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6-methylsalicylic acid
- Family: Fungi - Trichocomaceae
- Kingdom: Fungi
- Class: Monoaromatic
| Canonical Smiles | OC(=O)c1c(C)cccc1O |
|---|---|
| InChI | InChI=1S/C8H8O3/c1-5-3-2-4-6(9)7(5)8(10)11/h2-4,9H,1H3,(H,10,11) |
| InChIKey | HCJMNOSIAGSZBM-UHFFFAOYSA-N |
| Formula | C8H8O3 |
| HBA | 2 |
| HBD | 2 |
| MW | 152.15 |
| Rotatable Bonds | 1 |
| TPSA | 57.53 |
| LogP | 1.4 |
| Number Rings | 1 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 11 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.12 |
| Exact Mass | 152.05 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Geosmithia langdonii | Incertae sedis | Fungi | 240214 |
| 2 | Aspergillus flavipes | Trichocomaceae | Fungi | 41900 |
Showing of synonyms
6-methylsalicylic acid
2-HYDROXY-6-METHYLBENZOIC ACID
567-61-3
6-Hydroxy-o-toluic acid
2,6-Cresotic acid
Benzoic acid, 2-hydroxy-6-methyl-
6-MSA
Methylsalicylic acid
NSC 403256
UNII-L5352FE23Y
BRN 2208693
CHEBI:17637
L5352FE23Y
NSC-403256
DTXSID20205257
4-10-00-00594 (Beilstein Handbook Reference)
DTXCID20127748
6-Methyl-2-hydroxybenzenecarboxylic acid
Benzoic acid, 2-hydroxy-6-methyl-(9CI)
35745-30-3
2-hydroxymethylbenzoate
Hcjmnosiagszbm-uhfffaoysa-n
6-MS
MFCD01194284
6-Methyl-2-hydroxybenzenecarboxylate
2-Hydroxy-6-methylbenzoicacid
2-hydroxy-6-methyl-benzoic acid
SCHEMBL147955
CHEMBL510026
2-Hydroxy-6-methylbenzoic acid #
BCP05389
GEO-04151
LMPK13010002
NSC403256
AKOS004907081
AC-5291
CS-W002751
FH69926
FS-2603
MB01720
PD016989
SY030546
DB-006156
C02657
EN300-105059
Q6172528
- Malak LG, Ibrahim MA, et al. (2014). Antileishmanial metabolites from geosmithia langdonii. Journal of Natural Products,2014,77(9),1987-1991. [View] [PubMed]
- Nagia MM, El-Metwally MM, et al. (2012). Four butyrolactones and diverse bioactive secondary metabolites from terrestrial Aspergillus flavipes MM2: isolation and structure determination. Organic and Medicinal Chemistry Letters,2012,2(1),9. [View] [PubMed]
Pubchem:
11279
Cas:
567-61-3
Zinc:
ZINC000000901434
Kegg Ligand:
C02657
Chebi:
17637
Nmrshiftdb2:
60033064
Metabolights:
MTBLC17637
Chembl:
CHEMBL510026
Comptox:
DTXSID20205257
CPRiL:
95037
SMILES: c1ccccc1
Level: 0
Mol. Weight: 152.15 g/mol
Anti-leishmanial
Absorption
- Caco-2 (logPapp)
- -5.3
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -3.66
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.64
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.71
- Plasma Protein Binding
- 35.27
- 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
- 12.42
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 0.11
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 2.49
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 2.4
- 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
- 2.52
- Rat (Acute)
- 2.52
- Rat (Chronic Oral)
- 2.99
- Fathead Minnow
- 3.53
- 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
- 279.07
- Hydration Free Energy
- -5.51
- Log(D) at pH=7.4
- 0.47
- Log(P)
- 2.19
- Log S
- -2.36
- Log(Vapor Pressure)
- -5.85
- Melting Point
- 183.98
- pKa Acid
- 2.97
- pKa Basic
- 5.7
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9313 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9313 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.9286 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.9286 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9014 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9014 |
| Biotin carboxylase | P24182 | ACCC_ECOLI | Escherichia coli | 3 | 0.8747 |
| Biotin carboxylase | P24182 | ACCC_ECOLI | Escherichia coli | 3 | 0.8747 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.8700 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.8700 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.8400 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.8400 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.8384 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.8384 |
| glutaryl-CoA dehydrogenase (ETF) | Q3JP94 | Q3JP94_BURP1 | Burkholderia pseudomallei | 2 | 0.8331 |
| glutaryl-CoA dehydrogenase (ETF) | Q3JP94 | Q3JP94_BURP1 | Burkholderia pseudomallei | 2 | 0.8331 |
| Transcriptional activator, LuxR/UhpA family of regulators | Q7NQP7 | Q7NQP7_CHRVO | Chromobacterium violaceum | 3 | 0.8144 |
| Transcriptional activator, LuxR/UhpA family of regulators | Q7NQP7 | Q7NQP7_CHRVO | Chromobacterium violaceum | 3 | 0.8144 |
| Cytochrome P450 2E1 | P05181 | CP2E1_HUMAN | Homo sapiens | 3 | 0.8078 |
| Cytochrome P450 2E1 | P05181 | CP2E1_HUMAN | Homo sapiens | 3 | 0.8078 |
| Pteridine reductase, putative | Q581W1 | Q581W1_TRYB2 | Trypanosoma brucei brucei | 3 | 0.8044 |
| Pteridine reductase, putative | Q581W1 | Q581W1_TRYB2 | Trypanosoma brucei brucei | 3 | 0.8044 |
| Neutrophil gelatinase-associated lipocalin | P80188 | NGAL_HUMAN | Homo sapiens | 3 | 0.7918 |
| Neutrophil gelatinase-associated lipocalin | P80188 | NGAL_HUMAN | Homo sapiens | 3 | 0.7918 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7867 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7867 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7860 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7860 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7823 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7823 |
| Branched-chain-amino-acid aminotransferase, mitochondrial | O15382 | BCAT2_HUMAN | Homo sapiens | 3 | 0.7771 |
| Branched-chain-amino-acid aminotransferase, mitochondrial | O15382 | BCAT2_HUMAN | Homo sapiens | 3 | 0.7771 |
| Mandelate racemase | P11444 | MANR_PSEPU | Pseudomonas putida | 3 | 0.7674 |
| Mandelate racemase | P11444 | MANR_PSEPU | Pseudomonas putida | 3 | 0.7674 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7658 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7658 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7602 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7602 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7594 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7594 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7587 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7587 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7574 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7574 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7565 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7565 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7529 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7529 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7529 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7529 |
| Mandelate racemase | P11444 | MANR_PSEPU | Pseudomonas putida | 3 | 0.7527 |
| Mandelate racemase | P11444 | MANR_PSEPU | Pseudomonas putida | 3 | 0.7527 |
| Carbonic anhydrase 13 | Q8N1Q1 | CAH13_HUMAN | Homo sapiens | 3 | 0.7525 |
| Carbonic anhydrase 13 | Q8N1Q1 | CAH13_HUMAN | Homo sapiens | 3 | 0.7525 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | P13922 | DRTS_PLAFK | Plasmodium falciparum | 2 | 0.7500 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | P13922 | DRTS_PLAFK | Plasmodium falciparum | 2 | 0.7500 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7455 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7455 |
| Dicamba O-demethylase, oxygenase component | Q5S3I3 | DDMC_STEMA | Stenotrophomonas maltophilia | 3 | 0.7426 |
| Dicamba O-demethylase, oxygenase component | Q5S3I3 | DDMC_STEMA | Stenotrophomonas maltophilia | 3 | 0.7426 |
| L-lactate dehydrogenase A chain | P04642 | LDHA_RAT | Rattus norvegicus | 3 | 0.7416 |
| L-lactate dehydrogenase A chain | P04642 | LDHA_RAT | Rattus norvegicus | 3 | 0.7416 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7399 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7399 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7387 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7387 |
| Xanthine dehydrogenase/oxidase | P22985 | XDH_RAT | Rattus norvegicus | 3 | 0.7369 |
| Xanthine dehydrogenase/oxidase | P22985 | XDH_RAT | Rattus norvegicus | 3 | 0.7369 |
| Gibberellin receptor GID1A | Q9MAA7 | GID1A_ARATH | Arabidopsis thaliana | 3 | 0.7344 |
| Gibberellin receptor GID1A | Q9MAA7 | GID1A_ARATH | Arabidopsis thaliana | 3 | 0.7344 |
| Methionine aminopeptidase | P0AE18 | MAP1_ECOLI | Escherichia coli | 3 | 0.7333 |
| Methionine aminopeptidase | P0AE18 | MAP1_ECOLI | Escherichia coli | 3 | 0.7333 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.7312 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.7312 |
| Gibberellin receptor GID1 | Q6L545 | GID1_ORYSJ | Oryza sativa subsp. japonica | 3 | 0.7284 |
| Gibberellin receptor GID1 | Q6L545 | GID1_ORYSJ | Oryza sativa subsp. japonica | 3 | 0.7284 |
| Aldo-keto reductase family 1 member B1 | P80276 | ALDR_PIG | Sus scrofa | 2 | 0.7259 |
| Aldo-keto reductase family 1 member B1 | P80276 | ALDR_PIG | Sus scrofa | 2 | 0.7259 |
| Acetylcholinesterase | P22303 | ACES_HUMAN | Homo sapiens | 3 | 0.7220 |
| Acetylcholinesterase | P22303 | ACES_HUMAN | Homo sapiens | 3 | 0.7220 |
| Poly [ADP-ribose] polymerase 1 | P09874 | PARP1_HUMAN | Homo sapiens | 3 | 0.7217 |
| Poly [ADP-ribose] polymerase 1 | P09874 | PARP1_HUMAN | Homo sapiens | 3 | 0.7217 |
| Deacetoxycephalosporin C synthase | P18548 | CEFE_STRCL | Streptomyces clavuligerus | 3 | 0.7210 |
| Deacetoxycephalosporin C synthase | P18548 | CEFE_STRCL | Streptomyces clavuligerus | 3 | 0.7210 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7202 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7202 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7177 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7177 |
| Gastrotropin | Q6IMW5 | Q6IMW5_DANRE | Danio rerio | 2 | 0.7157 |
| Gastrotropin | Q6IMW5 | Q6IMW5_DANRE | Danio rerio | 2 | 0.7157 |
| N-acyl-aromatic-L-amino acid amidohydrolase (carboxylate-forming) | Q91XE4 | ACY3_MOUSE | Mus musculus | 3 | 0.7127 |
| N-acyl-aromatic-L-amino acid amidohydrolase (carboxylate-forming) | Q91XE4 | ACY3_MOUSE | Mus musculus | 3 | 0.7127 |
| Catechol 2,3-dioxygenase | Q6REQ5 | Q6REQ5_9NOCA | Rhodococcus sp. DK17 | 3 | 0.7077 |
| Catechol 2,3-dioxygenase | Q6REQ5 | Q6REQ5_9NOCA | Rhodococcus sp. DK17 | 3 | 0.7077 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7068 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7068 |
| Cyclic GMP-AMP phosphodiesterase SMPDL3A | Q92484 | ASM3A_HUMAN | Homo sapiens | 2 | 0.7013 |
| Cyclic GMP-AMP phosphodiesterase SMPDL3A | Q92484 | ASM3A_HUMAN | Homo sapiens | 2 | 0.7013 |