Compounds > 5-hydroxynicotinic acid
Page last updated: 2024-12-06

5-hydroxynicotinic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

5-hydroxynicotinic acid (5-HNA) is a pyridine derivative and a naturally occurring compound found in various plants, such as corn and rice. It is a key intermediate in the biosynthesis of nicotinic acid (niacin), an essential vitamin. 5-HNA has garnered attention for its potential biological activities. Studies have indicated that it possesses antioxidant properties, which may contribute to its protective effects against oxidative stress. Furthermore, 5-HNA has been shown to exhibit anti-inflammatory and anti-proliferative activities. Research has explored its potential therapeutic applications in conditions like cancer, diabetes, and neurodegenerative diseases. The compound's ability to modulate cellular signaling pathways and its interactions with specific receptors are areas of ongoing investigation. 5-HNA is also being studied as a potential precursor for the synthesis of various pharmaceuticals and agrochemicals. Its relatively simple structure and availability make it an attractive starting point for developing new bioactive compounds.'

Cross-References

ID SourceID
PubMed CID34037
CHEMBL ID2146902
CHEBI ID169995
SCHEMBL ID186161
MeSH IDM0277897

Synonyms (52)

Synonym
HMS1671H22
AC-2839
27828-71-3
CHEBI:169995
nsc-606891
nsc606891
OPREA1_193943
5-hydroxynicotinic acid
AE-848/00984004
brn 0115847
5-hydroxy-3-pyridinecarboxylic acid
nicotinic acid, 5-hydroxy-
3-pyridinecarboxylic acid, 5-hydroxy-
5-hydroxy-nicotinic acid
OPREA1_058796
H1226
AKOS000272822
STK801985
5-hydroxypyridine-3-carboxylic acid
A5346
AKOS005463460
5-hydroxypyridinium-3-carboxylate
STK531022
5-hydroxynicotinicacid
EN300-73559
BBL010930
5-22-05-00113 (beilstein handbook reference)
chembl2146902 ,
bdbm50391823
FT-0621168
FT-0602367
AM20051033
5-hydroxy nicotinic acid
PB33816
BP-21442
5hn ,
AB01334129-02
SCHEMBL186161
mfcd00129117
SY003082
PS-5446
ATTDCVLRGFEHEO-UHFFFAOYSA-N
J-400705
DTXSID50182143
CS-W009148
5-hydroxynicotinic acid, 97%
Z57124104
3-hydroxypyridine-5-carboxylic acid
BCP27371
3-hydroxy-5-pyridinecarboxylic acid
Q27455772
NCGC00342404-01
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
aromatic carboxylic acidAny carboxylic acid in which the carboxy group is directly bonded to an aromatic ring.
pyridinesAny organonitrogen heterocyclic compound based on a pyridine skeleton and its substituted derivatives.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
D-amino-acid oxidaseHomo sapiens (human)IC50 (µMol)10,000.00000.00401.119910.0000AID1247844
D-aspartate oxidaseHomo sapiens (human)IC50 (µMol)3,351.00000.00400.39370.8550AID1247843
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Hydroxycarboxylic acid receptor 2Homo sapiens (human)EC50 (µMol)368.00000.00871.20176.3096AID689540
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (19)

Processvia Protein(s)Taxonomy
proline catabolic processD-amino-acid oxidaseHomo sapiens (human)
digestionD-amino-acid oxidaseHomo sapiens (human)
D-amino acid catabolic processD-amino-acid oxidaseHomo sapiens (human)
D-serine catabolic processD-amino-acid oxidaseHomo sapiens (human)
dopamine biosynthetic processD-amino-acid oxidaseHomo sapiens (human)
D-alanine catabolic processD-amino-acid oxidaseHomo sapiens (human)
D-serine metabolic processD-amino-acid oxidaseHomo sapiens (human)
neutrophil-mediated killing of gram-negative bacteriumD-amino-acid oxidaseHomo sapiens (human)
neutrophil apoptotic processHydroxycarboxylic acid receptor 2Homo sapiens (human)
positive regulation of neutrophil apoptotic processHydroxycarboxylic acid receptor 2Homo sapiens (human)
negative regulation of lipid catabolic processHydroxycarboxylic acid receptor 2Homo sapiens (human)
positive regulation of adiponectin secretionHydroxycarboxylic acid receptor 2Homo sapiens (human)
G protein-coupled receptor signaling pathwayHydroxycarboxylic acid receptor 2Homo sapiens (human)
inseminationD-aspartate oxidaseHomo sapiens (human)
grooming behaviorD-aspartate oxidaseHomo sapiens (human)
regulation of cell communicationD-aspartate oxidaseHomo sapiens (human)
D-amino acid catabolic processD-aspartate oxidaseHomo sapiens (human)
hormone metabolic processD-aspartate oxidaseHomo sapiens (human)
nervous system processD-aspartate oxidaseHomo sapiens (human)
aspartate catabolic processD-aspartate oxidaseHomo sapiens (human)
negative regulation of lipid catabolic processHydroxycarboxylic acid receptor 1Homo sapiens (human)
G protein-coupled receptor signaling pathwayHydroxycarboxylic acid receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
D-amino-acid oxidase activityD-amino-acid oxidaseHomo sapiens (human)
protein bindingD-amino-acid oxidaseHomo sapiens (human)
identical protein bindingD-amino-acid oxidaseHomo sapiens (human)
FAD bindingD-amino-acid oxidaseHomo sapiens (human)
nicotinic acid receptor activityHydroxycarboxylic acid receptor 2Homo sapiens (human)
protein bindingD-aspartate oxidaseHomo sapiens (human)
D-aspartate oxidase activityD-aspartate oxidaseHomo sapiens (human)
D-glutamate oxidase activityD-aspartate oxidaseHomo sapiens (human)
FAD bindingD-aspartate oxidaseHomo sapiens (human)
G protein-coupled receptor activityHydroxycarboxylic acid receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (10)

Processvia Protein(s)Taxonomy
mitochondrial outer membraneD-amino-acid oxidaseHomo sapiens (human)
extracellular regionD-amino-acid oxidaseHomo sapiens (human)
cytoplasmD-amino-acid oxidaseHomo sapiens (human)
peroxisomal matrixD-amino-acid oxidaseHomo sapiens (human)
cytosolD-amino-acid oxidaseHomo sapiens (human)
cell projectionD-amino-acid oxidaseHomo sapiens (human)
presynaptic active zoneD-amino-acid oxidaseHomo sapiens (human)
cytoplasmD-amino-acid oxidaseHomo sapiens (human)
plasma membraneHydroxycarboxylic acid receptor 2Homo sapiens (human)
cell junctionHydroxycarboxylic acid receptor 2Homo sapiens (human)
plasma membraneHydroxycarboxylic acid receptor 2Homo sapiens (human)
peroxisomeD-aspartate oxidaseHomo sapiens (human)
peroxisomeD-aspartate oxidaseHomo sapiens (human)
peroxisomal matrixD-aspartate oxidaseHomo sapiens (human)
cytosolD-aspartate oxidaseHomo sapiens (human)
cytoplasmD-aspartate oxidaseHomo sapiens (human)
plasma membraneHydroxycarboxylic acid receptor 1Homo sapiens (human)
plasma membraneHydroxycarboxylic acid receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID689539Agonist activity at human recombinant GPR81 transfected in african green monkey COS-7 cells after 20 mins by [35S]GTPgammaS binding assay2012ACS medicinal chemistry letters, Aug-09, Volume: 3, Issue:8
Identification of Hydroxybenzoic Acids as Selective Lactate Receptor (GPR81) Agonists with Antilipolytic Effects.
AID689540Agonist activity at human recombinant GPR109a transfected in african green monkey COS-7 cells after 20 mins by [35S]GTPgammaS binding assay2012ACS medicinal chemistry letters, Aug-09, Volume: 3, Issue:8
Identification of Hydroxybenzoic Acids as Selective Lactate Receptor (GPR81) Agonists with Antilipolytic Effects.
AID1247843Inhibition of human recombinant DDO expressed in Escherichia coli BL21(DE3) using D-Asp and D-Ala assessed as 2-oxo acid production after 10 mins by colorimetric assay2015Journal of medicinal chemistry, Sep-24, Volume: 58, Issue:18
Identification of Novel D-Aspartate Oxidase Inhibitors by in Silico Screening and Their Functional and Structural Characterization in Vitro.
AID1247844Inhibition of human recombinant DAO expressed in Escherichia coli BL21(DE3) using D-Asp and D-Ala assessed as 2-oxo acid production after 10 mins by colorimetric assay2015Journal of medicinal chemistry, Sep-24, Volume: 58, Issue:18
Identification of Novel D-Aspartate Oxidase Inhibitors by in Silico Screening and Their Functional and Structural Characterization in Vitro.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (14.29)18.2507
2000's0 (0.00)29.6817
2010's6 (85.71)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 20.76

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index20.76 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index5.21 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.76)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
benzoic acid
Benzoic Acid: A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid.. benzoic acid : A compound comprising a benzene ring core carrying a carboxylic acid substituent.. aromatic carboxylic acid : Any carboxylic acid in which the carboxy group is directly bonded to an aromatic ring.		2.1110benzoic acidsalgal metabolite;
antimicrobial food preservative;
drug allergen;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
EC 3.1.1.3 (triacylglycerol lipase) inhibitor;
human xenobiotic metabolite;
plant metabolite
malonic acid
malonic acid : An alpha,omega-dicarboxylic acid in which the two carboxy groups are separated by a single methylene group.. dicarboxylic acid : Any carboxylic acid containing two carboxy groups.		2.1110alpha,omega-dicarboxylic acidhuman metabolite
niacin
Niacin: A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has PELLAGRA-curative, vasodilating, and antilipemic properties.. vitamin B3 : Any member of a group of vitamers that belong to the chemical structural class called pyridines that exhibit biological activity against vitamin B3 deficiency. Vitamin B3 deficiency causes a condition known as pellagra whose symptoms include depression, dermatitis and diarrhea. The vitamers include nicotinic acid and nicotinamide (and their ionized and salt forms).. nicotinic acid : A pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group.		2.4920pyridine alkaloid;
pyridinemonocarboxylic acid;
vitamin B3		antidote;
antilipemic drug;
EC 3.5.1.19 (nicotinamidase) inhibitor;
Escherichia coli metabolite;
human urinary metabolite;
metabolite;
mouse metabolite;
plant metabolite;
vasodilator agent
tyrosine
Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.		2.5320amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
proteinogenic amino acid;
tyrosine		EC 1.3.1.43 (arogenate dehydrogenase) inhibitor;
fundamental metabolite;
micronutrient;
nutraceutical
3-aminobenzoic acid
3-aminobenzoic acid: RN given refers to parent cpd. 3-aminobenzoic acid : An aminobenzoic acid carrying an amino group at position 3.		2.1110aminobenzoic acid
3-hydroxybenzoic acid
3-hydroxybenzoic acid: RN given refers to parent cpd. 3-hydroxybenzoic acid : A monohydroxybenzoic acid that is benzoic acid substituted by a hydroxy group at position 3. It has been isolated from Taxus baccata. It is used as an intermediate in the synthesis of plasticisers, resins, pharmaceuticals, etc.		2.0710monohydroxybenzoic acidbacterial metabolite;
plant metabolite
alpha-resorcylic acid
alpha-resorcylic acid: RN given refers to parent cpd. 3,5-dihydroxybenzoic acid : A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 5.		2.0710dihydroxybenzoic acid;
resorcinols		metabolite
5-chlorosalicylic acid
5-chlorosalicylic acid: major metabolite of meseclazone; RN given refers to parent cpd. 5-chlorosalicylic acid : A monohydroxybenzoic acid that is 2-hydroxybenzoic acid (salicylic acid) in which the hydrogen at position 5 is replaced by chlorine.		2.1110chlorobenzoic acid;
monochlorobenzenes;
monohydroxybenzoic acid
3-aminopyridine
[no description available]		2.1110
3,5-pyridinedicarboxylic acid
3,5-pyridinedicarboxylic acid: structure in first source		2.1110pyridinedicarboxylic acid
3-hydroxypicolinic acid
[no description available]		2.1110monocarboxylic acid;
monohydroxypyridine		MALDI matrix material
6-aminonicotinic acid
6-aminonicotinic acid: RN given refers to parent cpd. 6-aminonicotinic acid : An aminonicotinic acid in which the amino group is situated at position 6 of the pyridine ring.		2.1110aminonicotinic acid;
aminopyridine;
aromatic amine		metabolite
sodium azide
Sodium Azide: A cytochrome oxidase inhibitor which is a nitridizing agent and an inhibitor of terminal oxidation. (From Merck Index, 12th ed). sodium azide : The sodium salt of hydrogen azide (hydrazoic acid).		2.1110inorganic sodium saltantibacterial agent;
explosive;
mitochondrial respiratory-chain inhibitor;
mutagen
azides
Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.		1.9910pseudohalide anionmitochondrial respiratory-chain inhibitor
5-fluorosalicylic acid
5-fluorosalicylic acid: structure given in first source; product from action of alkaline phosphatase on 5-fluorosalicyl phosphate; forms highly fluorescent terbium ternary complex		2.1110
2-aminonicotinic acid
2-aminonicotinic acid: structure in first source. 2-aminonicotinic acid : An aminonicotinic acid in which the amino group is situated at position 2 of the pyridine ring.. aminonicotinic acid : An aromatic amino acid that is nicotinic acid in which one of the hydrogens attached to the pyridine ring is replaced by an amino group. A 'closed class'.		2.1110aminonicotinic acid;
aminopyridine		metabolite
3-aminopicolinic acid
[no description available]		2.1110
5-bromonicotinic acid
5-bromonicotinic acid: structure given in first source		2.1110
5-fluoro-3-pyridinecarboxylic acid
[no description available]		2.1110
5-aminonicotinic acid
5-aminonicotinic acid: an inhibitor of D-aspartate oxidase; structure in first source. 5-aminonicotinic acid : An aminonicotinic acid in which the amino group is situated at position 5 of the pyridine ring.		2.1110aminonicotinic acid;
aminopyridine;
aromatic amine		metabolite
2-methyl-3-hydroxypyridine-5-carboxylic acid
2-methyl-3-hydroxypyridine-5-carboxylic acid: structure given in first source. 5-hydroxy-6-methylpyridine-3-carboxylic acid : The 5-hydroxy-6-methyl derivative of nicotinic acid.		2.7430methylpyridines;
monohydroxypyridine
nad
NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.		2.1510organophosphate oxoanioncofactor;
human metabolite;
hydrogen acceptor;
Saccharomyces cerevisiae metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Encephalitis, Polio
[description not available]		02.0610
Poliomyelitis
An acute infectious disease of humans, particularly children, caused by any of three serotypes of human poliovirus (POLIOVIRUS). Usually the infection is limited to the gastrointestinal tract and nasopharynx, and is often asymptomatic. The central nervous system, primarily the spinal cord, may be affected, leading to rapidly progressive paralysis, coarse FASCICULATION and hyporeflexia. Motor neurons are primarily affected. Encephalitis may also occur. The virus replicates in the nervous system, and may cause significant neuronal loss, most notably in the spinal cord. A rare related condition, nonpoliovirus poliomyelitis, may result from infections with nonpoliovirus enteroviruses. (From Adams et al., Principles of Neurology, 6th ed, pp764-5)		02.0610