AFCDB: Prangolarin (FDB012667)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:18 UTC

Update date

2019-11-26 03:07:20 UTC

Primary ID

FDB012667

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Prangolarin

Description

(r)-oxypeucedanin, also known as hishigado or phosphine, is a member of the class of compounds known as psoralens. Psoralens are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one (r)-oxypeucedanin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (r)-oxypeucedanin can be found in carrot, lemon, parsley, and wild carrot, which makes (r)-oxypeucedanin a potential biomarker for the consumption of these food products.

CAS Number

737-52-0

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	0.052 g/L	ALOGPS
logP	2.79	ALOGPS
logP	2.32	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.2 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	74.65 m³·mol⁻¹	ChemAxon
Polarizability	28.89 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

C16H14O5

IUPAC name

4-[(3,3-dimethyloxiran-2-yl)methoxy]-7H-furo[3,2-g]chromen-7-one

InChI Identifier

InChI=1S/C16H14O5/c1-16(2)13(21-16)8-19-15-9-3-4-14(17)20-12(9)7-11-10(15)5-6-18-11/h3-7,13H,8H2,1-2H3

InChI Key

QTAGQHZOLRFCBU-UHFFFAOYSA-N

Isomeric SMILES

CC1(C)OC1COC1=C2C=CC(=O)OC2=CC2=C1C=CO2

Average Molecular Weight

286.2794

Monoisotopic Molecular Weight

286.084123558

Classification

Description

Belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Psoralens

Alternative Parents

Substituents

Psoralen
Benzopyran
1-benzopyran
Benzofuran
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Furan
Lactone
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 67.13%; H 4.93%; O 27.94%	DFC
Melting Point	Not Available
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	(R)-Oxypeucedanin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fdo-9370000000-ba212a82c604298e7a11	Spectrum
Predicted GC-MS	(R)-Oxypeucedanin, 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-1090000000-9a62441281765dc2937c	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-5090000000-679a16d82a5c237ca58a	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-5920000000-f745046aa1802d326ac6	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f79-0090000000-0276fe8d4f2cf6a09bf7	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0490000000-21dbeed560117c8c5381	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a59-0910000000-06c5b56d971bd3d4bdb8	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-c2309c473ed29ebdc7af	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f79-0090000000-830ea8c1ff4ebfba1bd2	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pb9-2930000000-9716abcf4cc48c836f41	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0090000000-5fe777fd006230f677fa	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0090000000-ad2862cb9064408fae7f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-6890000000-c716dea4ef6d24e6db79	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

HJP78-H:HJP78-H

EAFUS ID

Not Available

Dr. Duke ID

OXYPEUCEDANIN

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

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
antitumor promoter	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
calcium antagonist	48706	Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.	DUKE
diabetic-macular-edema inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
lipolytic			DUKE
mutagenic			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).

Prangolarin (FDB012667)

Structure for FDB012667 (Prangolarin)