Showing Compound Lucernol (FDB012284)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:05 UTC

Update date

2019-11-26 03:06:31 UTC

Primary ID

FDB012284

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Lucernol

Description

Lucernol belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Thus, lucernol is considered to be a flavonoid. Lucernol has been detected, but not quantified in, alfalfas (Medicago sativa) and pulses. This could make lucernol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Lucernol.

CAS Number

15402-22-9

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

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Synonym	Source
2,3,9-Trihydroxy-6H-benzofuro(3,2-c)(1)benzopyran-6-one	HMDB
2,3,9-Trihydroxy-6H-benzofuro[3,2-c][1]benzopyran-6-one, 9ci	HMDB
2,3,9-Trihydroxy-6H-benzofuro[3,2-c][1]benzopyran-6-one, 9CI	db_source
2,3-Dimethoxy-alpha-methyl-benzeneethanamine	HMDB
6,7,12-Trihydroxycoumestan	HMDB
6H-Benzofuro(3,2-c)(1)benzopyran-6-one, 2,3,9-trihydroxy-	biospider
Benzeneethanamine, 2,3-dimethoxy-alpha-methyl-	biospider
Lucernol	db_source

Showing 1 to 8 of 8 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.79 g/L	ALOGPS
logP	2.68	ALOGPS
logP	2.09	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.22	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.13 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.6 m³·mol⁻¹	ChemAxon
Polarizability	27.39 Å³	ChemAxon
Number of Rings	4	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

C15H8O6

IUPAC name

4,5,14-trihydroxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

InChI Identifier

InChI=1S/C15H8O6/c16-6-1-2-7-11(3-6)20-14-8-4-9(17)10(18)5-12(8)21-15(19)13(7)14/h1-5,16-18H

InChI Key

CJPXZAMCIOOMNF-UHFFFAOYSA-N

Isomeric SMILES

OC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C(O)=C2

Average Molecular Weight

284.2204

Monoisotopic Molecular Weight

284.032087988

Classification

Description

Belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Coumestans

Direct Parent

Coumestans

Alternative Parents

Substituents

Coumestan
Angular furanocoumarin
Furanocoumarin
6,7-dihydroxycoumarin
Coumarin
Benzopyran
1-benzopyran
Benzofuran
Furopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Furan
Lactone
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Coumestan flavonoids (LMPK12090032 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Source:

Food

Biological:

Plant:

Fabaceae

Role

Biological role:

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 63.39%; H 2.84%; O 33.77%	DFC
Melting Point	Mp 350°	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	Lucernol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ac3-0290000000-490add647a516af40030	Spectrum
Predicted GC-MS	Lucernol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0109-3143900000-70e72686245c2ab072c2	Spectrum
Predicted GC-MS	Lucernol, 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	splash10-000i-0090000000-970c7dc3bfdf907374e5	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0090000000-e96e1332ac342e95a4c4	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05mo-1390000000-85a3101defc1543edc9c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-e33e03a4d2dee4f0bd0b	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0090000000-6ea3c5a5902c921c073a	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01q3-0390000000-7738ed36b3907a963288	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-3896d645ce486a1e32ca	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0090000000-3896d645ce486a1e32ca	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ar9-0090000000-3f59b3ef30e10083f467	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-279002154c712db975df	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0090000000-279002154c712db975df	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001r-0090000000-fd747db13c238936914b	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4678030

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

5748586

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB34042

CRC / DFC (Dictionary of Food Compounds) ID

HFP93-G:HFP93-G

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

C00009759

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

Processing...

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

— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Showing Compound Lucernol (FDB012284)

Structure for FDB012284 (Lucernol)