4-Pyridoxolactone (YMDB00787)

Identification

YMDB ID

YMDB00787

Name

4-Pyridoxolactone

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

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. Based on a literature review a significant number of articles have been published on 4-Pyridoxolactone.

Structure

MOL SDF PDB SMILES InChI

Synonyms

.beta.-Pyracin
4-pyridoxic acid lactone
4-Pyridoxolactone
beta-Pyracin
Furo[3,4-c]pyridin-1(3H)-one, 7-hydroxy-6-methyl-
4-Pyridoxate lactone

CAS number

4753-19-9

Weight

Average: 165.1461
Monoisotopic: 165.042593095

InChI Key

HHPDVQLBYQFYFA-UHFFFAOYSA-N

InChI

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

IUPAC Name

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

Traditional IUPAC Name

4-pyridoxolactone

Chemical Formula

C₈H₇NO₃

SMILES

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

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 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	18.6 g/L	ALOGPS
logP	0.44	ALOGPS
logP	0.79	ChemAxon
logS	-0.95	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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Vitamin B6 metabolism

ec00750

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ri-2900000000-5f6a91d1eeb5eaa49adc	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-5950000000-11ff12c2dd36530c4236	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-aa1266c816944909b39a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-d0258c632349f5e836e0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dj-7900000000-30cd1dadf39f33995b09	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-3fd21d96beb6c70780d6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-2b177a3586d7e6d68836	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00e9-9800000000-3abeb7516d954dda95b1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-65490e650f013cfe115e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03k9-0900000000-7ece33897451c1af0c35	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4v-7900000000-3ee7b8f8ce87fd24b311	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-52879b1c24e4e827f43a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-1dc0c584a9bf4ad25064	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0072-5900000000-8631bb6ae260af7ebb9b	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer

References

References:

Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Nishimura, S., Nagano, S., A Crai, C., Yokochi, N., Yoshikane, Y., Ge, F., Yagi, T. (2008). "Determination of individual vitamin B(6) compounds based on enzymatic conversion to 4-pyridoxolactone." J Nutr Sci Vitaminol (Tokyo) 54:18-24.18388403

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.

External Links:

Resource	Link
CHEBI ID	16871
HMDB ID	HMDB03454
Pubchem Compound ID	151228
Kegg ID	C00971
ChemSpider ID	133287
FOODB ID	FDB023177
Wikipedia ID	Not Available
BioCyc ID	CPD-375

Structure for #<Compound:0xad3da5d8>