NP-MRD: Showing NP-Card for dihydromyricetin (NP0024994)

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Record Information

Version

1.0

Created at

2021-06-19 17:13:53 UTC

Updated at

2021-06-29 23:49:40 UTC

NP-MRD ID

NP0024994

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dihydromyricetin

Provided By

JEOL Database JEOL Logo

Description

Dihydromyricetin is also known as ampelopsin. dihydromyricetin is found in Berberis duclouxiana, Brassica carinata, Burkea africana, Catha edulis, Catharanthus roseus, Cistus incanus, Cyphostemma digitatum, Hovenia dulcis , Manilkara zapota, Gymnosporia senegalensis, Morella rubra, Ampelopsis grossendentata, Nympaea spp., Onobrychis viciifolia, Petunia hybrida, Pinus contorta, Punica granatum L. , Rhododendron decorum, Rhododendron spinuliferum, Salix sachalinensis, Sedum rupestre, Shuteria involucrata, Stachyurus himalaicus, Wedelia prostrata, Xanthoceras sorbifolia and Zea mays . It was first documented in 2003 (PMID: 12889119). Based on a literature review a significant number of articles have been published on Dihydromyricetin (PMID: 17059013) (PMID: 22693649) (PMID: 34583588) (PMID: 34539879).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119133D          

 35 37  0  0  0  0            999 V2000
   -2.1298   -2.5652    0.3422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6387   -1.6537    1.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0736   -1.9369    2.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1406   -3.2164    2.9037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6951   -4.2900    2.2602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6376   -3.4490    4.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0741   -2.3923    4.8898 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4238   -2.5674    6.1467 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0012   -1.1171    4.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4853   -0.8920    3.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3763    0.3847    2.5739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3979    0.4871    1.1397 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3819    1.9673    0.7724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471    2.3830   -0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2452    3.7291   -0.7765 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375    4.1749   -1.9254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3757    4.6675    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3821    5.9925   -0.3063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0047    4.2690    1.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6222    5.1920    2.0005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0170    2.9308    1.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6205   -0.2139    0.5369 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5693   -0.2264   -0.8946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0069   -3.9956    1.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6997   -4.4468    4.6044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984   -3.4948    6.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4459   -0.3046    4.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5328    0.0402    0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7187    1.6437   -1.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1829    3.4023   -2.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1104    6.0201   -1.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4769    6.0441    1.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5192    2.6481    2.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5595    0.2561    0.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2283   -0.8891   -1.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  7  6  2  0  0  0  0
 13 21  2  0  0  0  0
  7  9  1  0  0  0  0
 21 19  1  0  0  0  0
  6  4  1  0  0  0  0
 19 17  2  0  0  0  0
  4  3  2  0  0  0  0
 17 15  1  0  0  0  0
 10  9  2  0  0  0  0
 15 14  2  0  0  0  0
 14 13  1  0  0  0  0
 12 13  1  0  0  0  0
 10 11  1  0  0  0  0
 17 18  1  0  0  0  0
  3  2  1  0  0  0  0
  7  8  1  0  0  0  0
  2 22  1  0  0  0  0
  4  5  1  0  0  0  0
 22 12  1  0  0  0  0
 15 16  1  0  0  0  0
 12 11  1  0  0  0  0
 19 20  1  0  0  0  0
 10  3  1  0  0  0  0
 22 23  1  0  0  0  0
  6 25  1  0  0  0  0
  9 27  1  0  0  0  0
 22 34  1  6  0  0  0
 12 28  1  6  0  0  0
 21 33  1  0  0  0  0
 14 29  1  0  0  0  0
 18 31  1  0  0  0  0
  8 26  1  0  0  0  0
  5 24  1  0  0  0  0
 16 30  1  0  0  0  0
 20 32  1  0  0  0  0
 23 35  1  0  0  0  0
M  END

