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Showing Compound Arctiopicrin (FDB001526)

Record Information
Version1.0
Creation date2010-04-08 22:05:00 UTC
Update date2019-11-26 02:56:34 UTC
Primary IDFDB001526
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameArctiopicrin
DescriptionArctiopicrin 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. Arctiopicrin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Arctiopicrin can be found in burdock, which makes arctiopicrin a potential biomarker for the consumption of this food product.
CAS Number19889-01-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Arctiopicrinebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.48 g/LALOGPS
logP1.53ALOGPS
logP1.59ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)6.19ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity93.42 m³·mol⁻¹ChemAxon
Polarizability36.35 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC19H26O6
IUPAC name(3aR,4S,11aR)-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl 3-hydroxy-2-methylpropanoate
InChI IdentifierInChI=1S/C19H26O6/c1-11-5-4-6-14(10-21)8-16-17(13(3)19(23)25-16)15(7-11)24-18(22)12(2)9-20/h5,8,12,15-17,20-21H,3-4,6-7,9-10H2,1-2H3/b11-5+,14-8-/t12?,15-,16+,17+/m0/s1
InChI KeyVOOFFTMORIBISQ-UMRVURNHSA-N
Isomeric SMILESCC(CO)C(=O)O[C@H]1C\C(C)=C\CC\C(CO)=C\[C@H]2OC(=O)C(=C)[C@H]12
Average Molecular Weight350.4061
Monoisotopic Molecular Weight350.172938564
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
  • Germacrane sesquiterpenoid
  • Sesquiterpenoid
  • Beta-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Hydroxy acid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Lactone
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water Solubility2 mg/mL at 25 oCBEILSTEIN
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, Positivesplash10-0f89-2039000000-68c42594e4b85bd072bc2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ns-6197000000-e93d0da833f4bb338a3e2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-9110000000-d5cd0917bfa8221b6edc2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0019000000-9f11535b555d9419b4e52016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pwa-4159000000-cab34407a76bf2e6749c2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbi-5930000000-0035e2e8f0c39f71f7fd2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-ec632ef45f55ea86b2c72021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-9aea08757b7861de4ebd2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-4090000000-e0691aedac3acf6bd88f2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000j-9232000000-7f20cecc951b6e6d58602021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dr-9010000000-5b615e6bc4cc8f907e642021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mk-4090000000-bfdd537bdd238ce9c5bc2021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC09297
Pubchem Compound ID5281423
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 IDARCTIOPICRIN
BIGG IDNot Available
KNApSAcK IDC00003215
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
Antibiotic22582 An agent that inhibits the growth of or destroys microorganisms, particularly bacteria. Therapeutically, antibiotics are used to treat bacterial infections, such as pneumonia, tuberculosis, and skin infections, by targeting specific biochemical processes essential for microbial survival.DUKE
BitterA taste receptor stimulant, bitter substances play a biological role in toxin detection and expulsion. Therapeutically, they stimulate digestion and appetite. Key medical uses includeDUKE
Gram(+)icide33282 An agent that targets and kills Gram-positive bacteria, playing a crucial role in treating bacterial infections. Therapeutically, it is used to combat infections caused by Gram-positive microorganisms, with key medical applications including treating skin infections, pneumonia, and sepsis.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.