NP-MRD: Showing NP-Card for Pinocembrin (NP0044446)

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Record Information

Version

2.0

Created at

2022-02-14 20:56:53 UTC

Updated at

2022-03-10 22:22:12 UTC

NP-MRD ID

NP0044446

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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. Outside of the human body, (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. A dihydroxyflavanone in which the two hydroxy groups are located at positions 5 and 7. Pinocembrin is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
   -0.9236   -2.6468    1.6684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7628   -1.7037    0.8784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5897   -1.3193    0.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7371    0.2008    0.5777 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0945    0.5286    0.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0843    0.8237    0.9894 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3759    1.1401    0.6062 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7184    1.1704   -0.7287 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7406    0.8777   -1.6598 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4399    0.5599   -1.2532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2769    0.8418   -0.1321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5618    0.3608   -0.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6403    1.1002   -0.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9347    0.6266   -0.6191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0007    1.3800   -1.1067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1836   -0.6346   -0.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1404   -1.4273    0.3762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4672   -2.6475    0.8401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8891   -0.9104    0.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3987   -1.7697    1.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7214   -1.5215   -0.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6651    0.4700    1.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8188    0.8017    2.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1532    1.3716    1.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7205    1.4138   -1.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9993    0.8988   -2.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6682    0.3295   -1.9723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4583    2.0971   -1.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5154    1.9923   -0.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2137   -1.0139   -0.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9569   -3.3906    1.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4 11  1  0
 11 12  1  0
 12 13  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 13 14  1  0
 10  5  1  0
 12 19  1  0
 15 29  1  0
 16 30  1  0
 18 31  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  1
 13 28  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
M  END


  Mrv1652309272007322D          

 19 21  0  0  0  0            999 V2000
10000.0175 9998.1294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5927 9998.1294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.165910000.6151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.592810000.6104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.878210000.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8782 9999.3729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5927 9998.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.017910000.6105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.303410000.1980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3034 9999.3729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0179 9998.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7324 9999.3729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.732410000.1980    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.874310001.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.159810001.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.445310001.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.445210000.6144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.159710000.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.874310000.6144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 14  1  0  0  0  0
  5  3  1  0  0  0  0
  7  2  1  0  0  0  0
  1 11  2  0  0  0  0
 13 17  1  6  0  0  0
  9  4  2  0  0  0  0
  7 10  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0044446

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(O)=C2C(=O)C[C@H](OC2=C1)C1=CC=CC=C1

> <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/t13-/m0/s1

> <INCHI_KEY>
URFCJEUYXNAHFI-ZDUSSCGKSA-N

> <FORMULA>
C15H12O4

> <MOLECULAR_WEIGHT>
256.2534

> <EXACT_MASS>
256.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
26.272466547500862

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.85

> <JCHEM_LOGP>
3.1386733719999995

> <ALOGPS_LOGS>
-3.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.508211062918406

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.866811828409287

> <JCHEM_PKA_STRONGEST_BASIC>
-4.950227971056941

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
69.30890000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.88e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pinocembrin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8666.6998663.175   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8664.0408663.175   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8661.3768667.815   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8664.0408667.806   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8662.7068667.036   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8662.7068665.496   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8664.0408664.726   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8666.7008667.806   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8665.3668667.036   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8665.3668665.496   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8666.7008664.726   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8668.0348665.496   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8668.0348667.036   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8672.0328669.354   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8670.6988670.124   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8669.3658669.353   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8669.3648667.814   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8670.6988667.044   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8672.0328667.814   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2    7                                                            
CONECT    3    5                                                            
CONECT    4    5    9                                                       
CONECT    5    4    6    3                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2   10                                                  
CONECT    8    9   13                                                       
CONECT    9   10    8    4                                                  
CONECT   10    9   11    7                                                  
CONECT   11   10   12    1                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8   17                                                  
CONECT   14   15   19                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   13                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₁₅H₁₂O₄

Average Mass

256.2534 Da

Monoisotopic Mass

256.07356 Da

IUPAC Name

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

Traditional Name

pinocembrin

CAS Registry Number

Not Available

SMILES

OC1=CC(O)=C2C(=O)C[C@H](OC2=C1)C1=CC=CC=C1

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/t13-/m0/s1

InChI Key

URFCJEUYXNAHFI-ZDUSSCGKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abelmoschus esculentus	FooDB	FooDB
Acritopappus confertus	LOTUS Database	35616633
Actinidia chinensis	FooDB	FooDB
Adenostoma sparsifolium	LOTUS Database	35616633
Agaricus bisporus	FooDB	FooDB
Agave	FooDB	FooDB
Allium ampeloprasum	FooDB	FooDB
Allium ascalonicum	FooDB	FooDB
Allium cepa	FooDB	FooDB
Allium cepa L.	FooDB	FooDB
Allium fistulosum	FooDB	FooDB
Allium sativum	FooDB	FooDB
Allium schoenoprasum	FooDB	FooDB
Allium tuberosum	FooDB	FooDB
Alnus sieboldiana	LOTUS Database	35616633
Aloysia triphylla	FooDB	FooDB
Alpinia mutica	LOTUS Database	35616633
Alpinia rafflesiana	LOTUS Database	35616633
Alpinia zerumbet	LOTUS Database	35616633
Amaranthus	FooDB	FooDB
Amelanchier alnifolia	FooDB	FooDB
Anacardium occidentale	FooDB	FooDB
Ananas comosus	FooDB	FooDB
Anethum graveolens	FooDB	FooDB
Angelica keiskei	FooDB	FooDB
Annona cherimola	FooDB	FooDB
Annona muricata	FooDB	FooDB
Annona reticulata	FooDB	FooDB
Annona squamosa	FooDB	FooDB
Anthriscus cerefolium	FooDB	FooDB
Apis mellifera	LOTUS Database	35616633
Apium graveolens	FooDB	FooDB
Apium graveolens var. dulce	FooDB	FooDB
Apium graveolens var. rapaceum	FooDB	FooDB
Apium graveolens var. secalinum	FooDB	FooDB
Arachis hypogaea	FooDB	FooDB
Arctium lappa	FooDB	FooDB
Armoracia rusticana	FooDB	FooDB
Artemisia campestris	LOTUS Database	35616633
Artemisia dracunculus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Artemisia vulgaris	FooDB	FooDB
Artocarpus altilis	FooDB	FooDB
Artocarpus heterophyllus	FooDB	FooDB
Asparagus officinalis	FooDB	FooDB
Attalea speciosa	FooDB	FooDB
Auricularia auricula-judae	FooDB	FooDB
Auricularia polytricha	FooDB	FooDB
Avena sativa L.	FooDB	FooDB
Averrhoa carambola	FooDB	FooDB
Baccharis aliena	LOTUS Database	35616633
Baccharis salicifolia	LOTUS Database	35616633
Basella alba	FooDB	FooDB
Benincasa hispida	FooDB	FooDB
Bertholletia excelsa	FooDB	FooDB
Beta vulgaris	FooDB	FooDB
Beta vulgaris ssp. cicla	FooDB	FooDB
Boesenbergia pandurata	Plant	KNApSAcK
Boesenbergia rotunda	LOTUS Database	35616633
Borago officinalis	FooDB	FooDB
Brassica alboglabra	FooDB	FooDB
Brassica juncea	FooDB	FooDB
Brassica napus	FooDB	FooDB
Brassica napus var. napus	FooDB	FooDB
Brassica oleracea	FooDB	FooDB
Brassica oleracea var. botrytis	FooDB	FooDB
Brassica oleracea var. capitata	FooDB	FooDB
Brassica oleracea var. gemmifera	FooDB	FooDB
Brassica oleracea var. gongylodes	FooDB	FooDB