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -2.1298   -2.5652    0.3422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6387   -1.6537    1.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0736   -1.9369    2.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1406   -3.2164    2.9037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6951   -4.2900    2.2602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6376   -3.4490    4.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0741   -2.3923    4.8898 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4238   -2.5674    6.1467 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0012   -1.1171    4.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4853   -0.8920    3.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3763    0.3847    2.5739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3979    0.4871    1.1397 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3819    1.9673    0.7724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471    2.3830   -0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2452    3.7291   -0.7765 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375    4.1749   -1.9254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3757    4.6675    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3821    5.9925   -0.3063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0047    4.2690    1.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6222    5.1920    2.0005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0170    2.9308    1.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6205   -0.2139    0.5369 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5693   -0.2264   -0.8946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0069   -3.9956    1.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6997   -4.4468    4.6044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984   -3.4948    6.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4459   -0.3046    4.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5328    0.0402    0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7187    1.6437   -1.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1829    3.4023   -2.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1104    6.0201   -1.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4769    6.0441    1.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5192    2.6481    2.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5595    0.2561    0.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2283   -0.8891   -1.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  7  6  2  0
 13 21  2  0
  7  9  1  0
 21 19  1  0
  6  4  1  0
 19 17  2  0
  4  3  2  0
 17 15  1  0
 10  9  2  0
 15 14  2  0
 14 13  1  0
 12 13  1  0
 10 11  1  0
 17 18  1  0
  3  2  1  0
  7  8  1  0
  2 22  1  0
  4  5  1  0
 22 12  1  0
 15 16  1  0
 12 11  1  0
 19 20  1  0
 10  3  1  0
 22 23  1  0
  6 25  1  0
  9 27  1  0
 22 34  1  6
 12 28  1  6
 21 33  1  0
 14 29  1  0
 18 31  1  0
  8 26  1  0
  5 24  1  0
 16 30  1  0
 20 32  1  0
 23 35  1  0
M  END


  Mrv1652306192119133D          

 35 37  0  0  0  0            999 V2000
   -2.1298   -2.5652    0.3422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6387   -1.6537    1.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0736   -1.9369    2.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1406   -3.2164    2.9037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6951   -4.2900    2.2602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6376   -3.4490    4.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0741   -2.3923    4.8898 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4238   -2.5674    6.1467 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0012   -1.1171    4.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4853   -0.8920    3.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3763    0.3847    2.5739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3979    0.4871    1.1397 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3819    1.9673    0.7724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471    2.3830   -0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2452    3.7291   -0.7765 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375    4.1749   -1.9254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3757    4.6675    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3821    5.9925   -0.3063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0047    4.2690    1.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6222    5.1920    2.0005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0170    2.9308    1.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6205   -0.2139    0.5369 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5693   -0.2264   -0.8946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0069   -3.9956    1.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6997   -4.4468    4.6044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984   -3.4948    6.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4459   -0.3046    4.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5328    0.0402    0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7187    1.6437   -1.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1829    3.4023   -2.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1104    6.0201   -1.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4769    6.0441    1.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5192    2.6481    2.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5595    0.2561    0.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2283   -0.8891   -1.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  7  6  2  0  0  0  0
 13 21  2  0  0  0  0
  7  9  1  0  0  0  0
 21 19  1  0  0  0  0
  6  4  1  0  0  0  0
 19 17  2  0  0  0  0
  4  3  2  0  0  0  0
 17 15  1  0  0  0  0
 10  9  2  0  0  0  0
 15 14  2  0  0  0  0
 14 13  1  0  0  0  0
 12 13  1  0  0  0  0
 10 11  1  0  0  0  0
 17 18  1  0  0  0  0
  3  2  1  0  0  0  0
  7  8  1  0  0  0  0
  2 22  1  0  0  0  0
  4  5  1  0  0  0  0
 22 12  1  0  0  0  0
 15 16  1  0  0  0  0
 12 11  1  0  0  0  0
 19 20  1  0  0  0  0
 10  3  1  0  0  0  0
 22 23  1  0  0  0  0
  6 25  1  0  0  0  0
  9 27  1  0  0  0  0
 22 34  1  6  0  0  0
 12 28  1  6  0  0  0
 21 33  1  0  0  0  0
 14 29  1  0  0  0  0
 18 31  1  0  0  0  0
  8 26  1  0  0  0  0
  5 24  1  0  0  0  0
 16 30  1  0  0  0  0
 20 32  1  0  0  0  0
 23 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0024994

> <DATABASE_NAME>
NP-MRD

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

> <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+/m0/s1

> <INCHI_KEY>
KJXSIXMJHKAJOD-LSDHHAIUSA-N

> <FORMULA>
C15H12O8

> <MOLECULAR_WEIGHT>
320.251

> <EXACT_MASS>
320.05321736

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
29.1969978170371

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.89

> <JCHEM_LOGP>
1.5128189463333332

> <ALOGPS_LOGS>
-2.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.754019780264306

> <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

> <ALOGPS_SOLUBILITY>
1.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-dihydromyricetin

