3-amino-4-hydroxybenzoic acid profile

3-amino-4-hydroxybenzoic acid, also known as 4-hydroxyanthranilic acid, is an organic compound with the formula C7H7NO3. It is a white solid that is soluble in water. This compound is an intermediate in the biosynthesis of the amino acid tryptophan, which is an essential amino acid in humans and other animals. 3-amino-4-hydroxybenzoic acid is also a precursor to the synthesis of many other important compounds, including the antibiotic streptomycin. The compound has also been shown to have antioxidant and anti-inflammatory properties. Research into this compound is driven by its biological importance as an intermediate in tryptophan biosynthesis and its potential as a therapeutic agent.'

3-amino-4-hydroxybenzoic acid : A monohydroxybenzoic acid that is 4-hydroxybenzoic acid carrying an additional amino substitutent at position 3. [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]

ID Source	ID
PubMed CID	65083
CHEMBL ID	242963
CHEBI ID	29476
SCHEMBL ID	79989
MeSH ID	M0287417

Synonym
AC-2757
nsc-700601
nsc700601
3-amino-4-hydroxy-benzoic acid
OPREA1_298249
inchi=1/c7h7no3/c8-5-3-4(7(10)11)1-2-6(5)9/h1-3,9h,8h2,(h,10,11
1571-72-8
3,4-ahba
3-amino-4-hydroxybenzoic acid
benzoic acid, 3-amino-4-hydroxy-
3-amino-4-hydroxybenzoic acid, 97%
A0859
AKOS000113937
ksc-11-207-15
CHEBI:29476 ,
KUC106684N
CHEMBL242963 ,
BBL012255
STL163577
unii-n155er48et
nsc 700601
einecs 216-390-2
n155er48et ,
FT-0614976
AN-584/40209222
AM20030061
S6361
SCHEMBL79989
mfcd00007697
SY002820
3-amino-4-hydroxy benzoic acid
J-640249
W-108006
BS-3844
DTXSID60166212
J-800248
bdbm50478480
CS-W010940
3-amino-4-hydroxylbenzoic acid
4-hydroxy-3-aminobenzoic acid
HY-W010224
Z190662426
Q27104072
3-amino-4-hydroxybenzenecarboxylic acid
1h-indole,4,5-difluoro-2-methyl-
EN300-24391
PD054438

Excerpt	Reference	Relevance
" Treatment is however still problematic given the poor bioavailability of CoQ10."	( Effect of vanillic acid on COQ6 mutants identified in patients with coenzyme Q10 deficiency. Airik, R; Bergdoll, M; Doimo, M; Hildebrandt, F; Navas, P; Pierrel, F; Salviati, L; Santos-Ocaña, C; Trevisson, E, 2014)	0.4

Class	Description
aminobenzoic acid
monohydroxybenzoic acid	Any hydroxybenzoic acid having a single phenolic hydroxy substituent on the benzene ring.
[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]

Assay ID	Title	Year	Journal	Article
AID714147	Activity of Trametes versicolor laccase by spectrophotometric analysis	2012	Bioorganic & medicinal chemistry, Mar-01, Volume: 20, Issue:5	Redox potentials, laccase oxidation, and antilarval activities of substituted phenols.
AID714146	Ratio of kcat to Km for Trametes versicolor laccase	2012	Bioorganic & medicinal chemistry, Mar-01, Volume: 20, Issue:5	Redox potentials, laccase oxidation, and antilarval activities of substituted phenols.
AID293934	Inhibition of pieris rapae Phenoloxidase	2007	Bioorganic & medicinal chemistry, Mar-01, Volume: 15, Issue:5	3D-QSAR and molecular docking studies of benzaldehyde thiosemicarbazone, benzaldehyde, benzoic acid, and their derivatives as phenoloxidase inhibitors.
AID337238	Inhibition of mouse EGFR by liquid scintillation counting
AID714148	Inhibition of Trametes versicolor laccase	2012	Bioorganic & medicinal chemistry, Mar-01, Volume: 20, Issue:5	Redox potentials, laccase oxidation, and antilarval activities of substituted phenols.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	1 (9.09)	18.2507
2000's	4 (36.36)	29.6817
2010's	4 (36.36)	24.3611
2020's	2 (18.18)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	1 (8.33%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	11 (91.67%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
protocatechuic acid protocatechuic acid: RN given refers to parent cpd; structure. 3,4-dihydroxybenzoic acid : A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4.	2.03	1	catechols; dihydroxybenzoic acid	antineoplastic agent; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor; human xenobiotic metabolite; plant metabolite
3-hydroxybenzaldehyde [no description available]	2.03	1	hydroxybenzaldehyde
4-hydroxybenzaldehyde [no description available]	2.03	1	hydroxybenzaldehyde	EC 1.14.17.1 (dopamine beta-monooxygenase) inhibitor; mouse metabolite; plant metabolite
4-hydroxybenzoic acid 4-hydroxybenzoic acid : A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring.	2.03	1	monohydroxybenzoic acid	algal metabolite; plant metabolite
benzaldehyde [no description available]	2.03	1	benzaldehydes	EC 3.1.1.3 (triacylglycerol lipase) inhibitor; EC 3.5.5.1 (nitrilase) inhibitor; flavouring agent; fragrance; odorant receptor agonist; plant metabolite
benzene [no description available]	2.03	1	aromatic annulene; benzenes; volatile organic compound	carcinogenic agent; environmental contaminant; non-polar solvent
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.	2.03	1	benzoic acids	algal 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
catechol [no description available]	2.07	1	catechols	allelochemical; genotoxin; plant metabolite
cuminaldehyde cuminaldehyde : A member of the class of benzaldehydes that is benzaldehyde substituted by an isopropyl group at position 4. It is a component of essential oils from Cumin and exhibits insecticidal activities.	2.03	1	benzaldehydes	insecticide; plant metabolite; volatile oil component
salicylic acid Scalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).	2.03	1	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
hydroquinone [no description available]	2.07	1	benzenediol; hydroquinones	antioxidant; carcinogenic agent; cofactor; Escherichia coli metabolite; human xenobiotic metabolite; mouse metabolite; skin lightening agent
vanillin Vanilla: A plant genus of the family ORCHIDACEAE that is the source of the familiar flavoring used in foods and medicines (FLAVORING AGENTS).	2.03	1	benzaldehydes; monomethoxybenzene; phenols	anti-inflammatory agent; anticonvulsant; antioxidant; flavouring agent; plant metabolite
beta-resorcylic acid beta-resorcylic acid: RN given refers to parent cpd; structure	2.03	1
2,5-dihydroxybenzoic acid 2,5-dihydroxybenzoic acid: RN given refers to parent cpd; a oxidative product of saligenin. 2,5-dihydroxybenzoic acid : A dihydroxybenzoic acid having the two hydroxy groups at the 2- and 5-positions.	2.03	1	dihydroxybenzoic acid	EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; fungal metabolite; human metabolite; MALDI matrix material; mouse metabolite
2-aminophenol [no description available]	2.46	2	aminophenol	bacterial metabolite
salicylaldehyde o-hydroxybenzaldehyde: structure in first source	2.03	1	hydroxybenzaldehyde	nematicide; plant metabolite
2,4-dihydroxybenzaldehyde 2,4-dihydroxybenzaldehyde : A dihydroxybenzaldehyde that is resorcinol which has been substituted by a formyl group para to one of the hydroxy groups.	2.03	1	dihydroxybenzaldehyde
1,2-diaminobenzene 1,2-diaminobenzene: RN given refers to parent cpd. 1,2-phenylenediamine : A phenylenediamine in which the two amino groups are ortho to each other.	2.07	1	phenylenediamine	hydrogen donor
2-amino-4-methylphenol 2-amino-4-methylphenol: structure in first source	2.07	1
4-tert-butylbenzoic acid 4-tert-butylbenzoic acid: RN given refers to parent cpd	2.03	1	alkylbenzene
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.	2.03	1	monohydroxybenzoic acid	bacterial metabolite; plant metabolite
4-anisic acid 4-methoxybenzoic acid: structure in first source. 4-methoxybenzoic acid : A methoxybenzoic acid substituted with a methoxy group at position C-4.	2.03	1	methoxybenzoic acid	plant metabolite
vanillic acid Vanillic Acid: A flavoring agent. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13).. vanillic acid : A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3.	2.46	2	methoxybenzoic acid; monohydroxybenzoic acid	plant metabolite
2-Methoxybenzaldehyde [no description available]	2.03	1	carbonyl compound
protocatechualdehyde protocatechualdehyde: found in wheat grains, wheat seedlings, & other plants; RN given refers to parent cpd; see also rancinamycins; structure	2.03	1	dihydroxybenzaldehyde
2-vanillin ortho-vanillin : A member of the class of benzaldehydes that is salicylaldehyde substituted by a methoxy group at position 3.	2.03	1	benzaldehydes; guaiacols	antimutagen; plant metabolite
cumic acid cumic acid : A member of the class of benzoic acids that is cumene substituted by at least one carboxy group.. p-cumic acid : A cumic acid that consists of benzoic acid substituted by an isopropyl group at position 4.	2.03	1	cumic acid	plant metabolite
3-methoxybenzoic acid [no description available]	2.03	1	methoxybenzoic acid	flavouring agent; human urinary metabolite
3-methoxybenzaldehyde 3-methoxybenzaldehyde : A member of the class of benzaldehydes in which the hydrogen at position 3 of benzaldehyde has been replaced by a methoxy group.	2.03	1	benzaldehydes; monomethoxybenzene	Brassica napus metabolite
isovanillin isovanillin: inhibits aldehyde oxidase. isovanillin : A member of the class of benzaldehydes that is 4-methoxybenzaldehyde substituted by a hydroxy group at position 3. It is an inhibitor of aldehyde oxidase.	2.03	1	benzaldehydes; monomethoxybenzene; phenols	animal metabolite; antidiarrhoeal drug; antifungal agent; EC 1.2.3.1 (aldehyde oxidase) inhibitor; HIV protease inhibitor; plant metabolite
isovanillic acid 3-hydroxy-4-methoxybenzoic acid : A methoxybenzoic acid that is 4-methoxybenzoic acid bearing a hydroxy substituent at position 3.	2.03	1	methoxybenzoic acid; monohydroxybenzoic acid	antibacterial agent; plant metabolite
4-anisaldehyde 4-anisaldehyde: RN given refers to cpd with specified locants for methoxy moieties; structure in Merck, 9th ed, #696. p-methoxybenzaldehyde : A member of the class of benzaldehydes consisting of benzaldehyde itself carrying a methoxy substituent at position 4.	2.03	1	benzaldehydes	bacterial metabolite; human urinary metabolite; insect repellent; plant metabolite
2-hydroxy-4-methoxybenzaldehyde 2-hydroxy-4-methoxybenzaldehyde: from African medicinal plants: Mondia whitei (Apocynaceae), Rhus vulagaris (Anacardiaceae), Sclerocarya caffra (Anacardiaceae)	2.03	1	methoxybenzenes; phenols
2,5-dihydroxybenzaldehyde 2,5-dihydroxybenzaldehyde: structure in first source. 2,5-dihydroxybenzaldehyde : A dihydroxybenzaldehyde carrying hydroxy groups at positions 2 and 5.	2.03	1	dihydroxybenzaldehyde	human metabolite; mouse metabolite; Penicillium metabolite
xylose xylopyranose: structure in first source	7.41	1	D-xylose
4-amino-3-hydroxybenzoic acid [no description available]	2.46	2
4-propylbenzoic acid [no description available]	2.03	1	alkylbenzene
coenzyme q10 coenzyme Q10: Ubiquinone ring with a chain of 10 isoprene units; redox equilibrium with ubiqunol serving in mitochondrial inner membrane to transfer electrons; presence during reconstitution of acetylcholine receptor into phospholipid vesicles yields vesicles active in catalyzing carbamylcholine-sensitive Na+ flux; coenzyme Q10 depletion has been noted with use of statins. coenzyme Q10 : A ubiquinone having a side chain of 10 isoprenoid units. In the naturally occurring isomer, all isoprenyl double bonds are in the E- configuration.	2.1	1	ubiquinones	antioxidant; ferroptosis inhibitor; human metabolite
ubiquinone 6 [no description available]	2.1	1	ubiquinones	Saccharomyces cerevisiae metabolite
4-isopropylbenzaldehyde thiosemicarbazone 4-isopropylbenzaldehyde thiosemicarbazone: structure in first source	2.03	1
3-hydroxy-4-methoxybenzaldehyde thiosemicarbazone 3-hydroxy-4-methoxybenzaldehyde thiosemicarbazone: inhibits cabbage butterfly larvae phenoloxidase; structure in first source	2.03	1
ubiquinone Ubiquinone: A lipid-soluble benzoquinone which is involved in ELECTRON TRANSPORT in mitochondrial preparations. The compound occurs in the majority of aerobic organisms, from bacteria to higher plants and animals.	2.1	1
salicylaldehyde thiosemicarbazone salicylaldehyde thiosemicarbazone: structure given in first source	2.03	1

Condition	Relationship Strength	Studies	Trials
Muscular Weakness [description not available]	2.1	1	0
Electron Transport Chain Deficiencies, Mitochondrial [description not available]	2.1	1	0
Ataxia Impairment of the ability to perform smoothly coordinated voluntary movements. This condition may affect the limbs, trunk, eyes, pharynx, larynx, and other structures. Ataxia may result from impaired sensory or motor function. Sensory ataxia may result from posterior column injury or PERIPHERAL NERVE DISEASES. Motor ataxia may be associated with CEREBELLAR DISEASES; CEREBRAL CORTEX diseases; THALAMIC DISEASES; BASAL GANGLIA DISEASES; injury to the RED NUCLEUS; and other conditions.	2.1	1	0
Muscle Weakness A vague complaint of debility, fatigue, or exhaustion attributable to weakness of various muscles. The weakness can be characterized as subacute or chronic, often progressive, and is a manifestation of many muscle and neuromuscular diseases. (From Wyngaarden et al., Cecil Textbook of Medicine, 19th ed, p2251)	2.1	1	0
Mitochondrial Diseases Diseases caused by abnormal function of the MITOCHONDRIA. They may be caused by mutations, acquired or inherited, in mitochondrial DNA or in nuclear genes that code for mitochondrial components. They may also be the result of acquired mitochondria dysfunction due to adverse effects of drugs, infections, or other environmental causes.	2.1	1	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	3.38	1	1
HIV Coinfection [description not available]	3.38	1	1
HIV Infections Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).	3.38	1	1

3-amino-4-hydroxybenzoic acid

Description

Cross-References

Synonyms (47)

Research Excerpts

Bioavailability

Drug Classes (2)

Bioassays (5)

Research

Studies (11)

Market Indicators

Research Demand Index: 28.88

Study Types