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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:21:03 UTC

Update Date

2022-03-07 02:56:43 UTC

HMDB ID

HMDB0040768

Secondary Accession Numbers

HMDB40768

Metabolite Identification

Common Name

N-(2,5-Dihydroxyphenyl)pyridinium(1+)

Description

N-(2,5-Dihydroxyphenyl)pyridinium(1+) belongs to the class of organic compounds known as hydroquinones. Hydroquinones are compounds containing a hydroquinone moiety, which consists of a benzene ring with a hydroxyl groups at positions 1 and 4. N-(2,5-Dihydroxyphenyl)pyridinium(1+) is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, N-(2,5-dihydroxyphenyl)pyridinium(1+) has been detected, but not quantified in, fruits. This could make N-(2,5-dihydroxyphenyl)pyridinium(1+) a potential biomarker for the consumption of these foods.

Structure

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


  Mrv0541 05061312072D          

 14 15  0  0  0  0            999 V2000
    2.8579    0.8250    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
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    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
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  9  4  1  0  0  0  0
  9  8  2  0  0  0  0
 10  8  1  0  0  0  0
 11  5  1  0  0  0  0
 11 10  2  0  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 12 10  1  0  0  0  0
 13  9  1  0  0  0  0
 14 11  1  0  0  0  0
M  CHG  1  12   1
M  END
> <DATABASE_ID>
HMDB0040768

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC(=C(O)C=C1)[N+]1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H9NO2/c13-9-4-5-11(14)10(8-9)12-6-2-1-3-7-12/h1-8H,(H-,13,14)/p+1

> <INCHI_KEY>
BYQQTWROSPBRIU-UHFFFAOYSA-O

> <FORMULA>
C11H10NO2

> <MOLECULAR_WEIGHT>
188.2026

> <EXACT_MASS>
188.071153569

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
19.478352489245772

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(2,5-dihydroxyphenyl)-1λ⁵-pyridin-1-ylium

> <ALOGPS_LOGP>
-0.78

> <JCHEM_LOGP>
-0.7552270908050792

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.454013339711484

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.701455522248698

> <JCHEM_PKA_STRONGEST_BASIC>
-6.044530672367263

> <JCHEM_POLAR_SURFACE_AREA>
44.34

> <JCHEM_REFRACTIVITY>
64.1152

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.00e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(2,5-dihydroxyphenyl)-1λ⁵-pyridin-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

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       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       5.335   4.620   0.000  0.00  0.00           N+1
HETATM   13  O   UNK     0       8.002   9.240   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1    7                                                       
CONECT    4    5    9                                                       
CONECT    5    4   11                                                       
CONECT    6    2   12                                                       
CONECT    7    3   12                                                       
CONECT    8    9   10                                                       
CONECT    9    4    8   13                                                  
CONECT   10    8   11   12                                                  
CONECT   11    5   10   14                                                  
CONECT   12    6    7   10                                                  
CONECT   13    9                                                            
CONECT   14   11                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₁H₁₀NO₂

Average Molecular Weight

188.2026

Monoisotopic Molecular Weight

188.071153569

IUPAC Name

1-(2,5-dihydroxyphenyl)-1λ⁵-pyridin-1-ylium

Traditional Name

1-(2,5-dihydroxyphenyl)-1λ⁵-pyridin-1-ylium

CAS Registry Number

33354-74-4

SMILES

OC1=CC(=C(O)C=C1)[N+]1=CC=CC=C1

InChI Identifier

InChI=1S/C11H9NO2/c13-9-4-5-11(14)10(8-9)12-6-2-1-3-7-12/h1-8H,(H-,13,14)/p+1

InChI Key

BYQQTWROSPBRIU-UHFFFAOYSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroquinones. Hydroquinones are compounds containing a hydroquinone moiety, which consists of a benzene ring with a hydroxyl groups at positions 1 and 4.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Hydroquinone
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Pyridine
Pyridinium
Heteroaromatic compound
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic cation
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040768)
Cytoplasm (HMDB: HMDB0040768)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040768)

Source

Exogenous

Food

Food (HMDB: HMDB0040768)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0040768)

Not Available

Nutrient (HMDB: HMDB0040768)

