Anthranilic acid - Compound Card

Anthranilic acid

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Anthranilic acid

Structure
Zoomed Structure
  • Family: Monera - Streptomycetaceae
  • Kingdom: Monera
  • Class: Monoaromatic
Canonical Smiles OC(=O)c1ccccc1N
InChI InChI=1S/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10)
InChIKey RWZYAGGXGHYGMB-UHFFFAOYSA-N
Formula C7H7NO2
HBA 2
HBD 2
MW 137.14
Rotatable Bonds 1
TPSA 63.32
LogP 0.97
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 10
Formal Charge 0
Fraction CSP3 0.0
Exact Mass 137.05
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Streptomyces species Eg8. Streptomycetaceae Monera 1883

Showing of synonyms

  • Abdelfattah MS (2014). Isolation and crystal structure of a new anthraquinone derivative from Actinomycete.. Chemistry of Natural Compounds,2014,50(4),613-616. [View]
Pubchem: 227
Kegg Ligand: C00108
Chebi: 30754
Nmrshiftdb2: 10008784
Metabolights: MTBLC30754
Drugbank: DB04166
Pdb Ligand: BE2
Bindingdb: 50376751
CPRiL: 7053
Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 137.14 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.72
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.37
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.92

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
-0.37
Plasma Protein Binding
33.79
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.47
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.35
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
2.44
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
2.65
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
1.23
Rat (Acute)
1.6
Rat (Chronic Oral)
2.98
Fathead Minnow
2.97
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
285.97
Hydration Free Energy
-9.29
Log(D) at pH=7.4
-1.29
Log(P)
1.12
Log S
-1.76
Log(Vapor Pressure)
-4.63
Melting Point
185.51
pKa Acid
1.92
pKa Basic
5.01
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.9194
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.9194
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 3 0.9111
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 3 0.9111
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.9061
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.9061
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8936
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8936
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8915
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8915
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.8858
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.8858
Isochorismate pyruvate lyase Q51507 PCHB_PSEAE Pseudomonas aeruginosa 3 0.8685
Isochorismate pyruvate lyase Q51507 PCHB_PSEAE Pseudomonas aeruginosa 3 0.8685
Ornithine transcarbamylase, mitochondrial P00480 OTC_HUMAN Homo sapiens 3 0.8562
Ornithine transcarbamylase, mitochondrial P00480 OTC_HUMAN Homo sapiens 3 0.8562
rRNA methylase Q8DSS3 Q8DSS3_STRMU Streptococcus mutans serotype c 2 0.8504
rRNA methylase Q8DSS3 Q8DSS3_STRMU Streptococcus mutans serotype c 2 0.8504
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8504
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8504
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.8457
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.8457
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8372
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8372
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8347
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8347
L-lactate dehydrogenase (cytochrome) P00175 CYB2_YEAST Saccharomyces cerevisiae 3 0.8341
L-lactate dehydrogenase (cytochrome) P00175 CYB2_YEAST Saccharomyces cerevisiae 3 0.8341
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8261
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8261
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8204
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8204
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 3 0.8148
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 3 0.8148
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8122
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8122
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8064
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8064
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 3 0.7959
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 3 0.7959
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 2 0.7950
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 2 0.7950
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7935
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7935
Nicotinamide phosphoribosyltransferase P43490 NAMPT_HUMAN Homo sapiens 3 0.7891
Nicotinamide phosphoribosyltransferase P43490 NAMPT_HUMAN Homo sapiens 3 0.7891
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7859
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7859
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7849
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7849
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7839
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7839
Class 10 plant pathogenesis-related protein 2B Q9LLQ2 P102B_LUPLU Lupinus luteus 2 0.7752
Class 10 plant pathogenesis-related protein 2B Q9LLQ2 P102B_LUPLU Lupinus luteus 2 0.7752
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7712
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7712
4-substituted benzoates-glutamate ligase GH3.12 Q9LYU4 GH312_ARATH Arabidopsis thaliana 3 0.7674
4-substituted benzoates-glutamate ligase GH3.12 Q9LYU4 GH312_ARATH Arabidopsis thaliana 3 0.7674
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7662
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7662
histone deacetylase A5H660 A5H660_SCHMA Schistosoma mansoni 3 0.7629
histone deacetylase A5H660 A5H660_SCHMA Schistosoma mansoni 3 0.7629
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7525
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7525
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7441
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7441
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7389
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7389
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7376
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7376
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7375
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7375
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7327
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7327
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 2 0.7320
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 2 0.7320
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7285
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7285
3-oxoacyl-[acyl-carrier-protein] synthase 1 Q2YQQ9 Q2YQQ9_BRUA2 Brucella abortus 3 0.7270
3-oxoacyl-[acyl-carrier-protein] synthase 1 Q2YQQ9 Q2YQQ9_BRUA2 Brucella abortus 3 0.7270
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7214
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7214
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7192
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7192
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7185
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7185
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7175
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7175
Feruloyl esterase A O42807 FAEA_ASPNG Aspergillus niger 2 0.7174
Feruloyl esterase A O42807 FAEA_ASPNG Aspergillus niger 2 0.7174
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7163
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7163
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7138
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7138
Genome polyprotein P27395 POLG_JAEV1 Japanese encephalitis virus 2 0.7126
Genome polyprotein P27395 POLG_JAEV1 Japanese encephalitis virus 2 0.7126
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7091
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7091
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7083
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7083
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7078
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7078
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 2 0.7068
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 2 0.7068
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7067
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7067
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 3 0.7065
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 3 0.7065
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7047
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7047
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 2 0.7043
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 2 0.7043
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 3 0.7039
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 3 0.7039
Carboxyethyl-arginine beta-lactam-synthase P0DJQ7 BLS_STRCL Streptomyces clavuligerus 2 0.7035
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 2 0.7035
Carboxyethyl-arginine beta-lactam-synthase P0DJQ7 BLS_STRCL Streptomyces clavuligerus 2 0.7035
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 2 0.7035
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7022
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7022
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7009
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7009
Anthranilate phosphoribosyltransferase P50384 TRPD_SACS2 Saccharolobus solfataricus 2 0.7002
Anthranilate phosphoribosyltransferase P50384 TRPD_SACS2 Saccharolobus solfataricus 2 0.7002

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