2-Aminobenzoic acid (YMDB00278)

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Identification

YMDB ID

YMDB00278

Name

2-Aminobenzoic acid

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

2-Aminobenzoic acid, also known as anthranilate or vitamin L1, belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety. 2-Aminobenzoic acid is a moderately basic compound (based on its pKa). 2-Aminobenzoic acid exists in all living species, ranging from bacteria to humans. Within yeast, 2-aminobenzoic acid participates in a number of enzymatic reactions. In particular, pyruvic acid, L-glutamic acid, and 2-aminobenzoic acid can be biosynthesized from chorismate and L-glutamine; which is catalyzed by the enzyme anthranilate synthase component. In addition, 2-aminobenzoic acid and phosphoribosyl pyrophosphate can be converted into N-(5-phosphoribosyl)-anthranilate through the action of the enzyme anthranilate phosphoribosyltransferase. In yeast, 2-aminobenzoic acid is involved in the metabolic pathway called the tryptophan metabolism pathway. 2-Aminobenzoic acid is a potentially toxic compound.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

1-Amino-2-carboxybenzene
2-amino-Benzoate
2-amino-Benzoic acid
2-Aminobenzoate
2-Aminobenzoic acid
2-Aminophenylacetate
2-Aminophenylacetic acid
2-Carboxyaniline
Aminobenzoic acid
Anthranate
Anthranic acid
Anthranilate
Anthranilic acid
anthranilic acid gr
Benzoic acid, 2-amino-
Benzoic acid, o-amino-
Carboxyaniline
Kyselina anthranilova
Kyselina o-aminobenzoova
o-amino-Benzoate
o-amino-Benzoic acid
o-Aminobenzoate
o-Aminobenzoic acid
o-Anthranilate
o-Anthranilic acid
o-Carboxyaniline
Ortho-amidobenzoate
Ortho-amidobenzoic acid
Ortho-aminobenzoate
Ortho-aminobenzoic acid
Vitamin L
Vitamin L1
2-Aminobenzoesaeure
O-Aminobenzoesaeure
Anthranilic acid, cadmium salt
Anthranilic acid, calcium (2:1) salt
Anthranilic acid, monolithium salt
Sodium anthranilate
Anthranilic acid, dihydrochloride
Anthranilic acid, hydrochloride
Anthranilic acid, monosodium salt
H-2-Abz-OH

CAS number

118-92-3

Weight

Average: 137.136
Monoisotopic: 137.047678473

InChI Key

RWZYAGGXGHYGMB-UHFFFAOYSA-N

InChI

InChI=1S/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10)

IUPAC Name

2-aminobenzoic acid

Traditional IUPAC Name

2-aminobenzoic acid

Chemical Formula

C₇H₇NO₂

SMILES

[H]OC(=O)C1=C([H])C([H])=C([H])C([H])=C1N([H])[H]

Chemical Taxonomy

Description

belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Aminobenzoic acids

Alternative Parents

Substituents

Aminobenzoic acid
Benzoic acid
Benzoyl
Aniline or substituted anilines
Vinylogous amide
Amino acid or derivatives
Amino acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Primary amine
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aminobenzoic acid (CHEBI:30754 )

Physical Properties

State

Solid

Charge

Melting point

146.5 °C

Experimental Properties

Property	Value	Reference
Water Solubility	3.5 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	1.21 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	6.81 g/L	ALOGPS
logP	0.78	ALOGPS
logP	1.45	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	4.89	ChemAxon
pKa (Strongest Basic)	1.95	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	38.01 m³·mol⁻¹	ChemAxon
Polarizability	13.29 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Tryptophan metabolism

PW002442

KEGG Pathways

Phenylalanine, tyrosine and tryptophan biosynthesis	ec00400
Tryptophan metabolism	ec00380

SMPDB Reactions

L-Kynurenine + water → hydron + L-Alanine + 2-Aminobenzoic acid

Chorismate + L-Glutamine → Pyruvic acid + L-Glutamic acid + hydron + 2-Aminobenzoic acid

2-Aminobenzoic acid + Phosphoribosyl pyrophosphate → Pyrophosphate + N-(5-Phosphonato-beta-D-ribosyl)anthranilate

KEGG Reactions

2-Aminobenzoic acid + Phosphoribosyl pyrophosphate → Pyrophosphate + N-(5-phospho-beta-D-ribosyl)anthranilic acid

Chorismate + L-Glutamine → 2-Aminobenzoic acid + Pyruvic acid + L-Glutamic acid + hydron

