NP-MRD: Showing NP-Card for 6-Demethylvignafuran (NP0056825)

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Record Information

Version

2.0

Created at

2022-04-28 02:28:13 UTC

Updated at

2022-04-28 02:28:13 UTC

NP-MRD ID

NP0056825

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-Demethylvignafuran

Description

6-Demethylvignafuran belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Thus, 6-demethylvignafuran is considered to be a flavonoid lipid molecule. 6-Demethylvignafuran is found in Anthyllis vulneraria , Coronilla emerus, Dalbergia odorifera, Hedysarum polybotrys, Lotus maritimus and Mucuna birdwoodiana. 6-Demethylvignafuran is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
   -2.5250   -2.3210    1.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6517   -1.3891    0.8618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1262   -0.2470    0.2116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4692    0.0103    0.1217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9585    1.1480   -0.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3099    1.4091   -0.6169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0665    2.0268   -1.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7180    1.7570   -0.9864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2294    0.6359   -0.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2191    0.3781   -0.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1909    1.2018   -0.7931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4332    0.6510   -0.5260 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7442    0.9870   -0.7839 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8045    0.2096   -0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4901   -0.9543    0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5536   -1.7344    0.7343 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1869   -1.3097    0.5930 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1375   -0.5198    0.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8302   -0.6123    0.2908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9719   -3.2672    1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9429   -1.8823    2.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3843   -2.4978    0.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2149   -0.6469    0.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8272    1.9384    0.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3659    2.9279   -1.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0003    2.4383   -1.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0542    2.1362   -1.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9559    1.8951   -1.3278 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8355    0.4642   -0.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3561   -2.5977    1.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9699   -2.2350    1.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  9  2  0
  9  8  1  0
  8  7  2  0
  7  5  1  0
  5  6  1  0
  5  4  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 18  2  0
 18 19  1  0
 18 17  1  0
 17 15  2  0
 15 16  1  0
 15 14  1  0
 14 13  2  0
  4  3  1  0
 19 10  1  0
 13 12  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  8 26  1  0
  7 25  1  0
  6 24  1  0
  4 23  1  0
 11 27  1  0
 17 31  1  0
 16 30  1  0
 14 29  1  0
 13 28  1  0
M  END

  Mrv1652310051705382D          

 19 21  0  0  0  0            999 V2000
   -0.6284    2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
   -2.6909    0.8085    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
   -0.1435    0.8555    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
   -2.6909    2.2374    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
    2.0701    1.9354    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
   -1.4534    1.5229    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
   -1.8659    2.2374    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
    2.7845    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    2.9519    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
  3  2  2  0  0  0  0
  5  4  2  0  0  0  0
  9  2  1  0  0  0  0
  9  6  1  0  0  0  0
 10  3  1  0  0  0  0
 10  7  2  0  0  0  0
 11  4  1  0  0  0  0
 11  8  2  0  0  0  0
 12  5  1  0  0  0  0
 13  7  1  0  0  0  0
 13  9  2  0  0  0  0
 14  8  1  0  0  0  0
 14 12  2  0  0  0  0
 15  6  2  0  0  0  0
 15 12  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18  1  1  0  0  0  0
 18 14  1  0  0  0  0
 19 13  1  0  0  0  0
 19 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056825

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C=CC(O)=C1)C1=CC2=C(O1)C=C(O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O4/c1-18-14-8-11(17)4-5-12(14)15-6-9-2-3-10(16)7-13(9)19-15/h2-8,16-17H,1H3

> <INCHI_KEY>
QTFMQWQJMAKEOI-UHFFFAOYSA-N

> <FORMULA>
C15H12O4

> <MOLECULAR_WEIGHT>
256.257

> <EXACT_MASS>
256.073558866

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
26.868880121176943

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-hydroxy-2-methoxyphenyl)-1-benzofuran-6-ol

> <ALOGPS_LOGP>
3.26

> <JCHEM_LOGP>
2.9347937933333332

> <ALOGPS_LOGS>
-3.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.37954610838865

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.765177595632592

> <JCHEM_PKA_STRONGEST_BASIC>
-2.873342392630984

> <JCHEM_POLAR_SURFACE_AREA>
62.83

> <JCHEM_REFRACTIVITY>
70.33780000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-demethylvignafuran

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-OCT-17         0                                  
HETATM    1  C   UNK     0      -1.173   5.510   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.023   1.509   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.483   1.509   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.023   4.177   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.793   2.843   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.713   2.843   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.483   4.177   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -7.333   2.843   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.713   5.510   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   18                                                            
CONECT    2    3    9                                                       
CONECT    3    2   10                                                       
CONECT    4    5   11                                                       
CONECT    5    4   12                                                       
CONECT    6    9   15                                                       
CONECT    7   10   13                                                       
CONECT    8   11   14                                                       
CONECT    9    2    6   13                                                  
CONECT   10    3    7   16                                                  
CONECT   11    4    8   17                                                  
CONECT   12    5   14   15                                                  
CONECT   13    7    9   19                                                  
CONECT   14    8   12   18                                                  
CONECT   15    6   12   19                                                  
CONECT   16   10                                                            
CONECT   17   11                                                            
CONECT   18    1   14                                                       
CONECT   19   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₂O₄

Average Mass

256.2570 Da

Monoisotopic Mass

256.07356 Da

IUPAC Name

2-(4-hydroxy-2-methoxyphenyl)-1-benzofuran-6-ol

Traditional Name

6-demethylvignafuran

CAS Registry Number

Not Available

SMILES

COC1=C(C=CC(O)=C1)C1=CC2=C(O1)C=C(O)C=C2

InChI Identifier

InChI=1S/C15H12O4/c1-18-14-8-11(17)4-5-12(14)15-6-9-2-3-10(16)7-13(9)19-15/h2-8,16-17H,1H3

InChI Key

QTFMQWQJMAKEOI-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
Anthyllis vulneraria	Plant	KNApSAcK
Coronilla emerus	Plant	KNApSAcK
Dalbergia odorifera	LOTUS Database	35616633
Hedysarum polybotrys	LOTUS Database	35616633
Lotus maritimus	Plant	KNApSAcK
Mucuna birdwoodiana	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
Methoxyphenol
Benzofuran
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Furan
Ether
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Other Flavonoids (LMPK12160038 )

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	3.26	ALOGPS
logP	2.93	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	8.77	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	70.34 m³·mol⁻¹	ChemAxon
Polarizability	26.87 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

HMDB0147270

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

14887925

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 6-Demethylvignafuran (NP0056825)

MOL for NP0056825 (6-Demethylvignafuran)

3D MOL for NP0056825 (6-Demethylvignafuran)

3D SDF for NP0056825 (6-Demethylvignafuran)

3D-SDF for NP0056825 (6-Demethylvignafuran)

PDB for NP0056825 (6-Demethylvignafuran)

3D PDB for NP0056825 (6-Demethylvignafuran)

SMILES for NP0056825 (6-Demethylvignafuran)

INCHI for NP0056825 (6-Demethylvignafuran)

Structure for NP0056825 (6-Demethylvignafuran)

3D Structure for NP0056825 (6-Demethylvignafuran)