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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 22:46:42 UTC

Update Date

2021-09-26 23:17:39 UTC

HMDB ID

HMDB0259840

Secondary Accession Numbers

None

Metabolite 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. visnagin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on visnagin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Visnagin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Visnagin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D 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>
HMDB0259840

> <DATABASE_NAME>
hmdb

> <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

COMPND    HMDB0259840
HETATM    1  C1  UNL     1      -2.216  -2.489  -0.056  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.656  -1.581   0.843  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.087  -0.367   0.502  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.865   0.768   0.457  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.200   1.009   0.692  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.412   2.341   0.492  1.00  0.00           C  
HETATM    7  O2  UNL     1      -2.302   2.899   0.158  1.00  0.00           O  
HETATM    8  C6  UNL     1      -1.333   2.007   0.119  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.013   2.055  -0.171  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.845   0.940  -0.141  1.00  0.00           C  
HETATM   11  O3  UNL     1       2.133   1.054  -0.431  1.00  0.00           O  
HETATM   12  C9  UNL     1       2.942   0.026  -0.411  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.404   0.184  -0.746  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.427  -1.209  -0.078  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.094  -1.374   0.231  1.00  0.00           C  
HETATM   16  O4  UNL     1       0.574  -2.470   0.540  1.00  0.00           O  
HETATM   17  C13 UNL     1       0.255  -0.259   0.202  1.00  0.00           C  
HETATM   18  H1  UNL     1      -2.201  -3.508   0.413  1.00  0.00           H  
HETATM   19  H2  UNL     1      -1.686  -2.544  -1.025  1.00  0.00           H  
HETATM   20  H3  UNL     1      -3.267  -2.188  -0.306  1.00  0.00           H  
HETATM   21  H4  UNL     1      -3.924   0.279   0.976  1.00  0.00           H  
HETATM   22  H5  UNL     1      -4.353   2.902   0.586  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.456   2.990  -0.434  1.00  0.00           H  
HETATM   24  H7  UNL     1       4.955   0.468   0.185  1.00  0.00           H  
HETATM   25  H8  UNL     1       4.776  -0.820  -1.023  1.00  0.00           H  
HETATM   26  H9  UNL     1       4.557   0.944  -1.517  1.00  0.00           H  
HETATM   27  H10 UNL     1       3.071  -2.057  -0.058  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3
CONECT    3    4    4   17
CONECT    4    5    8
CONECT    5    6    6   21
CONECT    6    7   22
CONECT    7    8
CONECT    8    9    9
CONECT    9   10   23
CONECT   10   11   17   17
CONECT   11   12
CONECT   12   13   14   14
CONECT   13   24   25   26
CONECT   14   15   27
CONECT   15   16   16   17
END

View in JSmol View Stereo Labels

Synonyms

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

Chemical Formula

C₁₃H₁₀O₄

Average Molecular Weight

230.219

Monoisotopic Molecular Weight

230.057908802

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

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 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	148.146	32859911
AllCCS	[M+H-H2O]+	143.89	32859911
AllCCS	[M+Na]+	153.249	32859911
AllCCS	[M+NH4]+	152.107	32859911
AllCCS	[M-H]-	151.555	32859911
AllCCS	[M+Na-2H]-	151.001	32859911
AllCCS	[M+HCOO]-	150.501	32859911
DeepCCS	[M+H]+	155.131	30932474
DeepCCS	[M-H]-	152.774	30932474
DeepCCS	[M-2H]-	185.973	30932474
DeepCCS	[M+Na]+	161.225	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Visnagin	COC1=C2C=COC2=CC2=C1C(=O)C=C(C)O2	3040.3	Standard polar	33892256
Visnagin	COC1=C2C=COC2=CC2=C1C(=O)C=C(C)O2	2081.8	Standard non polar	33892256
Visnagin	COC1=C2C=COC2=CC2=C1C(=O)C=C(C)O2	2033.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Visnagin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0hhi-1490000000-a3000242afb978b50c53	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Visnagin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Visnagin 40V, Positive-QTOF	splash10-02jr-0910000000-b6fd8506a0bb464b4980	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Visnagin 20V, Positive-QTOF	splash10-014i-0090000000-8b8f26b2bb74658dec53	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Visnagin 40V, Positive-QTOF	splash10-02jr-0910000000-43fd6fc14bd1f0459616	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Visnagin 20V, Positive-QTOF	splash10-014i-0090000000-b4951998b2b77ddf01dc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Visnagin 10V, Positive-QTOF	splash10-001i-0090000000-96a6abc9e460d4484c38	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Visnagin 10V, Positive-QTOF	splash10-001i-0090000000-1e35007777aa589ea2bb	2021-09-20	HMDB team, MONA	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00002447

Chemspider ID

6460

KEGG Compound ID

C09049

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Visnagin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

10002

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1296971

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Visnagin (HMDB0259840)

MOL for HMDB0259840 (Visnagin)

3D MOL for HMDB0259840 (Visnagin)

3D SDF for HMDB0259840 (Visnagin)

3D-SDF for HMDB0259840 (Visnagin)

PDB for HMDB0259840 (Visnagin)

3D PDB for HMDB0259840 (Visnagin)

SMILES for HMDB0259840 (Visnagin)

INCHI for HMDB0259840 (Visnagin)

Structure for HMDB0259840 (Visnagin)

3D Structure for HMDB0259840 (Visnagin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra