AFCDB: Xanthotoxol (FDB000578)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:38 UTC

Update date

2020-02-24 19:10:09 UTC

Primary ID

FDB000578

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Xanthotoxol

Description

Xanthotoxol, also known as 8-hydroxypsoralen, belongs to the class of organic compounds known as 8-hydroxypsoralens. These are psoralens containing a hydroxyl group attached at the C8 position of the psoralen group. Xanthotoxol exists in all living organisms, ranging from bacteria to humans. Xanthotoxol has been detected, but not quantified in, several different foods, such as figs (Ficus carica), parsleys (Petroselinum crispum), herbs and spices, green vegetables, and fats and oils. This could make xanthotoxol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Xanthotoxol.

CAS Number

2009-24-7

Structure

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

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.78 g/L	ALOGPS
logP	1.9	ALOGPS
logP	2.29	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	8.19	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.67 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	52.37 m³·mol⁻¹	ChemAxon
Polarizability	19.01 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

C11H6O4

IUPAC name

9-hydroxy-7H-furo[3,2-g]chromen-7-one

InChI Identifier

InChI=1S/C11H6O4/c12-8-2-1-6-5-7-3-4-14-10(7)9(13)11(6)15-8/h1-5,13H

InChI Key

JWVYQQGERKEAHW-UHFFFAOYSA-N

Isomeric SMILES

[H]OC1=C2OC(=O)C([H])=C([H])C2=C([H])C2=C1OC([H])=C2[H]

Average Molecular Weight

202.165

Monoisotopic Molecular Weight

202.026608673

Classification

Description

Belongs to the class of organic compounds known as 8-hydroxypsoralens. These are psoralens containing a hydroxyl group attached at the C8 position of the psoralen group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

8-hydroxypsoralens

Alternative Parents

Substituents

8-hydroxypsoralen
Benzopyran
1-benzopyran
Benzofuran
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Furan
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

8-hydroxyfurocoumarin (CHEBI:15709 )
Furanocoumarins (C00841 )
an 8-hydroxyfurocoumarin (CPD-13041 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 65.35%; H 2.99%; O 31.66%	DFC
Melting Point	Mp 251-252°	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	Not Available
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	Xanthotoxol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fk9-0920000000-f2a166594cf283c47f5c	Spectrum
Predicted GC-MS	Xanthotoxol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00e9-4090000000-dca534ef96e39d848c13	Spectrum
Predicted GC-MS	Xanthotoxol, 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	splash10-0udi-0090000000-c09589cc1f633fd56111	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0190000000-3ab98291b26fe8eeb4e8	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pb9-2930000000-4691abe312d6e6ecb939	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0290000000-c887179a30886be5e421	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0390000000-4c461f4a9306d3586bfd	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0aor-0900000000-b332ff7a37ce35057295	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0090000000-2e5a86e101fa40f235c9	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0290000000-f0e15e059d45f78f5b76	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0560-0900000000-5f24b0525848ab617753	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-6f70ceb2368baddf4f40	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0090000000-6f70ceb2368baddf4f40	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-0090000000-1553b0f99d6356baaebd	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

15709

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB29457

CRC / DFC (Dictionary of Food Compounds) ID

BDW00-J:BDW00-J

EAFUS ID

Not Available

Dr. Duke ID

XANTHOTOXOL

BIGG ID

Not Available

KNApSAcK ID

C00000582

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
anti histaminic	37956	Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.	DUKE
anti mitotic			DUKE
anti nicotinic	38323	Any drug used for its actions on cholinergic systems. Included here are agonists and antagonists, drugs that affect the life cycle of acetylcholine, and drugs that affect the survival of cholinergic neurons.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
cytotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE

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

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Xanthotoxol (FDB000578)

Structure for FDB000578 (Xanthotoxol)