NP-MRD: Showing NP-Card for Peonidin (NP0046032)

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Record Information

Version

2.0

Created at

2022-03-17 19:47:17 UTC

Updated at

2022-03-17 19:47:17 UTC

NP-MRD ID

NP0046032

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Peonidin

Description

Peonidin is found in Dioscorea alata , Ginkgo biloba , Solanum tuberosum subsp. Andigena and Valeriana spryginii. Peonidin was first documented in 2013 (PMID: 23419638).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305221920052D          

 22 24  0  0  0  0            999 V2000
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  8  2  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  2  0  0  0  0
 11  3  1  0  0  0  0
 12  5  2  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 14  6  1  0  0  0  0
 14 10  1  0  0  0  0
 15  4  1  0  0  0  0
 15 11  2  0  0  0  0
 16  8  1  0  0  0  0
 16 13  2  0  0  0  0
 17  9  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20 13  1  0  0  0  0
 21  1  1  0  0  0  0
 21 15  1  0  0  0  0
 22 14  2  0  0  0  0
 22 16  1  0  0  0  0
M  CHG  1  22   1
M  END
> <DATABASE_ID>
NP0046032

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(=C1)C1=C(O)C=C2C(O)=CC(O)=CC2=[O+]1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O6/c1-21-15-4-8(2-3-11(15)18)16-13(20)7-10-12(19)5-9(17)6-14(10)22-16/h2-7H,1H3,(H3-,17,18,19,20)/p+1

> <INCHI_KEY>
XFDQJKDGGOEYPI-UHFFFAOYSA-O

> <FORMULA>
C16H13O6

> <MOLECULAR_WEIGHT>
301.2708

> <EXACT_MASS>
301.071213148

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
30.137943363322044

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1lambda4-chromen-1-ylium

> <ALOGPS_LOGP>
1.90

> <JCHEM_LOGP>
3.082

> <ALOGPS_LOGS>
-4.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.8248954317188755

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.012336535390854

> <JCHEM_PKA_STRONGEST_BASIC>
-4.90136353188422

> <JCHEM_POLAR_SURFACE_AREA>
103.29

> <JCHEM_REFRACTIVITY>
88.59539999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1lambda4-chromen-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+1
CONECT    1   21                                                            
CONECT    2    3    8                                                       
CONECT    3    2   11                                                       
CONECT    4    8   15                                                       
CONECT    5    9   12                                                       
CONECT    6    9   14                                                       
CONECT    7   10   13                                                       
CONECT    8    2    4   16                                                  
CONECT    9    5    6   17                                                  
CONECT   10    7   12   14                                                  
CONECT   11    3   15   18                                                  
CONECT   12    5   10   19                                                  
CONECT   13    7   16   20                                                  
CONECT   14    6   10   22                                                  
CONECT   15    4   11   21                                                  
CONECT   16    8   13   22                                                  
CONECT   17    9                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21    1   15                                                       
CONECT   22   14   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
3,4',5,7-Tetrahydroxy-3'-methoxyflavylium	ChEBI
3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-benzopyrylium	ChEBI
3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-benzopyrylium chloride	ChEBI
Peonidin cation	ChEBI
Peonidin(1+)	ChEBI

Chemical Formula

C₁₆H₁₃O₆

Average Mass

301.2708 Da

Monoisotopic Mass

301.07121 Da

IUPAC Name

3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1lambda4-chromen-1-ylium

Traditional Name

3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1lambda4-chromen-1-ylium

CAS Registry Number

134-01-0

SMILES

COC1=C(O)C=CC(=C1)C1=C(O)C=C2C(O)=CC(O)=CC2=[O+]1

InChI Identifier

InChI=1S/C16H12O6/c1-21-15-4-8(2-3-11(15)18)16-13(20)7-10-12(19)5-9(17)6-14(10)22-16/h2-7H,1H3,(H3-,17,18,19,20)/p+1

