NP-MRD: Showing NP-Card for 2-(3,5-dihydroxyphenyl)-1-benzofuran-6,7-diol (NP0296497)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 06:06:36 UTC

Updated at

2022-09-10 06:06:36 UTC

NP-MRD ID

NP0296497

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(3,5-dihydroxyphenyl)-1-benzofuran-6,7-diol

Description

2-(3,5-Dihydroxyphenyl)-1-benzofuran-6,7-diol belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. 2-(3,5-Dihydroxyphenyl)-1-benzofuran-6,7-diol is an extremely weak basic (essentially neutral) compound (based on its pKa). This aromatic-hydroxylation-of-fused-benzene-ring-pattern2 occurs in humans. It is generated by cyp1a2, cyp2b6, cyp2c9, and cyp2c19 enzymes via an aromatic-hydroxylation-of-fused-benzene-ring-pattern2 reaction. 2-(3,5-dihydroxyphenyl)-1-benzofuran-6,7-diol is found in Morus alba. 2-(3,5-Dihydroxyphenyl)-1-benzofuran-6,7-diol is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -4.1053   -2.7933   -0.2206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5699   -1.5367   -0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3941   -0.4568    0.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7979    0.7722    0.3786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5998    1.8897    0.6245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4467    0.9610    0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6148   -0.1099    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1703    0.0856    0.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4809    1.2878    0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8537    1.0743    0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9326    1.9165    0.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1946    1.3840   -0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3572    0.0361   -0.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6404   -0.4495   -0.4432 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2490   -0.7752   -0.3453 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4203   -2.1488   -0.5948 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9560   -0.2853   -0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7697   -0.7998   -0.1894 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1978   -1.3484   -0.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3828   -3.1788   -1.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4756   -0.5473    0.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8546    2.1746    1.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0243    1.9649    0.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0240    2.2595    0.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7574    2.9695    0.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0571    2.0345    0.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8602   -1.4122   -0.6246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6265   -2.7593   -0.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5456   -2.2088   -0.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 19  2  0
 19  7  1  0
  7  6  2  0
  6  4  1  0
  4  5  1  0
  4  3  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 17  2  0
 17 18  1  0
 17 15  1  0
 15 16  1  0
 15 13  2  0
 13 14  1  0
 13 12  1  0
 12 11  2  0
  3  2  1  0
 18  8  1  0
 11 10  1  0
  1 20  1  0
 19 29  1  0
  6 23  1  0
  5 22  1  0
  3 21  1  0
  9 24  1  0
 16 28  1  0
 14 27  1  0
 12 26  1  0
 11 25  1  0
M  END


  Mrv1652308231919092D          

 19 21  0  0  0  0            999 V2000
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    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
   -1.4534    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    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
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    0.0940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    2.9519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  7  1  1  0  0  0  0
  7  5  1  0  0  0  0
  8  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  3  1  0  0  0  0
  9  6  2  0  0  0  0
 10  4  2  0  0  0  0
 10  6  1  0  0  0  0
 11  2  1  0  0  0  0
 12  5  2  0  0  0  0
 12  8  1  0  0  0  0
 13 11  2  0  0  0  0
 14  7  2  0  0  0  0
 14 13  1  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 13  1  0  0  0  0
 19 12  1  0  0  0  0
 19 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0296497

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(=CC(O)=C1)C1=CC2=C(O1)C(O)=C(O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C14H10O5/c15-9-3-8(4-10(16)6-9)12-5-7-1-2-11(17)13(18)14(7)19-12/h1-6,15-18H

> <INCHI_KEY>
VOEMDQMSOKXQNY-UHFFFAOYSA-N

> <FORMULA>
C14H10O5

> <MOLECULAR_WEIGHT>
258.229

> <EXACT_MASS>
258.052823422

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
25.94998658133253

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,5-dihydroxyphenyl)-1-benzofuran-6,7-diol

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
2.4853344156666664

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.850463293057729

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.528271855152629

> <JCHEM_PKA_STRONGEST_BASIC>
-2.909015386095647

> <JCHEM_POLAR_SURFACE_AREA>
94.06

> <JCHEM_REFRACTIVITY>
67.83640000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.50e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,5-dihydroxyphenyl)-1-benzofuran-6,7-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-AUG-19         0                                  
HETATM    1  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.483   1.509   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.483   4.176   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.793   2.843   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.713   2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.023   1.509   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.023   4.176   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.793   0.175   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -5.793   5.510   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1   11                                                       
CONECT    3    8    9                                                       
CONECT    4    8   10                                                       
CONECT    5    7   12                                                       
CONECT    6    9   10                                                       
CONECT    7    1    5   14                                                  
CONECT    8    3    4   12                                                  
CONECT    9    3    6   15                                                  
CONECT   10    4    6   16                                                  
CONECT   11    2   13   17                                                  
CONECT   12    5    8   19                                                  
CONECT   13   11   14   18                                                  
CONECT   14    7   13   19                                                  
CONECT   15    9                                                            
CONECT   16   10                                                            
CONECT   17   11                                                            
CONECT   18   13                                                            
CONECT   19   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₀O₅

Average Mass

258.2290 Da

Monoisotopic Mass

258.05282 Da

IUPAC Name

2-(3,5-dihydroxyphenyl)-1-benzofuran-6,7-diol

Traditional Name

2-(3,5-dihydroxyphenyl)-1-benzofuran-6,7-diol

CAS Registry Number

Not Available

SMILES

OC1=CC(=CC(O)=C1)C1=CC2=C(O1)C(O)=C(O)C=C2

InChI Identifier

InChI=1S/C14H10O5/c15-9-3-8(4-10(16)6-9)12-5-7-1-2-11(17)13(18)14(7)19-12/h1-6,15-18H

InChI Key

VOEMDQMSOKXQNY-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
Morus alba	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
2-phenylbenzofuran
Phenylbenzofuran
Benzofuran
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Furan
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
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	2.17	ALOGPS
logP	2.49	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	7.53	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	94.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	67.84 m³·mol⁻¹	ChemAxon
Polarizability	25.95 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

HMDB0138548

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

58964617

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

118735933

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(3,5-dihydroxyphenyl)-1-benzofuran-6,7-diol (NP0296497)

MOL for NP0296497 (2-(3,5-dihydroxyphenyl)-1-benzofuran-6,7-diol)

3D MOL for NP0296497 (2-(3,5-dihydroxyphenyl)-1-benzofuran-6,7-diol)

3D SDF for NP0296497 (2-(3,5-dihydroxyphenyl)-1-benzofuran-6,7-diol)

3D-SDF for NP0296497 (2-(3,5-dihydroxyphenyl)-1-benzofuran-6,7-diol)

PDB for NP0296497 (2-(3,5-dihydroxyphenyl)-1-benzofuran-6,7-diol)

3D PDB for NP0296497 (2-(3,5-dihydroxyphenyl)-1-benzofuran-6,7-diol)

SMILES for NP0296497 (2-(3,5-dihydroxyphenyl)-1-benzofuran-6,7-diol)

INCHI for NP0296497 (2-(3,5-dihydroxyphenyl)-1-benzofuran-6,7-diol)

Structure for NP0296497 (2-(3,5-dihydroxyphenyl)-1-benzofuran-6,7-diol)

3D Structure for NP0296497 (2-(3,5-dihydroxyphenyl)-1-benzofuran-6,7-diol)