L-Kynurenine + water → 2-Aminobenzoic acid + L-Alanine + hydron

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-014i-1950000000-5595652a2e8f93679437	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-014i-1960000000-889ed538406d5aa57a5d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00xr-9650000000-e0611721f0bf7b5bb2f8	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-00r6-2910000000-0daf33fe6231b5e15b0e	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-014i-3970000000-3351c7d8036c42c4cd41	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00kf-9400000000-b65ee27505e8c4bcca28	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-0490000000-4165d1d7b8fff53889dd	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-1950000000-5595652a2e8f93679437	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-1960000000-889ed538406d5aa57a5d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00xr-9650000000-e0611721f0bf7b5bb2f8	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00r6-2910000000-0daf33fe6231b5e15b0e	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-3970000000-3351c7d8036c42c4cd41	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kr-7900000000-a9c510a71b30a8fcc1b8	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-7900000000-cb7be965685a5ee30fbd	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-00kf-9400000000-395d42e11895b80f4e9c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-8c390367e035aea8527a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0006-9000000000-899b596a227cd9a1769d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-0900000000-3cc9be013399e30d7eae	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-655ef8fc722e0b1b6d14	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-4d0520217d12a10f9273	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0006-9000000000-bab8539624c8af4e6434	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-0900000000-f51f2db6bf1da2e26d20	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-86d698a8c81a3e765840	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-0900000000-6df94712ad580bebfd21	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0006-9100000000-a1ce64280c2d7f3b85df	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0006-9000000000-454f848122c778e951ad	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-7de473c1ca6bf702b2ac	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-94f19baa1ae36f43be60	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-00di-2900000000-c2bbbe5e00434e635ad2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-4900000000-f8f84a5536375300afbd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00r6-9200000000-fccd86d3a0a4bfe2e5d7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-014i-9000000000-91ceb340e5cf91473cba	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014i-9000000000-80972c552b97ae764bc4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-4900000000-f494672ce9de4818b8c5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0006-9300000000-9bbb2f00817538e072d5	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0079-0900000000-e7e07e78dd5baa5c3f87	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1900000000-54a3d793d6fbf0220b47	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0umi-9200000000-bd780d6ca957af006488	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000f-9800000000-93111d593c96a3298a6c	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-014u-9600000000-5b8e271f29d04a87c89a	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Crombie, T., Boyle, J. P., Coggins, J. R., Brown, A. J. (1994). "The folding of the bifunctional TRP3 protein in yeast is influenced by a translational pause which lies in a region of structural divergence with Escherichia coli indoleglycerol-phosphate synthase." Eur J Biochem 226:657-664.8001582
Panozzo, C., Nawara, M., Suski, C., Kucharczyka, R., Skoneczny, M., Becam, A. M., Rytka, J., Herbert, C. J. (2002). "Aerobic and anaerobic NAD+ metabolism in Saccharomyces cerevisiae." FEBS Lett 517:97-102.12062417

Synthesis Reference:

Wang, Chengyin; Yang, Jisheng; Wang, Honghai. Production of o-aminobenzoic acid from by-product o-nitrobenzoic acid. Huaxue Shijie (1999), 40(5), 274-277.

External Links:

Resource	Link
CHEBI ID	30754
HMDB ID	HMDB01123
Pubchem Compound ID	227
Kegg ID	C00108
ChemSpider ID	222
FOODB ID	FDB000896
Wikipedia	Anthranilic_acid
BioCyc ID	ANTHRANILATE

Enzymes

Protein Details

1. Anthranilate synthase component 2

General function:: Involved in catalytic activity
Specific function:: Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate
Gene Name:: TRP3
Uniprot ID:: P00937
Molecular weight:: 53488.89844

Reactions

Chorismate + L-glutamine → anthranilate + pyruvate + L-glutamate.
1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate → 1-C-(3-indolyl)-glycerol 3-phosphate + CO(2) + H(2)O.

Protein Details

2. Anthranilate synthase component 1

General function:: Involved in biosynthetic process
Specific function:: Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate
Gene Name:: TRP2
Uniprot ID:: P00899
Molecular weight:: 56767.0

Reactions

Chorismate + L-glutamine → anthranilate + pyruvate + L-glutamate.

Protein Details

3. Anthranilate phosphoribosyltransferase

General function:: Involved in anthranilate phosphoribosyltransferase activity
Specific function:: N-(5-phospho-D-ribosyl)-anthranilate + diphosphate = anthranilate + 5-phospho-alpha-D-ribose 1- diphosphate
Gene Name:: TRP4
Uniprot ID:: P07285
Molecular weight:: 41374.0

Reactions

N-(5-phospho-D-ribosyl)-anthranilate + diphosphate → anthranilate + 5-phospho-alpha-D-ribose 1-diphosphate.

Protein Details

4. 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
Gene Name:: BNA5
Uniprot ID:: Q05979
Molecular weight:: 51031.60156

Reactions

L-kynurenine + H(2)O → anthranilate + L-alanine.
L-3-hydroxykynurenine + H(2)O → 3-hydroxyanthranilate + L-alanine.

Protein Details

5. Probable kynurenine formamidase

General function:: Involved in hydrolase activity
Specific function:: Catalyzes the hydrolysis of N-formyl-L-kynurenine to L- kynurenine, the second step in the conversion of tryptophan to nicotinic acid, NAD(H) and NADP(H)
Gene Name:: BNA7
Uniprot ID:: Q04066
Molecular weight:: 29991.0

Reactions

N-formyl-L-kynurenine + H(2)O → formate + L-kynurenine.

Structure for #<Compound:0xb3d6b254>

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions