AFCDB: 6alpha-Hydroxyphaseollin (FDB002706)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:29 UTC

Update date

2020-02-24 19:10:35 UTC

Primary ID

FDB002706

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

6alpha-Hydroxyphaseollin

Description

6alpha-Hydroxyphaseollin 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. 6alpha-Hydroxyphaseollin is an extremely weak basic (essentially neutral) compound (based on its pKa). 6alpha-Hydroxyphaseollin has been detected, but not quantified in, several different foods, such as common beans, green beans, pulses, soy beans, and yellow wax beans. This could make 6alpha-hydroxyphaseollin a potential biomarker for the consumption of these foods.

CAS Number

34144-10-0

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	0.058 g/L	ALOGPS
logP	3.25	ALOGPS
logP	2.91	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.41	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.15 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	92.08 m³·mol⁻¹	ChemAxon
Polarizability	35.76 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

C20H18O5

IUPAC name

6,6-dimethyl-5,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁴,¹⁹]henicosa-2(11),3,7,9,14(19),15,17-heptaene-1,17-diol

InChI Identifier

InChI=1S/C20H18O5/c1-19(2)6-5-11-7-17-14(9-15(11)25-19)20(22)10-23-16-8-12(21)3-4-13(16)18(20)24-17/h3-9,18,21-22H,10H2,1-2H3

InChI Key

KVUZVBGGLCNPQI-UHFFFAOYSA-N

Isomeric SMILES

CC1(C)OC2=CC3=C(OC4C5=C(OCC34O)C=C(O)C=C5)C=C2C=C1

Average Molecular Weight

338.3539

Monoisotopic Molecular Weight

338.115423686

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
Coumaran
Benzofuran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Tertiary alcohol
Ether
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 71.00%; H 5.36%; O 23.64%	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	[a]20D -207 (EtOAc)	DFC
Spectroscopic UV Data	318 (e 3100) (EtOH-NaOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	6alpha-Hydroxyphaseollin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-0719000000-cf3c2e08ef3bd2364382	Spectrum
Predicted GC-MS	6alpha-Hydroxyphaseollin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00xr-9421800000-24030aa0a1bd1bf04638	Spectrum
Predicted GC-MS	6alpha-Hydroxyphaseollin, 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-0119000000-9d0e8ebca7f968413587	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-2179000000-f30cc34b053beadc9793	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0159-3930000000-23c01d50a8c57c7571b6	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-f60e3ca95575fcd65339	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0029000000-e6e1cf7fd10e01016945	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gk9-0291000000-ad33ac8b7e4d4ad274b1	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-2b8ef97f349df851f3ad	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0029000000-d05b5990aa58cc0a95ba	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00s2-1495000000-29b08f31042c3c70b30a	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-fba49930c01349472a4d	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0009000000-1fd324b854bd3d9f5ddc	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05tr-0149000000-711f552084263e83749e	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

3084583

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB30771

CRC / DFC (Dictionary of Food Compounds) ID

CND49-Q:CND49-Q

EAFUS ID

Not Available

Dr. Duke ID

HYDROXYPHASEOLIN|6-ALPHA-HYDROXYPHASEOLLIN

BIGG ID

Not Available

KNApSAcK ID

C00020214

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
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.

6alpha-Hydroxyphaseollin (FDB002706)

Structure for FDB002706 (6alpha-Hydroxyphaseollin)