Milk Composition Database: Showing metabocard for Pyridoxine (BMDB0000239)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:27:13 UTC

Update Date

2020-06-04 20:48:26 UTC

MCDB ID

BMDB0000239

Secondary Accession Numbers

BMDB00239

Metabolite Identification

Common Name

Pyridoxine

Description

Pyridoxine, also known as pyridoxol or vitamin B6, belongs to the class of organic compounds known as pyridoxines. These are pyridoxal derivatives in which the carbaldehyde group at position 2 of the pyridoxal moiety is replaced by a hydroxymethyl group. Pyridoxine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Pyridoxine exists in all living species, ranging from bacteria to humans. Pyridoxine participates in a number of enzymatic reactions, within cattle. In particular, Pyridoxine can be converted into pyridoxal; which is catalyzed by the enzyme pyridoxine-5'-phosphate oxidase. In addition, Pyridoxine can be converted into pyridoxine 5'-phosphate; which is catalyzed by the enzyme pyridoxal kinase. In cattle, pyridoxine is involved in the metabolic pathway called the vitamin B6 metabolism pathway. Pyridoxine is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Methyl-3-hydroxy-4,5-dihydroxymethylpyridine	ChEBI
3-Hydroxy-4,5-bis(hydroxymethyl)-2-methylpyridine	ChEBI
3-Hydroxy-4,5-dimethylol-alpha-picoline	ChEBI
5-Hydroxy-6-methyl-3,4-pyridinedimethanol	ChEBI
Pyridoxol	ChEBI
Vitamin b6	ChEBI
3-Hydroxy-4,5-dimethylol-a-picoline	Generator
3-Hydroxy-4,5-dimethylol-α-picoline	Generator
2-Methyl-3-hydroxy-4,5-bis(hydroxymethyl)pyridine	HMDB
2-Methyl-3-hydroxy-4,5-di(hydroxymethyl)pyridine	HMDB
2-Methyl-4,5-bis(hydroxymethyl)-3-hydroxypyridine	HMDB
3-Hydroxy-2-picoline-4,5-dimethanol	HMDB
Adermine	HMDB
Gravidox	HMDB
Hydoxin	HMDB
Piridossina	HMDB
Piridoxina	HMDB
Pyridoxin	HMDB
Pyridoxinum	HMDB
Pyridoxolum	HMDB
Pyridoxol hydrochloride	HMDB
Rodex	HMDB
Pyridoxine hydrochloride	HMDB

Chemical Formula

C₈H₁₁NO₃

Average Molecular Weight

169.1778

Monoisotopic Molecular Weight

169.073893223

IUPAC Name

4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol

Traditional Name

pyridoxine

CAS Registry Number

65-23-6

SMILES

CC1=C(O)C(CO)=C(CO)C=N1

InChI Identifier

InChI=1S/C8H11NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,10-12H,3-4H2,1H3

InChI Key

LXNHXLLTXMVWPM-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pyridoxines. These are pyridoxal derivatives in which the carbaldehyde group at position 2 of the pyridoxal moiety is replaced by a hydroxymethyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridoxines

Direct Parent

Pyridoxines

Alternative Parents

Substituents

Pyridoxine
Methylpyridine
Hydroxypyridine
Heteroaromatic compound
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Aromatic alcohol
Primary alcohol
Organooxygen compound
Organonitrogen compound
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monohydroxypyridine (CHEBI:16709 )
methylpyridines (CHEBI:16709 )
vitamin B6 (CHEBI:16709 )
hydroxymethylpyridine (CHEBI:16709 )
Water-soluble vitamins (C00314 )
a vitamin B6 (PYRIDOXINE )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	159 - 162 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	79 mg/mL	Not Available
LogP	-0.77	SANGSTER (1993)

Predicted Properties

Property	Value	Source
logP	-0.57	ALOGPS
logP	-0.95	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	5.58	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	73.58 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.11 m³·mol⁻¹	ChemAxon
Polarizability	17.11 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-000t-0940000000-30b4702623a6d8fcb4bb	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-001j-0690000000-0581e2b42fa48c1ea498	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00di-9330000000-32929ff06762b9f5887f	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-001i-0490000000-34a09ddbbb462aeb02a6	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0f6x-9400000000-486db54a30b61c2eb9d4	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000t-0940000000-30b4702623a6d8fcb4bb	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-001j-0690000000-0581e2b42fa48c1ea498	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9330000000-32929ff06762b9f5887f	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001i-0490000000-34a09ddbbb462aeb02a6	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-001j-0790000000-6f8f6e679e03f9119a65	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f79-0900000000-0f727b3e23c2481951e8	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00di-7079000000-2f143e187cb8c078f936	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0vi0-0900000000-bd0de86c072765a5caad	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-3900000000-2018b406a3c75213b733	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0059-9200000000-e69bb531deb2a103a476	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0f6x-9400000000-77c43a946c4ae1abf3b9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-014i-0900000000-479d4492cc8d634fa366	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0udi-0900000000-486d6a4e5e1a731b7c54	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-05fr-0900000000-4ef09ce9c04561a1085e	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0ab9-1900000000-3298adf6db36689d5d43	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a6r-7900000000-6711954ee96f08344434	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-00di-0900000000-234e90d43a7febd7a098	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0udi-0900000000-137080765c0035b45258	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-001i-0900000000-882ee900a8bba08e2c7c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-003r-8900000000-e0e11797b63cea991d81	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0059-9100000000-c25384179219411af02c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0ue9-0900000000-c0e149ce890192397b7f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0v4i-0900000000-f9f378af3d47ab006806	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-479d4492cc8d634fa366	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0900000000-486d6a4e5e1a731b7c54	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-05fr-0900000000-4ef09ce9c04561a1085e	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uk9-0900000000-eab5b3411261744df750	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ue9-0900000000-cc4dc8719602182ef1eb	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-5900000000-1c2637733578fcdd7c6a	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-e89cc69d8b21012ff982	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-059i-0900000000-0ad8d09e042015cb2e33	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9500000000-577a3d87899ca47d539f	2015-05-27	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-1003-6900000000-1237eaf82dfadfd54d4b	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Not Available	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	41 uM	PMID: 17558655	details
Detected and Quantified	2.364 uM	USDA Food Co...	details
Detected and Quantified	2.364 uM	USDA Food Co...	details
Detected and Quantified	2.187 uM	USDA Food Co...	details
Detected and Quantified	2.364 uM	USDA Food Co...	details
Detected and Quantified	2.01 uM	USDA Food Co...	details
Detected and Quantified	2.955 uM	USDA Food Co...	details
Detected and Quantified	2.66 uM	USDA Food Co...	details
Detected and Quantified	2.187 uM	USDA Food Co...	details
Detected and Quantified	2.955 uM	USDA Food Co...	details
Detected and Quantified	2.719 uM	USDA Food Co...	details
Detected and Quantified	2.187 uM	USDA Food Co...	details
Detected and Quantified	2.187 uM	USDA Food Co...	details
Detected and Quantified	2.896 uM	Fooddata+, T...	details
Detected and Quantified	2.955 uM	Fooddata+, T...	details
Detected and Quantified	2.483 uM	USDA Food Co...	details
Detected and Quantified	3.015 uM	USDA Food Co...	details
Detected and Quantified	2.66 uM	USDA Food Co...	details
Detected and Quantified	2.719 uM	USDA Food Co...	details
Detected and Quantified	2.246 uM	USDA Food Co...	details
Detected and Quantified	2.246 uM	USDA Food Co...	details
Detected and Quantified	2.955 uM	Fooddata+, T...	details
Detected and Quantified	2.896 uM	Fooddata+, T...	details
Detected and Quantified	2.955 uM	Fooddata+, T...	details
Detected and Quantified	2.128 uM	USDA Food Co...	details
Detected and Quantified	2.128 uM	USDA Food Co...	details
Detected and Quantified	2.778 uM	Fooddata+, T...	details
Detected and Quantified	2.719 uM	Fooddata+, T...	details
Detected and Quantified	2.955 uM	Fooddata+, T...	details
Detected and Quantified	2.483 uM	Park, Y. W; Juáre...	details
Detected and Quantified	1.8 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	1.8 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	1.8 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	2.0 +/- 0.1 uM	PMID: 30994344	details

External Links

HMDB ID

HMDB0000239

DrugBank ID

DB00165

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Pyridoxine

METLIN ID

Not Available

PubChem Compound

1054

PDB ID

Not Available

ChEBI ID

16709

References

Synthesis Reference

Itov, Z. I.; Stepanova, S. V.; El'yanov, B. S.; Gunar, V. I. Synthesis of pyridoxine under high pressure. Khimiko-Farmatsevticheskii Zhurnal (1987), 21(7), 858-62.

Material Safety Data Sheet (MSDS)

Not Available

General References

Agostini TS, Scherer R, Godoy HT: Simultaneous determination of B-group vitamins in enriched Brazilian dairy products. Crit Rev Food Sci Nutr. 2007;47(5):435-9. doi: 10.1080/10408390600846309. [PubMed:17558655 ]
Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W. (2007). Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113 doi: 10.1016/j.smallrumres.2006.09.013. Small Ruminant Research.
A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
USDA Food Composition Databases [Link]
Fooddata+, The Technical University of Denmark (DTU) [Link]

Showing metabocard for Pyridoxine (BMDB0000239)

Structure for BMDB0000239 (Pyridoxine)