AFCDB: Leucodelphinidin (FDB018307)

Record Information

Version

1.0

Creation date

2010-04-08 22:13:38 UTC

Update date

2020-02-24 19:11:09 UTC

Primary ID

FDB018307

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Leucodelphinidin

Description

Leucodelphinidin, also known as leucoefdin or 3,4,5,7,3',4',5'-heptahydroxyflavan, is a member of the class of compounds known as epigallocatechins. Epigallocatechins are compounds containing epigallocatechin or a derivative. Epigallocatechin is a flavan-3-ol containing a benzopyran-3,5,7-triol linked to a 3,4,5-hydroxyphenyl moiety. Leucodelphinidin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Leucodelphinidin can be found in a number of food items such as black mulberry, sunburst squash (pattypan squash), groundcherry, and yautia, which makes leucodelphinidin a potential biomarker for the consumption of these food products. Other species containing leucodelphinidin include Aesculus hippocastanum (Horse chestnut, in rind/bark/cortex), Arachis hypogaea (Earth nut in seeds), Arbutus unedo (Arbutus, in the leaf), Caesalpinia pulcherrima (Barbados pride), Ceratonia siliqua (Carob, in the fruit), Hamamelis virginiana (American witch hazel, in the leaf), Hippophae rhamnoides (Hippophae berry, in the leaf), Humulus lupulus (bine flower / blossom, in the leaf), Musa acuminata × balbisiana (Banana, in the fruit), Nelumbo nucifera (Baladi bean, in the leaf), Phyllanthus emblica (Emblic, Indian gooseberry, in the rind/bark/cortex), Quercus alba (White oak, in the rind/bark/cortex), Quercus robur (Common oak, in the rind/bark/cortex), Rumex hymenosepalus (Arizona dock, in the root), Schinus molle (California peppertree, in the leaf) and Vicia faba (bell-bean, in the seed) .

CAS Number

491-52-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.53 g/L	ALOGPS
logP	0.4	ALOGPS
logP	0.57	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	8.7	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	150.84 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	77.19 m³·mol⁻¹	ChemAxon
Polarizability	30.54 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C15H14O8

IUPAC name

2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol

InChI Identifier

InChI=1S/C15H14O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,13-22H

InChI Key

ZEACOKJOQLAYTD-UHFFFAOYSA-N

Isomeric SMILES

OC1C(O)C2=C(O)C=C(O)C=C2OC1C1=CC(O)=C(O)C(O)=C1

Average Molecular Weight

322.2669

Monoisotopic Molecular Weight

322.068867424

Classification

Description

Belongs to the class of organic compounds known as epigallocatechins. Epigallocatechins are compounds containing epigallocatechin or a derivative. Epigallocatechin is a flavan-3-ol containing a benzopyran-3,5,7-triol linked to a 3,4,5-hydroxyphenyl moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Epigallocatechins

Alternative Parents

Substituents

Epigallocatechin
Leucoanthocyanidin-skeleton
7-hydroxyflavonoid
Hydroxyflavonoid
5-hydroxyflavonoid
4-hydroxyflavonoid
4'-hydroxyflavonoid
3-hydroxyflavonoid
3'-hydroxyflavonoid
Chromane
1-benzopyran
Benzopyran
Pyrogallol derivative
Benzenetriol
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
1,2-diol
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

secondary alcohol (CHEBI:71216 )
catechols (CHEBI:71216 )
polyphenol (CHEBI:71216 )
resorcinols (CHEBI:71216 )
glycol (CHEBI:71216 )
hydroxyflavan (CHEBI:71216 )
a leucoanthocyanidin (CPD-7088 )

Ontology

Disposition

Source:

Endogenous

Biological:

Plant

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 55.90%; H 4.38%; O 39.72%	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	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Leucodelphinidin, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-1000019000-06e1c92dd6bab901e43f	Spectrum
Predicted GC-MS	Leucodelphinidin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000i-0931000000-246efdb8bd053f3bed33	Spectrum
Predicted GC-MS	Leucodelphinidin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Leucodelphinidin, 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-0209000000-67a36854da3cd48e1a1d	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0abi-0912000000-82ea3703abc74646fea1	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0k9i-1900000000-adef4ec8c1bd878b886a	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0309000000-2f116d9edb31b6e02ef3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0uk9-0925000000-e3f556483d696229fcf8	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-3900000000-7e8050a9b9304b3817d5	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0009000000-311ce388518b76d24bd6	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0uki-0934000000-16fe20933e63c348851d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udr-0910000000-e81b0f29708f5217a590	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0009000000-f6db70837ba5cef7382b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00y1-0913000000-cbd38f186b7d509542eb	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052r-1920000000-8bccc0f1f15a107b06df	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

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

LJH91-K:LJH91-K

EAFUS ID

Not Available

Dr. Duke ID

LEUCODELPHINIDIN

BIGG ID

Not Available

KNApSAcK ID

Not Available

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 inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti neoplastic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	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).

Leucodelphinidin (FDB018307)

Structure for FDB018307 (Leucodelphinidin)