Showing Compound Pinocembrin (FDB002758)

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

FDB002758

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Pinocembrin

Description

(s)-pinocembrin, also known as 5,7-dihydroxyflavanone or dihydrochrysin, is a member of the class of 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 (s)-pinocembrin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (s)-pinocembrin is a bitter tasting compound found in mexican oregano and tarragon, which makes (s)-pinocembrin a potential biomarker for the consumption of these food products.

CAS Number

68745-38-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(S)-5,7-Dihydroxyflavanone	HMDB
5,7-Dihydroxyflavanone	HMDB
Dihydrochrysin	HMDB
Galangin flavanone	HMDB
Pinocembrin (6ci)	HMDB
Pinocembrin	MeSH, HMDB
Pinocembrine	MeSH, HMDB
(+)-Pinocoembrin	MeSH
2,3-Dihydro-5,7-dihydroxy-2-phenyl-4H-1-benzopyran-4-one, 9CI	db_source

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

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

Not Available

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 70.31%; H 4.72%; O 24.97%	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	325 () (MeOH/NaOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Pinocembrin, non-derivatized, GC-MS Spectrum	splash10-0zi0-4940000000-e82938be666b8efbd57d	Spectrum
GC-MS	Pinocembrin, non-derivatized, GC-MS Spectrum	splash10-0zi0-4940000000-e82938be666b8efbd57d	Spectrum
Predicted GC-MS	Pinocembrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0kdr-2390000000-e5b2a24d0f85221b06d5	Spectrum
Predicted GC-MS	Pinocembrin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-024i-7359000000-bbe602140f5eb8e64c35	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0a4i-0980000000-1e2fb974e66fdf1905de	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a4i-0090000000-e7a2d42e43fa0b871d58	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a4i-0490000000-db48745a3d543c14c6fc	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0pi0-0900000000-31c7469fd05b2dfa0d26	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-03di-0590000000-a0bd5e67864cbcce0ef1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-0490000000-e3e0fd288f81b7d8a9f6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0900000000-bb65e58e45d6926a4d0e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0900000000-405d5e70eb1870fb79b7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-004i-0890000000-53a90fbc9a29bf0adf0a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0udi-0900000000-20e5dc727e70bdfb32ad	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0udi-0920000000-51d135533a4a8f649cba	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0290000000-b164f424f75fa66b547a	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pbi-0970000000-077fc628bf2155480d1e	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f79-3900000000-cfbae6b4977762472890	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-cc887329ec72033da059	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1390000000-73b4983f6ed53a910578	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ufr-5910000000-d0b4a2815a601b641cdb	2015-04-25	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

CNM52-F:CNM52-F

EAFUS ID

Not Available

Dr. Duke ID

PINOCEMBRIN

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
anesthetic			DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti leukemic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
artemicide			DUKE
candidicide			DUKE
cytotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	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

Flavor	Citations
bitter	Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755

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).