Andrographolide (CED0003543)

Record Information
Version1.0
Creation Date2016-05-22 05:26:40 UTC
Update Date2026-05-14 18:16:10 UTC
Accession NumberCHEM018679
Identification
Common NameAndrographolide
ClassSmall Molecule
Description
Andrographolide is an organoheterocyclic compound with the formula C20H30O5 and an average molecular weight of 350.45 g/mol. Andrographolide belongs to the gamma butyrolactones, a subclass of lactones within the organic compounds. It is recorded as being released from several sources, including amplifiers within electrical and electronic equipment, as well as household cleaning and consumer products such as pipe accessories, other smoking requisites, and non electric simulated smoking devices. In industrial applications, the compound is used as a conditioner and softener. Biologically, it serves as an analgesic (PMC7285361) and an anti-inflammatory agent (PMC8069343). It has a therapeutic effect on inflammation (PMC11086401, PMC5695812). The compound interacts with five recorded protein targets, including interleukin-6 (IL6), tumor necrosis factor (TNF), nuclear factor NF-kappa-B p100 subunit (NFKB2), interleukin-1 beta (IL1B), and one other protein.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
(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)-furanoneChEBI
3-(2-(Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenenaphthyl)ethylidene)dihydro-4-hydroxyfuran-2(3H)-oneChEBI
3alpha,14,15,18-Tetrahydroxy-5b,9BH,10a-labda-8(20),12-dien-16-Oic acid gamma-lactoneChEBI
(1R-(1-a(e(S)),4Abeta,5a,6a,8aalpha))-3-(2-(decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethylidene)dihydro-4-hydroxy-2(3H)-furanoneGenerator
(1R-(1-Α(e(S)),4abeta,5α,6α,8aalpha))-3-(2-(decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethylidene)dihydro-4-hydroxy-2(3H)-furanoneGenerator
3a,14,15,18-Tetrahydroxy-5b,9BH,10a-labda-8(20),12-dien-16-Oate g-lactoneGenerator
3a,14,15,18-Tetrahydroxy-5b,9BH,10a-labda-8(20),12-dien-16-Oic acid g-lactoneGenerator
3alpha,14,15,18-Tetrahydroxy-5b,9BH,10a-labda-8(20),12-dien-16-Oate gamma-lactoneGenerator
3Α,14,15,18-tetrahydroxy-5b,9BH,10a-labda-8(20),12-dien-16-Oate γ-lactoneGenerator
3Α,14,15,18-tetrahydroxy-5b,9BH,10a-labda-8(20),12-dien-16-Oic acid γ-lactoneGenerator
IsoandrographolideMeSH
17-hydro-9-dehydro-AndrographolideMeSH
AndrographisPhytoBank
Andrographiside aglyconPhytoBank
AndrographolidPhytoBank
Chemical FormulaC20H30O5
Average Molecular Mass350.455 g/mol
Monoisotopic Mass350.209 g/mol
CAS Registry Number5508-58-7
IUPAC Name(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
Traditional Name(3E,4S)-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]ethylidene}-4-hydroxyoxolan-2-one
SMILES[H]\C(C[C@]1([H])C(=C)CC[C@]2([H])[C@](C)(CO)[C@]([H])(O)CC[C@@]12C)=C1/C(=O)OC[C@@]1([H])O
InChI IdentifierInChI=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 KeyBOJKULTULYSRAS-OTESTREVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
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
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.28 g/LALOGPS
logP1.57ALOGPS
logP1.66ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)13.48ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity94.93 m³·mol⁻¹ChemAxon
Polarizability38.31 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f89-0019000000-ff2f9c9f0fd8276fc1c3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00lr-0294000000-742cbb13e8f32e3df8d5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-02t9-1791000000-1dcc78d4fd79a42d2409Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0009000000-6fab8fd176ce3be51828Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ku2-1039000000-5f4277e95ecebeef0cd1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05dl-5092000000-6566c7bfb33d17b2318dNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
226.0Log mg/kg[130:400]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
inflammationhas_therapeutic_effect_onNot AvailablePMC11086401 , PMC5695812
Exposure Sources
Source IDSourceSectorReference
505AmplifiersElectrical & Electronic EquipmentNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
634BucklesTextiles, leather & furnishingsNot Available
649Pins ClothesTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Bile acid receptor structureClick to view 3D structureBile acid receptorQ96RI1HumansPredicted (SEA)24.6782
Signal transducer and activator of transcription 3 structureClick to view 3D structureSignal transducer and activator of transcription 3P40763HumansPredicted (SEA)6.53933
Fatty acid-binding protein, adipocyte structureClick to view 3D structureFatty acid-binding protein, adipocyteP15090HumansPredicted (SEA)12.5337
Tyrosine-protein phosphatase non-receptor type 1 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 1P18031HumansPredicted (SEA)774.288
G-protein coupled bile acid receptor 1 structureClick to view 3D structureG-protein coupled bile acid receptor 1Q8TDU6HumansPredicted (SEA)330.781
Click to view 3D structureCMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1P54751Mus musculusPredicted (SEA)6.61718
Click to view 3D structureVitamin D3 receptorP13053Rattus norvegicusPredicted (SEA)7.31783
Vitamin D3 receptor structureClick to view 3D structureVitamin D3 receptorP11473HumansPredicted (SEA)439.77
Click to view 3D structureAndrogen receptorP15207Rattus norvegicusPredicted (SEA)225.607
Sex hormone-binding globulin structureClick to view 3D structureSex hormone-binding globulinP04278HumansPredicted (SEA)49.8235
Corticosteroid-binding globulin structureClick to view 3D structureCorticosteroid-binding globulinP08185HumansPredicted (SEA)36.5891
Click to view 3D structureProgesterone receptorQ690N0Bos taurusPredicted (SEA)71.0763
Androgen receptor structureClick to view 3D structureAndrogen receptorP10275HumansPredicted (SEA)1999.79
Click to view 3D structureVitamin D3 receptorO42392Gallus gallusPredicted (SEA)10.1204
Solute carrier organic anion transporter family member 1B1 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B1Q9Y6L6HumansPredicted (SEA)1079.38
Aldo-keto reductase family 1 member B10 structureClick to view 3D structureAldo-keto reductase family 1 member B10O60218HumansPredicted (SEA)643.268
Mineralocorticoid receptor structureClick to view 3D structureMineralocorticoid receptorP08235HumansPredicted (SEA)899.47
Ferritin heavy chain structureClick to view 3D structureFerritin heavy chainP02794HumansPredicted (SEA)0.700643
Click to view 3D structureVitamin D3 receptor AQ9PTN2Danio rerioPredicted (SEA)8.64126
Click to view 3D structureAndrogen receptorP19091Mus musculusPredicted (SEA)158.267
3-oxo-5-alpha-steroid 4-dehydrogenase 2 structureClick to view 3D structure3-oxo-5-alpha-steroid 4-dehydrogenase 2P31213HumansPredicted (SEA)65.7047
Click to view 3D structureSolute carrier family 22 member 3O88446Rattus norvegicusPredicted (SEA)24.1333
Click to view 3D structureVitamin D3 receptorA3RGC1Sus scrofaPredicted (SEA)12.0666
Vitamin D-binding protein structureClick to view 3D structureVitamin D-binding proteinP02774HumansPredicted (SEA)12.0666
Glucocorticoid receptor structureClick to view 3D structureGlucocorticoid receptorP04150HumansPredicted (SEA)2257.16
Concentrations
Not Available
External Links
DrugBank IDDB05767
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00023362
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAndrographolide
Chemspider IDNot Available
ChEBI ID65408
PubChem Compound IDNot Available
Kegg Compound IDC20214
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15894448
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18464090
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19110075
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22026410
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22512591
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22858223