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Orsellinic acid
- Family: Fungi - Trichocomaceae
- Kingdom: Fungi
- Class: Monoaromatic
| Canonical Smiles | Oc1cc(C)c(c(c1)O)C(=O)O |
|---|---|
| InChI | InChI=1S/C8H8O4/c1-4-2-5(9)3-6(10)7(4)8(11)12/h2-3,9-10H,1H3,(H,11,12) |
| InChIKey | AMKYESDOVDKZKV-UHFFFAOYSA-N |
| Formula | C8H8O4 |
| HBA | 3 |
| HBD | 3 |
| MW | 168.15 |
| Rotatable Bonds | 1 |
| TPSA | 77.76 |
| LogP | 1.1 |
| Number Rings | 1 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 12 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.12 |
| Exact Mass | 168.04 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Aspergillus terreus | Trichocomaceae | Fungi | 33178 |
Showing of synonyms
Orsellinic acid
Benzoic acid, 2,4-dihydroxy-6-methyl-
610-404-4
2,4-Dihydroxy-6-methylbenzoic acid
480-64-8
O-Orsellinic acid
Orsellic acid
Orcinolcarboxylic acid
2,4-dihydroxy-6-methyl-benzoic acid
4,6-Dihydroxy-o-toluic acid
MFCD00210536
CHEBI:32807
2,4-Dihydroxy-6-methylbenzenecarboxylic acid
6-Methyl-.beta.-resorcylic acid
11XLA0494B
Orsellinate
4,6-Dihydroxy-2-methylbenzoic acid
2,4-Dihydroxy-6-methyl benzoic acid
2,4-Dihydroxy-6-methylbenzoate
6-Methyl-beta-resorcylic acid
Orsellinicacid
Orsellinsaeure
UNII-11XLA0494B
Spectrum_000594
SpecPlus_000120
Spectrum2_000305
Spectrum3_001284
Spectrum4_001598
Spectrum5_000316
6-Methyl- -resorcylic acid
BSPBio_002887
KBioGR_002216
KBioSS_001074
SPECTRUM300001
DivK1c_006216
SCHEMBL522294
SPBio_000270
CHEMBL457583
MEGxm0_000096
O-ORSELLINIC ACID [MI]
KBio1_001160
KBio2_001074
KBio2_003642
KBio2_006210
KBio3_002107
DTXSID20197385
HY-N3126
.beta.-Resorcylic acid, 6-methyl-
BBL103122
BDBM50104645
CCG-38582
LMPK13010001
STL556932
AKOS000349074
AB92942
FO67708
SDCCGMLS-0066472.P001
NCGC00095565-01
NCGC00095565-02
DA-56464
DS-17030
SY110288
CS-0023315
NS00031754
C01839
6-Methyl--resorcylic acid
Q414421
SR-05000002400
SR-05000002400-1
6X7
- Chen H, Daletos G, et al. (2015). Inducing secondary metabolite production by the soil-dwelling fungus Aspergillus terreus through bacterial co-culture. Phytochemistry Letters,2015,12,35-41. [View]
Pubchem:
68072
Cas:
480-64-8
Gnps:
CCMSLIB00005719618
Zinc:
ZINC000000901157
Kegg Ligand:
C01839
Chebi:
32807
Nmrshiftdb2:
60061725
Metabolights:
MTBLC32807
Chembl:
CHEMBL457583
Comptox:
DTXSID20197385
Pdb Ligand:
6X7
Bindingdb:
50104645
CPRiL:
287395
SMILES: c1ccccc1
Level: 0
Mol. Weight: 168.15 g/mol
Antibacterial
Absorption
- Caco-2 (logPapp)
- -5.41
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.230
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.39
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.700
- Plasma Protein Binding
- 28.94
- 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
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 13.040
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 0.650
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 2.280
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 2.150
- 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
- 3.890
- Rat (Acute)
- 2.110
- Rat (Chronic Oral)
- 3.130
- Fathead Minnow
- 3.560
- 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
- 304.280
- Hydration Free Energy
- -6.600
- Log(D) at pH=7.4
- 0.140
- Log(P)
- 1.79
- Log S
- -2.03
- Log(Vapor Pressure)
- -7.17
- Melting Point
- 256.1
- pKa Acid
- 3.35
- pKa Basic
- 6.7
| 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 | 0.9294 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9294 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.9044 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.9044 |
| Polymerase acidic protein | Q5EP34 | Q5EP34_9INFA | Influenza A virus | 3 | 0.8921 |
| Polymerase acidic protein | Q5EP34 | Q5EP34_9INFA | Influenza A virus | 3 | 0.8921 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 3 | 0.8909 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 3 | 0.8909 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8897 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8897 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.8880 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.8880 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.8801 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.8801 |
| LysR-type regulatory protein | Q7WT50 | Q7WT50_9BURK | Burkholderia sp. DNT | 3 | 0.8694 |
| LysR-type regulatory protein | Q7WT50 | Q7WT50_9BURK | Burkholderia sp. DNT | 3 | 0.8694 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.8636 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.8636 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 3 | 0.8606 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 3 | 0.8606 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 3 | 0.8602 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 3 | 0.8602 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.8473 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.8473 |
| Carbonic anhydrase 13 | Q8N1Q1 | CAH13_HUMAN | Homo sapiens | 3 | 0.8470 |
| Carbonic anhydrase 13 | Q8N1Q1 | CAH13_HUMAN | Homo sapiens | 3 | 0.8470 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8448 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8448 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8446 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8446 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8376 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8376 |
| Aromatic-amino-acid aminotransferase | P95468 | TYRB_PARDE | Paracoccus denitrificans | 3 | 0.8373 |
| Aromatic-amino-acid aminotransferase | P95468 | TYRB_PARDE | Paracoccus denitrificans | 3 | 0.8373 |
