NP-MRD: Showing NP-Card for 3,5,7-trihydroxy-2-{4-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}chromen-4-one (NP0266701)

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Record Information

Version

2.0

Created at

2022-09-08 11:07:54 UTC

Updated at

2022-09-08 11:07:54 UTC

NP-MRD ID

NP0266701

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,5,7-trihydroxy-2-{4-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}chromen-4-one

Description

3,5,7-Trihydroxy-2-{4-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}-4H-chromen-4-one belongs to the class of organic compounds known as homolycorine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds containing the homolycorine skeleton, made up of a [3,4-g]benzopyranone ring due to the oxidation of the hydroxyl group at the C6. They are biogenetically formed through a restructuring of lycorine-type alkaloids. 3,5,7-trihydroxy-2-{4-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}chromen-4-one is found in Oenothera speciosa. 3,5,7-Trihydroxy-2-{4-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}-4H-chromen-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241505292D          

 32 35  0  0  0  0            999 V2000
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    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
   -2.8579   -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
   -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
   -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
    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 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
    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
    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
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 13 26  1  0  0  0  0
  4 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
   -5.1319    2.6174   -0.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3110    1.4226    0.0619 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1855    0.5888   -1.0362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4661   -0.5799   -0.7351 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1565   -0.3798   -0.4727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9573   -0.7490   -0.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2264   -0.2816   -0.3595 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4851   -0.5744   -0.7719 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7248   -0.1286   -0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8630   -0.5176   -0.7152 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0389   -0.1718   -0.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1962   -0.6231   -0.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4452   -0.2803   -0.4218 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6032   -0.7512   -1.0772 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5852    0.5156    0.6676 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4525    0.9981    1.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6022    1.7946    2.4287 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1953    0.6479    0.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0356    1.0753    1.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0781    1.8099    2.4720 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8143    0.6734    0.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6873    1.1386    1.5734 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5621   -1.4016   -1.9058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4404   -1.8701   -2.5377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8405   -1.5468   -2.0834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9423   -2.0392   -2.7480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1740   -1.3297    0.4072 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4482   -2.6354    0.0901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4577   -0.6178    0.7781 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0061   -1.3071    1.8553 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0286    0.7871    1.2189 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1983    1.4648    1.5559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5192    3.2095    0.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0393    2.1826   -0.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6131    3.2211   -1.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3208    1.7803    0.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6303   -1.2244   -1.6162 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0726    0.3341    0.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0677   -1.2629   -1.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9382   -0.1378   -1.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5542    0.8203    1.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0746    2.2633    3.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7441    1.7239    2.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5622   -1.6605   -2.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5224   -2.5096   -3.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8252   -2.6313   -3.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4995   -1.2289    1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3614   -3.2558    0.8616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1594   -0.5385   -0.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8819   -1.7246    1.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3964    0.6904    2.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0216    2.1998    2.1929 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
  8  9  1  0
  9 21  2  0
 21 22  1  0
 21 19  1  0
 19 20  2  0
 19 18  1  0
 18 16  2  0
 16 17  1  0
 16 15  1  0
 15 13  2  0
 13 14  1  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
  4 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31  2  1  0
 25  6  1  0
 10  9  1  0
 11 18  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  1
  4 37  1  6
  7 38  1  0
 23 44  1  0
 24 45  1  0
 26 46  1  0
 22 43  1  0
 17 42  1  0
 15 41  1  0
 14 40  1  0
 12 39  1  0
 27 47  1  1
 28 48  1  0
 29 49  1  6
 30 50  1  0
 31 51  1  1
 32 52  1  0
M  END


  Mrv1533004241505292D          

 32 35  0  0  0  0            999 V2000
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    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
   -2.8579   -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
   -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
   -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
    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 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
    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
    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
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 13 26  1  0  0  0  0
  4 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0266701

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(OC2=CC(=CC=C2O)C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2)C(O)C(O)C1O

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

> <INCHI_KEY>
KCPGPFNOACHSRM-UHFFFAOYSA-N

> <FORMULA>
C21H20O11

> <MOLECULAR_WEIGHT>
448.38

> <EXACT_MASS>
448.100561464

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
43.01508801869887

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.55

> <JCHEM_LOGP>
0.935141337333333

> <ALOGPS_LOGS>
-2.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.898207661042272

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.381015591046147

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6122003788295034

> <JCHEM_POLAR_SURFACE_AREA>
186.37

> <JCHEM_REFRACTIVITY>
107.4629

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.51e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5,7-trihydroxy-2-{4-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -9.336  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   27                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11                                                            
CONECT   13    8   14   26                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   25                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   18   26                                                  
CONECT   26   25   13                                                       
CONECT   27    4   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    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

3,5,7-trihydroxy-2-{4-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}-4H-chromen-4-one

Traditional Name

3,5,7-trihydroxy-2-{4-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}chromen-4-one

CAS Registry Number

Not Available

SMILES

CC1OC(OC2=CC(=CC=C2O)C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2)C(O)C(O)C1O

InChI Identifier

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

InChI Key

KCPGPFNOACHSRM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Oenothera speciosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as homolycorine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds containing the homolycorine skeleton, made up of a [3,4-g]benzopyranone ring due to the oxidation of the hydroxyl group at the C6. They are biogenetically formed through a restructuring of lycorine-type alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Amaryllidaceae alkaloids

Sub Class

Homolycorine-type amaryllidaceae alkaloids

Direct Parent

Homolycorine-type amaryllidaceae alkaloids

Alternative Parents

Substituents

Homolycorine skeleton
Benzopyran
Isochromane
2-benzopyran
Indole or derivatives
Benzodioxole
Beta-hydroxy acid
Fatty acid ester
Aralkylamine
Dicarboxylic acid or derivatives
N-alkylpyrrolidine
Benzenoid
Hydroxy acid
Fatty acyl
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Lactone
Carboxylic acid ester
Amino acid or derivatives
Secondary alcohol
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Oxacycle
Acetal
Organic nitrogen compound
Organonitrogen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
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	1.55	ALOGPS
logP	0.94	ChemAxon
logS	-2.5	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	107.46 m³·mol⁻¹	ChemAxon
Polarizability	43.02 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

76507972

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,5,7-trihydroxy-2-{4-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}chromen-4-one (NP0266701)

MOL for NP0266701 (3,5,7-trihydroxy-2-{4-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}chromen-4-one)

3D MOL for NP0266701 (3,5,7-trihydroxy-2-{4-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}chromen-4-one)

3D SDF for NP0266701 (3,5,7-trihydroxy-2-{4-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}chromen-4-one)

3D-SDF for NP0266701 (3,5,7-trihydroxy-2-{4-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}chromen-4-one)

PDB for NP0266701 (3,5,7-trihydroxy-2-{4-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}chromen-4-one)

3D PDB for NP0266701 (3,5,7-trihydroxy-2-{4-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}chromen-4-one)

SMILES for NP0266701 (3,5,7-trihydroxy-2-{4-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}chromen-4-one)

INCHI for NP0266701 (3,5,7-trihydroxy-2-{4-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}chromen-4-one)

Structure for NP0266701 (3,5,7-trihydroxy-2-{4-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}chromen-4-one)

3D Structure for NP0266701 (3,5,7-trihydroxy-2-{4-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}chromen-4-one)