Survey with prize
Record Information
Version1.0
Creation date2010-04-08 22:11:57 UTC
Update date2019-11-26 03:11:58 UTC
Primary IDFDB015628
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameArgophyllin B
DescriptionArgophyllin B 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. Argophyllin B is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number81686-18-2
Structure
Thumb
Synonyms
SynonymSource
Argophyllin Bdb_source
Predicted Properties
PropertyValueSource
Water Solubility1.82 g/LALOGPS
logP0.83ALOGPS
logP1.18ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)14.69ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area105.59 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity96.75 m³·mol⁻¹ChemAxon
Polarizability38.88 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H28O7
IUPAC name(1S,2R,4R,6R,8S,9S,11R)-8-hydroxy-9-(hydroxymethyl)-4-methyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradecan-2-yl (2Z)-2-methylbut-2-enoate
InChI IdentifierInChI=1S/C20H28O7/c1-5-10(2)18(23)26-15-8-20(4)16(27-20)7-13(22)12(9-21)6-14-17(15)11(3)19(24)25-14/h5,12-17,21-22H,3,6-9H2,1-2,4H3/b10-5-/t12-,13-,14+,15+,16+,17-,20-/m0/s1
InChI KeyFWOAAAUYUVVHOD-FYYQHIOXSA-N
Isomeric SMILESC\C=C(\C)C(=O)O[C@@H]1C[C@@]2(C)O[C@@H]2C[C@H](O)[C@H](CO)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
  • Tetrahydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Oxacycle
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Primary alcohol
  • Alcohol
  • 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 CompositionC 63.14%; H 7.42%; O 29.44%DFC
Melting PointMp 63-69°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]22D -137.5 (c, 0.14 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-1029000000-6ec013e0b7994bd23777JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01qa-7089000000-2b59810b803f83a0d62fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-9030000000-f1183e96a144e42eccb0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0019000000-ab0a909e34b014cda4a4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ot-3029000000-8a2a9bd8aff5a02dd730JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kft-9451000000-b173fca9c7bab32502baJSpectraViewer
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) IDHNB36-D:KFF24-V
EAFUS IDNot Available
Dr. Duke IDARGOPHYLLIN-B|AGROPHYLLIN-B
BIGG IDNot Available
KNApSAcK IDC00012152
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).