| Toxoflavin degrading enzyme | E3SET7 | E3SET7_PAEPO | Paenibacillus polymyxa | 3 | 0.8365 |
| Toxoflavin degrading enzyme | E3SET7 | E3SET7_PAEPO | Paenibacillus polymyxa | 3 | 0.8365 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8286 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8286 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8281 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8281 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8273 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8273 |
| L-lactate dehydrogenase A chain | P04642 | LDHA_RAT | Rattus norvegicus | 3 | 0.8172 |
| L-lactate dehydrogenase A chain | P04642 | LDHA_RAT | Rattus norvegicus | 3 | 0.8172 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.8139 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.8139 |
| Vanillate porin OpdK | Q9HUR5 | Q9HUR5_PSEAE | Pseudomonas aeruginosa | 3 | 0.8023 |
| Vanillate porin OpdK | Q9HUR5 | Q9HUR5_PSEAE | Pseudomonas aeruginosa | 3 | 0.8023 |
| Nitric oxide synthase 3 | P29474 | NOS3_HUMAN | Homo sapiens | 3 | 0.8016 |
| Nitric oxide synthase 3 | P29474 | NOS3_HUMAN | Homo sapiens | 3 | 0.8016 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7946 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7946 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7924 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7924 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7857 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7857 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 4 | 0.7729 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 4 | 0.7729 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 3 | 0.7727 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 3 | 0.7727 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP8 | DEOD_ECOLI | Escherichia coli | 3 | 0.7703 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP8 | DEOD_ECOLI | Escherichia coli | 3 | 0.7703 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7693 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7693 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7658 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7658 |
| Pteridine reductase, putative | Q581W1 | Q581W1_TRYB2 | Trypanosoma brucei brucei | 3 | 0.7628 |
| Pteridine reductase, putative | Q581W1 | Q581W1_TRYB2 | Trypanosoma brucei brucei | 3 | 0.7628 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 3 | 0.7588 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 3 | 0.7588 |
| Dihydropteroate synthase | Q81VW8 | Q81VW8_BACAN | Bacillus anthracis | 3 | 0.7568 |
| Dihydropteroate synthase | Q81VW8 | Q81VW8_BACAN | Bacillus anthracis | 3 | 0.7568 |
| Chorismate pyruvate-lyase | P26602 | UBIC_ECOLI | Escherichia coli | 3 | 0.7555 |
| Chorismate pyruvate-lyase | P26602 | UBIC_ECOLI | Escherichia coli | 3 | 0.7555 |
| Pantothenate synthetase | P9WIL4 | PANC_MYCTO | Mycobacterium tuberculosis | 3 | 0.7479 |
| Pantothenate synthetase | P9WIL4 | PANC_MYCTO | Mycobacterium tuberculosis | 3 | 0.7479 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.7464 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.7464 |
| glutaryl-CoA dehydrogenase (ETF) | Q3JP94 | Q3JP94_BURP1 | Burkholderia pseudomallei | 2 | 0.7425 |
| glutaryl-CoA dehydrogenase (ETF) | Q3JP94 | Q3JP94_BURP1 | Burkholderia pseudomallei | 2 | 0.7425 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7422 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7422 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7382 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7382 |
| LysR-type regulatory protein | Q7WT50 | Q7WT50_9BURK | Burkholderia sp. DNT | 3 | 0.7364 |
| LysR-type regulatory protein | Q7WT50 | Q7WT50_9BURK | Burkholderia sp. DNT | 3 | 0.7364 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.7275 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.7275 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7273 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7273 |
| Dicamba O-demethylase, oxygenase component | Q5S3I3 | DDMC_STEMA | Stenotrophomonas maltophilia | 3 | 0.7258 |
| Dicamba O-demethylase, oxygenase component | Q5S3I3 | DDMC_STEMA | Stenotrophomonas maltophilia | 3 | 0.7258 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7251 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7251 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7229 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7229 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7216 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7216 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7199 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7199 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7154 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7154 |
| Thiamine-phosphate synthase | P39594 | THIE_BACSU | Bacillus subtilis | 3 | 0.7136 |
| Thiamine-phosphate synthase | P39594 | THIE_BACSU | Bacillus subtilis | 3 | 0.7136 |
| cAMP-dependent protein kinase catalytic subunit alpha | P17612 | KAPCA_HUMAN | Homo sapiens | 3 | 0.7111 |
| cAMP-dependent protein kinase catalytic subunit alpha | P17612 | KAPCA_HUMAN | Homo sapiens | 3 | 0.7111 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.7087 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.7087 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7072 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7072 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7039 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7039 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 2 | 0.7008 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 2 | 0.7008 |