AFCDB: Isopimpinellin (FDB012661)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:17 UTC

Update date

2019-11-26 03:07:20 UTC

Primary ID

FDB012661

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Isopimpinellin

Description

Isopimpinellin belongs to the class of organic compounds known as 8-methoxypsoralens. These are psoralens containing a methoxy group attached at the C8 position of the psoralen group. Isopimpinellin is found, on average, in the highest concentration within a few different foods, such as parsleys (Petroselinum crispum), celery stalks (Apium graveolens var. dulce), and fennels (Foeniculum vulgare). Isopimpinellin has also been detected, but not quantified in, several different foods, such as parsnips (Pastinaca sativa), wild celeries (Apium graveolens), wild carrots (Daucus carota), limes (Citrus aurantiifolia), and anises (Pimpinella anisum). This could make isopimpinellin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Isopimpinellin.

CAS Number

482-27-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	2.01	ALOGPS
logP	1.63	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	63.32 m³·mol⁻¹	ChemAxon
Polarizability	23.84 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

C13H10O5

IUPAC name

4,9-dimethoxy-7H-furo[3,2-g]chromen-7-one

InChI Identifier

InChI=1S/C13H10O5/c1-15-10-7-3-4-9(14)18-12(7)13(16-2)11-8(10)5-6-17-11/h3-6H,1-2H3

InChI Key

DFMAXQKDIGCMTL-UHFFFAOYSA-N

Isomeric SMILES

COC1=C2OC=CC2=C(OC)C2=C1OC(=O)C=C2

Average Molecular Weight

246.218

Monoisotopic Molecular Weight

246.052823422

Classification

Description

Belongs to the class of organic compounds known as 8-methoxypsoralens. These are psoralens containing a methoxy 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-methoxypsoralens

Alternative Parents

Substituents

5-methoxypsoralen
8-methoxypsoralen
1-benzopyran
Benzopyran
Benzofuran
Anisole
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Furan
Lactone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

psoralens (CHEBI:28853 )
Furanocoumarins (C02162 )

Ontology

Physiological effect

Health effect:

Health condition:

Skin and subcutaneous tissue disorders:

Erythema

Observation:

Edema

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 63.42%; H 4.09%; O 32.49%	DFC
Melting Point	Mp 151°	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	311 (e 13800) (EtOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-000t-7690000000-e6fa32711c30bc186816	2014-09-20	View Spectrum
Predicted GC-MS	Isopimpinellin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-1190000000-275fee6a0dc6bf75820a	Spectrum
Predicted GC-MS	Isopimpinellin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isopimpinellin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-001i-0090000000-a0c532fce25db07d90ef	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-001i-0090000000-54e2a9d485cc8bdceb6d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-001i-0090000000-1032f4d166b576b7ff20	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-001i-0090000000-9c87bfda7e5ffe9c5af4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0udi-0190000000-ea38f4e14acc089f6b51	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0udi-0190000000-a3f55b3b5507de3ae999	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-014i-0970000000-1e191da648efe9b73b12	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-014i-0290000000-bdc222e3350bd6ef6486	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-014j-0190000000-908c9053908baf8cf954	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-07vr-0920000000-5af7d91dde7af1b89547	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0190000000-dfa5b17d7b2df4661d05	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-278fc8d7828591790af9	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-49418fa141b50d6f7f71	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0090000000-730804c160e7a2b01bf9	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0390000000-ee25336a941ea1bf779b	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-bbb8af93a94542f5b653	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0090000000-cef1eff8d1ded6b77f3d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fki-0960000000-d96e6099792968341c94	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-f541a876b9ec3249e209	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0090000000-05d9c28202aea63dacbe	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-0920000000-1148e3f152ca14bca10d	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-14343c13950e873267f5	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0090000000-14343c13950e873267f5	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0090000000-aa4ade1addb5f0cbc93a	2021-09-24	View Spectrum

NMR

Type	Description		View

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

28853

Phenol-Explorer ID

720

DrugBank ID

Not Available

HMDB ID

HMDB34312

CRC / DFC (Dictionary of Food Compounds) ID

HJP62-Y:HJP62-Y

EAFUS ID

Not Available

Dr. Duke ID

ISOPIMPINELLIN

BIGG ID

Not Available

KNApSAcK ID

C00000583

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 appetant	50780	An agent which regulates the physiologic mechanisms that control the appetite and food intake.	DUKE
anti feedant			DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti lipogenic			DUKE
anti mitotic			DUKE
anti tubercular	33282	A substance that kills or slows the growth of bacteria.	DUKE
calcium antagonist	48706	Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
diuretic	35498	An agent that promotes the excretion of urine through its effects on kidney function.	DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
insecticide	24852	Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.	DUKE
molluscicide	33904	A substance used to destroy pests of the phylum Mollusca.	DUKE
mutagenic			DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
piscicide			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

— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.

Isopimpinellin (FDB012661)

Structure for FDB012661 (Isopimpinellin)