NP-MRD: Showing NP-Card for Visnagin (NP0051432)

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Record Information

Version

2.0

Created at

2022-04-27 22:48:02 UTC

Updated at

2022-04-27 22:48:02 UTC

NP-MRD ID

NP0051432

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Visnagin

Description

Visnagin, also known as desmethoxykhellin or FUK-724, belongs to the class of organic compounds known as furanochromones. These are polycyclic aromatic compounds containing a furan ring fused to a 1-benzopyran-4-one ring system. Thus, visnagin is considered to be an aromatic polyketide lipid molecule. Visnagin is found in Cimicifuga dahurica , Ammi visnaga and Musineon divaricatum. Visnagin was first documented in 2000 (PMID: 10705731). Visnagin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 21069311) (PMID: 19188097) (PMID: 20036111) (PMID: 21116788).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171523312D          

 17 19  0  0  0  0            999 V2000
    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 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 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    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
  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
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
  3 17  2  0  0  0  0
 13 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051432

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C=COC2=CC2=C1C(=O)C=C(C)O2

> <INCHI_IDENTIFIER>
InChI=1S/C13H10O4/c1-7-5-9(14)12-11(17-7)6-10-8(3-4-16-10)13(12)15-2/h3-6H,1-2H3

> <INCHI_KEY>
NZVQLVGOZRELTG-UHFFFAOYSA-N

> <FORMULA>
C13H10O4

> <MOLECULAR_WEIGHT>
230.219

> <EXACT_MASS>
230.057908802

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
23.118621902295093

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methoxy-7-methyl-5H-furo[3,2-g]chromen-5-one

> <ALOGPS_LOGP>
2.32

> <JCHEM_LOGP>
1.8730054043333328

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.778840578179562

> <JCHEM_PKA_STRONGEST_BASIC>
-2.817212502984345

> <JCHEM_POLAR_SURFACE_AREA>
48.67

> <JCHEM_REFRACTIVITY>
62.4115

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.94e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
visnagin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.258  -0.533   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.925  -0.533   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.592  -5.153   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.925  -5.153   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.459  -4.859   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.554  -3.613   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.459  -2.367   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    4   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    3   13                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Value	Source
5-Methoxy-2-methylfuranochromone	ChEBI
Desmethoxykhellin	ChEBI
FUK-724	ChEBI
Visnagidin	ChEBI
Visnagine	ChEBI

Chemical Formula

C₁₃H₁₀O₄

Average Mass

230.2190 Da

Monoisotopic Mass

230.05791 Da

IUPAC Name

4-methoxy-7-methyl-5H-furo[3,2-g]chromen-5-one

Traditional Name

visnagin

CAS Registry Number

Not Available

SMILES

COC1=C2C=COC2=CC2=C1C(=O)C=C(C)O2

InChI Identifier

InChI=1S/C13H10O4/c1-7-5-9(14)12-11(17-7)6-10-8(3-4-16-10)13(12)15-2/h3-6H,1-2H3

InChI Key

NZVQLVGOZRELTG-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
Actaea dahurica	Plant	KNApSAcK
Ammi visnaga	Plant	KNApSAcK
Musineon divaricatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanochromones. These are polycyclic aromatic compounds containing a furan ring fused to a 1-benzopyran-4-one ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Furanochromones

Alternative Parents

Substituents

Furanochromone
Benzofuran
Anisole
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous ester
Furan
Ether
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotricyclic compound (CHEBI:10002 )
oxacycle (CHEBI:10002 )
chromones (C09049 )
Benzopyranoids (C09049 )
Benzopyranoids (LMPK13110003 )

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	2.32	ALOGPS
logP	1.87	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	14.78	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	48.67 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	62.41 m³·mol⁻¹	ChemAxon
Polarizability	23.12 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

C00002447

Chemspider ID

Not Available

KEGG Compound ID

C09049

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Visnagin

METLIN ID

Not Available

PubChem Compound

6716

PDB ID

Not Available

ChEBI ID

10002

Good Scents ID

Not Available

References

General References

Vanachayangkul P, Chow N, Khan SR, Butterweck V: Prevention of renal crystal deposition by an extract of Ammi visnaga L. and its constituents khellin and visnagin in hyperoxaluric rats. Urol Res. 2011 Jun;39(3):189-95. doi: 10.1007/s00240-010-0333-y. Epub 2010 Nov 11. [PubMed:21069311 ]
Duarte J, Torres AI, Zarzuelo A: Cardiovascular effects of visnagin on rats. Planta Med. 2000 Feb;66(1):35-9. doi: 10.1055/s-2000-11108. [PubMed:10705731 ]
Vanachayangkul P, Butterweck V, Frye RF: Determination of visnagin in rat plasma by liquid chromatography with tandem mass spectrometry and its application to in vivo pharmacokinetic studies. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Mar 1;877(7):653-6. doi: 10.1016/j.jchromb.2009.01.014. Epub 2009 Jan 21. [PubMed:19188097 ]
Vanachayangkul P, Byer K, Khan S, Butterweck V: An aqueous extract of Ammi visnaga fruits and its constituents khellin and visnagin prevent cell damage caused by oxalate in renal epithelial cells. Phytomedicine. 2010 Jul;17(8-9):653-8. doi: 10.1016/j.phymed.2009.10.011. Epub 2009 Dec 29. [PubMed:20036111 ]
Lee JK, Jung JS, Park SH, Park SH, Sim YB, Kim SM, Ha TS, Suh HW: Anti-inflammatory effect of visnagin in lipopolysaccharide-stimulated BV-2 microglial cells. Arch Pharm Res. 2010 Nov;33(11):1843-50. doi: 10.1007/s12272-010-1117-1. Epub 2010 Nov 30. [PubMed:21116788 ]

Showing NP-Card for Visnagin (NP0051432)

MOL for NP0051432 (Visnagin)

3D MOL for NP0051432 (Visnagin)

3D SDF for NP0051432 (Visnagin)

3D-SDF for NP0051432 (Visnagin)

PDB for NP0051432 (Visnagin)

3D PDB for NP0051432 (Visnagin)

SMILES for NP0051432 (Visnagin)

INCHI for NP0051432 (Visnagin)

Structure for NP0051432 (Visnagin)

3D Structure for NP0051432 (Visnagin)