InChI Key

XFDQJKDGGOEYPI-UHFFFAOYSA-O

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
Actinidia chinensis	FooDB	USDA
Allium cepa	FooDB	USDA
Allium cepa L.	FooDB	USDA
Amelanchier alnifolia	FooDB	USDA
Anacardium occidentale	FooDB	USDA
Ananas comosus	FooDB	USDA
Apium graveolens	FooDB	USDA
Arachis hypogaea	FooDB	USDA
Bertholletia excelsa	FooDB	USDA
Brassica oleracea	FooDB	USDA
Brassica oleracea var. italica	FooDB	USDA
Brassica ruvo	FooDB	USDA
Carya illinoinensis	FooDB	USDA
Citrullus lanatus	FooDB	USDA
Citrus paradisi	FooDB	USDA
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	KNAPSACK
Corylus	FooDB	USDA
Cucumis melo	FooDB	USDA
Cynara scolymus	FooDB	USDA
Daucus carota ssp. sativus	FooDB	USDA
Dioscorea alata	Plant	KNApSAcK
Ficus carica	FooDB	USDA
Fragaria x ananassa	FooDB	USDA
Ginkgo biloba	Plant	KNApSAcK
Hippophae rhamnoides	FooDB	USDA
Ipomoea batatas	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Juglans regia	FooDB	USDA
Lactuca sativa	FooDB	USDA
Macadamia	FooDB	USDA
Malus pumila	FooDB	USDA
Musa acuminata	FooDB	USDA
Musa x paradisiaca	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Olea europaea	FooDB	KNAPSACK
Origanum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Persea americana	FooDB	USDA
Phaseolus vulgaris	FooDB	PHENOL EXPLORER
Phoenix dactylifera	FooDB	USDA
Photinia melanocarpa	FooDB	USDA
Pinus edulis	FooDB	USDA
Pistacia vera	FooDB	USDA
Pisum sativum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus avium	FooDB	USDA
Prunus avium L.	FooDB	USDA
Prunus cerasus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus domestica	FooDB	PHENOL EXPLORER
Prunus dulcis	FooDB	USDA
Prunus persica	FooDB	USDA
Prunus persica var. nucipersica	FooDB	USDA
Punica granatum	FooDB	USDA
Pyrus communis	FooDB	USDA
Raphanus sativus	FooDB	USDA
Ribes nigrum	FooDB	USDA
Ribes rubrum	FooDB	USDA
Ribes uva-crispa	FooDB	USDA
Rosa	FooDB	KNAPSACK
Rubus occidentalis	FooDB	USDA
Solanum lycopersicum	FooDB	USDA
Solanum tuberosum	FooDB	USDA
Solanum tuberosum subsp. Andigena	Plant	KNApSAcK
Syzygium cumini	FooDB	USDA
Triticum	FooDB	USDA
Vaccinium	FooDB	USDA
Vaccinium corymbosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vaccinium macrocarpon	FooDB	USDA
Vaccinium myrtillus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Valeriana spryginii	Plant	KNApSAcK
Vigna unguiculata	FooDB	USDA
Vitis	FooDB	USDA
Vitis vinifera L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3' atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

3'-O-methylated flavonoids

Alternative Parents

Substituents

3p-methoxyflavonoid-skeleton
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Anthocyanidin
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Organoheterocyclic compound
Ether
Oxacycle
Polyol
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

anthocyanidin cation (CHEBI:75314 )
Anthocyanidins (C08726 )
Anthocyanidins (LMPK12010006 )

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	1.9	ALOGPS
logP	3.08	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	6.01	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	103.29 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	88.6 m³·mol⁻¹	ChemAxon
Polarizability	30.14 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017306

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-15052

BiGG ID

Not Available

Wikipedia Link

Peonidin

METLIN ID

Not Available

PubChem Compound

441773

PDB ID

Not Available

ChEBI ID

75314

Good Scents ID

Not Available

References

General References

Kamenickova A, Anzenbacherova E, Pavek P, Soshilov AA, Denison MS, Anzenbacher P, Dvorak Z: Pelargonidin activates the AhR and induces CYP1A1 in primary human hepatocytes and human cancer cell lines HepG2 and LS174T. Toxicol Lett. 2013 Apr 26;218(3):253-9. doi: 10.1016/j.toxlet.2013.01.020. Epub 2013 Feb 16. [PubMed:23419638 ]
Ngo QA, Albrecht H, Tsuchimatsu T, Grossniklaus U: The differentially regulated genes TvQR1 and TvPirin of the parasitic plant Triphysaria exhibit distinctive natural allelic diversity. BMC Plant Biol. 2013 Feb 18;13:28. doi: 10.1186/1471-2229-13-28. [PubMed:23419068 ]

Showing NP-Card for Peonidin (NP0046032)

MOL for NP0046032 (Peonidin)

3D MOL for NP0046032 (Peonidin)

3D SDF for NP0046032 (Peonidin)

3D-SDF for NP0046032 (Peonidin)

PDB for NP0046032 (Peonidin)

3D PDB for NP0046032 (Peonidin)

SMILES for NP0046032 (Peonidin)

INCHI for NP0046032 (Peonidin)

Structure for NP0046032 (Peonidin)

3D Structure for NP0046032 (Peonidin)