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -2.1298   -2.5652    0.3422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6387   -1.6537    1.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0736   -1.9369    2.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1406   -3.2164    2.9037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6951   -4.2900    2.2602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6376   -3.4490    4.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0741   -2.3923    4.8898 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4238   -2.5674    6.1467 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0012   -1.1171    4.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4853   -0.8920    3.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3763    0.3847    2.5739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3979    0.4871    1.1397 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3819    1.9673    0.7724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471    2.3830   -0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2452    3.7291   -0.7765 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375    4.1749   -1.9254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3757    4.6675    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3821    5.9925   -0.3063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0047    4.2690    1.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6222    5.1920    2.0005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0170    2.9308    1.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6205   -0.2139    0.5369 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5693   -0.2264   -0.8946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0069   -3.9956    1.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6997   -4.4468    4.6044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984   -3.4948    6.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4459   -0.3046    4.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5328    0.0402    0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7187    1.6437   -1.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1829    3.4023   -2.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1104    6.0201   -1.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4769    6.0441    1.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5192    2.6481    2.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5595    0.2561    0.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2283   -0.8891   -1.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  7  6  2  0
 13 21  2  0
  7  9  1  0
 21 19  1  0
  6  4  1  0
 19 17  2  0
  4  3  2  0
 17 15  1  0
 10  9  2  0
 15 14  2  0
 14 13  1  0
 12 13  1  0
 10 11  1  0
 17 18  1  0
  3  2  1  0
  7  8  1  0
  2 22  1  0
  4  5  1  0
 22 12  1  0
 15 16  1  0
 12 11  1  0
 19 20  1  0
 10  3  1  0
 22 23  1  0
  6 25  1  0
  9 27  1  0
 22 34  1  6
 12 28  1  6
 21 33  1  0
 14 29  1  0
 18 31  1  0
  8 26  1  0
  5 24  1  0
 16 30  1  0
 20 32  1  0
 23 35  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  O   UNK     0      -2.130  -2.565   0.342  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.639  -1.654   1.010  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.074  -1.937   2.338  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.141  -3.216   2.904  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.695  -4.290   2.260  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.638  -3.449   4.181  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.074  -2.392   4.890  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.424  -2.567   6.147  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.001  -1.117   4.336  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.485  -0.892   3.049  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.376   0.385   2.574  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.398   0.487   1.140  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.382   1.967   0.772  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.247   2.383  -0.420  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.245   3.729  -0.777  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.838   4.175  -1.925  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.376   4.668   0.037  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.382   5.992  -0.306  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.005   4.269   1.207  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.622   5.192   2.001  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.017   2.931   1.580  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.621  -0.214   0.537  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.569  -0.226  -0.895  0.00  0.00           O+0
HETATM   24  H   UNK     0      -2.007  -3.996   1.375  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.700  -4.447   4.604  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.298  -3.495   6.410  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.446  -0.305   4.905  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.533   0.040   0.760  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.719   1.644  -1.062  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.183   3.402  -2.406  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.110   6.020  -1.152  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.477   6.044   1.542  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.519   2.648   2.502  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.559   0.256   0.852  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.228  -0.889  -1.184  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    4    2   10                                                  
CONECT    4    6    3    5                                                  
CONECT    5    4   24                                                       
CONECT    6    7    4   25                                                  
CONECT    7    6    9    8                                                  
CONECT    8    7   26                                                       
CONECT    9    7   10   27                                                  
CONECT   10    9   11    3                                                  
CONECT   11   10   12                                                       
CONECT   12   13   22   11   28                                             
CONECT   13   21   14   12                                                  
CONECT   14   15   13   29                                                  
CONECT   15   17   14   16                                                  
CONECT   16   15   30                                                       
CONECT   17   19   15   18                                                  
CONECT   18   17   31                                                       
CONECT   19   21   17   20                                                  
CONECT   20   19   32                                                       
CONECT   21   13   19   33                                                  
CONECT   22    2   12   23   34                                             
CONECT   23   22   35                                                       
CONECT   24    5                                                            
CONECT   25    6                                                            
CONECT   26    8                                                            
CONECT   27    9                                                            
CONECT   28   12                                                            
CONECT   29   14                                                            
CONECT   30   16                                                            
CONECT   31   18                                                            
CONECT   32   20                                                            
CONECT   33   21                                                            
CONECT   34   22                                                            
CONECT   35   23                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

RDKit          3D

35 37  0  0  0  0  0  0  0  0999 V2000
   -2.1298   -2.5652    0.3422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6387   -1.6537    1.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0736   -1.9369    2.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1406   -3.2164    2.9037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6951   -4.2900    2.2602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6376   -3.4490    4.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0741   -2.3923    4.8898 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4238   -2.5674    6.1467 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0012   -1.1171    4.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4853   -0.8920    3.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3763    0.3847    2.5739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3979    0.4871    1.1397 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3819    1.9673    0.7724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471    2.3830   -0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2452    3.7291   -0.7765 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375    4.1749   -1.9254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3757    4.6675    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3821    5.9925   -0.3063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0047    4.2690    1.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6222    5.1920    2.0005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0170    2.9308    1.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6205   -0.2139    0.5369 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5693   -0.2264   -0.8946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0069   -3.9956    1.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6997   -4.4468    4.6044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984   -3.4948    6.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4459   -0.3046    4.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5328    0.0402    0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7187    1.6437   -1.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1829    3.4023   -2.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1104    6.0201   -1.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4769    6.0441    1.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5192    2.6481    2.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5595    0.2561    0.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2283   -0.8891   -1.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  7  6  2  0
 13 21  2  0
  7  9  1  0
 21 19  1  0
  6  4  1  0
 19 17  2  0
  4  3  2  0
 17 15  1  0
 10  9  2  0
 15 14  2  0
 14 13  1  0
 12 13  1  0
 10 11  1  0
 17 18  1  0
  3  2  1  0
  7  8  1  0
  2 22  1  0
  4  5  1  0
 22 12  1  0
 15 16  1  0
 12 11  1  0
 19 20  1  0
 10  3  1  0
 22 23  1  0
  6 25  1  0
  9 27  1  0
 22 34  1  6
 12 28  1  6
 21 33  1  0
 14 29  1  0
 18 31  1  0
  8 26  1  0
  5 24  1  0
 16 30  1  0
 20 32  1  0
 23 35  1  0
M  END

View in JSmol

Synonyms

Value	Source
(+)-Ampelopsin	ChEBI
(2R,3R)-2,3-Dihydro-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one	ChEBI
(2R,3R)-3,3',4',5,5',7-Hexahydroxy-2,3-dihydroflavanonol	ChEBI
(2R,3R)-3,5,7,3',4',5'-Hexahydroxyflavanone	ChEBI
(2R,3R)-Dihydromyricetin	ChEBI
Ampelopsin	ChEBI
Ampeloptin	ChEBI
(+)-Dihydromyricetin	Kegg
3,3',4',5,5',7-Hexahydroxyflavanone	PhytoBank
3,3’,4’,5,5’,7-Hexahydroxyflavanone	PhytoBank
Dihydromyricetin	PhytoBank
Dihydromyrcetin	PhytoBank

