AFCDB: Tuberosin (FDB007156)

Record Information

Version

1.0

Creation date

2010-04-08 22:07:28 UTC

Update date

2019-11-26 03:01:32 UTC

Primary ID

FDB007156

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Tuberosin

Description

Tuberosin is a member of the class of compounds known as pterocarpans. Pterocarpans are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. Tuberosin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Tuberosin can be found in potato, which makes tuberosin a potential biomarker for the consumption of this food product.

CAS Number

Not Available

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	0.057 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	35.43 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

(1R,13R)-7,7-dimethyl-8,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁴,¹⁹]henicosa-2(11),3,5,9,14(19),15,17-heptaene-1,17-diol

InChI Identifier

InChI=1S/C20H18O5/c1-19(2)6-5-11-7-14-17(9-15(11)25-19)24-18-13-4-3-12(21)8-16(13)23-10-20(14,18)22/h3-9,18,21-22H,10H2,1-2H3/t18-,20+/m1/s1

InChI Key

ZBTYHECJEINCMD-QUCCMNQESA-N

Isomeric SMILES

CC1(C)OC2=CC3=C(C=C2C=C1)[C@@]1(O)COC2=C(C=CC(O)=C2)[C@H]1O3

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

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
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	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0119000000-df9f4425637b6301e703	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-2179000000-757a5e5208bd65ce59cd	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-3940000000-2502b239ff537bdabb9d	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-cf891640ed06d1c5a988	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0029000000-d7af978acbbeb8e519f7	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gk9-0291000000-6f290d80619700e4f8ef	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-2b8ef97f349df851f3ad	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0029000000-e411c5da20629bf15abf	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0079-0924000000-81554335715e2b05d3f6	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-fba49930c01349472a4d	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000j-0069000000-bec49912c40f8cd6cd12	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06rb-1986000000-fbec1bed01bcf6a77288	2021-10-21	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

5318770

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

TUBEROSIN

BIGG ID

Not Available

KNApSAcK ID

C00009684

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 staphylococcic	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti tubercular	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

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).

Tuberosin (FDB007156)

Structure for FDB007156 (Tuberosin)