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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7) Show 7 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:44 UTC

HMDB ID

HMDB0001476

Secondary Accession Numbers

HMDB01476

Metabolite Identification

Common Name

3-Hydroxyanthranilic acid

Description

3-Hydroxyanthranilic acid, also known as 2-amino-3-hydroxy-benzoate or 3-ohaa, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 3-Hydroxyanthranilic acid is a drug. 3-Hydroxyanthranilic acid exists in all living species, ranging from bacteria to humans. Within humans, 3-hydroxyanthranilic acid participates in a number of enzymatic reactions. In particular, 3-hydroxyanthranilic acid and L-alanine can be biosynthesized from L-3-hydroxykynurenine through the action of the enzyme kynureninase. In addition, 3-hydroxyanthranilic acid can be converted into cinnavalininate through the action of the enzyme catalase. 3-Hydroxyanthranilic acid is an intermediate in the metabolism of tryptophan. In humans, 3-hydroxyanthranilic acid is involved in tryptophan metabolism. Outside of the human body, 3-hydroxyanthranilic acid has been detected, but not quantified in brassicas. This could make 3-hydroxyanthranilic acid a potential biomarker for the consumption of these foods. It is new antioxidant isolated from methanol extract of tempeh. It is effective in preventing autoxidation of soybean oil and powder, while antioxidant 6,7,4'-trihydroxyisoflavone is not.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Amino-3-hydroxy-benzoic acid	ChEBI
2-Amino-3-hydroxybenzoic acid	ChEBI
3-Ohaa	ChEBI
3-Oxyanthranilic acid	ChEBI
2-Amino-3-hydroxy-benzoate	Generator
2-Amino-3-hydroxybenzoate	Generator
3-Oxyanthranilate	Generator
3-Hydroxyanthranilate	Generator
3-Hydroxanthranilate	HMDB
3-Hydroxy-2-aminobenzoate	HMDB
3-Hydroxy-2-aminobenzoic acid	HMDB
3-Hydroxy-anthranilate	HMDB
3-Hydroxy-anthranilic acid	HMDB
3-Hydroxy-anthranilsaeure	HMDB
3-Hydroxyantranilic acid	HMDB
3-OH-Anthranilic acid	HMDB
3 Hydroxyanthranilic acid	HMDB
Acid, 3-hydroxyanthranilic	HMDB

Chemical Formula

C₇H₇NO₃

Average Molecular Weight

153.1354

Monoisotopic Molecular Weight

153.042593095

IUPAC Name

2-amino-3-hydroxybenzoic acid

Traditional Name

3-hydroxyanthranilic acid

CAS Registry Number

548-93-6

SMILES

NC1=C(O)C=CC=C1C(O)=O

InChI Identifier

InChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11)

InChI Key

WJXSWCUQABXPFS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hydroxybenzoic acid derivatives

Alternative Parents

Substituents

Aminobenzoic acid
Aminobenzoic acid or derivatives
Hydroxybenzoic acid
Benzoic acid
O-aminophenol
Aminophenol
Benzoyl
Aniline or substituted anilines
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous amide
Amino acid or derivatives
Amino acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organonitrogen compound
Hydrocarbon derivative
Amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Primary amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monohydroxybenzoic acid (CHEBI:15793 )
aminobenzoic acid (CHEBI:15793 )

Ontology

Physiological effect

Health effect

Circulatory system disorder

Vascular disorder

Cerebral infarction (HMDB: HMDB0001476)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 8634758)

Cellular substructure

Organ

Bladder (HMDB: HMDB0001476)

Tissue

Epithelium

Epidermis (HMDB: HMDB0001476)

Cell

Leukocyte (HMDB: HMDB0001476)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001476)

Source

Exogenous

Exogenous (HMDB: HMDB0001476)

Food

Food (HMDB: HMDB0001476)

Animal origin

Poultry

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)

Vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Endogenous

Endogenous (HMDB: HMDB0001476)

Plant

Plant (HMDB: HMDB0001476)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tryptophan Metabolism (PathBank: SMP0063693)
Tryptophan Metabolism (HMDB: HMDB0001476)
NAD Metabolism (PathBank: SMP0002338)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0001476)

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	128.9	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002099
[M+H]+	Not Available	131.3	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002099

Predicted Molecular Properties

Property	Value	Source
Water Solubility	10.5 g/L	ALOGPS
logP	0.81	ALOGPS
logP	1.15	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	1.94	ChemAxon
pKa (Strongest Basic)	4.82	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	83.55 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	40 m³·mol⁻¹	ChemAxon
Polarizability	14.18 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]+	131.531	31661259
DarkChem	[M-H]-	127.128	31661259
AllCCS	[M+H]+	133.241	32859911
AllCCS	[M-H]-	126.842	32859911
DeepCCS	[M+H]+	131.029	30932474
DeepCCS	[M-H]-	127.201	30932474
DeepCCS	[M-2H]-	164.254	30932474
DeepCCS	[M+Na]+	139.721	30932474
AllCCS	[M+H]+	133.2	32859911
AllCCS	[M+H-H2O]+	128.7	32859911
AllCCS	[M+NH4]+	137.5	32859911
AllCCS	[M+Na]+	138.7	32859911
AllCCS	[M-H]-	126.8	32859911
AllCCS	[M+Na-2H]-	128.2	32859911
AllCCS	[M+HCOO]-	129.7	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.	2.07 minutes	32390414
Predicted by Siyang on May 30, 2022	10.9236 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.31 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	52.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1340.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	352.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	89.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	230.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	100.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	349.1 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	447.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	145.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	799.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	182.2 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	1014.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	262.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	366.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	530.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	230.8 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	227.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxyanthranilic acid	NC1=C(O)C=CC=C1C(O)=O	2894.2	Standard polar	33892256
3-Hydroxyanthranilic acid	NC1=C(O)C=CC=C1C(O)=O	1628.5	Standard non polar	33892256
3-Hydroxyanthranilic acid	NC1=C(O)C=CC=C1C(O)=O	1610.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxyanthranilic acid,1TMS,isomer #1	C[Si](C)(C)OC1=CC=CC(C(=O)O)=C1N	1728.0	Semi standard non polar	33892256
3-Hydroxyanthranilic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC=CC(O)=C1N	1748.9	Semi standard non polar	33892256
3-Hydroxyanthranilic acid,1TMS,isomer #3	C[Si](C)(C)NC1=C(O)C=CC=C1C(=O)O	1793.1	Semi standard non polar	33892256
3-Hydroxyanthranilic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=CC(O[Si](C)(C)C)=C1N	1746.9	Semi standard non polar	33892256
3-Hydroxyanthranilic acid,2TMS,isomer #2	C[Si](C)(C)NC1=C(O[Si](C)(C)C)C=CC=C1C(=O)O	1829.3	Semi standard non polar	33892256
3-Hydroxyanthranilic acid,2TMS,isomer #3	C[Si](C)(C)NC1=C(O)C=CC=C1C(=O)O[Si](C)(C)C	1788.5	Semi standard non polar	33892256
3-Hydroxyanthranilic acid,2TMS,isomer #4	C[Si](C)(C)N(C1=C(O)C=CC=C1C(=O)O)[Si](C)(C)C	1850.4	Semi standard non polar	33892256
3-Hydroxyanthranilic acid,3TMS,isomer #1	C[Si](C)(C)NC1=C(O[Si](C)(C)C)C=CC=C1C(=O)O[Si](C)(C)C	1857.7	Semi standard non polar	33892256
3-Hydroxyanthranilic acid,3TMS,isomer #1	C[Si](C)(C)NC1=C(O[Si](C)(C)C)C=CC=C1C(=O)O[Si](C)(C)C	1856.9	Standard non polar	33892256
3-Hydroxyanthranilic acid,3TMS,isomer #1	C[Si](C)(C)NC1=C(O[Si](C)(C)C)C=CC=C1C(=O)O[Si](C)(C)C	1948.5	Standard polar	33892256
3-Hydroxyanthranilic acid,3TMS,isomer #2	C[Si](C)(C)OC1=CC=CC(C(=O)O)=C1N([Si](C)(C)C)[Si](C)(C)C	1863.7	Semi standard non polar	33892256
3-Hydroxyanthranilic acid,3TMS,isomer #2	C[Si](C)(C)OC1=CC=CC(C(=O)O)=C1N([Si](C)(C)C)[Si](C)(C)C	1964.0	Standard non polar	33892256
3-Hydroxyanthranilic acid,3TMS,isomer #2	C[Si](C)(C)OC1=CC=CC(C(=O)O)=C1N([Si](C)(C)C)[Si](C)(C)C	1908.7	Standard polar	33892256
3-Hydroxyanthranilic acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC=CC(O)=C1N([Si](C)(C)C)[Si](C)(C)C	1815.4	Semi standard non polar	33892256
3-Hydroxyanthranilic acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC=CC(O)=C1N([Si](C)(C)C)[Si](C)(C)C	1884.2	Standard non polar	33892256
3-Hydroxyanthranilic acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC=CC(O)=C1N([Si](C)(C)C)[Si](C)(C)C	1962.5	Standard polar	33892256
3-Hydroxyanthranilic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=CC(O[Si](C)(C)C)=C1N([Si](C)(C)C)[Si](C)(C)C	1909.2	Semi standard non polar	33892256
3-Hydroxyanthranilic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=CC(O[Si](C)(C)C)=C1N([Si](C)(C)C)[Si](C)(C)C	1937.3	Standard non polar	33892256
3-Hydroxyanthranilic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=CC(O[Si](C)(C)C)=C1N([Si](C)(C)C)[Si](C)(C)C	1820.5	Standard polar	33892256
3-Hydroxyanthranilic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC(C(=O)O)=C1N	2011.6	Semi standard non polar	33892256
3-Hydroxyanthranilic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC(O)=C1N	2037.1	Semi standard non polar	33892256
3-Hydroxyanthranilic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=C(O)C=CC=C1C(=O)O	2063.8	Semi standard non polar	33892256
3-Hydroxyanthranilic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1N	2247.2	Semi standard non polar	33892256
3-Hydroxyanthranilic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=C(O[Si](C)(C)C(C)(C)C)C=CC=C1C(=O)O	2351.3	Semi standard non polar	33892256
3-Hydroxyanthranilic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=C(O)C=CC=C1C(=O)O[Si](C)(C)C(C)(C)C	2283.5	Semi standard non polar	33892256
3-Hydroxyanthranilic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C1=C(O)C=CC=C1C(=O)O)[Si](C)(C)C(C)(C)C	2328.7	Semi standard non polar	33892256
3-Hydroxyanthranilic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=C(O[Si](C)(C)C(C)(C)C)C=CC=C1C(=O)O[Si](C)(C)C(C)(C)C	2529.0	Semi standard non polar	33892256
3-Hydroxyanthranilic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=C(O[Si](C)(C)C(C)(C)C)C=CC=C1C(=O)O[Si](C)(C)C(C)(C)C	2471.3	Standard non polar	33892256
3-Hydroxyanthranilic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=C(O[Si](C)(C)C(C)(C)C)C=CC=C1C(=O)O[Si](C)(C)C(C)(C)C	2347.5	Standard polar	33892256
3-Hydroxyanthranilic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CC(C(=O)O)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2550.8	Semi standard non polar	33892256
3-Hydroxyanthranilic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CC(C(=O)O)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2560.4	Standard non polar	33892256
3-Hydroxyanthranilic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CC(C(=O)O)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2286.0	Standard polar	33892256
3-Hydroxyanthranilic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC(O)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2500.5	Semi standard non polar	33892256
3-Hydroxyanthranilic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC(O)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2460.6	Standard non polar	33892256
3-Hydroxyanthranilic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC(O)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2320.9	Standard polar	33892256
3-Hydroxyanthranilic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2770.7	Semi standard non polar	33892256
3-Hydroxyanthranilic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2686.1	Standard non polar	33892256
3-Hydroxyanthranilic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2317.0	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Bladder
Epidermis
Leukocyte

Pathways

Name	SMPDB/PathBank	KEGG
Tryptophan metabolism	Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.079 (0.015-0.209) uM	Adult (>18 years old)	Both	Normal	8634758	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	3.28 (0.46-5.19) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.01 (0.007-0.011) uM	Adult (>18 years old)	Both	Stroke	17892481	details
Blood	Detected and Quantified	37.82 uM	Infant (0-1 year old)	Female	Nicotinamide Adenine Dinucleotide Deficiency	28792876	details

Associated Disorders and Diseases

Disease References

Stroke
Darlington LG, Mackay GM, Forrest CM, Stoy N, George C, Stone TW: Altered kynurenine metabolism correlates with infarct volume in stroke. Eur J Neurosci. 2007 Oct;26(8):2211-21. Epub 2007 Sep 24. [PubMed:17892481 ]
Nicotinamide Adenine Dinucleotide Deficiency
Shi H, Enriquez A, Rapadas M, Martin EMMA, Wang R, Moreau J, Lim CK, Szot JO, Ip E, Hughes JN, Sugimoto K, Humphreys DT, McInerney-Leo AM, Leo PJ, Maghzal GJ, Halliday J, Smith J, Colley A, Mark PR, Collins F, Sillence DO, Winlaw DS, Ho JWK, Guillemin GJ, Brown MA, Kikuchi K, Thomas PQ, Stocker R, Giannoulatou E, Chapman G, Duncan EL, Sparrow DB, Dunwoodie SL: NAD Deficiency, Congenital Malformations, and Niacin Supplementation. N Engl J Med. 2017 Aug 10;377(6):544-552. doi: 10.1056/NEJMoa1616361. [PubMed:28792876 ]

Associated OMIM IDs

601367 (Stroke)

External Links

DrugBank ID

DB03644

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB010582

KNApSAcK ID

C00007568

Chemspider ID

KEGG Compound ID

C00632

BioCyc ID

3-HYDROXY-ANTHRANILATE

BiGG ID

1485273

Wikipedia Link

3-hydroxyanthranilic_acid

METLIN ID

3275

PubChem Compound

PDB ID

Not Available

ChEBI ID

15793

Food Biomarker Ontology

Not Available

VMH ID

3HANTHRN

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Warnell, J. L. 3-Hydroxyanthranilic acid. Biochemical Preparations (1958), 6 20-4.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

De Antoni A, Rubaltelli FF, Costa C, Allegri G: Effect of phototherapy on the urinary excretion of tryptophan metabolites in neonatal hyperbilirubinemia. Acta Vitaminol Enzymol. 1975;29(1-6):145-50. [PubMed:1244083 ]
Calandra P: Research on tryptophan metabolites "via kynurenine" in epidermis of man and mouse. Acta Vitaminol Enzymol. 1975;29(1-6):158-60. [PubMed:1244085 ]
Hegedus ZL, Frank HA, Altschule MD, Nayak U: Human plasma lipofuscin melanins formed from tryptophan metabolites. Arch Int Physiol Biochim. 1986 Dec;94(5):339-48. [PubMed:2440410 ]
Werner ER, Lutz H, Fuchs D, Hausen A, Huber C, Niederwieser D, Pfleiderer W, Reibnegger G, Troppmair J, Wachter H: Identification of 3-hydroxyanthranilic acid in mixed lymphocyte cultures. Biol Chem Hoppe Seyler. 1985 Jan;366(1):99-102. [PubMed:3159398 ]
Teulings FA, Mulder-Kooy GE, Peters HA, Fokkens W, Van Der Werf-Messing B: The excretion of 3-hydroxyanthranilic acid in patients with bladder and kidney carcinoma. Acta Vitaminol Enzymol. 1975;29(1-6):108-12. [PubMed:1244078 ]
Lopez AS, Alegre E, LeMaoult J, Carosella E, Gonzalez A: Regulatory role of tryptophan degradation pathway in HLA-G expression by human monocyte-derived dendritic cells. Mol Immunol. 2006 Jul;43(14):2151-60. Epub 2006 Feb 21. [PubMed:16490253 ]
Yeh JK, Brown RR: Effects of vitamin B-6 deficiency and tryptophan loading on urinary excretion of tryptophan metabolites in mammals. J Nutr. 1977 Feb;107(2):261-71. [PubMed:833687 ]
Herve C, Beyne P, Jamault H, Delacoux E: Determination of tryptophan and its kynurenine pathway metabolites in human serum by high-performance liquid chromatography with simultaneous ultraviolet and fluorimetric detection. J Chromatogr B Biomed Appl. 1996 Jan 12;675(1):157-61. [PubMed:8634758 ]
Teulings FA, Lems PH, Portengen H, Henkelman MS, Blonk DI: The action of 3-hydroxyanthranilic acid and other tryptophan metabolites on stimulated human lymphocytes. Acta Vitaminol Enzymol. 1975;29(1-6):113-6. [PubMed:1244079 ]

Enzymes

Enzyme Details

1. Kynureninase

General function:: Involved in metabolic process
Specific function:: Catalyzes the cleavage of L-kynurenine (L-Kyn) and L-3-hydroxykynurenine (L-3OHKyn) into anthranilic acid (AA) and 3-hydroxyanthranilic acid (3-OHAA), respectively. Has a preference for the L-3-hydroxy form. Also has cysteine-conjugate-beta-lyase activity.
Gene Name:: KYNU
Uniprot ID:: Q16719
Molecular weight:: 34634.47

Reactions

L-3-Hydroxykynurenine + Water → 3-Hydroxyanthranilic acid + L-Alanine	details

Enzyme Details

2. 3-hydroxyanthranilate 3,4-dioxygenase

General function:: Involved in 3-hydroxyanthranilate 3,4-dioxygenase activity
Specific function:: Catalyzes the oxidative ring opening of 3-hydroxyanthranilate to 2-amino-3-carboxymuconate semialdehyde, which spontaneously cyclizes to quinolinate.
Gene Name:: HAAO
Uniprot ID:: P46952
Molecular weight:: 32555.935

Reactions

3-Hydroxyanthranilic acid + Oxygen → 2-Amino-3-carboxymuconic acid semialdehyde	details

Enzyme Details

3. Catalase

General function:: Involved in catalase activity
Specific function:: Occurs in almost all aerobically respiring organisms and serves to protect cells from the toxic effects of hydrogen peroxide. Promotes growth of cells including T-cells, B-cells, myeloid leukemia cells, melanoma cells, mastocytoma cells and normal and transformed fibroblast cells.
Gene Name:: CAT
Uniprot ID:: P04040
Molecular weight:: 59755.82

Reactions

3-Hydroxyanthranilic acid + Oxygen → Cinnabarinic acid + Superoxide + Hydrogen peroxide + Hydrogen Ion	details

Enzyme Details

4. HemK methyltransferase family member 1

General function:: Not Available
Specific function:: N5-glutamine methyltransferase responsible for the methylation of the GGQ triplet of the mitochondrial translation release factor MTRF1L.
Gene Name:: HEMK1
Uniprot ID:: Q9Y5R4
Molecular weight:: Not Available

Reactions

3-Hydroxyanthranilic acid + S-Adenosylmethionine → 3-Methoxyanthranilate + S-Adenosylhomocysteine	details

Enzyme Details

5. Methyltransferase-like protein 2B

General function:: Not Available
Specific function:: Probable methyltransferase (By similarity).
Gene Name:: METTL2B
Uniprot ID:: Q6P1Q9
Molecular weight:: Not Available

Reactions

3-Hydroxyanthranilic acid + S-Adenosylmethionine → 3-Methoxyanthranilate + S-Adenosylhomocysteine	details

Enzyme Details

6. Methyltransferase-like protein 6

General function:: Not Available
Specific function:: Probable methyltransferase (By similarity).
Gene Name:: METTL6
Uniprot ID:: Q8TCB7
Molecular weight:: Not Available

Reactions

3-Hydroxyanthranilic acid + S-Adenosylmethionine → 3-Methoxyanthranilate + S-Adenosylhomocysteine	details

Enzyme Details

7. Uncharacterized methyltransferase WBSCR22

General function:: Not Available
Specific function:: Methyltransferase that may act on DNA.
Gene Name:: WBSCR22
Uniprot ID:: O43709
Molecular weight:: Not Available

Reactions

3-Hydroxyanthranilic acid + S-Adenosylmethionine → 3-Methoxyanthranilate + S-Adenosylhomocysteine	details

Showing metabocard for 3-Hydroxyanthranilic acid (HMDB0001476)

MOL for HMDB0001476 (3-Hydroxyanthranilic acid)

3D MOL for HMDB0001476 (3-Hydroxyanthranilic acid)

3D SDF for HMDB0001476 (3-Hydroxyanthranilic acid)

3D-SDF for HMDB0001476 (3-Hydroxyanthranilic acid)

PDB for HMDB0001476 (3-Hydroxyanthranilic acid)

3D PDB for HMDB0001476 (3-Hydroxyanthranilic acid)

SMILES for HMDB0001476 (3-Hydroxyanthranilic acid)

INCHI for HMDB0001476 (3-Hydroxyanthranilic acid)

Structure for HMDB0001476 (3-Hydroxyanthranilic acid)

3D Structure for HMDB0001476 (3-Hydroxyanthranilic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

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