Showing Compound Toralactone (FDB017935)

Record Information

Version

1.0

Creation date

2010-04-08 22:13:24 UTC

Update date

2019-11-26 03:15:28 UTC

Primary ID

FDB017935

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Toralactone

Description

Toralactone belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. Toralactone has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, herbs and spices, pulses, and robusta coffees (Coffea canephora). This could make toralactone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Toralactone.

CAS Number

41743-74-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
9,10-Dihydroxy-7-methoxy-3-methyl-1H-naphtho(2,3-c)pyran-1-one	ChEBI
9,10-Dihydroxy-7-methoxy-3-methyl-1H-naphtho[2,3-c]pyran-1-one, 9ci	HMDB
9,10-Dihydroxy-7-methoxy-3-methyl-1H-naphtho[2,3-c]pyran-1-one, 9CI	db_source

Showing 1 to 3 of 3 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.13 g/L	ALOGPS
logP	2.68	ALOGPS
logP	3.13	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	8.45	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.18 m³·mol⁻¹	ChemAxon
Polarizability	27.48 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

C15H12O5

IUPAC name

9,10-dihydroxy-7-methoxy-3-methyl-1H-benzo[g]isochromen-1-one

InChI Identifier

InChI=1S/C15H12O5/c1-7-3-8-4-9-5-10(19-2)6-11(16)12(9)14(17)13(8)15(18)20-7/h3-6,16-17H,1-2H3

InChI Key

WEHXAEGTVPWKDY-UHFFFAOYSA-N

Isomeric SMILES

COC1=CC(O)=C2C(O)=C3C(=O)OC(C)=CC3=CC2=C1

Average Molecular Weight

272.2528

Monoisotopic Molecular Weight

272.068473494

Classification

Description

Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
Isocoumarin
1-naphthol
Benzopyran
Naphthalene
2-benzopyran
Anisole
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Lactone
Ether
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:78029 )
organic heterotricyclic compound (CHEBI:78029 )
phenols (CHEBI:78029 )
polyketide (CHEBI:78029 )
lactone (CHEBI:78029 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Source:

Food

Nutrient

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 66.17%; H 4.44%; O 29.38%	DFC
Melting Point	Mp 252-254°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Toralactone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0abc-0190000000-0b6644937e0069cfba34	Spectrum
Predicted GC-MS	Toralactone, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0uk9-2009400000-28388824cb8fdaf3e748	Spectrum
Predicted GC-MS	Toralactone, 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	splash10-00di-0090000000-af0e4aa15b772877e705	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0090000000-67a31feccf2de0c2d09c	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002b-0890000000-b766d9ba09c1aa5c07ac	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-a304bd0b8e4313937885	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0090000000-b199e2cdf9b618446ccb	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004j-1980000000-284d4a71b00b8c9cc8c5	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0090000000-031a5312b116bdf1aa4a	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0090000000-e8cad39c3f9c861b9b61	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fi9-0490000000-d32339d75f0f0ea86780	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-d6b6f6391b4e9f4522f4	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0090000000-d6b6f6391b4e9f4522f4	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dj-3970000000-0694d792101fade0dd10	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4479581

ChEMBL ID

Not Available

KEGG Compound ID

C17673

Pubchem Compound ID

5321980

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB38549

CRC / DFC (Dictionary of Food Compounds) ID

LCB72-E:LCB72-E

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

C00032364

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

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Food	Content Range	Average	Reference

Arabica coffee	Expected but not quantified	Not Available	DFC CODES
Robusta coffee	Expected but not quantified	Not Available	DFC CODES

Showing 1 to 2 of 2 entries

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Toralactone (FDB017935)

Structure for FDB017935 (Toralactone)