Showing Compound (S)-Pinocembrin (FDB002759)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:30 UTC

Update date

2019-11-26 02:57:55 UTC

Primary ID

FDB002759

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(S)-Pinocembrin

Description

(S)-Pinocembrin, also known as dihydrochrysin, belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. Thus, (S)-pinocembrin is considered to be a flavonoid lipid molecule (S)-Pinocembrin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (S)-Pinocembrin is found, on average, in the highest concentration within mexican oregano (S)-Pinocembrin has also been detected, but not quantified in, pine nuts and prunus (cherry, plum). This could make (S)-pinocembrin a potential biomarker for the consumption of these foods.

CAS Number

480-39-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(+)-Pinocembrin	PhytoBank
(+)-Pinocoembrin	MeSH
(2S)-Pinocembrin	ChEBI
(S)-2,3-Dihydro-5,7-dihydroxy-2-phenyl-4H-1-benzopyran-4-one	ChEBI
(S)-5,7-Dihydroxyflavanone	ChEBI
(S)-5,7-dihydroxyflavanone	biospider
(S)-Pinocembrin	ChEBI
5,7-Dihydroxyflavanone	ChEBI
Dihydrochrysin	ChEBI
Galangin flavanone	ChEBI

Showing 1 to 10 of 12 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.19 g/L	ALOGPS
logP	2.85	ALOGPS
logP	3.14	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.87	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.31 m³·mol⁻¹	ChemAxon
Polarizability	26.27 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

C15H12O4

IUPAC name

(2S)-5,7-dihydroxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

InChI Identifier

InChI=1S/C15H12O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-7,13,16-17H,8H2

InChI Key

URFCJEUYXNAHFI-UHFFFAOYSA-N

Isomeric SMILES

OC1=CC(O)=C2C(=O)CC(OC2=C1)C1=CC=CC=C1

Average Molecular Weight

256.257

Monoisotopic Molecular Weight

256.073558866

Classification

Description

Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanones

Alternative Parents

Substituents

Flavanone
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Chromone
Benzopyran
Chromane
1-benzopyran
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyflavanone (CHEBI:28157 )
flavanones (C09827 )
Flavanones (LMPK12140214 )

Ontology

No ontology term

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 70.31%; H 4.72%; O 24.97%	DFC
Melting Point	Mp 192-193°	DFC
Optical Rotation	[a]15D -45.3 (c, 0.9 in Me2CO)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(2S)-pinocembrin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-024i-7359000000-bbe602140f5eb8e64c35	Spectrum
Predicted GC-MS	(2S)-pinocembrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0553-2490000000-ab0d5fb04a17ac900f46	Spectrum
Predicted GC-MS	(2S)-pinocembrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(2S)-pinocembrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(2S)-pinocembrin, 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-0290000000-da83748cebaf2aff41e7	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pbi-0970000000-4da94433e475e4b0655c	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-4900000000-2027700d1a9013d79861	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-3e50055087cb60de2aa7	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0290000000-047a6df1cc7ac9b1ae05	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ufr-5910000000-bfc1ff4fa9dc8cd944c8	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-74e7833e04a924835b1e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-0980000000-884390bd07a6c6de61c4	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-0900000000-2e4404a2a08d29364139	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-95fde3556f3ac1e6ef94	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zfs-0940000000-6587ef358d202da97874	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0900000000-fc81a674baf331f83b9b	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

208593

ChEMBL ID

Not Available

KEGG Compound ID

C09827

Pubchem Compound ID

238782

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

220

DrugBank ID

Not Available

HMDB ID

HMDB30808

CRC / DFC (Dictionary of Food Compounds) ID

CNM52-F:CNM53-G

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

C00000992

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

— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Showing Compound (S)-Pinocembrin (FDB002759)

Structure for FDB002759 ((S)-Pinocembrin)