NP-MRD: Showing NP-Card for 2-(3,4-dihydroxyphenyl)-4,6-dihydroxy-2-methoxy-1-benzofuran-3-one (NP0329373)

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Record Information

Version

2.0

Created at

2022-09-12 13:41:49 UTC

Updated at

2022-09-12 13:41:49 UTC

NP-MRD ID

NP0329373

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(3,4-dihydroxyphenyl)-4,6-dihydroxy-2-methoxy-1-benzofuran-3-one

Description

2-(3,4-Dihydroxyphenyl)-4,6-dihydroxy-2-methoxy-2,3-dihydro-1-benzofuran-3-one belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. 2-(3,4-dihydroxyphenyl)-4,6-dihydroxy-2-methoxy-1-benzofuran-3-one is found in Allium cepa. 2-(3,4-Dihydroxyphenyl)-4,6-dihydroxy-2-methoxy-2,3-dihydro-1-benzofuran-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004161522102D          

 22 24  0  0  0  0            999 V2000
    0.2122   -2.0569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0407   -1.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0407   -0.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7439   -0.4008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3570    0.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1855    0.9582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7986    1.5102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4009    1.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2293    2.0201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2122    0.6611    0.0000 C   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  2  0  0  0  0
  3 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 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
 15 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0329373

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O7/c1-21-15(7-2-3-9(17)10(18)4-7)14(20)13-11(19)5-8(16)6-12(13)22-15/h2-6,16-19H,1H3

> <INCHI_KEY>
LMUQMEDGLAEQEK-UHFFFAOYSA-N

> <FORMULA>
C15H12O7

> <MOLECULAR_WEIGHT>
304.254

> <EXACT_MASS>
304.058302726

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
28.603998156439964

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-4,6-dihydroxy-2-methoxy-2,3-dihydro-1-benzofuran-3-one

> <ALOGPS_LOGP>
1.90

> <JCHEM_LOGP>
3.0523508896666662

> <ALOGPS_LOGS>
-2.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.825573175730975

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.563553200812091

> <JCHEM_PKA_STRONGEST_BASIC>
-4.311489206256554

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
74.94000000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)-4,6-dihydroxy-2-methoxy-1-benzofuran-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       0.396  -3.840   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.076  -2.333   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.126  -0.057   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.650  -4.013   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.076  -0.272   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.389  -0.748   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.533   0.282   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.213   1.789   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.357   2.819   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.748   2.264   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.428   3.771   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.396   1.234   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13   15                                             
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5   13                                                  
CONECT   13   12    3   14                                                  
CONECT   14   13                                                            
CONECT   15    3   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₂O₇

Average Mass

304.2540 Da

Monoisotopic Mass

304.05830 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-4,6-dihydroxy-2-methoxy-2,3-dihydro-1-benzofuran-3-one

Traditional Name

2-(3,4-dihydroxyphenyl)-4,6-dihydroxy-2-methoxy-1-benzofuran-3-one

CAS Registry Number

Not Available

SMILES

COC1(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C15H12O7/c1-21-15(7-2-3-9(17)10(18)4-7)14(20)13-11(19)5-8(16)6-12(13)22-15/h2-6,16-19H,1H3

InChI Key

LMUQMEDGLAEQEK-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Allium cepa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Benzofuran
Benzylether
Coumaran
Catechol
Aryl ketone
Aryl alkyl ketone
Ketal
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Oxacycle
Organoheterocyclic compound
Acetal
Organic oxide
Organooxygen compound
Organic oxygen compound
Aldehyde
Hydrocarbon derivative
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	1.9	ALOGPS
logP	3.05	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	7.56	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	74.94 m³·mol⁻¹	ChemAxon
Polarizability	28.6 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

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

51136531

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)-4,6-dihydroxy-2-methoxy-1-benzofuran-3-one (NP0329373)

MOL for NP0329373 (2-(3,4-dihydroxyphenyl)-4,6-dihydroxy-2-methoxy-1-benzofuran-3-one)

3D MOL for NP0329373 (2-(3,4-dihydroxyphenyl)-4,6-dihydroxy-2-methoxy-1-benzofuran-3-one)

3D SDF for NP0329373 (2-(3,4-dihydroxyphenyl)-4,6-dihydroxy-2-methoxy-1-benzofuran-3-one)

3D-SDF for NP0329373 (2-(3,4-dihydroxyphenyl)-4,6-dihydroxy-2-methoxy-1-benzofuran-3-one)

PDB for NP0329373 (2-(3,4-dihydroxyphenyl)-4,6-dihydroxy-2-methoxy-1-benzofuran-3-one)

3D PDB for NP0329373 (2-(3,4-dihydroxyphenyl)-4,6-dihydroxy-2-methoxy-1-benzofuran-3-one)

SMILES for NP0329373 (2-(3,4-dihydroxyphenyl)-4,6-dihydroxy-2-methoxy-1-benzofuran-3-one)

INCHI for NP0329373 (2-(3,4-dihydroxyphenyl)-4,6-dihydroxy-2-methoxy-1-benzofuran-3-one)

Structure for NP0329373 (2-(3,4-dihydroxyphenyl)-4,6-dihydroxy-2-methoxy-1-benzofuran-3-one)

3D Structure for NP0329373 (2-(3,4-dihydroxyphenyl)-4,6-dihydroxy-2-methoxy-1-benzofuran-3-one)