ContaminantDB: Sorgolactone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 03:48:37 UTC

Update Date

2016-11-09 01:20:49 UTC

Accession Number

CHEM032931

Identification

Common Name

Sorgolactone

Class

Small Molecule

Description

Sorgolactone is found in cereals and cereal products. Sorgolactone is isolated from the roots of Sorghum bicolor (sorghum) (genuine host plant for Striga species) 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.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₁₈H₂₀O₅

Average Molecular Mass

316.348 g/mol

Monoisotopic Mass

316.131 g/mol

CAS Registry Number

141262-39-7

IUPAC Name

3-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

Traditional Name

3-methyl-5-{[(3Z)-8-methyl-2-oxo-3aH,4H,5H,6H,7H,8H,8bH-indeno[1,2-b]furan-3-ylidene]methoxy}-5H-furan-2-one

SMILES

CC1CCCC2=C1C1OC(=O)\C(=C/OC3OC(=O)C(C)=C3)C1C2

InChI Identifier

InChI=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 Key

KHSREFIWULNDAB-JYRVWZFOSA-N

Chemical Taxonomy

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Strigolactones

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 Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.088 g/L	ALOGPS
logP	2.84	ALOGPS
logP	3.28	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	15.2	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	82.88 m³·mol⁻¹	ChemAxon
Polarizability	33.59 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fk9-7790000000-be3cc93ca40e046dc606	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uxu-1393000000-f5919a1eec109b201d5c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-8690000000-32e64c360041dac42003	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9310000000-8a106779cf7ce5e88f81	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-3296000000-3d3649a1f8a9f6899f80	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03y1-9871000000-5553b98954c347420696	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000b-9410000000-59c100dcaa69de274e87	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0129000000-c6bcafcc571e7c92bebc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1191000000-8d98d394275ffde0f468	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-029i-7960000000-ae0e38fa02a3301d4016	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0039000000-fd450661b5cb073f6994	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-4296000000-b6ddf7c157ae44be1986	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-003r-2950000000-43868db7aa53b7ecf072	Spectrum