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Showing Compound Sorgolactone (FDB019234)

Record Information
Version1.0
Creation date2010-04-08 22:14:13 UTC
Update date2019-11-26 03:17:16 UTC
Primary IDFDB019234
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSorgolactone
DescriptionIsolated from the roots of Sorghum bicolor (sorghum) (genuine host plant for Striga subspecies) Strigolactones are plant hormones that have been implicated in inhibition of shoot branching. Strigolactones are carotenoid-derived and trigger germination of parasitic plant seeds (for example striga from which they gained their name) and stimulate symbiotic mycorrhizal fungi. Strigolactones contain a labile ether bond that is easily hydrolysed in the rhizosphere meaning that there is a large concentration gradient between areas near the root and those further away. Sorgolactone is found in cereals and cereal products and sorghum.
CAS Number141262-39-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.088 g/LALOGPS
logP2.84ALOGPS
logP3.28ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)15.2ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area61.83 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity82.88 m³·mol⁻¹ChemAxon
Polarizability33.59 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H20O5
IUPAC name3-methyl-5-{[(3Z)-8-methyl-2-oxo-2H,3H,3aH,4H,5H,6H,7H,8H,8bH-indeno[1,2-b]furan-3-ylidene]methoxy}-2,5-dihydrofuran-2-one
InChI IdentifierInChI=1S/C18H20O5/c1-9-4-3-5-11-7-12-13(18(20)23-16(12)15(9)11)8-21-14-6-10(2)17(19)22-14/h6,8-9,12,14,16H,3-5,7H2,1-2H3/b13-8-
InChI KeyKHSREFIWULNDAB-JYRVWZFOSA-N
Isomeric SMILESCC1CCCC2=C1C1OC(=O)\C(=C/OC3OC(=O)C(C)=C3)C1C2
Average Molecular Weight316.3484
Monoisotopic Molecular Weight316.13107375
Classification
Description Belongs to the class of organic compounds known as strigolactones. These are terpene lactones structurally characterized by the presence of an indeno[1,2-b]furan and a 2,5-dihydrofuran-2-one linked together to form a 3-methyl-5-{8-methyl-2-oxo-indeno[1,2-b]furan-3-ylidene]methoxy}-2,5-dihydrofuran-2-one skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentStrigolactones
Alternative Parents
Substituents
  • Strigolactone
  • 2-furanone
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Dihydrofuran
  • Vinylogous ester
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Lactone
  • Oxacycle
  • Acetal
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSSorgolactone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fk9-7790000000-be3cc93ca40e046dc606Spectrum
Predicted GC-MSSorgolactone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSorgolactone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxu-1393000000-f5919a1eec109b201d5c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-8690000000-32e64c360041dac420032016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9310000000-8a106779cf7ce5e88f812016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3296000000-3d3649a1f8a9f6899f802016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03y1-9871000000-5553b98954c3474206962016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000b-9410000000-59c100dcaa69de274e872016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0129000000-c6bcafcc571e7c92bebc2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1191000000-8d98d394275ffde0f4682021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-029i-7960000000-ae0e38fa02a3301d40162021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0039000000-fd450661b5cb073f69942021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-4296000000-b6ddf7c157ae44be19862021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003r-2950000000-43868db7aa53b7ecf0722021-09-25View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC09186
Pubchem Compound ID5281395
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB39607
CRC / DFC (Dictionary of Food Compounds) IDLVS95-X:LVS95-X
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00003483
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDSorgolactone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.