AFCDB: Pisatin (FDB011855)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:52 UTC

Update date

2019-11-26 03:05:35 UTC

Primary ID

FDB011855

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Pisatin

Description

Pisatin belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. Pisatin is an extremely weak basic (essentially neutral) compound (based on its pKa). Pisatin has been detected, but not quantified in, several different foods, such as common pea, herbs and spices, pulses, and tea. This could make pisatin a potential biomarker for the consumption of these foods.

CAS Number

469-01-2

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	0.77 g/L	ALOGPS
logP	1.75	ALOGPS
logP	1.78	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	11.98	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	77.94 m³·mol⁻¹	ChemAxon
Polarizability	31.73 Å³	ChemAxon
Number of Rings	5	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

C17H14O6

IUPAC name

16-methoxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2(10),3,8,13,15,17-hexaen-1-ol

InChI Identifier

InChI=1S/C17H14O6/c1-19-9-2-3-10-12(4-9)20-7-17(18)11-5-14-15(22-8-21-14)6-13(11)23-16(10)17/h2-6,16,18H,7-8H2,1H3

InChI Key

LZMRDTLRSDRUSU-UHFFFAOYSA-N

Isomeric SMILES

COC1=CC=C2C3OC4=C(C=C5OCOC5=C4)C3(O)COC2=C1

Average Molecular Weight

314.2895

Monoisotopic Molecular Weight

314.07903818

Classification

Description

Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Furanoisoflavonoids

Direct Parent

Pterocarpans

Alternative Parents

Substituents

Isoflavanol
Pterocarpan
Isoflavan
Chromane
Benzopyran
1-benzopyran
Benzodioxole
Benzofuran
Coumaran
Anisole
Alkyl aryl ether
Benzenoid
Tertiary alcohol
Oxacycle
Ether
Acetal
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (CPD-3944 )

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

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 64.97%; H 4.49%; O 30.54%	DFC
Melting Point	Mp 61°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	2.58	ARNOLDI,A & MERLINI,L (1990)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]20D +280 (c, 0.11 in EtOH)	DFC
Spectroscopic UV Data	309 (e 7250) (EtOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Pisatin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-06sa-1691000000-274d0a6517fe3252562b	Spectrum
Predicted GC-MS	Pisatin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9328000000-e689e98a16aeffb2e091	Spectrum
Predicted GC-MS	Pisatin, 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	splash10-014i-0009000000-51ff895d3d542958b762	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0039000000-0352732548637eab03f8	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-7930000000-ac982921a96b24070af6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-226bc1be39e0a6889bbb	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0039000000-32e07322e048d0dfd736	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fr2-1090000000-82ba48e1b539fc3da501	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-7c7169b7540bc9455826	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0049000000-3be945fe734b9b554664	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0101-1690000000-1c2eba349da0683de3b2	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-2ba875095a8aafa31ef7	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0119000000-4b39bd2e26b1cc32f4d0	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004r-0922000000-d989845b9f9595ff4ac4	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

3682780

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

4484953

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB33732

CRC / DFC (Dictionary of Food Compounds) ID

GZS70-L:HBB41-V

EAFUS ID

Not Available

Dr. Duke ID

PISATIN

BIGG ID

Not Available

KNApSAcK ID

C00000651

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 bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
fungicide	24127	A substance used to destroy fungal pests.	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
phytoalexin	26115	A toxin made by a plant that acts against an organism attacking it.	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.

Pisatin (FDB011855)

Structure for FDB011855 (Pisatin)