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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:53:09 UTC

Update Date

2022-03-07 02:53:33 UTC

HMDB ID

HMDB0032998

Secondary Accession Numbers

HMDB32998

Metabolite Identification

Common Name

2-Methoxyxanthone

Description

2-Methoxyxanthone belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. 2-Methoxyxanthone has been detected, but not quantified in, fruits and herbs and spices. This could make 2-methoxyxanthone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2-Methoxyxanthone.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 05061306512D          

 17 19  0  0  0  0            999 V2000
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  7  6  2  0  0  0  0
  9  6  1  0  0  0  0
  9  8  2  0  0  0  0
 10  4  2  0  0  0  0
 11  8  1  0  0  0  0
 12  5  2  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  2  0  0  0  0
 14 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 14  2  0  0  0  0
 16  1  1  0  0  0  0
 16  9  1  0  0  0  0
 17 12  1  0  0  0  0
 17 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032998

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(OC3=CC=CC=C3C2=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H10O3/c1-16-9-6-7-13-11(8-9)14(15)10-4-2-3-5-12(10)17-13/h2-8H,1H3

> <INCHI_KEY>
DVZCOQQFPCMIPO-UHFFFAOYSA-N

> <FORMULA>
C14H10O3

> <MOLECULAR_WEIGHT>
226.2274

> <EXACT_MASS>
226.062994186

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.44620740625432

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methoxy-9H-xanthen-9-one

> <ALOGPS_LOGP>
3.19

> <JCHEM_LOGP>
2.801968954666667

> <ALOGPS_LOGS>
-4.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.82088509097043

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
63.27950000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.23e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methoxyxanthen-9-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   10                                                       
CONECT    5    3   12                                                       
CONECT    6    7    9                                                       
CONECT    7    6   13                                                       
CONECT    8    9   11                                                       
CONECT    9    6    8   16                                                  
CONECT   10    4   12   14                                                  
CONECT   11    8   13   14                                                  
CONECT   12    5   10   17                                                  
CONECT   13    7   11   17                                                  
CONECT   14   10   11   15                                                  
CONECT   15   14                                                            
CONECT   16    1    9                                                       
CONECT   17   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0032998
HETATM    1  C1  UNL     1       4.686   0.833   0.312  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.090  -0.436   0.386  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.739  -0.684   0.370  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.300  -1.978   0.450  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.949  -2.235   0.435  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.005  -1.244   0.343  1.00  0.00           C  
HETATM    7  O2  UNL     1      -1.273  -1.540   0.333  1.00  0.00           O  
HETATM    8  C6  UNL     1      -2.183  -0.603   0.246  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.528  -0.970   0.239  1.00  0.00           C  
HETATM   10  C8  UNL     1      -4.486   0.013   0.147  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.068   1.333   0.066  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.746   1.685   0.073  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.787   0.718   0.164  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.451   1.077   0.171  1.00  0.00           C  
HETATM   15  O3  UNL     1      -0.076   2.267   0.097  1.00  0.00           O  
HETATM   16  C13 UNL     1       0.467   0.056   0.264  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.828   0.332   0.278  1.00  0.00           C  
HETATM   18  H1  UNL     1       4.072   1.531  -0.323  1.00  0.00           H  
HETATM   19  H2  UNL     1       4.693   1.257   1.337  1.00  0.00           H  
HETATM   20  H3  UNL     1       5.736   0.774  -0.094  1.00  0.00           H  
HETATM   21  H4  UNL     1       2.968  -2.836   0.525  1.00  0.00           H  
HETATM   22  H5  UNL     1       0.570  -3.257   0.496  1.00  0.00           H  
HETATM   23  H6  UNL     1      -3.794  -2.017   0.305  1.00  0.00           H  
HETATM   24  H7  UNL     1      -5.539  -0.268   0.141  1.00  0.00           H  
HETATM   25  H8  UNL     1      -4.847   2.076  -0.005  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.440   2.738   0.008  1.00  0.00           H  
HETATM   27  H10 UNL     1       2.114   1.379   0.212  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3
CONECT    3    4    4   17
CONECT    4    5   21
CONECT    5    6    6   22
CONECT    6    7   16
CONECT    7    8
CONECT    8    9    9   13
CONECT    9   10   23
CONECT   10   11   11   24
CONECT   11   12   25
CONECT   12   13   13   26
CONECT   13   14
CONECT   14   15   15   16
CONECT   16   17   17
CONECT   17   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Methoxy-9H-xanthen-9-one	HMDB
2-Methoxy-xanthen-9-one	HMDB
2-Methoxyxanthen-9-one	HMDB

