NP-MRD: Showing NP-Card for 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4r,5s,6r)-2,3,5-trihydroxy-6-methyloxan-4-yl]oxy}chromen-4-one (NP0160427)

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Record Information

Version

2.0

Created at

2022-09-02 18:22:47 UTC

Updated at

2022-09-02 18:22:47 UTC

NP-MRD ID

NP0160427

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4r,5s,6r)-2,3,5-trihydroxy-6-methyloxan-4-yl]oxy}chromen-4-one

Description

2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3S,4R,5S,6R)-2,3,5-trihydroxy-6-methyloxan-4-yl]oxy}-4H-chromen-4-one belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4r,5s,6r)-2,3,5-trihydroxy-6-methyloxan-4-yl]oxy}chromen-4-one is found in Metrosideros polymorpha. Based on a literature review very few articles have been published on 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3S,4R,5S,6R)-2,3,5-trihydroxy-6-methyloxan-4-yl]oxy}-4H-chromen-4-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022220222D          

 32 35  0  0  1  0            999 V2000
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  2  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
    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  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
   -1.4289    0.8250    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
   -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 O   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    0.0000    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
    4.2868   -0.0000    0.0000 O   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
    2.8579   -2.4750    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5350   -2.9737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 12 19  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 10 29  1  0  0  0  0
 29 30  2  0  0  0  0
  8 31  1  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  1  0  0  0
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    4.8184   -0.8054   -1.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1771    0.0091   -0.0029 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1884    1.3318   -0.3579 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3244    1.4230   -1.4684 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5517    2.6596   -2.0568 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9261    1.3949   -0.8612 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0647    1.5912   -1.9681 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6446    0.1732   -0.0964 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7109    0.3648    0.9809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5039   -0.3016    0.9999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7021    0.1525    0.5737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8555    1.4843    0.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9968    1.7516   -0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3076    2.9887   -1.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4659    4.0522   -0.9983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365    5.3169   -1.4921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3261    3.8181   -0.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4461    4.8872   -0.0270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0253    2.5536    0.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7856   -0.6340    0.6426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7785   -1.8485    1.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9268   -2.6204    1.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8512   -3.8985    1.6664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9991   -4.6846    1.7213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6690   -4.4368    2.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5178   -3.6838    2.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2919   -4.1567    2.5311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6072   -2.4054    1.5756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4709   -1.6128    1.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5819   -2.1101    1.9324 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8704   -0.5775    0.3669 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8738   -1.9209   -0.0813 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9969   -1.2985   -1.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4758   -0.2005   -1.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3860   -1.6621   -0.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9098   -0.0951    0.8510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4501    0.6138   -2.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0440    2.5129   -2.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8792    2.3106   -0.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2356    0.7859   -2.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1292   -0.5412   -0.8101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7183    0.9470   -0.9177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2195    3.1265   -1.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5646    5.5008   -2.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6135    5.8035   -0.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1326    2.4438    0.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8718   -2.1999    0.7947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1883   -5.2569    0.9056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5901   -5.4357    2.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1379   -5.0596    2.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8141   -0.6378    1.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2473   -1.9132   -0.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  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  1  0
 17 19  2  0
  8 31  1  0
 31 32  1  0
 31  2  1  0
 29 10  1  0
 19 12  1  0
 28 21  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  1
  4 37  1  6
  5 38  1  0
  6 39  1  1
  7 40  1  0
  8 41  1  6
 22 47  1  0
 24 48  1  0
 25 49  1  0
 27 50  1  0
 13 42  1  0
 14 43  1  0
 16 44  1  0
 18 45  1  0
 19 46  1  0
 31 51  1  1
 32 52  1  0
M  END


  Mrv1652309022220222D          

 32 35  0  0  1  0            999 V2000
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  2  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
    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  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
   -1.4289    0.8250    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
   -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 O   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    0.0000    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
    4.2868   -0.0000    0.0000 O   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
    2.8579   -2.4750    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5350   -2.9737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 12 19  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 10 29  1  0  0  0  0
 29 30  2  0  0  0  0
  8 31  1  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0160427

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1O[C@H](O)[C@@H](O)[C@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C(O)=C2)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O11/c1-7-15(26)19(17(28)21(29)30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-18(20)8-2-3-10(23)11(24)4-8/h2-7,15,17,19,21-26,28-29H,1H3/t7-,15+,17+,19-,21+/m1/s1

