Showing Compound (2S,3R,4R)-3,4,4'-Trihydroxyflavan (FDB020477)

Record Information

Version

1.0

Creation date

2010-04-08 22:15:03 UTC

Update date

2019-11-26 03:18:59 UTC

Primary ID

FDB020477

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(2S,3R,4R)-3,4,4'-Trihydroxyflavan

Description

(2S,3R,4R)-3,4,4'-Trihydroxyflavan 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 (2S,3R,4R)-3,4,4'-Trihydroxyflavan has been detected, but not quantified in, fruits. This could make (2S,3R,4R)-3,4,4'-trihydroxyflavan a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (2S,3R,4R)-3,4,4'-Trihydroxyflavan.

CAS Number

149747-10-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
4-Methylumbelliferyl-N,n'-diacetyl-beta-chitobiose	HMDB
4-Methylumbelliferyl-N,N'-diacetyl-beta-chitobiose	biospider
4-Methylumbelliferyl-N,N-diacetylchitobioside	HMDB
4-Mudacb	HMDB
GUM	HMDB
Me-dinag	HMDB

Showing 1 to 6 of 6 entries

Predicted Properties

Property	Value	Source
Water Solubility	1.56 g/L	ALOGPS
logP	1.2	ALOGPS
logP	1.79	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	9.47	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.26 m³·mol⁻¹	ChemAxon
Polarizability	26.36 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

C15H14O4

IUPAC name

2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4-diol

InChI Identifier

InChI=1S/C15H14O4/c16-10-7-5-9(6-8-10)15-14(18)13(17)11-3-1-2-4-12(11)19-15/h1-8,13-18H

InChI Key

HGNZPAIPVKRUKE-UHFFFAOYSA-N

Isomeric SMILES

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

Average Molecular Weight

258.2693

Monoisotopic Molecular Weight

258.089208936

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
Hydroxyflavonoid
Chromane
Benzopyran
1-benzopyran
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
1,2-diol
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 69.76%; H 5.46%; O 24.78%	DFC
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(2S,3R,4R)-3,4,4'-Trihydroxyflavan, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-0930000000-549a8fc2e62ffda69a30	Spectrum
Predicted GC-MS	(2S,3R,4R)-3,4,4'-Trihydroxyflavan, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-11b9-5425900000-6bed84fb61262afe7605	Spectrum
Predicted GC-MS	(2S,3R,4R)-3,4,4'-Trihydroxyflavan, 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	splash10-0a4i-0190000000-d10d3bb12067fbddcd77	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-1940000000-ab7a086c698c6a866a88	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9700000000-694e2686ae61bae74d76	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0190000000-ce7caccb44efb7ce8b01	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ab9-2970000000-b5351f379937670a13ab	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-054o-9600000000-3f6a211cc3dec3331622	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-7466f0ff4fc176d35adf	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0930000000-ee4dba855d471b8e6e1b	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-4900000000-6db2eb115d0f16420f17	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4r-0090000000-e0a309d8eb88e252f016	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-2960000000-0bf8678210a682cb61b6	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05mo-4900000000-2e452767f869fcc2f03e	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

171284

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB40679

CRC / DFC (Dictionary of Food Compounds) ID

MSS68-H:MSS69-I

EAFUS ID

Not Available

Dr. Duke ID

Not Available

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

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

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

Showing Compound (2S,3R,4R)-3,4,4'-Trihydroxyflavan (FDB020477)

Structure for FDB020477 ((2S,3R,4R)-3,4,4'-Trihydroxyflavan)