Showing Compound Lactucin (FDB014575)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:21 UTC

Update date

2019-11-26 03:10:21 UTC

Primary ID

FDB014575

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Lactucin

Description

Lactucin belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Lactucin has been detected, but not quantified in, several different foods, such as robusta coffees (Coffea canephora), green vegetables, coffee and coffee products, arabica coffees (Coffea arabica), and herbs and spices. This could make lactucin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Lactucin.

CAS Number

1891-29-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
11beta,13-Dihydrolactucin	HMDB
Lactucin	MeSH

Predicted Properties

Property	Value	Source
Water Solubility	6.84 g/L	ALOGPS
logP	-0.28	ALOGPS
logP	-0.018	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	13	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.87 m³·mol⁻¹	ChemAxon
Polarizability	27.92 Å³	ChemAxon
Number of Rings	3	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

C15H16O5

IUPAC name

4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

InChI Identifier

InChI=1S/C15H16O5/c1-6-3-9(17)12-7(2)15(19)20-14(12)13-8(5-16)4-10(18)11(6)13/h4,9,12-14,16-17H,2-3,5H2,1H3

InChI Key

VJQAFLAZRVKAKM-UHFFFAOYSA-N

Isomeric SMILES

CC1=C2C(C3OC(=O)C(=C)C3C(O)C1)C(CO)=CC2=O

Average Molecular Weight

276.288

Monoisotopic Molecular Weight

276.099773615

Classification

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Ketone
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Carbonyl group
Primary alcohol
Organooxygen compound
Organic oxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Coffea

Biological location:

Subcellular:

Cell and elements:

Extracellular

Process

Naturally occurring process:

Biological process:

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 65.21%; H 5.84%; O 28.95%	DFC
Melting Point	Mp 224-228°	DFC
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 +49 (c, 0.9 in MeOH)	DFC
Spectroscopic UV Data	[neutral] lmax 257 (e 14000) (EtOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Lactucin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052b-5790000000-b95d08ba5457bf6b2069	Spectrum
Predicted GC-MS	Lactucin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ab9-2139000000-fe4b945f22fd4dcc8988	Spectrum
Predicted GC-MS	Lactucin, 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	splash10-0a6r-0090000000-adba28495fd27a848006	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052u-0490000000-fb65751d00ebf7cfc048	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f76-5950000000-cc2ba0ae124168adaaa1	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-aa9e3a2cce7827efdc3a	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-057i-0090000000-48ae893a3deee473fadb	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-2910000000-9062473d504431458708	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-5eee9e278d85992a4bc3	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6u-0090000000-a5e6ac486e245f455cda	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00bd-0960000000-d62be5c7a1ff74131be2	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-aa99d0f367d18fe63c0c	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a6r-0090000000-9caf2622ff8214727496	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004r-0290000000-3d238649ddfe7d1c32b0	Spectrum

NMR

Not Available

External Links

ChemSpider ID

2985716

ChEMBL ID

Not Available

KEGG Compound ID

C09489

Pubchem Compound ID

3756497

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB35814

CRC / DFC (Dictionary of Food Compounds) ID

JFR52-Z:JSS68-A

EAFUS ID

Not Available

Dr. Duke ID

LACTUCIN

BIGG ID

Not Available

KNApSAcK ID

C00003311

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

Lactucin

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
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
bitter			DUKE
central nervous system depressant	35470	A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.	DUKE
cytotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE
sedative	35717	A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.	DUKE
tonic			DUKE