Showing Compound Ligustilide (FDB012613)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:16 UTC

Update date

2019-11-26 03:07:12 UTC

Primary ID

FDB012613

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Ligustilide

Description

Ligustilide belongs to the class of organic compounds known as isobenzofurans. These are organic aromatic compounds containing an isobenzofuran moiety. Ligustilide is found, on average, in the highest concentration within wild celeries (Apium graveolens). Ligustilide has also been detected, but not quantified in, a few different foods, such as celery stalks (Apium graveolens var. dulce), herbs and spices, and lovages (Levisticum officinale). This could make ligustilide a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Ligustilide.

CAS Number

4431-01-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(e)-Ligustilide	HMDB
3-Butylidene-4,5-dihydro-1(3H)-isobenzofuranone, 9ci	HMDB
3-Butylidene-4,5-dihydrophthalide, 8ci	HMDB
Z-Ligustilide	MeSH
Ligustilide, (e)-isomer	MeSH
Ligustilide, (Z)-isomer	MeSH
Ligustilide	MeSH
(E)-Ligustilide	biospider
3-Butylidene-4,5-dihydro-1(3H)-isobenzofuranone, 9CI	db_source
3-Butylidene-4,5-dihydrophthalide, 8CI	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.5 g/L	ALOGPS
logP	3.48	ALOGPS
logP	2.73	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	58.04 m³·mol⁻¹	ChemAxon
Polarizability	21.14 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C12H14O2

IUPAC name

(3E)-3-butylidene-1,3,4,5-tetrahydro-2-benzofuran-1-one

InChI Identifier

InChI=1S/C12H14O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h5,7-8H,2-4,6H2,1H3/b11-8+

InChI Key

IQVQXVFMNOFTMU-DHZHZOJOSA-N

Isomeric SMILES

CCC\C=C1\OC(=O)C2=C1CCC=C2

Average Molecular Weight

190.2384

Monoisotopic Molecular Weight

190.099379692

Classification

Description

Belongs to the class of organic compounds known as isobenzofurans. These are organic aromatic compounds containing an isobenzofuran moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isobenzofurans

Sub Class

Not Available

Direct Parent

Isobenzofurans

Alternative Parents

Substituents

Isobenzofuran
2-furanone
Dihydrofuran
Enol ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Source:

Food

Biological:

Plant

Role

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 75.76%; H 7.42%; O 16.82%	DFC
Melting Point	Not Available
Boiling Point	Bp6 168-169°	DFC
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	[neutral] lmax 320 (e 2400) (MeOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Ligustilide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004l-6900000000-19a1ca647a7e0491d8e1	Spectrum
Predicted GC-MS	Ligustilide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ligustilide, 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	splash10-0006-3900000000-df63f7ba708218730e1c	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-6900000000-bb0e90d13b2a41a2f252	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zi3-9100000000-a8552493184912c22439	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-da55f68b7672778c6684	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000j-1900000000-b2cafbc59a05197f25e3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004l-8900000000-fc5da55ccfb2f546ca15	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-02c830ea56178823e129	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000g-1900000000-ca00aa40e89649e134d3	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00or-9100000000-883a9cc29d1cd4ed674d	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-f778b0a41733b7c667b1	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-ce781099c44f51da042b	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05s1-3900000000-1cb74a6387e3878f4f59	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4731467

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

5877292

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB34277

CRC / DFC (Dictionary of Food Compounds) ID

DWL20-L:HJK13-L

EAFUS ID

Not Available

Dr. Duke ID

LIGUSTILIDE|TRANS-LIGUSTILIDE|E-LIGUSTILIDE

BIGG ID

Not Available

KNApSAcK ID

Not Available

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

HJK13-L:HJK13-L

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti arrhythmic	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
anti asthmatic	49167	A drug used to treat asthma.	DUKE
anti constrictive	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti prostaglandin	49020	A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.	DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
myorelaxant			DUKE
tracheorelaxant			DUKE