Andrographolide (CHEM018679)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:26:40 UTC
Update Date2016-11-09 01:15:51 UTC
Accession NumberCHEM018679
Identification
Common NameAndrographolide
ClassSmall Molecule
DescriptionA labdane diterpenoid isolated from the leaves and roots of Andrographis paniculata that exhibits anti-HIV, anti-inflammatory and antineoplastic properties.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0019000000-ff2f9c9f0fd8276fc1c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-0294000000-742cbb13e8f32e3df8d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02t9-1791000000-1dcc78d4fd79a42d2409Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-6fab8fd176ce3be51828Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ku2-1039000000-5f4277e95ecebeef0cd1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05dl-5092000000-6566c7bfb33d17b2318dSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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