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Showing NP-Card for 5-hydroxy-3-(4-hydroxy-2-methoxyphenyl)-7-methoxy-6-methyl-2,3-dihydro-1-benzopyran-4-one (NP0257551)

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Record Information
Version2.0
Created at2022-09-07 22:42:13 UTC
Updated at2022-09-07 22:42:13 UTC
NP-MRD IDNP0257551
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-hydroxy-3-(4-hydroxy-2-methoxyphenyl)-7-methoxy-6-methyl-2,3-dihydro-1-benzopyran-4-one
Description5-Hydroxy-3-(4-hydroxy-2-methoxyphenyl)-7-methoxy-6-methyl-3,4-dihydro-2H-1-benzopyran-4-one belongs to the class of organic compounds known as 7-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C7 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. 5-hydroxy-3-(4-hydroxy-2-methoxyphenyl)-7-methoxy-6-methyl-2,3-dihydro-1-benzopyran-4-one is found in Desmodium uncinatum. Based on a literature review very few articles have been published on 5-hydroxy-3-(4-hydroxy-2-methoxyphenyl)-7-methoxy-6-methyl-3,4-dihydro-2H-1-benzopyran-4-one.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0257551 (5-hydroxy-3-(4-hydroxy-2-methoxyphenyl)-7-methoxy-6-methyl-2,3-dihydro-1-benzopyran-4-one)


  Mrv1652309082200422D          

 24 26  0  0  0  0            999 V2000
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   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
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    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    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
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    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 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
  1  2  1  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  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
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  3  9  1  0  0  0  0
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M  END
Download

3D MOL for NP0257551 (5-hydroxy-3-(4-hydroxy-2-methoxyphenyl)-7-methoxy-6-methyl-2,3-dihydro-1-benzopyran-4-one)

Download
3D SDF for NP0257551 (5-hydroxy-3-(4-hydroxy-2-methoxyphenyl)-7-methoxy-6-methyl-2,3-dihydro-1-benzopyran-4-one)

  Mrv1652309082200422D          

 24 26  0  0  0  0            999 V2000
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   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
   -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
    0.7145   -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
    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
    4.2868    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   -1.6500    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
  1  2  1  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  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0257551

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=CC=C1C1COC2=CC(OC)=C(C)C(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O6/c1-9-13(22-2)7-15-16(17(9)20)18(21)12(8-24-15)11-5-4-10(19)6-14(11)23-3/h4-7,12,19-20H,8H2,1-3H3

> <INCHI_KEY>
UCMOEFQGLWWXJA-UHFFFAOYSA-N

> <FORMULA>
C18H18O6

> <MOLECULAR_WEIGHT>
330.336

> <EXACT_MASS>
330.1103383

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
33.646396655459775

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-3-(4-hydroxy-2-methoxyphenyl)-7-methoxy-6-methyl-3,4-dihydro-2H-1-benzopyran-4-one

> <JCHEM_LOGP>
3.2293022936666658

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.595751862852056

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.906558226444254

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3922853701118445

> <JCHEM_POLAR_SURFACE_AREA>
85.22

> <JCHEM_REFRACTIVITY>
87.66319999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-3-(4-hydroxy-2-methoxyphenyl)-7-methoxy-6-methyl-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0257551 (5-hydroxy-3-(4-hydroxy-2-methoxyphenyl)-7-methoxy-6-methyl-2,3-dihydro-1-benzopyran-4-one)
Download
PDB for NP0257551 (5-hydroxy-3-(4-hydroxy-2-methoxyphenyl)-7-methoxy-6-methyl-2,3-dihydro-1-benzopyran-4-one)
HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+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  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    3   10                                                  
CONECT   10    9   11   23                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   13   23                                                  
CONECT   23   22   10   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

Download
3D PDB for NP0257551 (5-hydroxy-3-(4-hydroxy-2-methoxyphenyl)-7-methoxy-6-methyl-2,3-dihydro-1-benzopyran-4-one)
Download
SMILES for NP0257551 (5-hydroxy-3-(4-hydroxy-2-methoxyphenyl)-7-methoxy-6-methyl-2,3-dihydro-1-benzopyran-4-one)
COC1=CC(O)=CC=C1C1COC2=CC(OC)=C(C)C(O)=C2C1=O
Download
INCHI for NP0257551 (5-hydroxy-3-(4-hydroxy-2-methoxyphenyl)-7-methoxy-6-methyl-2,3-dihydro-1-benzopyran-4-one)
InChI=1S/C18H18O6/c1-9-13(22-2)7-15-16(17(9)20)18(21)12(8-24-15)11-5-4-10(19)6-14(11)23-3/h4-7,12,19-20H,8H2,1-3H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC18H18O6
Average Mass330.3360 Da
Monoisotopic Mass330.11034 Da
IUPAC Name5-hydroxy-3-(4-hydroxy-2-methoxyphenyl)-7-methoxy-6-methyl-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name5-hydroxy-3-(4-hydroxy-2-methoxyphenyl)-7-methoxy-6-methyl-2,3-dihydro-1-benzopyran-4-one
CAS Registry NumberNot Available
SMILES
COC1=CC(O)=CC=C1C1COC2=CC(OC)=C(C)C(O)=C2C1=O
InChI Identifier
InChI=1S/C18H18O6/c1-9-13(22-2)7-15-16(17(9)20)18(21)12(8-24-15)11-5-4-10(19)6-14(11)23-3/h4-7,12,19-20H,8H2,1-3H3
InChI KeyUCMOEFQGLWWXJA-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Desmodium uncinatumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 7-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C7 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassIsoflavonoids  
Sub ClassO-methylated isoflavonoids  
Direct Parent7-O-methylated isoflavonoids  
Alternative Parents
Substituents
  • 2p-methoxyisoflavonoid-skeleton
    • 

  • 7-methoxyisoflavonoid-skeleton
    • 

  • Hydroxyisoflavonoid
    • 

  • Isoflavanol
    • 

  • Isoflavanone
    • 

  • Isoflavan
    • 

  • Chromone
    • 

  • Chromane
    • 

  • Benzopyran
    • 

  • Methoxyphenol
    • 

  • 1-benzopyran
    • 

  • Phenoxy compound
    • 

  • Anisole
    • 

  • Methoxybenzene
    • 

  • Phenol ether
    • 

  • Aryl ketone
    • 

  • Aryl alkyl ketone
    • 

  • Alkyl aryl ether
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Vinylogous acid
    • 

  • Ketone
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteropolycyclic compound
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
logP3.23ChemAxon
pKa (Strongest Acidic)8.91ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity87.66 m³·mol⁻¹ChemAxon
Polarizability33.65 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound91023830  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]