Anthranilic acid

Details

• Internal ID: 4165ac9f-f1a7-496b-9d16-716a2c86ae82
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Aminobenzoic acids and derivatives > Aminobenzoic acids
• IUPAC Name: 2-aminobenzoic acid
• SMILES (Canonical): C1=CC=C(C(=C1)C(=O)O)N
• SMILES (Isomeric): C1=CC=C(C(=C1)C(=O)O)N
• InChI: InChI=1S/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10)
• InChI Key: RWZYAGGXGHYGMB-UHFFFAOYSA-N
• Popularity: 4,534 references in papers

Physical and Chemical Properties

• Molecular Formula: C₇H₇NO₂
• Molecular Weight: 137.14 g/mol
• Exact Mass: 137.047678466 g/mol
• Topological Polar Surface Area (TPSA): 63.30 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 0.97
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 2-aminobenzoic acid
• 118-92-3
• o-aminobenzoic acid
• o-Carboxyaniline
• 2-Carboxyaniline
• vitamin L1
• o-Anthranilic acid
• anthranilate
• Benzoic acid, 2-amino-
• 1-Amino-2-carboxybenzene
• ortho-Aminobenzoic acid
• Benzoic acid, o-amino-
• Carboxyaniline
• Kyselina anthranilova
• NCI-C01730
• Benzoic acid, amino-
• Vitamin L
• Caswell No. 033G
• Kyselina o-aminobenzoova
• 2-azaniumylbenzoate
• 2-amino-Benzoic acid
• NSC 144
• CCRIS 49
• 2-amino benzoic acid
• Kyselina anthranilova [Czech]
• Antranilic Acid
• BRN 0471803
• HSDB 1321
• Kyselina o-aminobenzoova [Czech]
• AI3-02408
• EINECS 204-287-5
• o-Aminobenzoesaeure
• UNII-0YS975XI6W
• 2-Aminobenzoesaeure
• 0YS975XI6W
• DTXSID8020094
• CHEBI:30754
• alpha-Aminobenzoic acid
• Ortho-amidobenzoic acid
• NSC-144
• Anthranilic Acid-13C6
• Cupric anthranilate
• MFCD00007712
• NSC-40929
• DTXCID7094
• Bis(anthranilato)copper
• NSC 3937
• Bis(o-aminobenzoato)copper
• EC 204-287-5
• Copper, bis(anthranilato)-
• EINECS 215-310-3
• Anthranic acid
• NSC 173996
• Copper, bis(2-aminobenzoato)-
• NCGC00091175-01
• Copper, bis(2-aminobenzoato-N,O)-
• 1321-11-5
• 98072-80-1
• BE2
• ANTHRANILIC ACID (IARC)
• ANTHRANILIC ACID [IARC]
• C14H12CuN2O4
• NSC3937
• CAS-118-92-3
• C14-H12-Cu-N2-O4
• 15442-49-6
• Copper, bis(2-aminobenzoato-N,O)- (9CI)
• Anthranate
• anthanilic acid
• o-Anthranilate
• o-amino-Benzoate
• 4owv
• 2-amino-Benzoate
• Acide anthranilique
• Ortho-amidobenzoate
• Ortho-aminobenzoate
• 2-aminobezoic acid
• anthranilic acid gr
• Benzoic acid, 2-amino-, diazotized, coupled with 4-amino-5-hydroxy-2,7-naphthalenedisulfonic acid, diazotized 3,3'-dimethyl(1,1'-biphenyl)-4,4'-diamine and 5,5'-(oxybis((5-hydroxy-3,1-phenylene)oxy))bis(1,3-benzenediol), sodium salt
• Benzoic acid, 2-amino-, diazotized, coupled with 4-amino-5-hydroxy-2,7-naphthalenedisulfonic acid, diazotized 3,3'-dimethyl[1,1'-biphenyl]-4,4'-diamine and 5,5'-[oxybis[(5-hydroxy-3,1-phenylene)oxy]]bis[1,3-benzenediol], sodium salt
• Benzoic acid, 2-amino-, diazotized, coupled with diazotized 5-amino-2-((4-aminophenyl)amino)benzenesulfonic acid and 5,5'-(oxybis((5-hydroxy-3,1-phenylene)oxy))bis(1,3-benzenediol), sodium salt
• Benzoic acid, 2-amino-, diazotized, coupled with diazotized 5-amino-2-[(4-aminophenyl)amino]benzenesulfonic acid and 5,5'-[oxybis[(5-hydroxy-3,1-phenylene)oxy]]bis[1,3-benzenediol], sodium salt
• 2-Aminophenylacetate
• 2-Carboxyphenylamine
• o-amino-Benzoic acid
• 2-anilinecarboxylic acid
• H-2-Abz-OH
• DEA Code 8530
• SCHEMBL675
• bmse000067
• bmse000917
• H-(2)Abz-OH
• NCIOpen2_001191
• Oprea1_390012
• 80206-34-4
• CHEMBL14173
• NSC144
• ANTHRANILIC ACID [HSDB]
• 1-aminobenzene-2-carboxylic acid
• O-AMINOBENZOIC ACID [MI]
• ANTHRANILIC ACID [WHO-DD]
• NSC40929
• EINECS 307-609-3
• EINECS 308-537-5
• Tox21_111095
• Tox21_200703
• BBL025605
• BDBM50376751
• LS-608
• STK298716
• Anthranilic acid-ring-UL-14C, solid
• AKOS002667021
• Tox21_111095_1
• DB04166
• NCGC00091175-02
• NCGC00091175-03
• NCGC00258257-01
• 50816-84-7
• 97675-38-2
• AC-11503
• Anthranilic acid, reagent grade, >=98%
• BP-30147
• A0497
• C00108
• BENZOIC ACID,2-AMINO ANTHRANILIC ACID
• Benzoic acid,2-amino-,labeled with tritium(9ci)
• Anthranilic acid, puriss. p.a., >=99.5% (T)
• Q385140
• 3B851741-2A4D-440D-BB22-1A455121BA21
• InChI=1/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10
• Benzoic acid,2-amino-,diazotized,coupled with 4-amino-5-hydroxy-2,7-naphthalenedisulfonic acid,diazotized 3,3'-dimethyl[1,1'-biphenyl]-4,4'-diamine and 5,5'-[oxybis[(5-hydroxy-3,1-phenylene)oxy]]b

