AFCDB: Phaseollin (FDB012460)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:11 UTC

Update date

2019-11-26 03:06:51 UTC

Primary ID

FDB012460

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Phaseollin

Description

Phaseollin 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. Phaseollin is an extremely weak basic (essentially neutral) compound (based on its pKa). Phaseollin has been detected, but not quantified in, several different foods, such as green beans, cowpea, yellow wax beans, scarlet beans, and common beans. This could make phaseollin a potential biomarker for the consumption of these foods.

CAS Number

13401-40-6

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	0.007 g/L	ALOGPS
logP	4.14	ALOGPS
logP	3.57	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	9.42	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.92 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	90.99 m³·mol⁻¹	ChemAxon
Polarizability	34.66 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

C20H18O4

IUPAC name

17,17-dimethyl-4,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-1(13),5(10),6,8,14(19),15,20-heptaen-7-ol

InChI Identifier

InChI=1S/C20H18O4/c1-20(2)8-7-14-16(24-20)6-5-12-15-10-22-17-9-11(21)3-4-13(17)19(15)23-18(12)14/h3-9,15,19,21H,10H2,1-2H3

InChI Key

LWTDZKXXJRRKDG-UHFFFAOYSA-N

Isomeric SMILES

CC1(C)OC2=C(C=C1)C1=C(C=C2)C2COC3=C(C=CC(O)=C3)C2O1

Average Molecular Weight

322.3545

Monoisotopic Molecular Weight

322.120509064

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
2,2-dimethyl-1-benzopyran
Chromane
Benzopyran
1-benzopyran
Benzofuran
Coumaran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Ether
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a pterocarpan (CPD-4884 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Source:

Food

Nutrient

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 74.52%; H 5.63%; O 19.85%	DFC
Melting Point	Mp 177-178°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	pKa 9.13	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]D -145 (c, 0.17 in EtOH)	DFC
Spectroscopic UV Data	377 (e 2880) (EtOH/NaOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Phaseollin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0pba-0986000000-ef26fd9f571cb19c6da7	Spectrum
Predicted GC-MS	Phaseollin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00fr-4659000000-30489c44cd92abec518c	Spectrum
Predicted GC-MS	Phaseollin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Phaseollin, 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	splash10-00di-1019000000-4bbab45d581bac2b73b0	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01b9-1095000000-dc691a3331d87151164d	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-7390000000-d3aa381d2d66b3ecd240	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0009000000-eee8d60ede6b3ee25d06	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0069000000-190ffcf697fb9f20069b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-0190000000-a6a942d005a9696cc3be	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0009000000-a4f58630e05faac231a5	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00fr-0098000000-6433a047af8ecc8e05c1	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6r-1982000000-aef35370b06f5bbbb8e3	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0009000000-17eb34705e2ef23f703b	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0029000000-9d0ae020608ee5e985d1	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0avj-0932000000-f87d4a45a8e512e4f272	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

3279224

ChEMBL ID

Not Available

KEGG Compound ID

C10514

Pubchem Compound ID

4063834

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB34173

CRC / DFC (Dictionary of Food Compounds) ID

HHB31-I:HHB31-I

EAFUS ID

Not Available

Dr. Duke ID

PHASEOLLIN|PHASEOLIN

BIGG ID

Not Available

KNApSAcK ID

C00002559

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
anti feedant			DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	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

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.

Phaseollin (FDB012460)

Structure for FDB012460 (Phaseollin)