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
Water Solubility	0.2 g/L	ALOGPS
logP	-0.78	ALOGPS
logP	-0.76	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	6.7	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	44.34 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	64.12 m³·mol⁻¹	ChemAxon
Polarizability	19.48 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
DarkChem	[M+H]+	141.571	31661259
DarkChem	[M-H]-	143.506	31661259
DeepCCS	[M+H]+	142.357	30932474
DeepCCS	[M-H]-	139.961	30932474
DeepCCS	[M-2H]-	173.452	30932474
DeepCCS	[M+Na]+	148.269	30932474
AllCCS	[M+H]+	140.8	32859911
AllCCS	[M+H-H2O]+	136.5	32859911
AllCCS	[M+NH4]+	144.9	32859911
AllCCS	[M+Na]+	146.0	32859911
AllCCS	[M-H]-	142.4	32859911
AllCCS	[M+Na-2H]-	142.6	32859911
AllCCS	[M+HCOO]-	143.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-(2,5-Dihydroxyphenyl)pyridinium(1+)	OC1=CC(=C(O)C=C1)[N+]1=CC=CC=C1	3285.9	Standard polar	33892256
N-(2,5-Dihydroxyphenyl)pyridinium(1+)	OC1=CC(=C(O)C=C1)[N+]1=CC=CC=C1	1752.6	Standard non polar	33892256
N-(2,5-Dihydroxyphenyl)pyridinium(1+)	OC1=CC(=C(O)C=C1)[N+]1=CC=CC=C1	1822.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-(2,5-Dihydroxyphenyl)pyridinium(1+),1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(O)C([N+]2=CC=CC=C2)=C1	1871.9	Semi standard non polar	33892256
N-(2,5-Dihydroxyphenyl)pyridinium(1+),1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(O)C=C1[N+]1=CC=CC=C1	1878.3	Semi standard non polar	33892256
N-(2,5-Dihydroxyphenyl)pyridinium(1+),2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(O[Si](C)(C)C)C([N+]2=CC=CC=C2)=C1	1921.5	Semi standard non polar	33892256
N-(2,5-Dihydroxyphenyl)pyridinium(1+),1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(O)C([N+]2=CC=CC=C2)=C1	2155.7	Semi standard non polar	33892256
N-(2,5-Dihydroxyphenyl)pyridinium(1+),1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(O)C=C1[N+]1=CC=CC=C1	2162.1	Semi standard non polar	33892256
N-(2,5-Dihydroxyphenyl)pyridinium(1+),2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(O[Si](C)(C)C(C)(C)C)C([N+]2=CC=CC=C2)=C1	2424.6	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 - N-(2,5-Dihydroxyphenyl)pyridinium(1+) GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4r-0900000000-5fcbb2341da2bb2a4d2b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(2,5-Dihydroxyphenyl)pyridinium(1+) GC-MS (2 TMS) - 70eV, Positive	splash10-014i-5498000000-4adc7c89ffd687a7083d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(2,5-Dihydroxyphenyl)pyridinium(1+) 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2,5-Dihydroxyphenyl)pyridinium(1+) 10V, Positive-QTOF	splash10-000i-0900000000-78e0488e744bf47265e9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2,5-Dihydroxyphenyl)pyridinium(1+) 20V, Positive-QTOF	splash10-000i-0900000000-ebb16e4d9034d570afdd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2,5-Dihydroxyphenyl)pyridinium(1+) 40V, Positive-QTOF	splash10-0f89-9500000000-4b9b8d9863c52ac03e06	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2,5-Dihydroxyphenyl)pyridinium(1+) 10V, Positive-QTOF	splash10-000i-0900000000-3dd5a4be17fb2a2de83e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2,5-Dihydroxyphenyl)pyridinium(1+) 20V, Positive-QTOF	splash10-000i-0900000000-b1530805894ae58ea5fe	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2,5-Dihydroxyphenyl)pyridinium(1+) 40V, Positive-QTOF	splash10-0uei-9300000000-a73b71dc73cc4da960d4	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB020584

KNApSAcK ID

Not Available

Chemspider ID

364716

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

411955

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 N-(2,5-Dihydroxyphenyl)pyridinium(1+) (HMDB0040768)

MOL for HMDB0040768 (N-(2,5-Dihydroxyphenyl)pyridinium(1+))

3D MOL for HMDB0040768 (N-(2,5-Dihydroxyphenyl)pyridinium(1+))

3D SDF for HMDB0040768 (N-(2,5-Dihydroxyphenyl)pyridinium(1+))

3D-SDF for HMDB0040768 (N-(2,5-Dihydroxyphenyl)pyridinium(1+))

PDB for HMDB0040768 (N-(2,5-Dihydroxyphenyl)pyridinium(1+))

3D PDB for HMDB0040768 (N-(2,5-Dihydroxyphenyl)pyridinium(1+))

SMILES for HMDB0040768 (N-(2,5-Dihydroxyphenyl)pyridinium(1+))

INCHI for HMDB0040768 (N-(2,5-Dihydroxyphenyl)pyridinium(1+))

Structure for HMDB0040768 (N-(2,5-Dihydroxyphenyl)pyridinium(1+))

3D Structure for HMDB0040768 (N-(2,5-Dihydroxyphenyl)pyridinium(1+))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra