Showing Compound Desacetyllaurenobiolide (FDB015712)

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

FDB015712

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Desacetyllaurenobiolide

Description

Desacetyllaurenobiolide 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 small amount of articles have been published on Desacetyllaurenobiolide.

CAS Number

35001-24-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Chamissellin	HMDB
Deacetyllaurenobiolide	HMDB
Desacetyllaurenobiolide	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.72 g/L	ALOGPS
logP	2.45	ALOGPS
logP	2.47	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	6.62	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.52 m³·mol⁻¹	ChemAxon
Polarizability	26.78 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

C15H20O3

IUPAC name

4-hydroxy-6,10-dimethyl-3-methylidene-2H,3H,3aH,4H,7H,8H,11H,11aH-cyclodeca[b]furan-2-one

InChI Identifier

InChI=1S/C15H20O3/c1-9-5-4-6-10(2)8-13-14(12(16)7-9)11(3)15(17)18-13/h6-7,12-14,16H,3-5,8H2,1-2H3/b9-7-,10-6-

InChI Key

FRDLPOYYWWRSPZ-ZVEIMFCASA-N

Isomeric SMILES

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

Average Molecular Weight

248.3175

Monoisotopic Molecular Weight

248.141244506

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
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Alcohol
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 - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 72.55%; H 8.12%; O 19.33%	DFC
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]D +34.5 (c, 1.6 in CHCl3)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Desacetyllaurenobiolide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-9660000000-8c0c3ca8ca0a5980b822	Spectrum
Predicted GC-MS	Desacetyllaurenobiolide, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00bi-9042000000-ebf37e82b027d2dc9094	Spectrum
Predicted GC-MS	Desacetyllaurenobiolide, 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	splash10-001j-0190000000-b79f474eaa2b9ff09b73	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-053s-0790000000-5c61fe4f2045f5bade24	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gi3-9810000000-8555d8eaa3f10dbff010	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-379da8138a34c28b0659	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f92-0190000000-8a15f17be4738bc36dd5	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00r6-9410000000-533d56c2d7e164eebcc3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-7b3a58b796a0e4263959	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002b-0190000000-9f898299397f1c67c215	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0200-5890000000-48077b22a9ae77218d24	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-b1efe9307de63f05c06f	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000t-0390000000-4ede3bf6f793e6b7a0a4	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-0920000000-8e3849ce524657df3ca1	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB36770

CRC / DFC (Dictionary of Food Compounds) ID

KGM36-Q:KGM37-R

EAFUS ID

Not Available

Dr. Duke ID

DESACETYLLAURENOBIOLIDE|DEACETYLLAURENOBIOLIDE

BIGG ID

Not Available

KNApSAcK ID

C00012386

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files