Showing Compound Glyceollin III (FDB012283)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:05 UTC

Update date

2019-11-26 03:06:31 UTC

Primary ID

FDB012283

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Glyceollin III

Description

Glyceollin III 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. Glyceollin III is an extremely weak basic (essentially neutral) compound (based on its pKa). Glyceollin III has been detected, but not quantified in, a few different foods, such as fats and oils, pulses, and soy beans. This could make glyceollin III a potential biomarker for the consumption of these foods.

CAS Number

61080-23-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1,2-Dihydro-2-(1-methylethenyl)-6H-benzofuro[3,2-c]furo[3,2-g][1]benzopyran-6a,9(11ah)-diol, 9ci	HMDB
1,2-Dihydro-2-(1-methylethenyl)-6H-benzofuro[3,2-c]furo[3,2-g][1]benzopyran-6a,9(11aH)-diol, 9CI	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.17 g/L	ALOGPS
logP	2.57	ALOGPS
logP	2.93	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	9.4	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	1	ChemAxon
Refractivity	90.57 m³·mol⁻¹	ChemAxon
Polarizability	35.88 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C20H18O5

IUPAC name

6-(prop-1-en-2-yl)-7,11,20-trioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]icosa-2(10),3,8,14(19),15,17-hexaene-13,17-diol

InChI Identifier

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

InChI Key

MIYTVBARXCVVHZ-UHFFFAOYSA-N

Isomeric SMILES

CC(=C)C1CC2=CC3=C(OCC4(O)C3OC3=C4C=CC(O)=C3)C=C2O1

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (CPD-4407 )

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 71.00%; H 5.36%; O 23.64%	DFC
Melting Point	Mp 149-153°	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	292 (e 9600) (EtOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-059l-9748000000-0c8f6f42b908caad2956	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-01bl-9302700000-4a761389ba0b47aab22e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1209000000-36787a23fcfd732f5144	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-1819000000-4d66b9b9a426ed6600f2	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05mo-9500000000-7c7ec4875763a3f0c841	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-133c641ded1401e9d55b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0219000000-ba2ad87e769092cd90b7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05mt-3901000000-020981508ab46f0dc5f4	JSpectraViewer

External Links

ChemSpider ID

10174551

ChEMBL ID

Not Available

KEGG Compound ID

C15511

Pubchem Compound ID

12002084

Pubchem Substance ID

Not Available

ChEBI ID

52086

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB34041

CRC / DFC (Dictionary of Food Compounds) ID

HFP75-C:HFP75-C

EAFUS ID

Not Available

Dr. Duke ID

GLYCEOLLIN-III

BIGG ID

Not Available

KNApSAcK ID

C00009685

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
phytoalexin	26115	A toxin made by a plant that acts against an organism attacking it.	DUKE