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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:28:42 UTC

Update Date

2021-09-26 22:55:33 UTC

HMDB ID

HMDB0246459

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Hydroxynicotinamide

Description

4-Hydroxynicotinamide belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group. Based on a literature review very few articles have been published on 4-Hydroxynicotinamide. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-hydroxynicotinamide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Hydroxynicotinamide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-oxo-1,4-Dihydropyridine-3-carboximidate	Generator

Chemical Formula

C₆H₆N₂O₂

Average Molecular Weight

138.126

Monoisotopic Molecular Weight

138.042927441

IUPAC Name

4-hydroxypyridine-3-carboxamide

Traditional Name

4-hydroxypyridine-3-carboxamide

CAS Registry Number

Not Available

SMILES

NC(=O)C1=CN=CC=C1O

InChI Identifier

InChI=1S/C6H6N2O2/c7-6(10)4-3-8-2-1-5(4)9/h1-3H,(H2,7,10)(H,8,9)

InChI Key

UDTVJEZIOILIRG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridinecarboxylic acids and derivatives

Direct Parent

Nicotinamides

Alternative Parents

Substituents

Nicotinamide
Dihydropyridine
Hydropyridine
Vinylogous amide
Heteroaromatic compound
Cyclic ketone
Primary carboxylic acid amide
Carboxamide group
Azacycle
Carboxylic acid derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

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
logP	0.01	ALOGPS
logP	-0.047	ChemAxon
logS	-0.52	ALOGPS
pKa (Strongest Acidic)	8.84	ChemAxon
pKa (Strongest Basic)	2.32	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	76.21 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	34.96 m³·mol⁻¹	ChemAxon
Polarizability	12.54 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
DeepCCS	[M+H]+	130.569	30932474
DeepCCS	[M-H]-	128.122	30932474
DeepCCS	[M-2H]-	164.148	30932474
DeepCCS	[M+Na]+	139.115	30932474
AllCCS	[M+H]+	132.7	32859911
AllCCS	[M+H-H2O]+	128.2	32859911
AllCCS	[M+NH4]+	136.8	32859911
AllCCS	[M+Na]+	138.0	32859911
AllCCS	[M-H]-	124.2	32859911
AllCCS	[M+Na-2H]-	126.1	32859911
AllCCS	[M+HCOO]-	128.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxynicotinamide	NC(=O)C1=CN=CC=C1O	2203.4	Standard polar	33892256
4-Hydroxynicotinamide	NC(=O)C1=CN=CC=C1O	1546.1	Standard non polar	33892256
4-Hydroxynicotinamide	NC(=O)C1=CN=CC=C1O	1488.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxynicotinamide,2TMS,isomer #1	C[Si](C)(C)NC(=O)C1=CN=CC=C1O[Si](C)(C)C	1689.9	Semi standard non polar	33892256
4-Hydroxynicotinamide,2TMS,isomer #1	C[Si](C)(C)NC(=O)C1=CN=CC=C1O[Si](C)(C)C	1703.7	Standard non polar	33892256
4-Hydroxynicotinamide,2TMS,isomer #1	C[Si](C)(C)NC(=O)C1=CN=CC=C1O[Si](C)(C)C	1874.6	Standard polar	33892256
4-Hydroxynicotinamide,2TMS,isomer #2	C[Si](C)(C)N(C(=O)C1=CN=CC=C1O)[Si](C)(C)C	1588.0	Semi standard non polar	33892256
4-Hydroxynicotinamide,2TMS,isomer #2	C[Si](C)(C)N(C(=O)C1=CN=CC=C1O)[Si](C)(C)C	1706.5	Standard non polar	33892256
4-Hydroxynicotinamide,2TMS,isomer #2	C[Si](C)(C)N(C(=O)C1=CN=CC=C1O)[Si](C)(C)C	2065.2	Standard polar	33892256
4-Hydroxynicotinamide,3TMS,isomer #1	C[Si](C)(C)OC1=CC=NC=C1C(=O)N([Si](C)(C)C)[Si](C)(C)C	1713.6	Semi standard non polar	33892256
4-Hydroxynicotinamide,3TMS,isomer #1	C[Si](C)(C)OC1=CC=NC=C1C(=O)N([Si](C)(C)C)[Si](C)(C)C	1741.1	Standard non polar	33892256
4-Hydroxynicotinamide,3TMS,isomer #1	C[Si](C)(C)OC1=CC=NC=C1C(=O)N([Si](C)(C)C)[Si](C)(C)C	1834.2	Standard polar	33892256
4-Hydroxynicotinamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C1=CN=CC=C1O[Si](C)(C)C(C)(C)C	2145.3	Semi standard non polar	33892256
4-Hydroxynicotinamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C1=CN=CC=C1O[Si](C)(C)C(C)(C)C	2109.7	Standard non polar	33892256
4-Hydroxynicotinamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C1=CN=CC=C1O[Si](C)(C)C(C)(C)C	2159.6	Standard polar	33892256
4-Hydroxynicotinamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)C1=CN=CC=C1O)[Si](C)(C)C(C)(C)C	2095.7	Semi standard non polar	33892256
4-Hydroxynicotinamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)C1=CN=CC=C1O)[Si](C)(C)C(C)(C)C	2077.3	Standard non polar	33892256
4-Hydroxynicotinamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)C1=CN=CC=C1O)[Si](C)(C)C(C)(C)C	2203.7	Standard polar	33892256
4-Hydroxynicotinamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=NC=C1C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2372.3	Semi standard non polar	33892256
4-Hydroxynicotinamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=NC=C1C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2340.8	Standard non polar	33892256
4-Hydroxynicotinamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=NC=C1C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2213.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxynicotinamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-8900000000-4432f614c2387ead7f4d	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxynicotinamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxynicotinamide GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxynicotinamide GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxynicotinamide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxynicotinamide GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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-Hydroxynicotinamide 10V, Positive-QTOF	splash10-00di-0900000000-4f2d4df358e7b35defd9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxynicotinamide 20V, Positive-QTOF	splash10-00dl-8900000000-fc5b3466dd5d8d1804ed	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxynicotinamide 40V, Positive-QTOF	splash10-0udl-9000000000-22ac695b8e5d02621a9a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxynicotinamide 10V, Negative-QTOF	splash10-000i-3900000000-82f19cb2bc5dd0ff88e0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxynicotinamide 20V, Negative-QTOF	splash10-0006-9000000000-70602d62de50e26979d8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxynicotinamide 40V, Negative-QTOF	splash10-0006-9000000000-f2cb6e9a2b31c660f3e9	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

11633191

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12043122

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 4-Hydroxynicotinamide (HMDB0246459)

MOL for HMDB0246459 (4-Hydroxynicotinamide)

3D MOL for HMDB0246459 (4-Hydroxynicotinamide)

3D SDF for HMDB0246459 (4-Hydroxynicotinamide)

3D-SDF for HMDB0246459 (4-Hydroxynicotinamide)

PDB for HMDB0246459 (4-Hydroxynicotinamide)

3D PDB for HMDB0246459 (4-Hydroxynicotinamide)

SMILES for HMDB0246459 (4-Hydroxynicotinamide)

INCHI for HMDB0246459 (4-Hydroxynicotinamide)

Structure for HMDB0246459 (4-Hydroxynicotinamide)

3D Structure for HMDB0246459 (4-Hydroxynicotinamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra