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Showing NP-Card for 3,5-Dihydroxy-6,7-methylenedioxyflavanone (NP0047610)

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Record Information
Version2.0
Created at2022-03-17 20:43:00 UTC
Updated at2022-03-17 20:43:00 UTC
NP-MRD IDNP0047610
Secondary Accession NumbersNone
Natural Product Identification
Common Name3,5-Dihydroxy-6,7-methylenedioxyflavanone
Description3,5-Dihydroxy-6,7-methylenedioxyflavanone belongs to the class of organic compounds known as flavanonols. Flavanonols are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a hydroxyl group and a ketone at the carbon C2 and C3, respectively. 3,5-Dihydroxy-6,7-methylenedioxyflavanone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3,5-dihydroxy-6,7-methylenedioxyflavanone has been detected, but not quantified in, common beets. 3,5-Dihydroxy-6,7-methylenedioxyflavanone is found in Rhizoctonia solani. This could make 3,5-dihydroxy-6,7-methylenedioxyflavanone a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047610 (3,5-Dihydroxy-6,7-methylenedioxyflavanone)


  Mrv0541 05061307032D          

 22 25  0  0  0  0            999 V2000
    4.9279   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3429   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8580   -1.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8580   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  6  1  0  0  0  0
 11  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13 11  2  0  0  0  0
 14 12  1  0  0  0  0
 15  8  1  0  0  0  0
 15 14  1  0  0  0  0
 16 10  2  0  0  0  0
 16 13  1  0  0  0  0
 17 12  2  0  0  0  0
 18 13  1  0  0  0  0
 19 14  1  0  0  0  0
 20  7  1  0  0  0  0
 20 10  1  0  0  0  0
 21  7  1  0  0  0  0
 21 16  1  0  0  0  0
 22  9  1  0  0  0  0
 22 15  1  0  0  0  0
M  END
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3D MOL for NP0047610 (3,5-Dihydroxy-6,7-methylenedioxyflavanone)

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3D SDF for NP0047610 (3,5-Dihydroxy-6,7-methylenedioxyflavanone)

  Mrv0541 05061307032D          

 22 25  0  0  0  0            999 V2000
    4.9279   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3429   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8580   -1.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8580   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  6  1  0  0  0  0
 11  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13 11  2  0  0  0  0
 14 12  1  0  0  0  0
 15  8  1  0  0  0  0
 15 14  1  0  0  0  0
 16 10  2  0  0  0  0
 16 13  1  0  0  0  0
 17 12  2  0  0  0  0
 18 13  1  0  0  0  0
 19 14  1  0  0  0  0
 20  7  1  0  0  0  0
 20 10  1  0  0  0  0
 21  7  1  0  0  0  0
 21 16  1  0  0  0  0
 22  9  1  0  0  0  0
 22 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047610

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1C(OC2=CC3=C(OCO3)C(O)=C2C1=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O6/c17-12-11-9(6-10-16(13(11)18)21-7-20-10)22-15(14(12)19)8-4-2-1-3-5-8/h1-6,14-15,18-19H,7H2

> <INCHI_KEY>
WVADKXWSLHLDCL-UHFFFAOYSA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.2629

> <EXACT_MASS>
300.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
29.551803771666442

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,12-dihydroxy-11-phenyl-4,6,10-trioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-13-one

> <ALOGPS_LOGP>
1.51

> <JCHEM_LOGP>
2.350313700666667

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.222867136939515

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.172122826291885

> <JCHEM_PKA_STRONGEST_BASIC>
-3.088497201808936

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
74.43310000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,12-dihydroxy-11-phenyl-4,6,10-trioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0047610 (3,5-Dihydroxy-6,7-methylenedioxyflavanone)
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PDB for NP0047610 (3,5-Dihydroxy-6,7-methylenedioxyflavanone)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       9.199  -0.533   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.865   0.237   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.199  -2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.531  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.865  -2.843   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.507  -3.613   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.531  -2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.137  -2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.530  -4.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.864  -5.153   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.197  -5.153   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.198  -4.383   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.198  -2.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.137  -4.383   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.864  -6.693   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.197  -6.693   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.531  -5.153   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.602  -2.367   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.602  -4.859   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.864  -2.073   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3    8                                                       
CONECT    6    9   10                                                       
CONECT    7   20   21                                                       
CONECT    8    4    5   15                                                  
CONECT    9    6   11   22                                                  
CONECT   10    6   16   20                                                  
CONECT   11    9   12   13                                                  
CONECT   12   11   14   17                                                  
CONECT   13   11   16   18                                                  
CONECT   14   12   15   19                                                  
CONECT   15    8   14   22                                                  
CONECT   16   10   13   21                                                  
CONECT   17   12                                                            
CONECT   18   13                                                            
CONECT   19   14                                                            
CONECT   20    7   10                                                       
CONECT   21    7   16                                                       
CONECT   22    9   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

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3D PDB for NP0047610 (3,5-Dihydroxy-6,7-methylenedioxyflavanone)
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SMILES for NP0047610 (3,5-Dihydroxy-6,7-methylenedioxyflavanone)
OC1C(OC2=CC3=C(OCO3)C(O)=C2C1=O)C1=CC=CC=C1
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INCHI for NP0047610 (3,5-Dihydroxy-6,7-methylenedioxyflavanone)
InChI=1S/C16H12O6/c17-12-11-9(6-10-16(13(11)18)21-7-20-10)22-15(14(12)19)8-4-2-1-3-5-8/h1-6,14-15,18-19H,7H2
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View in JSmol
SynonymsNot Available
Chemical FormulaC16H12O6
Average Mass300.2629 Da
Monoisotopic Mass300.06339 Da
IUPAC Name2,12-dihydroxy-11-phenyl-4,6,10-trioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-13-one
Traditional Name2,12-dihydroxy-11-phenyl-4,6,10-trioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-13-one
CAS Registry Number110204-44-9
SMILES
OC1C(OC2=CC3=C(OCO3)C(O)=C2C1=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C16H12O6/c17-12-11-9(6-10-16(13(11)18)21-7-20-10)22-15(14(12)19)8-4-2-1-3-5-8/h1-6,14-15,18-19H,7H2
InChI KeyWVADKXWSLHLDCL-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Beta vulgarisFooDB
Rhizoctonia solaniFungi
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavanonols. Flavanonols are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a hydroxyl group and a ketone at the carbon C2 and C3, respectively.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentFlavanonols
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.51ALOGPS
logP2.35ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)10.17ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity74.43 m³·mol⁻¹ChemAxon
Polarizability29.55 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033321  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011348  
KNApSAcK IDC00008598  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound76390859  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available