Chemical Formula

C₁₅H₁₂O₈

Average Mass

320.2510 Da

Monoisotopic Mass

320.05322 Da

IUPAC Name

(2R,3R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(+)-dihydromyricetin

CAS Registry Number

Not Available

SMILES

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

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+/m0/s1

InChI Key

KJXSIXMJHKAJOD-LSDHHAIUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Adenanthera pavonina	KNApSAcK Database	22123792
Ampelopsis meliaefolia	KNApSAcK Database	22123792
Antirrhinum majus	KNApSAcK Database	22123792
Asparagus officinalis	KNApSAcK Database	22123792
Berberis duclouxiana	LOTUS Database	35616633
Brassica carinata	LOTUS Database	35616633
Brassica carinata Y line	KNApSAcK Database	22123792
Burkea africana	LOTUS Database	35616633
Capsicum annuum	KNApSAcK Database	22123792
Catha edulis	LOTUS Database	35616633
Catharanthus roseus	LOTUS Database	35616633
Cedrus deodara	KNApSAcK Database	22123792
Cercidiphyllum japonicum	KNApSAcK Database	22123792
Cistus incanus	LOTUS Database	35616633
Citrus incanus	KNApSAcK Database	22123792
Cyphostemma digitatum	LOTUS Database	35616633
Euscaphis konishii	KNApSAcK Database	22123792
Gentiana lutea L. var. aurantiaca	KNApSAcK Database	22123792
Ginkgo biloba	KNApSAcK Database	22123792
Heuchera villosa	KNApSAcK Database	22123792
Hovenia dulcis	Plant	KNApSAcK
Intsia bijuga	KNApSAcK Database	22123792
Leptarrhena pyrolifolia	KNApSAcK Database	22123792
Mahonia siamensis	KNApSAcK Database	22123792
Manilkara zapota	LOTUS Database	35616633
Manilkara zapota cv.Tikal	KNApSAcK Database	22123792
Maytenus senegalensis	LOTUS Database	35616633
Medicago truncatula	KNApSAcK Database	22123792
Morella rubra	LOTUS Database	35616633
Nekemias grossedentata	JEOL database	Zhang, Y., et al, Magn. Reson. Chem. 45, 909 (2007)
Nympaea spp.	-	KNApSAcK
Onobrychis viciifolia	LOTUS Database	35616633
Petunia hybrida	KNApSAcK Database	22123792
Petunia x hybrida	Plant	KNApSAcK
Picea abies	KNApSAcK Database	22123792
Pimenta dioica	KNApSAcK Database	22123792
Pinus contorta	LOTUS Database	35616633
Pinus spp.	KNApSAcK Database	22123792
Punica granatum	Plant	KNApSAcK
Punica granatum L.	KNApSAcK Database	22123792
Rhamnus pallasii	KNApSAcK Database	22123792
Rhododendron cinnabarinum	KNApSAcK Database	22123792
Rhododendron decorum	LOTUS Database	35616633
Rhododendron spinuliferum	LOTUS Database	35616633
Rhododendron spp.	KNApSAcK Database	22123792
Salix sachalinensis	LOTUS Database	35616633
Sedum reflexum	LOTUS Database	35616633
Shuteria involucrata	LOTUS Database	35616633
Soymida febrifuga	KNApSAcK Database	22123792
Stachyurus himalaicus	LOTUS Database	35616633
Syzygium cumini	KNApSAcK Database	22123792
Taxus chinensis	KNApSAcK Database	22123792
Vitis rotundifolia	KNApSAcK Database	22123792
Wedelia prostrata	LOTUS Database	35616633
Xanthoceras sorbifolia	KNApSAcK Database	22123792
Xanthoceras sorbifolium	Plant	KNApSAcK
Zea mays	KNApSAcK Database	22123792
Zea mays L.	Plant	KNApSAcK

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as epigallocatechins. These 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:28429 )
Dihyroflavonols (C02906 )

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	0.89	ALOGPS
logP	1.51	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	7.72	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	147.68 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.59 m³·mol⁻¹	ChemAxon
Polarizability	29.2 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Dihydromyricetin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

28429

Good Scents ID

rw1589001

References

General References

Zhang YS, Ning ZX, Yang SZ, Wu H: Antioxidation properties and mechanism of action of dihydromyricetin from Ampelopsis grossedentata. Yao Xue Xue Bao. 2003 Apr;38(4):241-4. [PubMed:12889119 ]
He ZF, Zeng S, Hou JJ, Liu DY: [Optimizing the extracting technique of ampelopsin from Ampelopsis cantoniensis Planch by a uniform design method]. Zhong Yao Cai. 2006 Jul;29(7):718-20. [PubMed:17059013 ]
Ni F, Gong Y, Li L, Abdolmaleky HM, Zhou JR: Flavonoid ampelopsin inhibits the growth and metastasis of prostate cancer in vitro and in mice. PLoS One. 2012;7(6):e38802. doi: 10.1371/journal.pone.0038802. Epub 2012 Jun 5. [PubMed:22693649 ]
Sun W, Liu S, Lu A, Yang F, Duan J: In vitro anti-PRV activity of dihydromyricetin from Ampelopsis grossedentata. Nat Prod Res. 2021 Sep 29:1-4. doi: 10.1080/14786419.2021.1982935. [PubMed:34583588 ]
Li X, Yang ZS, Cai WW, Deng Y, Chen L, Tan SL: Dihydromyricetin Inhibits Tumor Growth and Epithelial-Mesenchymal Transition through regulating miR-455-3p in Cholangiocarcinoma. J Cancer. 2021 Aug 22;12(20):6058-6070. doi: 10.7150/jca.61311. eCollection 2021. [PubMed:34539879 ]
Zhang, Y., et al. (2007). Zhang, Y., et al, Magn. Reson. Chem. 45, 909 (2007). Mag. Reson. Chem..

Showing NP-Card for dihydromyricetin (NP0024994)

MOL for NP0024994 (dihydromyricetin)

3D MOL for NP0024994 (dihydromyricetin)

3D SDF for NP0024994 (dihydromyricetin)

3D-SDF for NP0024994 (dihydromyricetin)

PDB for NP0024994 (dihydromyricetin)

3D PDB for NP0024994 (dihydromyricetin)

SMILES for NP0024994 (dihydromyricetin)

INCHI for NP0024994 (dihydromyricetin)

Structure for NP0024994 (dihydromyricetin)

3D Structure for NP0024994 (dihydromyricetin)