Showing Compound Laurenobiolide (FDB015713)

Record Information

Version

1.0

Creation date

2010-04-08 22:12:00 UTC

Update date

2019-11-26 03:12:05 UTC

Primary ID

FDB015713

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Laurenobiolide

Description

Laurenobiolide 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. Based on a literature review a significant number of articles have been published on Laurenobiolide.

CAS Number

35001-25-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Showing 1 to 3 of 3 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.083 g/L	ALOGPS
logP	3.31	ALOGPS
logP	2.91	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	6.21	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	80.67 m³·mol⁻¹	ChemAxon
Polarizability	30.89 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C17H22O4

IUPAC name

6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,7H,8H,11H,11aH-cyclodeca[b]furan-4-yl acetate

InChI Identifier

InChI=1S/C17H22O4/c1-10-6-5-7-11(2)9-15-16(12(3)17(19)21-15)14(8-10)20-13(4)18/h7-8,14-16H,3,5-6,9H2,1-2,4H3/b10-8-,11-7-

InChI Key

ORJVLIMAQARNOU-ACBQZUGDSA-N

Isomeric SMILES

CC(=O)OC1\C=C(C)/CC\C=C(C)/CC2OC(=O)C(=C)C12

Average Molecular Weight

290.3542

Monoisotopic Molecular Weight

290.151809192

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.

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
Dicarboxylic acid or derivatives
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 70.32%; H 7.64%; O 22.04%	DFC
Melting Point	Mp 101-103°	DFC
Optical Rotation	[a]D +17.1 (EtOH)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Laurenobiolide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001l-7290000000-42f5680cc8ce8d9d3bbc	Spectrum
Predicted GC-MS	Laurenobiolide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0090000000-5dd05d95f16c803a4875	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-003s-1690000000-603db850d843dbf236f2	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ftf-9840000000-ddd7810d621ff43e3546	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000j-0090000000-0c6ee6f48041152fa721	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000b-2090000000-be7ce9b54e80ed94245f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kfx-8940000000-c75c9d4e3c2cbee283e2	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9030000000-fbea22a3cc95a5df97e1	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9050000000-6e0edae293cab189749e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9010000000-f6230ad3cc97ec27ad71	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000t-0090000000-50e71a036f2205e62edc	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0290000000-36acec79491d6a3126f9	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ae9-1590000000-98ce2e8a788e952c73c4	2021-09-23	View Spectrum