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9774	97.74%
Caco-2	+	0.9281	92.81%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.8857	88.57%
Subcellular localzation	Mitochondria	0.6109	61.09%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9750	97.50%
OATP1B3 inhibitior	+	0.9554	95.54%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9492	94.92%
P-glycoprotein inhibitior	-	0.9861	98.61%
P-glycoprotein substrate	-	0.9836	98.36%
CYP3A4 substrate	-	0.8800	88.00%
CYP2C9 substrate	+	0.5802	58.02%
CYP2D6 substrate	-	0.8608	86.08%
CYP3A4 inhibition	-	0.9574	95.74%
CYP2C9 inhibition	-	0.5999	59.99%
CYP2C19 inhibition	-	0.9399	93.99%
CYP2D6 inhibition	-	0.9803	98.03%
CYP1A2 inhibition	+	0.5081	50.81%
CYP2C8 inhibition	-	0.9397	93.97%
CYP inhibitory promiscuity	-	0.9628	96.28%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5738	57.38%
Carcinogenicity (trinary)	Non-required	0.7800	78.00%
Eye corrosion	-	0.9858	98.58%
Eye irritation	+	1.0000	100.00%
Skin irritation	+	0.5076	50.76%
Skin corrosion	-	0.9811	98.11%
Ames mutagenesis	-	0.9500	95.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9217	92.17%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	+	0.8125	81.25%
skin sensitisation	-	0.7638	76.38%
Respiratory toxicity	-	0.8889	88.89%
Reproductive toxicity	-	0.6000	60.00%
Mitochondrial toxicity	-	0.8875	88.75%
Nephrotoxicity	+	0.6163	61.63%
Acute Oral Toxicity (c)	IV	0.6304	63.04%
Estrogen receptor binding	-	0.9519	95.19%
Androgen receptor binding	-	0.7187	71.87%
Thyroid receptor binding	-	0.7303	73.03%
Glucocorticoid receptor binding	-	0.9116	91.16%
Aromatase binding	-	0.8799	87.99%
PPAR gamma	-	0.5765	57.65%
Honey bee toxicity	-	0.9679	96.79%
Biodegradation	+	0.7250	72.50%
Crustacea aquatic toxicity	-	0.9300	93.00%
Fish aquatic toxicity	+	0.7420	74.20%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	35481.3 nM	Potency	via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	31622.8 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.57%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.61%	95.50%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.75%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	86.62%	83.82%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	86.33%	93.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.64%	91.11%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	82.04%	87.67%
CHEMBL221	P23219	Cyclooxygenase-1	80.33%	90.17%
CHEMBL5847	P52895	Aldo-keto reductase family 1 member C2	80.10%	92.50%

Plants that contains it

• Antirrhinum majus
• Arabidopsis thaliana
• Hunteria zeylanica
• Isatis tinctoria
• Pycnarrhena ozantha
• Tecoma stans
• Thymus quinquecostatus
• Thymus vulgaris

Cross-Links

• PubChem: 227
• NPASS: NPC130931
• ChEMBL: CHEMBL14173
• LOTUS: LTS0061170
• wikiData: Q385140