> <INCHI_KEY>
NSZQOXBBEWYGQH-BRMQXXNCSA-N

> <FORMULA>
C21H20O11

> <MOLECULAR_WEIGHT>
448.38

> <EXACT_MASS>
448.100561464

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
42.23957935135258

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3S,4R,5S,6R)-2,3,5-trihydroxy-6-methyloxan-4-yl]oxy}-4H-chromen-4-one

> <ALOGPS_LOGP>
1.33

> <JCHEM_LOGP>
0.9020746706666665

> <ALOGPS_LOGS>
-2.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.876145540694133

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.376531650747028

> <JCHEM_PKA_STRONGEST_BASIC>
-3.62473058857434

> <JCHEM_POLAR_SURFACE_AREA>
186.36999999999998

> <JCHEM_REFRACTIVITY>
107.73179999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.89e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3S,4R,5S,6R)-2,3,5-trihydroxy-6-methyloxan-4-yl]oxy}chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.865  -5.551   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   31                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   29                                                  
CONECT   11   10   12   20                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12                                                       
CONECT   20   11   21                                                       
CONECT   21   20   22   28                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   21   29                                                  
CONECT   29   28   10   30                                                  
CONECT   30   29                                                            
CONECT   31    8    2   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₀O₁₁

Average Mass

448.3800 Da

Monoisotopic Mass

448.10056 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3S,4R,5S,6R)-2,3,5-trihydroxy-6-methyloxan-4-yl]oxy}-4H-chromen-4-one

Traditional Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3S,4R,5S,6R)-2,3,5-trihydroxy-6-methyloxan-4-yl]oxy}chromen-4-one

CAS Registry Number

Not Available

SMILES

C[C@H]1O[C@H](O)[C@@H](O)[C@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C(O)=C2)[C@H]1O

InChI Identifier

InChI=1S/C21H20O11/c1-7-15(26)19(17(28)21(29)30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-18(20)8-2-3-10(23)11(24)4-8/h2-7,15,17,19,21-26,28-29H,1H3/t7-,15+,17+,19-,21+/m1/s1

InChI Key

NSZQOXBBEWYGQH-BRMQXXNCSA-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
Metrosideros polymorpha	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavones

Alternative Parents

Substituents

3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Hexose monosaccharide
Chromone
Benzopyran
1-benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Phenol
Monocyclic benzene moiety
Benzenoid
Pyran
Monosaccharide
Oxane
Vinylogous acid
Heteroaromatic compound
Hemiacetal
Secondary alcohol
Ether
Organoheterocyclic compound
Oxacycle
Polyol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
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
logP	1.33	ALOGPS
logP	0.9	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	6.38	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	107.73 m³·mol⁻¹	ChemAxon
Polarizability	42.24 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

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

163095367

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4r,5s,6r)-2,3,5-trihydroxy-6-methyloxan-4-yl]oxy}chromen-4-one (NP0160427)

MOL for NP0160427 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4r,5s,6r)-2,3,5-trihydroxy-6-methyloxan-4-yl]oxy}chromen-4-one)

3D MOL for NP0160427 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4r,5s,6r)-2,3,5-trihydroxy-6-methyloxan-4-yl]oxy}chromen-4-one)

3D SDF for NP0160427 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4r,5s,6r)-2,3,5-trihydroxy-6-methyloxan-4-yl]oxy}chromen-4-one)

3D-SDF for NP0160427 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4r,5s,6r)-2,3,5-trihydroxy-6-methyloxan-4-yl]oxy}chromen-4-one)

PDB for NP0160427 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4r,5s,6r)-2,3,5-trihydroxy-6-methyloxan-4-yl]oxy}chromen-4-one)

3D PDB for NP0160427 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4r,5s,6r)-2,3,5-trihydroxy-6-methyloxan-4-yl]oxy}chromen-4-one)

SMILES for NP0160427 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4r,5s,6r)-2,3,5-trihydroxy-6-methyloxan-4-yl]oxy}chromen-4-one)

INCHI for NP0160427 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4r,5s,6r)-2,3,5-trihydroxy-6-methyloxan-4-yl]oxy}chromen-4-one)

Structure for NP0160427 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4r,5s,6r)-2,3,5-trihydroxy-6-methyloxan-4-yl]oxy}chromen-4-one)

3D Structure for NP0160427 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4r,5s,6r)-2,3,5-trihydroxy-6-methyloxan-4-yl]oxy}chromen-4-one)