NP-MRD: Showing NP-Card for (-)-dihydromyricetin (NP0235786)

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Record Information

Version

2.0

Created at

2022-09-06 18:31:04 UTC

Updated at

2022-09-06 18:31:04 UTC

NP-MRD ID

NP0235786

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-dihydromyricetin

Description

(-)-Dihydromyricetin belongs to the class of organic compounds known as epigallocatechins. Epigallocatechins are compounds containing epigallocatechin or a derivative. Epigallocatechin is a flavan-3-ol containing a benzopyran-3,5,7-triol linked to a 3,4,5-hydroxyphenyl moiety. (-)-dihydromyricetin is found in Morella rubra, Rhododendron decorum and Rhododendron spinuliferum. Based on a literature review very few articles have been published on (-)-dihydromyricetin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -2.2679    3.0459   -0.8061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6388    2.0554   -0.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3541    0.8698    0.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5341    0.5112   -0.5718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1462    1.2250   -1.5685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1184   -0.6689   -0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5358   -1.4142    0.9096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1906   -2.5855    1.3372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3483   -1.0213    1.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7596    0.1161    1.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5801    0.5606    1.5327 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3956    1.2932    0.8225 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4777    0.3854    0.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2127   -0.8336   -0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1998   -1.6943   -0.6705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8243   -2.9045   -1.2487 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5298   -1.3231   -0.5224 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4793   -2.2164   -0.9788 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8278   -0.1119    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1465    0.2835    0.2181 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8288    0.7255    0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1686    2.1259   -0.2933 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1869    3.4660   -0.1570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7807    2.0442   -1.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0553   -0.9681   -0.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9290   -3.4288    0.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9209   -1.6391    2.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8630    1.9867    1.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1552   -1.1067   -0.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4687   -3.5774   -1.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4781   -2.0871   -0.9401 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9108   -0.3015   -0.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0287    1.6860    0.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2837    1.7797   -1.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0310    3.7222    0.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  2  0
  9  7  1  0
  7  8  1  0
  7  6  2  0
  6  4  1  0
  4  5  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
  2 22  1  0
 21 13  1  0
  3 10  1  0
 23 35  1  0
 22 34  1  6
 12 28  1  1
  9 27  1  0
  8 26  1  0
  6 25  1  0
  5 24  1  0
 14 29  1  0
 16 30  1  0
 18 31  1  0
 20 32  1  0
 21 33  1  0
M  END


  Mrv1652309062220312D          

 23 25  0  0  1  0            999 V2000
    1.4289    0.8250    0.0000 O   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
    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
    2.8579    0.8250    0.0000 O   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
    4.2868   -1.6500    0.0000 O   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
    0.7145   -1.2375    0.0000 C   0  0  1  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   -3.7125    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
   -2.1434   -2.8875    0.0000 O   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
   -2.1434   -1.2375    0.0000 O   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
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 13 21  1  0  0  0  0
 12 22  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0235786

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1[C@@H](OC2=CC(O)=CC(O)=C2C1=O)C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,14-20,22H/t14-,15+/m1/s1

> <INCHI_KEY>
KJXSIXMJHKAJOD-CABCVRRESA-N

> <FORMULA>
C15H12O8

> <MOLECULAR_WEIGHT>
320.253

> <EXACT_MASS>
320.053217346

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
29.20902060545665

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
1.5128189463333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.754019780264308

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.722177104215204

> <JCHEM_PKA_STRONGEST_BASIC>
-4.045614034631817

> <JCHEM_POLAR_SURFACE_AREA>
147.68

> <JCHEM_REFRACTIVITY>
76.58980000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(-)-dihydromyricetin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.000  -0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   22                                                  
CONECT   13   12   14   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   13                                                       
CONECT   22   12    2   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
(2S,3S)-3,5,7,3',4',5'-Hexahydroxyflavanone	ChEBI

Chemical Formula

C₁₅H₁₂O₈

Average Mass

320.2530 Da

Monoisotopic Mass

320.05322 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

O[C@H]1[C@@H](OC2=CC(O)=CC(O)=C2C1=O)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C15H12O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,14-20,22H/t14-,15+/m1/s1

InChI Key

KJXSIXMJHKAJOD-CABCVRRESA-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
Morella rubra	LOTUS Database	35616633
Rhododendron decorum	LOTUS Database	35616633
Rhododendron spinuliferum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as epigallocatechins. Epigallocatechins are compounds containing epigallocatechin or a derivative. Epigallocatechin is a flavan-3-ol containing a benzopyran-3,5,7-triol linked to a 3,4,5-hydroxyphenyl moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Epigallocatechins

Alternative Parents

Substituents

Epigallocatechin
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Flavanonol
Hydroxyflavonoid
Chromone
Chromane
Benzopyran
1-benzopyran
Benzenetriol
Pyrogallol derivative
Aryl alkyl ketone
Aryl ketone
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Secondary alcohol
Polyol
Ether
Organoheterocyclic compound
Oxacycle
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydromyricetin (CHEBI:48027 )

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

Not Available

Chemspider ID

16735660

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12306070

PDB ID

Not Available

ChEBI ID

48027

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (-)-dihydromyricetin (NP0235786)

MOL for NP0235786 ((-)-dihydromyricetin)

3D MOL for NP0235786 ((-)-dihydromyricetin)

3D SDF for NP0235786 ((-)-dihydromyricetin)

3D-SDF for NP0235786 ((-)-dihydromyricetin)

PDB for NP0235786 ((-)-dihydromyricetin)

3D PDB for NP0235786 ((-)-dihydromyricetin)

SMILES for NP0235786 ((-)-dihydromyricetin)

INCHI for NP0235786 ((-)-dihydromyricetin)

Structure for NP0235786 ((-)-dihydromyricetin)

3D Structure for NP0235786 ((-)-dihydromyricetin)