ContaminantDB: Cichoralexin

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

Record Information

Version

1.0

Creation Date

2016-05-26 02:03:25 UTC

Update Date

2016-11-09 01:19:07 UTC

Accession Number

CHEM030651

Identification

Common Name

Cichoralexin

Class

Small Molecule

Description

Cichoralexin is found in chicory. Cichoralexin is a constituent of Cichorium intybus (chicory) inoculated with Pseudomonas cichorii.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Carpesia lactone	HMDB

Chemical Formula

C₁₅H₂₀O₃

Average Molecular Mass

248.318 g/mol

Monoisotopic Mass

248.141 g/mol

CAS Registry Number

132296-37-8

IUPAC Name

3,6,9-trimethyl-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

Traditional Name

3,6,9-trimethyl-3H,3aH,4H,5H,6H,6aH,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

SMILES

CC1C2CCC(C)C3C(C2OC1=O)C(C)=CC3=O

InChI Identifier

InChI=1S/C15H20O3/c1-7-4-5-10-9(3)15(17)18-14(10)13-8(2)6-11(16)12(7)13/h6-7,9-10,12-14H,4-5H2,1-3H3

InChI Key

FJKWKEZAHVWIOR-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Guaiane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Organic oxygen 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	0.28 g/L	ALOGPS
logP	2.23	ALOGPS
logP	2.66	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	15.91	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.11 m³·mol⁻¹	ChemAxon
Polarizability	27.44 Å³	ChemAxon
Number of Rings	3	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	splash10-0fi0-9870000000-22437ede758350e45b6b	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	splash10-0002-0290000000-702a995926cd99706c4e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0032-1970000000-f6a95e91013309674f64	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9800000000-455f1856d23ce7f26a21	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-b8579944992ae1b57404	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6t-0190000000-8c513e252a133fddb263	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-114j-5910000000-72fabb7f1c1e5687c146	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-717909ee4df9ba3b89f8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0190000000-c41d861087afed3c0ac9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00bd-2960000000-bede17322bf322bf9fbf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-fab2e65b71aa23cc527f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001j-0390000000-503406b32624c89fe436	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-8910000000-b4a45e473036a835b788	Spectrum