Chemical Formula

C₁₄H₁₀O₃

Average Molecular Weight

226.2274

Monoisotopic Molecular Weight

226.062994186

IUPAC Name

2-methoxy-9H-xanthen-9-one

Traditional Name

2-methoxyxanthen-9-one

CAS Registry Number

1214-20-6

SMILES

COC1=CC2=C(OC3=CC=CC=C3C2=O)C=C1

InChI Identifier

InChI=1S/C14H10O3/c1-16-9-6-7-13-11(8-9)14(15)10-4-2-3-5-12(10)17-13/h2-8H,1H3

InChI Key

DVZCOQQFPCMIPO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthones

Alternative Parents

Substituents

Xanthone
Chromone
Anisole
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Heteroaromatic compound
Oxacycle
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0032998)

Cellular substructure

Membrane (HMDB: HMDB0032998)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032998)

Source

Exogenous

Food

Food (HMDB: HMDB0032998)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0032998)

Not Available

Nutrient (HMDB: HMDB0032998)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	134 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	142.364	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001138

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.022 g/L	ALOGPS
logP	3.19	ALOGPS
logP	2.8	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	63.28 m³·mol⁻¹	ChemAxon
Polarizability	23.45 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	151.419	31661259
DarkChem	[M-H]-	153.534	31661259
DeepCCS	[M+H]+	155.698	30932474
DeepCCS	[M-H]-	153.34	30932474
DeepCCS	[M-2H]-	186.226	30932474
DeepCCS	[M+Na]+	161.791	30932474
AllCCS	[M+H]+	148.9	32859911
AllCCS	[M+H-H2O]+	144.6	32859911
AllCCS	[M+NH4]+	152.9	32859911
AllCCS	[M+Na]+	154.0	32859911
AllCCS	[M-H]-	152.5	32859911
AllCCS	[M+Na-2H]-	151.9	32859911
AllCCS	[M+HCOO]-	151.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methoxyxanthone	COC1=CC2=C(OC3=CC=CC=C3C2=O)C=C1	3074.0	Standard polar	33892256
2-Methoxyxanthone	COC1=CC2=C(OC3=CC=CC=C3C2=O)C=C1	2122.0	Standard non polar	33892256
2-Methoxyxanthone	COC1=CC2=C(OC3=CC=CC=C3C2=O)C=C1	2164.8	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 - 2-Methoxyxanthone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0092-2930000000-60656bb032ab983207e9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxyxanthone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxyxanthone 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 - 2-Methoxyxanthone Linear Ion Trap , positive-QTOF	splash10-01ot-0960000000-fcfd600c3d94d23cc183	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxyxanthone 10V, Positive-QTOF	splash10-004i-0090000000-2a5c65fe5a667936fc27	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxyxanthone 20V, Positive-QTOF	splash10-004i-0090000000-46fe79245fabadcac768	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxyxanthone 40V, Positive-QTOF	splash10-0fft-3940000000-9ae565be24afc1c5c466	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxyxanthone 10V, Negative-QTOF	splash10-004i-0090000000-4c3cffeb3557a964a7f9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxyxanthone 20V, Negative-QTOF	splash10-004i-0090000000-e1a4043b89eb13f946d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxyxanthone 40V, Negative-QTOF	splash10-0002-1920000000-b489fa6f3d2f709f4b4c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxyxanthone 10V, Positive-QTOF	splash10-004i-0090000000-1158eb6b952d47f22859	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxyxanthone 20V, Positive-QTOF	splash10-004i-0090000000-1158eb6b952d47f22859	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxyxanthone 40V, Positive-QTOF	splash10-056r-5900000000-69820ec668c5b9d1a883	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxyxanthone 10V, Negative-QTOF	splash10-004i-0090000000-6929adb4eb50cc47a297	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxyxanthone 20V, Negative-QTOF	splash10-004i-0090000000-6929adb4eb50cc47a297	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxyxanthone 40V, Negative-QTOF	splash10-0002-0910000000-baf14d8249616d4fa3a1	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB010987

KNApSAcK ID

C00038230

Chemspider ID

64193

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71034

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2-Methoxyxanthone (HMDB0032998)

MOL for HMDB0032998 (2-Methoxyxanthone)

3D MOL for HMDB0032998 (2-Methoxyxanthone)

3D SDF for HMDB0032998 (2-Methoxyxanthone)

3D-SDF for HMDB0032998 (2-Methoxyxanthone)

PDB for HMDB0032998 (2-Methoxyxanthone)

3D PDB for HMDB0032998 (2-Methoxyxanthone)

SMILES for HMDB0032998 (2-Methoxyxanthone)

INCHI for HMDB0032998 (2-Methoxyxanthone)

Structure for HMDB0032998 (2-Methoxyxanthone)

3D Structure for HMDB0032998 (2-Methoxyxanthone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra