Welcome to FlavorDB

Content

Generals
Classification
Quality
Toxicity & Safety
Receptors

Compound Summary

General Compound Information

Andrographolide

Click to view/hide 3D structure

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.

Synonyms

Andrographolide; 5508-58-7; CHEBI:65408; (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(3H)-one; HMPL004;

Andro;DTXSID3045980;410105JHGR;NSC-383468;3alpha,14,15,18-tetrahydroxy-5b,9bH,10a-labda-8(20),12-dien-16-oic acid gamma-Lactone;(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;3-(2-(Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenenaphthyl)ethylidene)dihydro-4-hydroxyfuran-2(3H)-one;(1R-(1-alpha(E(S)),4abeta,5alpha,6alpha,8aalpha))-3-(2-(decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethylidene)dihydro-4-hydroxy-2(3H)-furanone;(3E,4S)-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]ethylidene}-4-hydroxyoxolan-2-one;(3E,4S)-4-hydroxy-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidenedecahydronaphthalen-1-yl]ethylidene}dihydrofuran-2(3H)-one;2(3H)-Furanone, 3-[2-[(1R,4aS,5R,6R,8aS)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-, (3E,4S)-;UNII-410105JHGR;HMPL-004;NSC383468;NCGC00095597-01;2(3H)-FURANONE, 3-(2-((1R,4AS,5R,6R,8AS)-DECAHYDRO-6-HYDROXY-5-(HYDROXYMETHYL)-5,8A-DIMETHYL-2-METHYLENE-1-NAPHTHALENYL)ETHYLIDENE)DIHYDRO-4-HYDROXY-, (3E,4S)-;869807-57-8;EINECS 226-852-5;NSC 383468;Andrographolide, 98%;ANDROGRAPHOLIDE [MI];ANDROGRAPHOLIDE [INCI];BIDD:ER0530;CHEMBL186141;GTPL9675;MEGxp0_000978;ANDROGRAPHOLIDE [USP-RS];ANDROGRAPHOLIDE [WHO-DD];DTXCID1025980;SCHEMBL12056309;ACon1_002113;(3E,4S)-3-(2-((1R,4AS,5R,6R,8AS)-DECAHYDRO-6-HYDROXY-5-(HYDROXYMETHYL)-5,8A-DIMETHYL-2-METHYLENE-1-NAPHTHALENYL)ETHYLIDENE)DIHYDRO-4-HYDROXY-2(3H)-FURANONE;ACT03252;Andrographolide, analytical standard;HY-N0191;ZINC3881797;Tox21_111508;BDBM50084419;MFCD07778082;AKOS015920075;CCG-208428;CS-3334;DB05767;NCGC00179817-01;NCGC00179817-02;AS-13637;CAS-5508-58-7;C20214;A830479;Q-100624;Q4759444;BRD-K89282837-001-01-0;ANDROGRAPHOLIDE (CONSTITUENT OF ANDROGRAPHIS) [DSC];Andrographolide, United States Pharmacopeia (USP) Reference Standard;(3E)-3-[2-[(1R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-decalin-1-yl]ethylidene]-4-hydroxy-tetrahydrofuran-2-one;Andrographolide;(3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-decalin-1-yl]ethylidene]-4-hydroxy-tetrahydrofuran-2-one;(5beta,9R,10alpha,14S)-3alpha,14,15,18-Tetrahydroxylabdane-8(20),12-diene-16-oic acid gamma-lactone;(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;2(3H)-Furanone, 3-(2-(decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethylidene)dihydro-4-hydroxy-, (1R-(1-alpha(E(S*)),4a-beta,5-alpha,6-alpha,8a-alpha))-;2(3H)-Furanone,3-[2-[(1R,4aS,5R,6R,8aS)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-,(3E,4S)-;3.ALPHA.,14,15,18-TETRAHYDROXY-5.BETA.,9.BETA.H,10.ALPHA.-LABDA-8(20),12-DIEN-16-OIC ACID .GAMMA.-LACTONE;

FlavorDB ID

53

PUBCHEM ID

5318517

Molecular Weight

350.4

Molecular Formula

C20H30O5

Openeye Can Smiles

CC12CCC(C(C1CCC(=C)C2CC=C3C(COC3=O)O)(C)CO)O

IUPAC Inchikey

BOJKULTULYSRAS-OTESTREVSA-N

Network

Shown in network

Similarity

Show/Hide similarity panel

Compound Classification

Classification (Parent Nodes)

ClassyFire Ontology

Compound Quality

Quality information of this compound is not available!

Compound Toxicity and Food Additive Safety (OFAS)

Toxicity Summary
Link to the Distributed Structure-Searchable Toxicity (DSSTox) Database

Receptors

Receptor	REFERENCE	EC50 [µM]	Effective Concentration [µM]
TAS2R8	details	Activated	Activated
TAS2R10	details	Activated	Activated
TAS2R20	details	Activated	Activated
TAS2R30	details	Activated	30.00
TAS2R31	details	>20.00	Activated
TAS2R39	details	Activated	Activated
TAS2R46	details	20.00	3.00
TAS2R50	details	27.80	10.00

GC-MS Consensus Spectra

GC-MS Consensus Spectra information of this compound is not available!