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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 16:13:54 UTC

Update Date

2023-02-21 17:16:59 UTC

HMDB ID

HMDB0004290

Secondary Accession Numbers

HMDB04290

Metabolite Identification

Common Name

Isopyridoxal

Description

Isopyridoxal belongs to the class of organic compounds known as pyridine carboxaldehydes. These are aromatic compounds containing a pyridine ring which bears a carboxaldehyde group. Isopyridoxal 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 isopyridoxal a potential biomarker for the consumption of these foods. Isopyridoxal 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 Isopyridoxal.

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      43.305 -26.100   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      45.710 -24.718   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      40.269 -20.740   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      44.892 -20.745   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      42.584 -24.747   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      47.201 -22.066   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      41.041 -22.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      45.662 -22.074   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      44.896 -23.410   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      43.357 -23.420   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      42.582 -22.084   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      43.351 -20.745   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2    9                                                            
CONECT    3    7                                                            
CONECT    4    8   12                                                       
CONECT    5    1   10                                                       
CONECT    6    8                                                            
CONECT    7    3   11                                                       
CONECT    8    4    6    9                                                  
CONECT    9    2    8   10                                                  
CONECT   10    5    9   11                                                  
CONECT   11    7   10   12                                                  
CONECT   12    4   11                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5-Hydroxy-4-(hydroxymethyl)-6-methyl-3-pyridinecarboxaldehyde	HMDB
5-Hydroxy-4-(hydroxymethyl)-6-methyl-nicotinaldehyde	HMDB
5-Hydroxy-4-(hydroxymethyl)-6-methylpyridine-3-carbaldehyde	HMDB

Chemical Formula

C₈H₉NO₃

Average Molecular Weight

167.162

Monoisotopic Molecular Weight

167.058243159

IUPAC Name

5-hydroxy-4-(hydroxymethyl)-6-methylpyridine-3-carbaldehyde

Traditional Name

isopyridoxal

CAS Registry Number

Not Available

SMILES

CC1=NC=C(C=O)C(CO)=C1O

InChI Identifier

InChI=1S/C8H9NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2-3,11-12H,4H2,1H3

InChI Key

GNKXHPULSPWUAK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridine carboxaldehydes. These are aromatic compounds containing a pyridine ring which bears a carboxaldehyde group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridine carboxaldehydes

Direct Parent

Pyridine carboxaldehydes

Alternative Parents

Substituents

3-pyridine carboxaldehyde
Aryl-aldehyde
Hydroxypyridine
Methylpyridine
Heteroaromatic compound
Azacycle
Hydrocarbon derivative
Organopnictogen compound
Alcohol
Organic oxygen compound
Aromatic alcohol
Organic nitrogen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Aldehyde
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monohydroxypyridine (CHEBI:17889 )
pyridinecarbaldehyde (CHEBI:17889 )
methylpyridines (CHEBI:17889 )
hydroxymethylpyridine (CHEBI:17889 )
a small molecule (CPD-383 )

Ontology

Not Available

Endogenous (HMDB: HMDB0004290)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

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	11.7 g/L	ALOGPS
logP	0.04	ALOGPS
logP	-0.47	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	9.02	ChemAxon
pKa (Strongest Basic)	4.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70.42 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	43.87 m³·mol⁻¹	ChemAxon
Polarizability	16.29 Å³	ChemAxon
Number of Rings	1	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]+	137.455	31661259
DarkChem	[M-H]-	134.022	31661259
DeepCCS	[M+H]+	139.499	30932474
DeepCCS	[M-H]-	136.919	30932474
DeepCCS	[M-2H]-	173.246	30932474
DeepCCS	[M+Na]+	148.554	30932474
AllCCS	[M+H]+	135.6	32859911
AllCCS	[M+H-H2O]+	131.2	32859911
AllCCS	[M+NH4]+	139.7	32859911
AllCCS	[M+Na]+	140.9	32859911
AllCCS	[M-H]-	133.1	32859911
AllCCS	[M+Na-2H]-	134.2	32859911
AllCCS	[M+HCOO]-	135.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.19 minutes	32390414
Predicted by Siyang on May 30, 2022	10.1011 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.22 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	58.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	614.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	310.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	79.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	175.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	55.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	285.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	453.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	395.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	675.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	57.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1038.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	219.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	315.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	590.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	365.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	376.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isopyridoxal	CC1=NC=C(C=O)C(CO)=C1O	2461.3	Standard polar	33892256
Isopyridoxal	CC1=NC=C(C=O)C(CO)=C1O	1597.3	Standard non polar	33892256
Isopyridoxal	CC1=NC=C(C=O)C(CO)=C1O	1687.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isopyridoxal,1TMS,isomer #1	CC1=NC=C(C=O)C(CO[Si](C)(C)C)=C1O	1743.3	Semi standard non polar	33892256
Isopyridoxal,1TMS,isomer #2	CC1=NC=C(C=O)C(CO)=C1O[Si](C)(C)C	1669.1	Semi standard non polar	33892256
Isopyridoxal,2TMS,isomer #1	CC1=NC=C(C=O)C(CO[Si](C)(C)C)=C1O[Si](C)(C)C	1797.5	Semi standard non polar	33892256
Isopyridoxal,1TBDMS,isomer #1	CC1=NC=C(C=O)C(CO[Si](C)(C)C(C)(C)C)=C1O	1980.4	Semi standard non polar	33892256
Isopyridoxal,1TBDMS,isomer #2	CC1=NC=C(C=O)C(CO)=C1O[Si](C)(C)C(C)(C)C	1937.5	Semi standard non polar	33892256
Isopyridoxal,2TBDMS,isomer #1	CC1=NC=C(C=O)C(CO[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	2244.8	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 - Isopyridoxal GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-1900000000-8a715833345d7b46b4e3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isopyridoxal GC-MS (2 TMS) - 70eV, Positive	splash10-00dj-6090000000-7c46aedf5b7518576b99	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isopyridoxal 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 - Isopyridoxal 10V, Positive-QTOF	splash10-0uxr-0900000000-8eed1e5e7dc5e8fbf4a2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopyridoxal 20V, Positive-QTOF	splash10-0udi-0900000000-0390e8fed2f93645c83a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopyridoxal 40V, Positive-QTOF	splash10-0fl3-9800000000-4ecec87f541a28020871	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopyridoxal 10V, Negative-QTOF	splash10-014i-0900000000-caeb2f57363d9b1653b0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopyridoxal 20V, Negative-QTOF	splash10-00kr-0900000000-95e90753a988082acd18	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopyridoxal 40V, Negative-QTOF	splash10-0a4i-9400000000-14698a7cadeade319518	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopyridoxal 10V, Negative-QTOF	splash10-00ks-0900000000-50026cd652cddee1b922	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopyridoxal 20V, Negative-QTOF	splash10-0abi-0900000000-eb81ea98de38aba535af	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopyridoxal 40V, Negative-QTOF	splash10-052g-9300000000-ce38bfd6d13e448bb963	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopyridoxal 10V, Positive-QTOF	splash10-0gb9-0900000000-fbae461839a1b7a22a77	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopyridoxal 20V, Positive-QTOF	splash10-0udi-0900000000-de018b2c6fdc4432edd6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopyridoxal 40V, Positive-QTOF	splash10-0089-7900000000-86b8875d760bf1ddbab4	2021-09-22	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

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

7046

PubChem Compound

440899

PDB ID

Not Available

ChEBI ID

17889

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

Garrido-Franco M: Pyridoxine 5'-phosphate synthase: de novo synthesis of vitamin B6 and beyond. Biochim Biophys Acta. 2003 Apr 11;1647(1-2):92-7. [PubMed:12686115 ]
Edwards P, Liu PK, Rose GA: Liquid chromatographic studies of vitamin B6 metabolism in man. Clin Chim Acta. 1990 Sep;190(1-2):67-80. [PubMed:2208740 ]
Bergen C, Compher C: Total homocysteine concentration and associated cardiovascular and renal implications in adults. J Cardiovasc Nurs. 2006 Jan-Feb;21(1):40-6. [PubMed:16407736 ]

Showing metabocard for Isopyridoxal (HMDB0004290)

MOL for HMDB0004290 (Isopyridoxal)

3D MOL for HMDB0004290 (Isopyridoxal)

3D SDF for HMDB0004290 (Isopyridoxal)

3D-SDF for HMDB0004290 (Isopyridoxal)

PDB for HMDB0004290 (Isopyridoxal)

3D PDB for HMDB0004290 (Isopyridoxal)

SMILES for HMDB0004290 (Isopyridoxal)

INCHI for HMDB0004290 (Isopyridoxal)

Structure for HMDB0004290 (Isopyridoxal)

3D Structure for HMDB0004290 (Isopyridoxal)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra