NP-MRD: Showing NP-Card for sakuranetin (NP0261618)

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Record Information

Version

2.0

Created at

2022-09-08 04:06:36 UTC

Updated at

2022-09-08 04:06:37 UTC

NP-MRD ID

NP0261618

Secondary Accession Numbers

None

Natural Product Identification

Common Name

sakuranetin

Description

5-Hydroxy-2-(4-hydroxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. sakuranetin is found in Artemisia campestris, Artemisia monosperma, Artemisia xanthochroa, Baccharis intermixta, Betula pubescens, Blumea fistulosa, Boesenbergia rotunda, Bonnetia paniculata, Brickellia vernicosa, Chromolaena odorata, Corymbia maculata, Cryptocarya obovata, Dittrichia graveolens, Dodonaea viscosa, Ageratina altissima, Heliotropium glutinosum, Isodon oresbius, Larrea tridentata, Lippia origanoides, Microtropis japonica, Mimosa tenuiflora, Oxytropis falcata, Phyla dulcis, Piper crassinervium, Piper marginatum, Plazia daphnoides, Poecilanthe parviflora, Populus tremuloides, Prunus avium, Prunus maximowiczii, Pyracantha coccinea and Xanthorrhoea resinosa. 5-Hydroxy-2-(4-hydroxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
    5.5358   -2.2355    0.6580 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1144   -2.4256    0.6136 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3169   -1.3113    0.3893 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8302   -0.0429    0.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0083    1.0428   -0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5189    2.2993   -0.1898 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6376    0.8528   -0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0749   -0.4025    0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9478   -1.4728    0.3431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2998   -0.6036    0.0819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1208    0.5138    0.3481 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5500    0.2205    0.2603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4145    0.6814    1.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7798    0.4208    1.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3257   -0.3138    0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6991   -0.5831    0.0843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4633   -0.7757   -0.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0951   -0.5128   -0.7685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6928    1.6008   -0.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7059    1.9511   -0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1280    3.1276   -0.1670 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0667   -3.1883    0.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8177   -1.5305    1.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8831   -1.7512   -0.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9184    0.0885    0.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5191    2.4369   -0.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5445   -2.4747    0.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8257    0.8917    1.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0327    1.2675    2.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4656    0.7774    1.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3436    0.0443   -0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8898   -1.3575   -1.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4431   -0.8911   -1.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3758    2.4826   -0.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7510    1.1731   -1.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7 20  1  0
 20 21  2  0
 20 19  1  0
 19 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  9  3  1  0
 18 12  1  0
  8  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
 19 34  1  0
 19 35  1  0
 11 28  1  1
  9 27  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
M  END

Sakuranetin
  Mrv1572001071617302D          

 21 23  0  0  0  0            999 V2000
   -0.7145   -1.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.3571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.1821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.3571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.1821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.7071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.7071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.7071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.7071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.5304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.5304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 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
  7 13  1  0  0  0  0
 13 14  2  0  0  0  0
  3 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0261618

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)CC(OC2=C1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-7,14,17-18H,8H2,1H3

> <INCHI_KEY>
DJOJDHGQRNZXQQ-UHFFFAOYSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.283

> <EXACT_MASS>
286.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
29.408474828418044

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.86

> <JCHEM_LOGP>
2.9810021063333334

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.5381887748914

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.624010049566934

> <JCHEM_PKA_STRONGEST_BASIC>
-4.601141020848354

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
75.77210000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.83e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sakuranetin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Sakuranetin                                       
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0      -1.334  -2.090   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -1.320   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.090   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -3.630   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -4.400   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667  -5.940   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -3.630   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -4.400   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335  -5.940   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668  -3.630   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.090   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335  -1.320   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -2.090   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -1.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -1.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -2.090   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669  -1.320   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669   0.220   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.003   0.990   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.336   0.990   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002   0.220   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   13                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13    3                                                       
CONECT   15   11   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
Sakuranetin	MeSH

Chemical Formula

C₁₆H₁₄O₅

Average Mass

286.2830 Da

Monoisotopic Mass

286.08412 Da

IUPAC Name

5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

sakuranetin

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)CC(OC2=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C16H14O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-7,14,17-18H,8H2,1H3

InChI Key

DJOJDHGQRNZXQQ-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Artemisia campestris	LOTUS Database	35616633
Artemisia monosperma	LOTUS Database	35616633
Artemisia xanthochroa	LOTUS Database	35616633
Baccharis intermixta	LOTUS Database	35616633
Betula pubescens	LOTUS Database	35616633
Blumea fistulosa	LOTUS Database	35616633
Boesenbergia rotunda	LOTUS Database	35616633
Bonnetia paniculata	LOTUS Database	35616633
Brickellia vernicosa	LOTUS Database	35616633
Chromolaena odorata	LOTUS Database	35616633
Corymbia maculata	LOTUS Database	35616633
Cryptocarya obovata	LOTUS Database	35616633
Dittrichia graveolens	LOTUS Database	35616633
Dodonaea viscosa	LOTUS Database	35616633
Eupatorium rugosum	LOTUS Database	35616633
Heliotropium glutinosum	LOTUS Database	35616633
Isodon oresbius	LOTUS Database	35616633
Larrea tridentata	LOTUS Database	35616633
Lippia origanoides	LOTUS Database	35616633
Microtropis japonica	LOTUS Database	35616633
Mimosa tenuiflora	LOTUS Database	35616633
Oxytropis falcata	LOTUS Database	35616633
Phyla dulcis	LOTUS Database	35616633
Piper crassinervium	LOTUS Database	35616633
Piper marginatum	LOTUS Database	35616633
Plazia daphnoides	LOTUS Database	35616633
Poecilanthe parviflora	LOTUS Database	35616633
Populus tremuloides	LOTUS Database	35616633
Prunus avium	LOTUS Database	35616633
Prunus maximowiczii	LOTUS Database	35616633
Pyracantha coccinea	LOTUS Database	35616633
Xanthorrhoea resinosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (CPD-7079 )

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	2.86	ALOGPS
logP	2.98	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	8.62	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	75.77 m³·mol⁻¹	ChemAxon
Polarizability	29.41 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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

348130

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for sakuranetin (NP0261618)

MOL for NP0261618 (sakuranetin)

3D MOL for NP0261618 (sakuranetin)

3D SDF for NP0261618 (sakuranetin)

3D-SDF for NP0261618 (sakuranetin)

PDB for NP0261618 (sakuranetin)

3D PDB for NP0261618 (sakuranetin)

SMILES for NP0261618 (sakuranetin)

INCHI for NP0261618 (sakuranetin)

Structure for NP0261618 (sakuranetin)

3D Structure for NP0261618 (sakuranetin)