AFCDB: Leucopelargonidin (FDB007686)

Record Information

Version

1.0

Creation date

2010-04-08 22:07:43 UTC

Update date

2019-11-26 03:01:45 UTC

Primary ID

FDB007686

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Leucopelargonidin

Description

Leucopelargonidin is a member of the class of compounds known as leucoanthocyanidins. Leucoanthocyanidins are flavonoids consisting of a flavan (3,4-dihydro-2-phenyl-2H-1-benzopyran) moiety that carries two hydroxy groups at the C3- and C4-positions. Leucopelargonidin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Leucopelargonidin can be found in a number of food items such as narrowleaf cattail, pepper (c. pubescens), macadamia nut (m. tetraphylla), and abiyuch, which makes leucopelargonidin a potential biomarker for the consumption of these food products. Leucopelargonidin is a colorless chemical compound related to leucoanthocyanins. It can be found in Albizia lebbeck (East Indian walnut), in the fruit of Anacardium occidentale (Cashew), in the fruit of Areca catechu (Areca nut), in the fruit of Hydnocarpus wightiana (Hindi Chaulmoogra), in the rhizome of Rumex hymenosepalus (Arizona dock), in Zea Mays (Corn) and in Ziziphus jujuba (Chinese date) .

CAS Number

520-17-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.84 g/L	ALOGPS
logP	0.62	ALOGPS
logP	1.18	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	9.08	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.23 m³·mol⁻¹	ChemAxon
Polarizability	28.28 Å³	ChemAxon
Number of Rings	3	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

C15H14O6

IUPAC name

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

InChI Identifier

InChI=1S/C15H14O6/c16-8-3-1-7(2-4-8)15-14(20)13(19)12-10(18)5-9(17)6-11(12)21-15/h1-6,13-20H

InChI Key

FSVMLWOLZHGCQX-UHFFFAOYSA-N

Isomeric SMILES

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

Average Molecular Weight

290.2681

Monoisotopic Molecular Weight

290.07903818

Classification

Description

Belongs to the class of organic compounds known as leucoanthocyanidins. These are flavonoids consisting of a flavan (3,4-dihydro-2-phenyl-2H-1-benzopyran) moiety that carries two hydroxy groups at the C3- and C4-positions.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Leucoanthocyanidins

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a leucoanthocyanidin (LEUCOPELARGONIDIN-CMPD )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 62.07%; H 4.86%; O 33.07%	CCD
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	splash10-0006-0190000000-8b627d02db62b9f1f86c	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0abc-0950000000-3dcdc08a99d216ad45ae	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05g0-4900000000-fc491a73d0ab243033bc	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0290000000-024e32ee1cac9733e4e9	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0079-1970000000-f54a3a9506a12cb6b90f	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056u-5900000000-b592b18055a33cf5d4f9	2015-05-27	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

3286789

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

KZD69-M:KZD69-M

EAFUS ID

Not Available

Dr. Duke ID

LEUCOPELARGONIDIN|LEUCOPELARGONIDINE

BIGG ID

Not Available

KNApSAcK ID

C00020638

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 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).

Leucopelargonidin (FDB007686)

Structure for FDB007686 (Leucopelargonidin)