Brassica oleracea var. italica	FooDB	FooDB
Brassica oleracea var. sabauda	FooDB	FooDB
Brassica oleracea var. viridis	FooDB	FooDB
Brassica rapa	FooDB	FooDB
Brassica rapa ssp. chinensis	FooDB	FooDB
Brassica rapa var. pekinensis	FooDB	FooDB
Brassica rapa var. rapa	FooDB	FooDB
Brassica ruvo	FooDB	FooDB
Brosimum alicastrum	FooDB	FooDB
Bursaphelenchus xylophilus	LOTUS Database	35616633
Byrsonima crassifolia	FooDB	FooDB
Cajanus cajan	FooDB	FooDB
Canarium ovatum	FooDB	FooDB
Cannabis sativa	CannabisDB	Not Available
Cantharellus cibarius	FooDB	FooDB
Capparis spinosa	FooDB	FooDB
Capsicum annuum	FooDB	FooDB
Capsicum annuum L.	FooDB	FooDB
Capsicum annuum var. annuum	FooDB	FooDB
Capsicum chinense	FooDB	FooDB
Capsicum pubescens	FooDB	FooDB
Carica papaya L.	FooDB	FooDB
Carissa macrocarpa	FooDB	FooDB
Carthamus tinctorius	FooDB	FooDB
Carum carvi	FooDB	FooDB
Carya	FooDB	FooDB
Carya illinoinensis	FooDB	FooDB
Cassinia arcuata	LOTUS Database	35616633
Castanea	FooDB	FooDB
Castanea crenata	FooDB	FooDB
Castanea mollissima	FooDB	FooDB
Castanea sativa	FooDB	FooDB
Ceratonia siliqua	FooDB	FooDB
Chamaemelum nobile	FooDB	FooDB
Chamerion angustifolium	FooDB	FooDB
Chenopodium album	FooDB	FooDB
Chenopodium quinoa	FooDB	FooDB
Chenopodium vulvaria	LOTUS Database	35616633
Chrysanthemum coronarium	FooDB	FooDB
Cicer arietinum	FooDB	FooDB
Cichorium endivia	FooDB	FooDB
Cichorium intybus	FooDB	FooDB
Cinnamomum	FooDB	FooDB
Cinnamomum aromaticum	FooDB	FooDB
Cinnamomum verum	FooDB	FooDB
Cirsium	FooDB	FooDB
Cistus laurifolius	LOTUS Database	35616633
Citrullus lanatus	FooDB	FooDB
Citrus ×limon (L.) Burm. f. (pro sp.)	FooDB	FooDB
Citrus aurantiifolia	FooDB	FooDB
Citrus latifolia	FooDB	FooDB
Citrus limon	FooDB	FooDB
Citrus maxima	FooDB	FooDB
Citrus paradisi	FooDB	FooDB
Citrus reticulata	FooDB	FooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	FooDB
Cocos nucifera	FooDB	FooDB
Coffea arabica L.	FooDB	FooDB
Coffea canephora	FooDB	FooDB
Colocasia esculenta	FooDB	FooDB
Combretum albopunctatum	LOTUS Database	35616633
Combretum apiculatum	LOTUS Database	35616633
Corchorus olitorius	FooDB	FooDB
Coriandrum sativum L.	FooDB	FooDB
Corylus	FooDB	FooDB
Corylus avellana	FooDB	FooDB
Crateva religiosa	FooDB	FooDB
Crocus sativus	FooDB	FooDB
Cryptocarya concinna	LOTUS Database	35616633
Cryptocarya obovata	LOTUS Database	35616633
Cucumis melo	FooDB	FooDB
Cucumis metuliferus	FooDB	FooDB
Cucumis sativus L.	FooDB	FooDB
Cucurbita	FooDB	FooDB
Cucurbita maxima	FooDB	FooDB
Cucurbita moschata	FooDB	FooDB
Cuminum cyminum	FooDB	FooDB
Curcuma longa	FooDB	FooDB
Cydonia oblonga	FooDB	FooDB
Cymbopogon citratus	FooDB	FooDB
Cynara cardunculus	FooDB	FooDB
Cynara scolymus	FooDB	FooDB
Dalbergia odorifera	LOTUS Database	35616633
Dalbergia parviflora	LOTUS Database	35616633
Dalbergia sissoo	LOTUS Database	35616633
Daucus carota	FooDB	FooDB
Daucus carota ssp. sativus	FooDB	FooDB
Dennstaedtia scabra	LOTUS Database	35616633
Desmos cochinchinensis	LOTUS Database	35616633
Dimocarpus longan	FooDB	FooDB
Dioscorea	FooDB	FooDB
Dioscorea pentaphylla	FooDB	FooDB
Diospyros	FooDB	FooDB
Diospyros kaki	FooDB	FooDB
Diospyros virginiana	FooDB	FooDB
Dodonaea viscosa	LOTUS Database	35616633
Dolichlasium lagascae	LOTUS Database	35616633
Durio zibethinus	FooDB	FooDB
Dysphania ambrosioides	FooDB	FooDB
Dysphania graveolens	LOTUS Database	35616633
Elaeis	FooDB	FooDB
Eleocharis dulcis	FooDB	FooDB
Elettaria cardamomum	FooDB	FooDB
Empetrum nigrum	FooDB	FooDB
Eragrostis tef	FooDB	FooDB
Eremophila flaccida	LOTUS Database	35616633
Eriobotrya japonica	FooDB	FooDB
Eriodictyon californicum	LOTUS Database	35616633
Eruca vesicaria subsp. Sativa	FooDB	FooDB
Eucalyptus sieberi	LOTUS Database	35616633
Eugenia javanica	FooDB	FooDB
Eugenia uniflora	FooDB	FooDB
Euphorbia hirta	LOTUS Database	35616633
Eutrema japonicum	FooDB	FooDB
Fagopyrum esculentum	FooDB	FooDB
Fagopyrum tataricum	FooDB	FooDB
Fagus	FooDB	FooDB
Feijoa sellowiana	FooDB	FooDB
Ficus carica	FooDB	FooDB
Flammulina velutipes	FooDB	FooDB
Flourensia retinophylla	LOTUS Database	35616633
Foeniculum vulgare	FooDB	FooDB
Fragaria x ananassa	FooDB	FooDB
Garcinia mangostana	FooDB	FooDB
Gaylussacia baccata	FooDB	FooDB
Ginkgo biloba	FooDB	FooDB
Glycine max	FooDB	FooDB
Glycyrrhiza glabra	LOTUS Database	35616633
Glycyrrhiza lepidota	LOTUS Database	35616633
Glycyrrhiza uralensis	LOTUS Database	35616633
Goniothalamus borneensis	LOTUS Database	35616633
Goniothalamus griffithii	LOTUS Database	35616633
Gossypium	FooDB	FooDB
Greyia flanaganii	LOTUS Database	35616633
Grifola frondosa	FooDB	FooDB
Hedysarum alpinum	FooDB	FooDB
Helianthus annuus L.	FooDB	FooDB
Helianthus tuberosus	FooDB	FooDB
Helichrysum cymosum	LOTUS Database	35616633
Helichrysum formosissimum	LOTUS Database	35616633
Helichrysum forskahlii	LOTUS Database	35616633
Helichrysum oreophilum	LOTUS Database	35616633
Helichrysum trilineatum	LOTUS Database	35616633
Hibiscus sabbariffa	FooDB	FooDB
Hippophae rhamnoides	FooDB	FooDB
Hordeum vulgare	FooDB	FooDB
Hymenoclea monogyra	LOTUS Database	35616633
Hyssopus officinalis L.	FooDB	FooDB
Illicium verum	FooDB	FooDB
Ipomoea aquatica	FooDB	FooDB
Ipomoea batatas	FooDB	FooDB
Juglans	FooDB	FooDB
Juglans ailanthifolia	FooDB	FooDB
Juglans cinerea	FooDB	FooDB
Juglans nigra L.	FooDB	FooDB
Juglans regia	FooDB	FooDB
Lablab purpureus	FooDB	FooDB
Lactuca sativa	FooDB	FooDB
Lagenaria siceraria	FooDB	FooDB
Lagochilus leiacanthus	LOTUS Database	35616633
Lathyrus sativus	FooDB	FooDB
Laurus nobilis L.	FooDB	FooDB
Lens culinaris	FooDB	FooDB
Lentinus edodes	FooDB	FooDB
Lepidium sativum	FooDB	FooDB
Levisticum officinale	FooDB	FooDB
Lindera umbellata	LOTUS Database	35616633
Linum usitatissimum	FooDB	FooDB
Lippia origanoides	LOTUS Database	35616633
Litchi chinensis	FooDB	FooDB
Litsea glaucescens	LOTUS Database	35616633
Litsea rubescens	LOTUS Database	35616633
Lophopappus tarapacanus	LOTUS Database	35616633
Luffa aegyptiaca	FooDB	FooDB
Lupinus	FooDB	FooDB
Lupinus albus	FooDB	FooDB
Lychnophora diamantinana	LOTUS Database	35616633
Macadamia	FooDB	FooDB
Macadamia tetraphylla	FooDB	FooDB
Malpighia emarginata	FooDB	FooDB
Malus	FooDB	FooDB
Malus pumila	FooDB	FooDB
Mammea americana	FooDB	FooDB
Mangifera indica	FooDB	FooDB
Manihot esculenta	FooDB	FooDB
Manilkara zapota	FooDB	FooDB
Maranta arundinacea	FooDB	FooDB
Matricaria recutita	FooDB	FooDB
Matteuccia struthiopteris	FooDB	FooDB
Medicago sativa	FooDB	FooDB
Melissa officinalis L.	FooDB	FooDB
Melodorum fruticosum	LOTUS Database	35616633
Mentha	FooDB	FooDB
Mentha aquatica	FooDB	FooDB
Mentha arvensis	FooDB	FooDB
Mentha spicata	FooDB	FooDB
Mentha x piperita	FooDB	FooDB
Mespilus germanica	FooDB	FooDB
Metroxylon sagu	FooDB	FooDB
Momordica charantia	FooDB	FooDB
Morchellaceae	FooDB	FooDB
Morella rubra	FooDB	FooDB
Moringa oleifera	FooDB	FooDB
Morus	FooDB	FooDB
Morus nigra	FooDB	FooDB
Muntingia calabura	LOTUS Database	35616633
Musa acuminata	FooDB	FooDB
Musa x paradisiaca	FooDB	FooDB
Myrica	FooDB	FooDB
Myristica fragrans	FooDB	FooDB
Nelumbo	FooDB	FooDB
Nelumbo nucifera	FooDB	FooDB
Nephelium lappaceum	FooDB	FooDB
Nuphar lutea	FooDB	FooDB
Ocimum basilicum	FooDB	FooDB
Oenothera biennis	FooDB	FooDB
Olea europaea	FooDB	FooDB
Ononis natrix	LOTUS Database	35616633
Opuntia	FooDB	FooDB
Opuntia cochenillifera	FooDB	FooDB
Opuntia macrorhiza	FooDB	FooDB
Origanum majorana	FooDB	FooDB
Origanum onites	FooDB	FooDB
Origanum vulgare	FooDB	FooDB
Origanum X majoricum	FooDB	FooDB
Oryza rufipogon	FooDB	FooDB
Oryza sativa	FooDB	FooDB
Oxytropis falcata	LOTUS Database	35616633
Ozothamnus stirlingii	LOTUS Database	35616633
Pachyrhizus erosus	FooDB	FooDB
Panax ginseng	FooDB	FooDB
Pangium edule	FooDB	FooDB
Panicum miliaceum	FooDB	FooDB
Passiflora edulis	FooDB	FooDB
Pastinaca sativa	FooDB	FooDB
Pediomelum esculentum	FooDB	FooDB
Perideridia oregana	FooDB	FooDB
Persea americana	FooDB	FooDB
Petasites japonicus	FooDB	FooDB
Petroselinum crispum	FooDB	FooDB
Phaseolus coccineus	FooDB	FooDB
Phaseolus lunatus	FooDB	FooDB
Phaseolus vulgaris	FooDB	FooDB
Phoenix dactylifera	FooDB	FooDB
Phonus arborescens	LOTUS Database	35616633
Photinia melanocarpa	FooDB	FooDB
Phyllostachys edulis	FooDB	FooDB
Physalis	FooDB	FooDB
Physalis philadelphica var. immaculata	FooDB	FooDB
Phytolacca americana	FooDB	FooDB
Pimenta dioica	FooDB	FooDB
Pimpinella anisum	FooDB	FooDB
Pinus	FooDB	FooDB
Pinus aristata	LOTUS Database	35616633
Pinus contorta	LOTUS Database	35616633
Pinus edulis	FooDB	FooDB
Pinus morrisonicola	LOTUS Database	35616633
Pinus sibirica	LOTUS Database	35616633
Pinus virginiana	LOTUS Database	35616633
Piper gaudichaudianum	LOTUS Database	35616633
Piper hispidum	LOTUS Database	35616633
Piper hostmannianum	LOTUS Database	35616633
Piper nigrum L.	FooDB	FooDB
Piper sarmentosum	LOTUS Database	35616633
Pistacia vera	FooDB	FooDB
Pisum sativum	FooDB	FooDB
Pleurotus ostreatus	FooDB	FooDB
Polygonum alpinum	FooDB	FooDB
Populus alba	LOTUS Database	35616633
Populus balsamifera	LOTUS Database	35616633
Populus canadensis	LOTUS Database	35616633
Populus deltoides	LOTUS Database	35616633
Populus laurifolia	LOTUS Database	35616633
Populus nigra	LOTUS Database	35616633
Populus simonii	LOTUS Database	35616633
Populus suaveolens	LOTUS Database	35616633
Populus szechuanica	LOTUS Database	35616633
Populus tremuloides	LOTUS Database	35616633
Portulaca oleracea	FooDB	FooDB
Pouteria sapota	FooDB	FooDB
Prunus armeniaca	FooDB	FooDB
Prunus avium	FooDB	FooDB
Prunus avium L.	FooDB	FooDB
Prunus cerasus	FooDB	FooDB
Prunus domestica	FooDB	FooDB
Prunus dulcis	FooDB	FooDB
Prunus persica	FooDB	FooDB
Prunus persica var. nucipersica	FooDB	FooDB
Prunus persica var. persica	FooDB	FooDB
Prunus tomentosa	FooDB	FooDB
Prunus verecunda	LOTUS Database	35616633
Prunus virginiana	FooDB	FooDB
Pseudotsuga menziesii	LOTUS Database	35616633
Psidium cattleianum	FooDB	FooDB
Psidium guajava	FooDB	FooDB
Psophocarpus tetragonolobus	FooDB	FooDB
Pterocaulon serrulatum	LOTUS Database	35616633
Punica granatum	FooDB	FooDB
Pyracantha coccinea	LOTUS Database	35616633
Pyrus communis	FooDB	FooDB
Pyrus pyrifolia	FooDB	FooDB
Quercus	FooDB	FooDB
Raphanus sativus	FooDB	FooDB
Raphanus sativus var. longipinnatus	FooDB	FooDB
Raphanus sativus var. sativus	FooDB	FooDB
Ratibida columnaris	LOTUS Database	35616633
Rheum rhabarbarum	FooDB	FooDB
Rhododendron dauricum	LOTUS Database	35616633
Ribes aureum	FooDB	FooDB
Ribes glandulosum	FooDB	FooDB
Ribes nigrum	FooDB	FooDB
Ribes rubrum	FooDB	FooDB
Ribes uva-crispa	FooDB	FooDB
Rosa	FooDB	FooDB
Rubus arcticus	FooDB	FooDB
Rubus chamaemorus	FooDB	FooDB
Rubus idaeus	FooDB	FooDB
Rubus occidentalis	FooDB	FooDB
Rubus spectabilis	FooDB	FooDB
Rumex	FooDB	FooDB
Rumex acetosa	FooDB	FooDB
Rumex articus	FooDB	FooDB
Sagittaria latifolia	FooDB	FooDB
Salix pulchra	FooDB	FooDB
Salvia elegans	FooDB	FooDB
Salvia hispanica	FooDB	FooDB
Salvia officinalis	FooDB	FooDB
Salvia rosmarinus	FooDB	FooDB
Sambucus nigra	FooDB	FooDB
Sambucus nigra L.	FooDB	FooDB
Satureja hortensis L.	FooDB	FooDB
Satureja montana	FooDB	FooDB
Scorzonera hispanica	FooDB	FooDB
Scutellaria discolor	LOTUS Database	35616633
Scutellaria lateriflora	LOTUS Database	35616633
Secale cereale	FooDB	FooDB
Sechium edule	FooDB	FooDB
Sesamum indicum	FooDB	FooDB
Sesbania bispinosa	FooDB	FooDB
Sinapis alba	FooDB	FooDB
Sisymbrium	FooDB	FooDB
Solanum lycopersicum	FooDB	FooDB
Solanum lycopersicum var. cerasiforme	FooDB	FooDB
Solanum lycopersicum var. lycopersicum	FooDB	FooDB
Solanum melongena	FooDB	FooDB
Solanum quitoense	FooDB	FooDB
Solanum tuberosum	FooDB	FooDB
Sorbus aucuparia	FooDB	FooDB
Sorghum bicolor	FooDB	FooDB
Soymida febrifuga	LOTUS Database	35616633
Spinacia oleracea	FooDB	FooDB
Stellaria dichotoma	LOTUS Database	35616633
Swartzia apetala	LOTUS Database	35616633
Syzygium aromaticum	FooDB	FooDB
Syzygium cumini	FooDB	FooDB
Syzygium jambos	FooDB	FooDB
Syzygium samarangense	LOTUS Database	35616633
Tamarindus indica	FooDB	FooDB
Taraxacum officinale	FooDB	FooDB
Tetragonia tetragonioides	FooDB	FooDB
Thelesperma	FooDB	FooDB
Thymus pulegioides	FooDB	FooDB
Thymus vulgaris	FooDB	FooDB
Tilia cordata	FooDB	FooDB
Tilia L.	FooDB	FooDB
Tragopogon porrifolius	FooDB	FooDB
Trigonella foenum-graecum	FooDB	FooDB
Triticum	FooDB	FooDB
Triticum aestivum	FooDB	FooDB
Triticum durum	FooDB	FooDB
Triticum spelta	FooDB	FooDB
Triticum turanicum	FooDB	FooDB
Turnera diffusa	LOTUS Database	35616633
Typha angustifolia	FooDB	FooDB
Uvaria chamae	LOTUS Database	35616633
Uvaria dulcis	LOTUS Database	35616633
Vaccinium	FooDB	FooDB
Vaccinium angustifolium	FooDB	FooDB
Vaccinium angustifolium X Vaccinium corymbosum	FooDB	FooDB
Vaccinium arboreum	FooDB	FooDB
Vaccinium corymbosum	FooDB	FooDB
Vaccinium deliciosum	FooDB	FooDB
Vaccinium elliottii	FooDB	FooDB
Vaccinium macrocarpon	FooDB	FooDB
Vaccinium myrtilloides	FooDB	FooDB
Vaccinium myrtillus	FooDB	FooDB
Vaccinium ovalifolium	FooDB	FooDB
Vaccinium ovatum	FooDB	FooDB
Vaccinium oxycoccos	FooDB	FooDB
Vaccinium parvifolium	FooDB	FooDB
Vaccinium reticulatum	FooDB	FooDB
Vaccinium stamineum	FooDB	FooDB
Vaccinium uliginosum	FooDB	FooDB
Vaccinium vitis-idaea	FooDB	FooDB
Vachellia constricta	LOTUS Database	35616633
Vachellia vernicosa	LOTUS Database	35616633
Valerianella locusta	FooDB	FooDB
Vanilla	FooDB	FooDB
Verbena officinalis	FooDB	FooDB
Viburnum edule	FooDB	FooDB
Vicia faba	FooDB	FooDB
Vigna aconitifolia	FooDB	FooDB
Vigna angularis	FooDB	FooDB
Vigna mungo	FooDB	FooDB
Vigna radiata	FooDB	FooDB
Vigna umbellata	FooDB	FooDB
Vigna unguiculata	FooDB	FooDB
Vigna unguiculata ssp. cylindrica	FooDB	FooDB
Vigna unguiculata ssp. unguiculata	FooDB	FooDB
Vigna unguiculata var. sesquipedalis	FooDB	FooDB
Viscum coloratum	LOTUS Database	35616633
Vitis	FooDB	FooDB
Vitis aestivalis	FooDB	FooDB
Vitis labrusca	FooDB	FooDB
Vitis rotundifolia	FooDB	FooDB
Vitis vinifera L.	FooDB	FooDB
Xanthosoma sagittifolium	FooDB	FooDB
Zea mays L.	FooDB	FooDB
Zingiber officinale	FooDB	FooDB
Zizania	FooDB	FooDB
Zizania aquatica	FooDB	FooDB
Ziziphus zizyphus	FooDB	FooDB
Zuccagnia punctata	LOTUS Database	35616633

Chemical Taxonomy

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 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0141337

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002759

KNApSAcK ID

C00000992

Chemspider ID

Not Available

KEGG Compound ID

C09827

BioCyc ID

CPD-6991

BiGG ID

Not Available

Wikipedia Link

Pinocembrin

METLIN ID

Not Available

PubChem Compound

68071

PDB ID

Not Available

ChEBI ID

28157

Good Scents ID

Not Available

References

General References

Pan L, Matthew S, Lantvit DD, Zhang X, Ninh TN, Chai H, Carcache de Blanco EJ, Soejarto DD, Swanson SM, Kinghorn AD: Bioassay-guided isolation of constituents of Piper sarmentosum using a mitochondrial transmembrane potential assay. J Nat Prod. 2011 Oct 28;74(10):2193-9. doi: 10.1021/np200557e. Epub 2011 Oct 5. [PubMed:21973101 ]
Allard PM, Dau ET, Eydoux C, Guillemot JC, Dumontet V, Poullain C, Canard B, Gueritte F, Litaudon M: Alkylated flavanones from the bark of Cryptocarya chartacea as dengue virus NS5 polymerase inhibitors. J Nat Prod. 2011 Nov 28;74(11):2446-53. doi: 10.1021/np200715v. Epub 2011 Nov 3. [PubMed:22050318 ]
Yang N, Qin S, Wang M, Chen B, Yuan N, Fang Y, Yao S, Jiao P, Yu Y, Zhang Y, Wang J: Pinocembrin, a major flavonoid in propolis, improves the biological functions of EPCs derived from rat bone marrow through the PI3K-eNOS-NO signaling pathway. Cytotechnology. 2013 Aug;65(4):541-51. doi: 10.1007/s10616-012-9502-x. Epub 2012 Nov 22. [PubMed:23179089 ]
Sayre CL, Takemoto JK, Martinez SE, Davies NM: Chiral analytical method development and application to pre-clinical pharmacokinetics of pinocembrin. Biomed Chromatogr. 2013 Jun;27(6):681-4. doi: 10.1002/bmc.2853. Epub 2012 Dec 5. [PubMed:23212747 ]
Soromou LW, Zhang Y, Cui Y, Wei M, Chen N, Yang X, Huo M, Balde A, Guan S, Deng X, Wang D: Subinhibitory concentrations of pinocembrin exert anti-Staphylococcus aureus activity by reducing alpha-toxin expression. J Appl Microbiol. 2013 Jul;115(1):41-9. doi: 10.1111/jam.12221. Epub 2013 May 20. [PubMed:23594163 ]

Showing NP-Card for Pinocembrin (NP0044446)

MOL for NP0044446 (Pinocembrin)

3D MOL for NP0044446 (Pinocembrin)

3D SDF for NP0044446 (Pinocembrin)

3D-SDF for NP0044446 (Pinocembrin)

PDB for NP0044446 (Pinocembrin)

3D PDB for NP0044446 (Pinocembrin)

SMILES for NP0044446 (Pinocembrin)

INCHI for NP0044446 (Pinocembrin)

Structure for NP0044446 (Pinocembrin)

3D Structure for NP0044446 (Pinocembrin)