Gentisic acid - Compound Card

Gentisic acid

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Gentisic acid

Structure
Zoomed Structure
  • Family: Plantae - Rhamnaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Phenolic Acid
Canonical Smiles Oc1ccc(c(c1)C(=O)O)O
InChI InChI=1S/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11)
InChIKey WXTMDXOMEHJXQO-UHFFFAOYSA-N
Formula C7H6O4
HBA 3
HBD 3
MW 154.12
Rotatable Bonds 1
TPSA 77.76
LogP 0.8
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 11
Formal Charge 0
Fraction CSP3 0.0
Exact Mass 154.03
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cotoneaster orbicularis Rosaceae Plantae 1851000
2 Achyranthes aspera Amaranthaceae Plantae 240005
3 Rhamnus disperma Rhamnaceae Plantae 1813078

Showing of synonyms

  • Ndhlala AR, Ghebrehiwot HM, et al. (2015). Antimicrobial, anthelmintic activities and characterisation of functional phenolic acids of Achyranthes aspera linn.: a medicinal plant used for the treatment of wounds and Ringworm in East Africa.. Frontiers in pharmacology,2015,6,274. [View] [PubMed]
  • Marzouk M, El-Toumy S, et al. (1999). Polyphenolic metabolites of Rhamnus disperma. Phytochemistry, 1999, 52(5), 943-946. [View]
  • El-Mousallamy AM, Hussein SA, et al. (2000). Unusual phenolic glycosides from Cotoneaster orbicularis. Phytochemistry,2000,53(6),699-704. [View] [PubMed]
Pubchem: 3469
Kegg Ligand: C00628
Chebi: 17189
Nmrshiftdb2: 10009263
Metabolights: MTBLC17189
Chembl: CHEMBL1461
Pdb Ligand: GTQ
Bindingdb: 50335808
CPRiL: 2008
Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 154.12 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.21
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.440
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.51

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.750
Plasma Protein Binding
19.56
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
Non-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
6.980
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.520
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.720
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.180
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
1.730
Rat (Acute)
2.130
Rat (Chronic Oral)
3.370
Fathead Minnow
3.730
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
329.950
Hydration Free Energy
-11.370
Log(D) at pH=7.4
-1.330
Log(P)
1.73
Log S
-1.24
Log(Vapor Pressure)
-5.05
Melting Point
202.4
pKa Acid
5.2
pKa Basic
1.26
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.9015
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.9015
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.8895
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.8895
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8878
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8878
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8870
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8870
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8607
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8607
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8523
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8523
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 3 0.8489
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 3 0.8489
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8412
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8412
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8252
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8252
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.8162
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.8162
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.8155
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.8155
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8093
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8093
Glycogenin-1 P46976 GLYG_HUMAN Homo sapiens 3 0.8041
Glycogenin-1 P46976 GLYG_HUMAN Homo sapiens 3 0.8041
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.8037
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.8037
4-substituted benzoates-glutamate ligase GH3.12 Q9LYU4 GH312_ARATH Arabidopsis thaliana 3 0.8006
4-substituted benzoates-glutamate ligase GH3.12 Q9LYU4 GH312_ARATH Arabidopsis thaliana 3 0.8006
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 3 0.7961
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 3 0.7961
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7941
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7941
Glycogen synthase P0A6U8 GLGA_ECOLI Escherichia coli 3 0.7938
Glycogen synthase P0A6U8 GLGA_ECOLI Escherichia coli 3 0.7938
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7926
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7926
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7922
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.7922
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.7922
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7922
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7861
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7861
SKP1-like protein 1A Q39255 SKP1A_ARATH Arabidopsis thaliana 3 0.7852
SKP1-like protein 1A Q39255 SKP1A_ARATH Arabidopsis thaliana 3 0.7852
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.7718
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.7718
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7699
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7699
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7549
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7549
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7532
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7532
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 3 0.7521
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 3 0.7521
Anthranilate phosphoribosyltransferase P50384 TRPD_SACS2 Saccharolobus solfataricus 3 0.7496
Anthranilate phosphoribosyltransferase P50384 TRPD_SACS2 Saccharolobus solfataricus 3 0.7496
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7491
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7491
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7463
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7463
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7422
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7422
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7412
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7412
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7399
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7399
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7391
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7391
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7362
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7362
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 3 0.7357
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 3 0.7357
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7345
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7345
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 3 0.7332
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 3 0.7332
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7328
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7328
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7326
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7326
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7311
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7311
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7293
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7293
Aminotransferase homolog Q9S5Y7 Q9S5Y7_CAMJU Campylobacter jejuni 3 0.7285
Aminotransferase homolog Q9S5Y7 Q9S5Y7_CAMJU Campylobacter jejuni 3 0.7285
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7274
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7274
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 4 0.7248
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 4 0.7248
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7245
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7245
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7238
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7238
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7234
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7234
Anthranilate phosphoribosyltransferase P50384 TRPD_SACS2 Saccharolobus solfataricus 3 0.7233
Anthranilate phosphoribosyltransferase P50384 TRPD_SACS2 Saccharolobus solfataricus 3 0.7233
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7230
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7230
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7227
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7227
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7219
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7219
Carboxyethyl-arginine beta-lactam-synthase P0DJQ7 BLS_STRCL Streptomyces clavuligerus 3 0.7197
Carboxyethyl-arginine beta-lactam-synthase P0DJQ7 BLS_STRCL Streptomyces clavuligerus 3 0.7197
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 3 0.7172
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 3 0.7172
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7169
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7169
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7162
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7162
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7161
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7161
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7160
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7160
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7147
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7147
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7144
Inosine-5'-monophosphate dehydrogenase P50097 IMDH_TRIFO Tritrichomonas foetus 2 0.7144
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7144
Inosine-5'-monophosphate dehydrogenase P50097 IMDH_TRIFO Tritrichomonas foetus 2 0.7144
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7138
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7138
tRNA-guanine(15) transglycosylase O58843 ATGT_PYRHO Pyrococcus horikoshii 3 0.7130
tRNA-guanine(15) transglycosylase O58843 ATGT_PYRHO Pyrococcus horikoshii 3 0.7130
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7099
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7099
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7094
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7094
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7074
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7074
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7064
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7064
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7043
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7043
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7013
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7013
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7007
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7007
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7000
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7000

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