NP-MRD: Showing NP-Card for 5,6-Dihydroxy-2-(2',4',6'-trihydroxyphenyl)benzofuran-3-carboxylic acid (NP0057046)

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Record Information

Version

2.0

Created at

2022-04-28 02:36:34 UTC

Updated at

2022-04-28 02:36:34 UTC

NP-MRD ID

NP0057046

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,6-Dihydroxy-2-(2',4',6'-trihydroxyphenyl)benzofuran-3-carboxylic acid

Description

Norwedelic acid, also known as norwedelate, belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. 5,6-Dihydroxy-2-(2',4',6'-trihydroxyphenyl)benzofuran-3-carboxylic acid is found in Sphagneticola calendulacea, Wedelia acapulcensis and Wedelia calendulacea . Norwedelic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
    0.5803   -1.1680   -3.1091 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6793   -0.1147   -2.3918 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8536    1.0790   -3.1136 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6312   -0.1014   -0.9654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3589    0.0126   -0.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7932    0.1683   -0.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5464    0.1994    1.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9026    0.0787    2.2265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8943    0.3433    1.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5707    0.4665   -0.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9499    0.6148   -0.1493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8719    0.4402   -1.3365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4761    0.2909   -1.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8594    0.2764   -2.5911 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2287   -0.0457    1.1307 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5013   -0.1864    1.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4952   -0.2908    2.0223 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8185   -0.4386    1.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8281   -0.5449    2.6267 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1747   -0.4852    0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5073   -0.6340    0.0018 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1726   -0.3798   -0.6084 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8713   -0.2344   -0.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7484    1.4232   -3.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3492    0.0901    3.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4351    0.3623    1.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6056   -0.1283   -0.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4106    0.5370   -2.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2731    0.3587   -3.4896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2415   -0.2571    3.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7947   -0.6531    2.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7312   -0.6640   -0.9837 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4393   -0.4147   -1.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  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
 20 22  1  0
 22 23  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 23  4  1  0
 13  6  1  0
 23 16  1  0
  3 24  1  0
 17 30  1  0
 19 31  1  0
 21 32  1  0
 22 33  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
M  END


  Mrv1533004161519482D          

 23 25  0  0  0  0            999 V2000
    1.4358   -2.7631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 O   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
    0.6538   -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
    4.0668   -1.5229    0.0000 O   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
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -2.1269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.7310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  4 14  1  0  0  0  0
  7 14  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0057046

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=C(OC2=CC(O)=C(O)C=C12)C1=C(O)C=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O8/c16-5-1-9(19)13(10(20)2-5)14-12(15(21)22)6-3-7(17)8(18)4-11(6)23-14/h1-4,16-20H,(H,21,22)

> <INCHI_KEY>
OYMZVRJQIIYPTP-UHFFFAOYSA-N

> <FORMULA>
C15H10O8

> <MOLECULAR_WEIGHT>
318.237

> <EXACT_MASS>
318.037567282

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
29.598838315924702

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,6-dihydroxy-2-(2,4,6-trihydroxyphenyl)-1-benzofuran-3-carboxylic acid

> <ALOGPS_LOGP>
2.20

> <JCHEM_LOGP>
1.8393520019999998

> <ALOGPS_LOGS>
-2.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.042406880979819

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.251988799215738

> <JCHEM_PKA_STRONGEST_BASIC>
-3.047932804436121

> <JCHEM_POLAR_SURFACE_AREA>
151.59

> <JCHEM_REFRACTIVITY>
77.07350000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.35e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
norwedelic acid

> <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  O   UNK     0       2.680  -5.158   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.143  -4.334   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.126  -0.057   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.591  -2.843   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.090  -2.637   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.320  -3.970   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.630  -2.637   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.400  -1.303   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.940  -1.303   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.630   0.031   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.090   0.031   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.320   1.365   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   14                                                  
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    4    7                                                  
CONECT   15    5   16   22                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   15   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
Norwedelate	Generator

Chemical Formula

C₁₅H₁₀O₈

Average Mass

318.2370 Da

Monoisotopic Mass

318.03757 Da

IUPAC Name

5,6-dihydroxy-2-(2,4,6-trihydroxyphenyl)-1-benzofuran-3-carboxylic acid

Traditional Name

norwedelic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=C(OC2=CC(O)=C(O)C=C12)C1=C(O)C=C(O)C=C1O

InChI Identifier

InChI=1S/C15H10O8/c16-5-1-9(19)13(10(20)2-5)14-12(15(21)22)6-3-7(17)8(18)4-11(6)23-14/h1-4,16-20H,(H,21,22)

InChI Key

OYMZVRJQIIYPTP-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Sphagneticola calendulacea	LOTUS Database	35616633
Wedelia acapulcensis	LOTUS Database	35616633
Wedelia calendulacea	Plant	KNApSAcK

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
Phenylbenzofuran
2-phenylbenzofuran
Phloroglucinol derivative
Benzenetriol
Benzofuran
Furoic acid or derivatives
Furan-3-carboxylic acid
Furan-3-carboxylic acid or derivatives
Furoic acid
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Furan
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Organoheterocyclic compound
Polyol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Other Flavonoids (LMPK12160052 )

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	2.2	ALOGPS
logP	1.84	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.25	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	151.59 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	77.07 m³·mol⁻¹	ChemAxon
Polarizability	29.6 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

44260115

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5,6-Dihydroxy-2-(2',4',6'-trihydroxyphenyl)benzofuran-3-carboxylic acid (NP0057046)

MOL for NP0057046 (5,6-Dihydroxy-2-(2',4',6'-trihydroxyphenyl)benzofuran-3-carboxylic acid)

3D MOL for NP0057046 (5,6-Dihydroxy-2-(2',4',6'-trihydroxyphenyl)benzofuran-3-carboxylic acid)

3D SDF for NP0057046 (5,6-Dihydroxy-2-(2',4',6'-trihydroxyphenyl)benzofuran-3-carboxylic acid)

3D-SDF for NP0057046 (5,6-Dihydroxy-2-(2',4',6'-trihydroxyphenyl)benzofuran-3-carboxylic acid)

PDB for NP0057046 (5,6-Dihydroxy-2-(2',4',6'-trihydroxyphenyl)benzofuran-3-carboxylic acid)

3D PDB for NP0057046 (5,6-Dihydroxy-2-(2',4',6'-trihydroxyphenyl)benzofuran-3-carboxylic acid)

SMILES for NP0057046 (5,6-Dihydroxy-2-(2',4',6'-trihydroxyphenyl)benzofuran-3-carboxylic acid)

INCHI for NP0057046 (5,6-Dihydroxy-2-(2',4',6'-trihydroxyphenyl)benzofuran-3-carboxylic acid)

Structure for NP0057046 (5,6-Dihydroxy-2-(2',4',6'-trihydroxyphenyl)benzofuran-3-carboxylic acid)

3D Structure for NP0057046 (5,6-Dihydroxy-2-(2',4',6'-trihydroxyphenyl)benzofuran-3-carboxylic acid)