Methyl 2,4-dihydroxy-6-methylbenzoate - Compound Card

Methyl 2,4-dihydroxy-6-methylbenzoate

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Methyl 2,4-dihydroxy-6-methylbenzoate

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi, Plantae
  • Class: Phenolic
    • Subclass: Phenolic Acid Derivative
Canonical Smiles COC(=O)c1c(C)cc(cc1O)O
InChI InChI=1S/C9H10O4/c1-5-3-6(10)4-7(11)8(5)9(12)13-2/h3-4,10-11H,1-2H3
InChIKey NCCWCZLEACWJIN-UHFFFAOYSA-N
Formula C9H10O4
HBA 4
HBD 2
MW 182.18
Rotatable Bonds 1
TPSA 66.76
LogP 1.19
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 13
Formal Charge 0
Fraction CSP3 0.22
Exact Mass 182.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Trilepisium madagascariense Moraceae Plantae 241931
2 Aspergillus versicolor Trichocomaceae Fungi 46472

Showing of synonyms

  • Abdelwahab M, Kurtán T, et al. (2018). Induced secondary metabolites from the endophytic fungus Aspergillus versicolor through bacterial co-culture and OSMAC approaches. Tetrahedron Letters,2018,59(27),2647-2652. [View]
  • Ango YP, Kapche GDWF, et al. (2016). Three New Derivatives and Others Constituents from the Roots and Twigs of Trilepisium madagascariense DC. Helvetica Chimica Acta, 2016, 99:642-649. [View]
Pubchem: 76658
Chebi: 67898
Nmrshiftdb2: 70000328
Metabolights: MTBLC67898
Bindingdb: 50294528

No compound-protein relationship available.

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 182.18 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.5
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.410
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.47

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.560
Plasma Protein Binding
16.23
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
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
8.910
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.770
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.600
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.010
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
3.390
Rat (Acute)
1.990
Rat (Chronic Oral)
2.670
Fathead Minnow
3.950
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
297.970
Hydration Free Energy
-10.910
Log(D) at pH=7.4
1.950
Log(P)
2.28
Log S
-2.5
Log(Vapor Pressure)
-3.65
Melting Point
102.02
pKa Acid
8.48
pKa Basic
4.41
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 0.9481
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9303
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.9215
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9101
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8974
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8933
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8932
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8909
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8882
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8823
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8806
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8747
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8742
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8639
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8627
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8509
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.8491
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8486
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8298
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8190
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8184
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.8180
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8161
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8153
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8119
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8086
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8081
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7982
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7982
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7958
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7955
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7923
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7908
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7853
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7827
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7802
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7788
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7777
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7741
orotidine-5'-phosphate decarboxylase Q8T6J6 Q8T6J6_PLAFA Plasmodium falciparum 4 0.7736
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7734
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 3 0.7723
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7674
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7597
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7567
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7551
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7544
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7508
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.7479
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7409
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7398
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7357
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7356
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7341
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7320
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 4 0.7312
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7310
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7290
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7289
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7255
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7242
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7223
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7223
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7218
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7202
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7200
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7199
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7195
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7162
Catechol 2,3-dioxygenase Q6REQ5 Q6REQ5_9NOCA Rhodococcus sp. DK17 3 0.7151
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7146
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7144
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7116
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7116
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7116
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7112
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7110
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7102
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7093
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7089
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.7078
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7075
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7074
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7071
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7071
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7060
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7059
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7043
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7028
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7019
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7017

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