ContaminantDB: Eucannabinolide

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

Record Information

Version

1.0

Creation Date

2016-05-26 01:50:15 UTC

Update Date

2016-11-09 01:19:03 UTC

Accession Number

CHEM030349

Identification

Common Name

Eucannabinolide

Class

Small Molecule

Description

Not Available

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
9-(Acetyloxy)-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-4-yl (2E)-4-hydroxy-2-(hydroxymethyl)but-2-enoic acid	Generator

Chemical Formula

C₂₂H₂₈O₈

Average Molecular Mass

420.453 g/mol

Monoisotopic Mass

420.178 g/mol

CAS Registry Number

38458-58-1

IUPAC Name

9-(acetyloxy)-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate

Traditional Name

9-(acetyloxy)-6,10-dimethyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate

SMILES

CC(=O)OC1C\C=C(C)\CC(OC(=O)C(\CO)=C\CO)C2C(OC(=O)C2=C)\C=C1/C

InChI Identifier

InChI=1S/C22H28O8/c1-12-5-6-17(28-15(4)25)13(2)10-19-20(14(3)21(26)29-19)18(9-12)30-22(27)16(11-24)7-8-23/h5,7,10,17-20,23-24H,3,6,8-9,11H2,1-2,4H3/b12-5+,13-10+,16-7+

InChI Key

XYPJAWWDSQFSQA-VISQRNLASA-N

Chemical Taxonomy

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Tricarboxylic acid or derivatives
Beta-hydroxy acid
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Hydroxy acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Primary alcohol
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	0.072 g/L	ALOGPS
logP	1.59	ALOGPS
logP	1.33	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	6.18	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	109.56 m³·mol⁻¹	ChemAxon
Polarizability	43.3 Å³	ChemAxon
Number of Rings	2	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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uki-0119700000-1c2a8dffe33e051d0d76	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000g-9126100000-1ffa3a1e0d98234171c0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9332000000-b0964192ade452b23c5f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0699-0009500000-be96c6fba2419512fd41	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-5009100000-b5973438f6ad7c467c26	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052r-9746000000-11c7a77e35cdbff83d09	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0091100000-4840a93a091cd1f3028a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002b-3092000000-35aae8077d997e5f698c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004j-5190000000-bc6c6245a3a24082637d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0bt9-2419300000-e78f461a8ad3eddcdaf2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-7063219681014e6db905	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-c4ec8bef9b894487e6b9	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0303565

FooDB ID

FDB015620

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

54600668

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Eucannabinolide (CHEM030349)

Structure for CHEM030349: Eucannabinolide