Record Information
Version1.0
Creation date2010-04-08 22:06:48 UTC
Update date2019-11-26 03:00:43 UTC
Primary IDFDB005709
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameArgophyllin A
DescriptionArgophyllin a belongs to germacranolides and derivatives class of compounds. Those are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Argophyllin a is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Argophyllin a can be found in sunflower, which makes argophyllin a a potential biomarker for the consumption of this food product.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
Predicted Properties
PropertyValueSource
Water Solubility1.7 g/LALOGPS
logP1.12ALOGPS
logP1.35ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)13.65ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area105.59 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity96.4 m³·mol⁻¹ChemAxon
Polarizability38.65 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H28O7
IUPAC name(1S,2R,4R,6R,8S,11R)-8,9-dihydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradecan-2-yl (2Z)-2-methylbut-2-enoate
InChI IdentifierInChI=1S/C20H28O7/c1-6-10(2)17(22)25-13-9-20(5)15(27-20)7-14(21)19(4,24)8-12-16(13)11(3)18(23)26-12/h6,12-16,21,24H,3,7-9H2,1-2,4-5H3/b10-6-/t12-,13-,14+,15-,16+,19+,20+/m1/s1
InChI KeyOFNWVOIJEOVYPP-CFUPXWRKSA-N
Isomeric SMILESC\C=C(\C)C(=O)O[C@@H]1C[C@@]2(C)O[C@@H]2C[C@H](O)C(C)(O)C[C@H]2OC(=O)C(=C)[C@H]12
Average Molecular Weight380.4321
Monoisotopic Molecular Weight380.18350325
Classification
Description Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentGermacranolides and derivatives
Alternative Parents
Substituents
  • Germacranolide
  • Sesquiterpenoid
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Fatty acyl
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Tertiary alcohol
  • 1,2-diol
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Oxacycle
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-2029000000-df1dafc7ccb375f0a3a0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-9085000000-4f1feff746571442d6e9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-9030000000-098504adee80c7002972Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0019000000-7a6efcf680b002aa15e3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06vs-5049000000-bab6a9d173f74f2be9a9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fdk-9350000000-4709d31fba74092e9160Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDARGOPHYLLIN-A|AGROPHYLLIN-A
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti feedantDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. Keisuke Watanabe et al., “Sesquiterpene lactones and diterpenoids from Helianthus argophyllus,” Phytochemistry 21, no. 3 (1982): 709-713. Article [Isolation]
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).