NP-MRD: Showing NP-Card for Hesperetin-7-methyl ether (NP0138737)

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Record Information

Version

1.0

Created at

2022-06-29 18:33:54 UTC

Updated at

2022-06-29 18:33:54 UTC

NP-MRD ID

NP0138737

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hesperetin-7-methyl ether

Description

28590-40-1 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. Hesperetin-7-methyl ether is found in Adenothamnus validus, Artemisia campestris, Chromolaena odorata and Heliotropium glutinosum. It was first documented in 1993 (PMID: 35862567). Based on a literature review a significant number of articles have been published on 28590-40-1 (PMID: 35863886) (PMID: 35863885) (PMID: 35863884) (PMID: 35863883).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -6.0744    0.1798    2.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6837    0.3595    2.3241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9259    0.1180    1.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5329   -0.3285    0.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7538   -0.5632   -1.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3710   -1.0144   -2.2080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3967   -0.3495   -1.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7535    0.0993    0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5740    0.3258    1.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3818    0.3095    0.1698 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3927   -0.4859   -0.7312 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8362   -0.2604   -0.5377 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3001   -0.2360    0.7676 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6185   -0.0357    1.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5240    0.1500    0.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8802    0.3577    0.3490 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3126    0.3761    1.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0863    0.1299   -1.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9747    0.3138   -2.2955 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7403   -0.0754   -1.5504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0927   -0.2041   -2.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5333   -0.5920   -2.1749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0636   -1.1161   -3.1714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5167    0.6192    1.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2911   -0.8960    2.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4469    0.7584    3.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6231   -0.5016    0.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3422   -1.1862   -2.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0709    0.6819    2.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2055   -1.5802   -0.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5977   -0.3815    1.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9827   -0.0168    2.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3979    0.4316    1.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0056   -0.5654    2.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8243    1.2085    2.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9474    0.4658   -2.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3842   -0.0937   -2.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4747   -0.7261   -2.8997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0574    0.9004   -2.2784 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 22  1  0
 22 23  2  0
 22 21  1  0
 21 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  2  0
 11 12  1  0
 12 20  2  0
 20 18  1  0
 18 19  1  0
 18 15  2  0
 15 16  1  0
 16 17  1  0
 15 14  1  0
 14 13  2  0
  9  3  1  0
 13 12  1  0
  8  7  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
 21 38  1  0
 21 39  1  0
 11 30  1  1
  9 29  1  0
 20 37  1  0
 19 36  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 14 32  1  0
 13 31  1  0
M  END


  Mrv1652306292220332D          

 23 25  0  0  1  0            999 V2000
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  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    0.0000    0.0000 C   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
    2.1434   -0.4125    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
    3.5724   -0.4125    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
    2.8579   -1.6500    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
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   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
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  9  6  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 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
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 14 22  1  0  0  0  0
  4 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138737

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)C[C@H](OC2=C1)C1=CC(O)=C(OC)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O6/c1-21-10-6-12(19)17-13(20)8-15(23-16(17)7-10)9-3-4-14(22-2)11(18)5-9/h3-7,15,18-19H,8H2,1-2H3/t15-/m0/s1

> <INCHI_KEY>
LWBHKKLWSUFUNZ-HNNXBMFYSA-N

> <FORMULA>
C17H16O6

> <MOLECULAR_WEIGHT>
316.309

> <EXACT_MASS>
316.094688235

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
32.36481405604477

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.80

> <JCHEM_LOGP>
2.8233308406666655

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.826704996459267

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.65756984104606

> <JCHEM_PKA_STRONGEST_BASIC>
-4.421349796173209

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
82.2353

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.31e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -5.390   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   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  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   23                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18    9                                                       
CONECT   20   16   21                                                       
CONECT   21   20                                                            
CONECT   22   14                                                            
CONECT   23    4                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₆O₆

Average Mass

316.3090 Da

Monoisotopic Mass

316.09469 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)C[C@H](OC2=C1)C1=CC(O)=C(OC)C=C1

InChI Identifier

InChI=1S/C17H16O6/c1-21-10-6-12(19)17-13(20)8-15(23-16(17)7-10)9-3-4-14(22-2)11(18)5-9/h3-7,15,18-19H,8H2,1-2H3/t15-/m0/s1

InChI Key

LWBHKKLWSUFUNZ-HNNXBMFYSA-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
Adenothamnus validus	LOTUS Database	35616633
Artemisia campestris	LOTUS Database	35616633
Chromolaena odorata	LOTUS Database	35616633
Heliotropium glutinosum	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
4p-methoxyflavonoid-skeleton
Flavanone
Hydroxyflavonoid
5-hydroxyflavonoid
3'-hydroxyflavonoid
Flavan
Chromone
Chromane
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Methoxybenzene
Aryl alkyl ketone
Anisole
Phenol ether
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00008300

Chemspider ID

31122037

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14157910

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Morales Corado JA, Lee CU, Enns GM: Carnitine-Acylcarnitine Translocase Deficiency. 1993. [PubMed:35862567 ]
Kaorop W, Maneechote C, Kumfu S, Chattipakorn SC, Chattipakorn N: Mitochondrial-derived peptides as a novel intervention for obesity and cardiac diseases: bench evidence for potential bedside application. J Clin Pathol. 2022 Jul 21. pii: jcp-2022-208321. doi: 10.1136/jcp-2022-208321. [PubMed:35863886 ]
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Showing NP-Card for Hesperetin-7-methyl ether (NP0138737)

MOL for NP0138737 (Hesperetin-7-methyl ether)

3D MOL for NP0138737 (Hesperetin-7-methyl ether)

3D SDF for NP0138737 (Hesperetin-7-methyl ether)

3D-SDF for NP0138737 (Hesperetin-7-methyl ether)

PDB for NP0138737 (Hesperetin-7-methyl ether)

3D PDB for NP0138737 (Hesperetin-7-methyl ether)

SMILES for NP0138737 (Hesperetin-7-methyl ether)

INCHI for NP0138737 (Hesperetin-7-methyl ether)

Structure for NP0138737 (Hesperetin-7-methyl ether)

3D Structure for NP0138737 (Hesperetin-7-methyl ether)