NP-MRD: Showing NP-Card for Robinetin (NP0043961)

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Record Information

Version

2.0

Created at

2021-06-22 17:42:57 UTC

Updated at

2021-08-20 00:00:49 UTC

NP-MRD ID

NP0043961

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Robinetin

Description

Robinetin, also known as 5-deoxymyricetin or 5-hydroxyfisetin, belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, robinetin is considered to be a flavonoid. Robinetin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Robinetin is found in Burkea africana. Robinetin was first documented in 2005 (PMID: 16132219). Based on a literature review a small amount of articles have been published on robinetin (PMID: 19914085) (PMID: 25313717) (PMID: 25482106).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

NP0043961
     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
   -2.3678    1.0584   -2.8656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8791    0.6472   -1.7827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5036    0.5701   -1.5819 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2963    0.9646   -2.6231 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0752    0.1301   -0.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4933    0.0244   -0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8573   -0.4557    1.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1599   -0.6025    1.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4719   -1.0855    2.7753 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1536   -0.2652    0.6114 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4895   -0.4128    0.9982 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8633    0.2109   -0.6432 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8210    0.5615   -1.5690 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5144    0.3459   -0.9965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7852   -0.2304    0.5285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0794   -0.1789    0.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8959   -0.5719    1.4325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2826   -0.5318    1.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0641   -0.9372    2.3992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8835   -0.0915    0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0876    0.3071   -0.8822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7012    0.2580   -0.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0052    1.3049   -3.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0967   -0.7329    1.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4534   -1.1691    2.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2269   -0.1684    0.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5432    0.9052   -2.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2951    0.7182   -1.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4290   -0.9235    2.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3222   -0.2211    3.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9626   -0.0798    0.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5617    0.6518   -1.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
  5 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22  2  1  0
 14  6  1  0
 22 16  1  0
  4 23  1  0
  7 24  1  0
  9 25  1  0
 11 26  1  0
 13 27  1  0
 14 28  1  0
 17 29  1  0
 19 30  1  0
 20 31  1  0
 21 32  1  0
M  END


  Mrv1652306222119422D          

 22 24  0  0  0  0            999 V2000
   -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
    0.7145   -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
   -0.7145   -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
    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
    2.1434   -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
    2.8579   -1.6500    0.0000 O   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 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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -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
    5.0013   -0.4125    0.0000 O   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
    3.5724    2.0625    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
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  2  0  0  0  0
 10 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  0  0  0  0
 17 21  1  0  0  0  0
 16 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043961

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(C=C1)C(=O)C(O)=C(O2)C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O7/c16-7-1-2-8-11(5-7)22-15(14(21)12(8)19)6-3-9(17)13(20)10(18)4-6/h1-5,16-18,20-21H

> <INCHI_KEY>
SOEDEYVDCDYMMH-UHFFFAOYSA-N

> <FORMULA>
C15H10O7

> <MOLECULAR_WEIGHT>
302.238

> <EXACT_MASS>
302.042652662

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
28.557530287238407

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
1.84

> <JCHEM_LOGP>
1.506299464

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.081257864106037

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.3130636699375415

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9230517537645673

> <JCHEM_POLAR_SURFACE_AREA>
127.45000000000002

> <JCHEM_REFRACTIVITY>
76.8622

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
robinetin

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043961
     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
   -2.3678    1.0584   -2.8656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8791    0.6472   -1.7827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5036    0.5701   -1.5819 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2963    0.9646   -2.6231 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0752    0.1301   -0.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4933    0.0244   -0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8573   -0.4557    1.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1599   -0.6025    1.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4719   -1.0855    2.7753 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1536   -0.2652    0.6114 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4895   -0.4128    0.9982 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8633    0.2109   -0.6432 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8210    0.5615   -1.5690 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5144    0.3459   -0.9965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7852   -0.2304    0.5285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0794   -0.1789    0.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8959   -0.5719    1.4325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2826   -0.5318    1.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0641   -0.9372    2.3992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8835   -0.0915    0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0876    0.3071   -0.8822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7012    0.2580   -0.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0052    1.3049   -3.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0967   -0.7329    1.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4534   -1.1691    2.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2269   -0.1684    0.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5432    0.9052   -2.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2951    0.7182   -1.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4290   -0.9235    2.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3222   -0.2211    3.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9626   -0.0798    0.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5617    0.6518   -1.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
  5 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22  2  1  0
 14  6  1  0
 22 16  1  0
  4 23  1  0
  7 24  1  0
  9 25  1  0
 11 26  1  0
 13 27  1  0
 14 28  1  0
 17 29  1  0
 19 30  1  0
 20 31  1  0
 21 32  1  0
M  END

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001  -0.770   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  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10    3   12                                                  
CONECT   12   11                                                            
CONECT   13   10                                                            
CONECT   14    9   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18                                                            
CONECT   21   17                                                            
CONECT   22   16                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    NP0043961
HETATM    1  O1  UNL     1      -2.368   1.058  -2.866  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.879   0.647  -1.783  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.504   0.570  -1.582  1.00  0.00           C  
HETATM    4  O2  UNL     1       0.296   0.965  -2.623  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.075   0.130  -0.423  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.493   0.024  -0.147  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.857  -0.456   1.118  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.160  -0.602   1.502  1.00  0.00           C  
HETATM    9  O3  UNL     1       3.472  -1.086   2.775  1.00  0.00           O  
HETATM   10  C7  UNL     1       4.154  -0.265   0.611  1.00  0.00           C  
HETATM   11  O4  UNL     1       5.490  -0.413   0.998  1.00  0.00           O  
HETATM   12  C8  UNL     1       3.863   0.211  -0.643  1.00  0.00           C  
HETATM   13  O5  UNL     1       4.821   0.561  -1.569  1.00  0.00           O  
HETATM   14  C9  UNL     1       2.514   0.346  -0.997  1.00  0.00           C  
HETATM   15  O6  UNL     1      -0.785  -0.230   0.529  1.00  0.00           O  
HETATM   16  C10 UNL     1      -2.079  -0.179   0.395  1.00  0.00           C  
HETATM   17  C11 UNL     1      -2.896  -0.572   1.432  1.00  0.00           C  
HETATM   18  C12 UNL     1      -4.283  -0.532   1.329  1.00  0.00           C  
HETATM   19  O7  UNL     1      -5.064  -0.937   2.399  1.00  0.00           O  
HETATM   20  C13 UNL     1      -4.884  -0.092   0.170  1.00  0.00           C  
HETATM   21  C14 UNL     1      -4.088   0.307  -0.882  1.00  0.00           C  
HETATM   22  C15 UNL     1      -2.701   0.258  -0.755  1.00  0.00           C  
HETATM   23  H1  UNL     1      -0.005   1.305  -3.520  1.00  0.00           H  
HETATM   24  H2  UNL     1       1.097  -0.733   1.850  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.453  -1.169   2.994  1.00  0.00           H  
HETATM   26  H4  UNL     1       6.227  -0.168   0.352  1.00  0.00           H  
HETATM   27  H5  UNL     1       4.543   0.905  -2.475  1.00  0.00           H  
HETATM   28  H6  UNL     1       2.295   0.718  -1.978  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.429  -0.924   2.358  1.00  0.00           H  
HETATM   30  H8  UNL     1      -5.322  -0.221   3.076  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.963  -0.080   0.141  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.562   0.652  -1.790  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   22
CONECT    3    4    5    5
CONECT    4   23
CONECT    5    6   15
CONECT    6    7    7   14
CONECT    7    8   24
CONECT    8    9   10   10
CONECT    9   25
CONECT   10   11   12
CONECT   11   26
CONECT   12   13   14   14
CONECT   13   27
CONECT   14   28
CONECT   15   16
CONECT   16   17   17   22
CONECT   17   18   29
CONECT   18   19   20   20
CONECT   19   30
CONECT   20   21   31
CONECT   21   22   22   32
END

NP0043961
     RDKit          3D

32 34  0  0  0  0  0  0  0  0999 V2000
   -2.3678    1.0584   -2.8656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8791    0.6472   -1.7827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5036    0.5701   -1.5819 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2963    0.9646   -2.6231 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0752    0.1301   -0.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4933    0.0244   -0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8573   -0.4557    1.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1599   -0.6025    1.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4719   -1.0855    2.7753 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1536   -0.2652    0.6114 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4895   -0.4128    0.9982 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8633    0.2109   -0.6432 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8210    0.5615   -1.5690 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5144    0.3459   -0.9965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7852   -0.2304    0.5285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0794   -0.1789    0.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8959   -0.5719    1.4325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2826   -0.5318    1.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0641   -0.9372    2.3992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8835   -0.0915    0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0876    0.3071   -0.8822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7012    0.2580   -0.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0052    1.3049   -3.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0967   -0.7329    1.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4534   -1.1691    2.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2269   -0.1684    0.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5432    0.9052   -2.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2951    0.7182   -1.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4290   -0.9235    2.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3222   -0.2211    3.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9626   -0.0798    0.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5617    0.6518   -1.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
  5 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22  2  1  0
 14  6  1  0
 22 16  1  0
  4 23  1  0
  7 24  1  0
  9 25  1  0
 11 26  1  0
 13 27  1  0
 14 28  1  0
 17 29  1  0
 19 30  1  0
 20 31  1  0
 21 32  1  0
M  END

View in JSmol

Synonyms

Value	Source
5-Deoxymyricetin	ChEBI
5-Hydroxyfisetin	ChEBI
3,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one	MeSH

Chemical Formula

C₁₅H₁₀O₇

Average Mass

302.2380 Da

Monoisotopic Mass

302.04265 Da

IUPAC Name

3,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one

Traditional Name

robinetin

CAS Registry Number

Not Available

SMILES

OC1=CC2=C(C=C1)C(=O)C(O)=C(O2)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C15H10O7/c16-7-1-2-8-11(5-7)22-15(14(21)12(8)19)6-3-9(17)13(20)10(18)4-6/h1-5,16-18,20-21H

InChI Key

SOEDEYVDCDYMMH-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Pyridine-d5, 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
Acacia dealbata	KNApSAcK Database	22123792
Acacia mearnsii	KNApSAcK Database	22123792
Adenanthera pavonina	KNApSAcK Database	22123792
Albizia pedicellata	KNApSAcK Database	22123792
Albizia splendens	KNApSAcK Database	22123792
Archidendron clypearia	KNApSAcK Database	22123792
Burkea africana	LOTUS Database	35616633
Butea spp.	KNApSAcK Database	22123792
Capsella bursa-pastoris	KNApSAcK Database	22123792
Gleditsia monosperma	KNApSAcK Database	22123792
Gliricidia sepium	KNApSAcK Database	22123792
Intsia bijuga	KNApSAcK Database	22123792
Intsia palembanica	KNApSAcK Database	22123792
Millettia stuhlmannii	KNApSAcK Database	22123792
Robinia pseudoacacia	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavonols

Alternative Parents

Substituents

3-hydroxyflavone
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
Hydroxyflavonoid
7-hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Benzenetriol
Pyrogallol derivative
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Benzenoid
Monocyclic benzene moiety
Pyran
Heteroaromatic compound
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pentahydroxyflavone (CHEBI:8876 )
7-hydroxyflavonol (CHEBI:8876 )
flavonols (C10177 )
Flavones and Flavonols (LMPK12111577 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	669.90 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	4972 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.550 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	1.84	ALOGPS
logP	1.51	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	6.31	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.45 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.86 m³·mol⁻¹	ChemAxon
Polarizability	28.56 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00001092

Chemspider ID

4445009

KEGG Compound ID

C10177

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

8876

Good Scents ID

rw1504511

References

General References

Nasir H, Iqbal Z, Hiradate S, Fujii Y: Allelopathic potential of Robinia pseudo-acacia L. J Chem Ecol. 2005 Sep;31(9):2179-92. doi: 10.1007/s10886-005-6084-5. Epub 2005 Aug 17. [PubMed:16132219 ]
Chaudhuri S, Pahari B, Sengupta B, Sengupta PK: Binding of the bioflavonoid robinetin with model membranes and hemoglobin: Inhibition of lipid peroxidation and protein glycosylation. J Photochem Photobiol B. 2010 Jan 21;98(1):12-9. doi: 10.1016/j.jphotobiol.2009.10.002. Epub 2009 Nov 13. [PubMed:19914085 ]
Pahari BP, Chaudhuri S, Chakraborty S, Sengupta PK: Ground and excited state proton transfer of the bioactive plant flavonol robinetin in a protein environment: spectroscopic and molecular modeling studies. J Phys Chem B. 2015 Feb 12;119(6):2533-45. doi: 10.1021/jp508410v. Epub 2014 Oct 27. [PubMed:25313717 ]
Germano MP, Certo G, D'Angelo V, Sanogo R, Malafronte N, De Tommasi N, Rapisarda A: Anti-angiogenic activity of Entada africana root. Nat Prod Res. 2015;29(16):1551-6. doi: 10.1080/14786419.2014.987773. Epub 2014 Dec 6. [PubMed:25482106 ]

Showing NP-Card for Robinetin (NP0043961)

MOL for NP0043961 (Robinetin)

3D MOL for NP0043961 (Robinetin)

3D SDF for NP0043961 (Robinetin)

3D-SDF for NP0043961 (Robinetin)

PDB for NP0043961 (Robinetin)

3D PDB for NP0043961 (Robinetin)

SMILES for NP0043961 (Robinetin)

INCHI for NP0043961 (Robinetin)

Structure for NP0043961 (Robinetin)

3D Structure for NP0043961 (Robinetin)