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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-12 21:21:04 UTC

Update Date

2020-02-26 21:24:38 UTC

HMDB ID

HMDB0003454

Secondary Accession Numbers

HMDB03454

Metabolite Identification

Common Name

4-Pyridoxolactone

Description

4-Pyridoxolactone belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group. 4-Pyridoxolactone exists in all eukaryotes, ranging from yeast to plants to humans. 4-Pyridoxolactone has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 4-pyridoxolactone a potential biomarker for the consumption of these foods. 4-Pyridoxolactone 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 4-Pyridoxolactone.

Structure

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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      22.372 -28.819   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      26.062 -31.900   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      25.642 -29.196   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      21.038 -32.670   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      19.704 -30.359   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.163 -33.139   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.163 -30.660   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.038 -31.129   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.372 -30.359   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.706 -32.670   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.706 -31.129   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.372 -33.440   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2    6    7                                                       
CONECT    3    7                                                            
CONECT    4    8   12                                                       
CONECT    5    8                                                            
CONECT    6    2   10                                                       
CONECT    7    2    3   11                                                  
CONECT    8    4    5    9                                                  
CONECT    9    1    8   11                                                  
CONECT   10    6   11   12                                                  
CONECT   11    7    9   10                                                  
CONECT   12    4   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Pyridoxic acid lactone	ChEBI
4-Pyridoxate lactone	Generator
beta-Pyracin	HMDB

Chemical Formula

C₈H₇NO₃

Average Molecular Weight

165.1461

Monoisotopic Molecular Weight

165.042593095

IUPAC Name

7-hydroxy-6-methyl-1H,3H-furo[3,4-c]pyridin-1-one

Traditional Name

4-pyridoxolactone

CAS Registry Number

4753-19-9

SMILES

CC1=NC=C2COC(=O)C2=C1O

InChI Identifier

InChI=1S/C8H7NO3/c1-4-7(10)6-5(2-9-4)3-12-8(6)11/h2,10H,3H2,1H3

InChI Key

HHPDVQLBYQFYFA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridinecarboxylic acids and derivatives

Direct Parent

Pyridinecarboxylic acids

Alternative Parents

Substituents

Pyridine carboxylic acid
Methylpyridine
Hydroxypyridine
Vinylogous acid
Heteroaromatic compound
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Azacycle
Oxacycle
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

lactone (CHEBI:16871 )
furopyridine (CHEBI:16871 )
a small molecule (CPD-375 )

Ontology

Disposition

Biological location

Cellular substructure

Cytoplasm

Ingestion

Physical Properties

State

Solid

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	18.6 g/L	ALOGPS
logP	10^(0.44) g/L	ALOGPS
logP	10^(0.79) g/L	ChemAxon
logS	10^(-0.95) g/L	ALOGPS
pKa (Strongest Acidic)	9.3	ChemAxon
pKa (Strongest Basic)	4.27	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.42 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	41.05 m³·mol⁻¹	ChemAxon
Polarizability	15.42 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]+	136.685	31661259
DarkChem	[M-H]-	132.125	31661259
DeepCCS	[M+H]+	136.132	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Pyridoxolactone	CC1=NC=C2COC(=O)C2=C1O	2538.4	Standard polar	33892256
4-Pyridoxolactone	CC1=NC=C2COC(=O)C2=C1O	1564.1	Standard non polar	33892256
4-Pyridoxolactone	CC1=NC=C2COC(=O)C2=C1O	1476.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Pyridoxolactone,1TMS,isomer #1	CC1=NC=C2COC(=O)C2=C1O[Si](C)(C)C	1723.2	Semi standard non polar	33892256
4-Pyridoxolactone,1TBDMS,isomer #1	CC1=NC=C2COC(=O)C2=C1O[Si](C)(C)C(C)(C)C	2005.4	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 - 4-Pyridoxolactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ri-2900000000-5f6a91d1eeb5eaa49adc	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Pyridoxolactone GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-5950000000-11ff12c2dd36530c4236	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Pyridoxolactone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Pyridoxolactone 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 - 4-Pyridoxolactone 10V, Positive-QTOF	splash10-014i-0900000000-aa1266c816944909b39a	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Pyridoxolactone 20V, Positive-QTOF	splash10-014i-0900000000-d0258c632349f5e836e0	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Pyridoxolactone 40V, Positive-QTOF	splash10-00dj-7900000000-30cd1dadf39f33995b09	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Pyridoxolactone 10V, Negative-QTOF	splash10-03di-0900000000-3fd21d96beb6c70780d6	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Pyridoxolactone 20V, Negative-QTOF	splash10-03di-0900000000-2b177a3586d7e6d68836	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Pyridoxolactone 40V, Negative-QTOF	splash10-00e9-9800000000-3abeb7516d954dda95b1	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Pyridoxolactone 10V, Negative-QTOF	splash10-03di-0900000000-65490e650f013cfe115e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Pyridoxolactone 20V, Negative-QTOF	splash10-03k9-0900000000-7ece33897451c1af0c35	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Pyridoxolactone 40V, Negative-QTOF	splash10-0a4v-7900000000-3ee7b8f8ce87fd24b311	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Pyridoxolactone 10V, Positive-QTOF	splash10-014i-0900000000-52879b1c24e4e827f43a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Pyridoxolactone 20V, Positive-QTOF	splash10-014i-0900000000-1dc0c584a9bf4ad25064	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Pyridoxolactone 40V, Positive-QTOF	splash10-0072-5900000000-8631bb6ae260af7ebb9b	2021-09-24	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 (predicted from logP)

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

FDB023177

KNApSAcK ID

Not Available

Chemspider ID

133287

KEGG Compound ID

C00971

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6936

PubChem Compound

151228

PDB ID

Not Available

ChEBI ID

16871

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Korte, Friedhelm; Bannuscher, Herbert. Heterocyclics in metabolism. V. The production of 4-pyridoxic acid and its lactone from pyridoxal-5-phosphate by liver homogenates. Biochemische Zeitschrift (1958), 329 451-7.

Material Safety Data Sheet (MSDS)

Not Available

General References

Ubbink JB, Serfontein WJ, Becker PJ, De Villiers LS: Determination of urinary 4-pyridoxic acid levels as 4-pyridoxic acid lactone using high-performance liquid chromatography. Am J Clin Nutr. 1986 Nov;44(5):698-703. [PubMed:3766456 ]

Showing metabocard for 4-Pyridoxolactone (HMDB0003454)

MOL for HMDB0003454 (4-Pyridoxolactone)

3D MOL for HMDB0003454 (4-Pyridoxolactone)

3D SDF for HMDB0003454 (4-Pyridoxolactone)

3D-SDF for HMDB0003454 (4-Pyridoxolactone)

PDB for HMDB0003454 (4-Pyridoxolactone)

3D PDB for HMDB0003454 (4-Pyridoxolactone)

SMILES for HMDB0003454 (4-Pyridoxolactone)

INCHI for HMDB0003454 (4-Pyridoxolactone)

Structure for HMDB0003454 (4-Pyridoxolactone)

3D Structure for HMDB0003454 (4-Pyridoxolactone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra