 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
RBL-2H3 (1162 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Vero (26788 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
BV-2 (3710 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
NIH3T3 (5395 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HT-22 (3261 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
rep Replicase polyprotein 1ab (378 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Protease (18 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
BCHE Cholinesterase (8742 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Akt1 RAC-alpha serine/threonine-protein kinase (147 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
[Candida] sake (415 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
dengue virus type 2 (2400 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
enterovirus D68 (324 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Mapk1 Mitogen-activated protein kinase 1 and 3 (ERK2 and ERK1) (70 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Henosepilachna vigintioctopunctata (143 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Mythimna separata (3306 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Influenza A virus H3N2 (588 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Chikungunya virus (1339 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Vero C1008 (1716 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Mechanisms of Action

Mechanism of Action Action Type target ID Target Name Target Type Target Organism Binding Site Name References

Names and Identifiers

Pubchem Sid 488195335
Pubchem Sid Url https://pubchem.ncbi.nlm.nih.gov/substance/488195335
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
InChIKey BOJKULTULYSRAS-OTESTREVSA-N
Smiles CC12CCC(C(C1CCC(=C)C2CC=C3C(COC3=O)O)(C)CO)O
Isomeric 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
WGK Germany 3
RTECS LU3490750
Alternate CAS 5508-58-7
MeSH Entry Terms 17-hydro-9-dehydro-andrographolide;andrographolide;isoandrographolide
Molecular Weight 350.45
Beilstein 42762
Reaxy-Rn 29234534
Reaxys-RN_link_address https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=29234534&ln=

Certificates(CoA,COO,BSE/TSE and Analysis Chart)

C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:

Find and download the COA for your product by matching the lot number on the packaging.

15 results found

Lot Number Certificate Type Date Item
E2114079 Certificate of Analysis Feb 07, 2025 A101649
D2303465 Certificate of Analysis Feb 13, 2023 A101649
D2303440 Certificate of Analysis Feb 13, 2023 A101649
D2303466 Certificate of Analysis Feb 13, 2023 A101649
D2303438 Certificate of Analysis Feb 13, 2023 A101649
D2303461 Certificate of Analysis Feb 13, 2023 A101649
D2303462 Certificate of Analysis Feb 13, 2023 A101649
F2527058 Certificate of Analysis Feb 13, 2023 A101649
D2303464 Certificate of Analysis Feb 13, 2023 A101649
D2303469 Certificate of Analysis Feb 13, 2023 A101649
B2321253 Certificate of Analysis May 21, 2022 A101649
F2209088 Certificate of Analysis May 21, 2022 A101649
F2209068 Certificate of Analysis May 21, 2022 A101649
F2209080 Certificate of Analysis May 21, 2022 A101649
G1813060 Certificate of Analysis May 10, 2022 A101649

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Chemical and Physical Properties

Solubility Solvent:DMSO, Max Conc. mg/mL: 35.05, Max Conc. mM: 100; Solvent:ethanol, Max Conc. mg/mL: 3.5, Max Conc. mM: 10
Specific Rotation[α] -126° (C=1.5,AcOH)
Melt Point(°C) 229-232°C
Molecular Weight 350.400 g/mol
XLogP3 2.200
Hydrogen Bond Donor Count 3
Hydrogen Bond Acceptor Count 5
Rotatable Bond Count 3
Exact Mass 350.209 Da
Monoisotopic Mass 350.209 Da
Topological Polar Surface Area 87.000 Ų
Heavy Atom Count 25
Formal Charge 0
Complexity 597.000
Isotope Atom Count 0
Defined Atom Stereocenter Count 6
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 1
Undefined Bond Stereocenter Count 0
The total count of all stereochemical bonds 1
Covalently-Bonded Unit Count 1

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