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Benzoic acid, 4‐hydroxy‐3‐methoxy‐, methyl ester
- Family: Plantae - Chenopodiaceae
- Kingdom: Plantae
- Class: Alkaloid
| Canonical Smiles | COC(=O)c1ccc(c(c1)OC)O |
|---|---|
| InChI | InChI=1S/C9H10O4/c1-12-8-5-6(9(11)13-2)3-4-7(8)10/h3-5,10H,1-2H3 |
| InChIKey | BVWTXUYLKBHMOX-UHFFFAOYSA-N |
| Formula | C9H10O4 |
| HBA | 4 |
| HBD | 1 |
| MW | 182.17 |
| Rotatable Bonds | 2 |
| TPSA | 55.76 |
| 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 | Haloxylon scoparium | Chenopodiaceae | Plantae | 1665493 |
Showing of synonyms
Benzoic acid, 4‐hydroxy‐3‐methoxy‐, methyl ester
Methyl vanillate
Methyl 4-hydroxy-3-methoxybenzoate
3943-74-6
Methyl 3-methoxy-4-hydroxybenzoate
Vanillic acid, methyl ester
4-Hydroxy-3-methoxybenzoic acid methyl ester
BENZOIC ACID, 4-HYDROXY-3-METHOXY-, METHYL ESTER
Methylvanillate
UNII-2HXG8QSO3D
2HXG8QSO3D
EINECS 223-525-9
NSC 74385
Vanillic acid methyl
BRN 1369113
Methyl Vanillic Acid
CHEBI:46477
AI3-20212
4-hydroxy-3-methoxy methyl benzoate
NSC-74385
DTXSID5074345
3-10-00-01410 (Beilstein Handbook Reference)
Methyl ester of 4-hydroxy-3-methoxybenzoic acid
DTXCID6039631
Vanillic acid, methyl ester (8CI)
223-525-9
Bvwtxuylkbhmox-uhfffaoysa-n
Inchi=1/c9h10o4/c1-12-8-5-6(9(11)13-2)3-4-7(8)10/h3-5,10h,1-2h
Vanillic acid methyl ester
MFCD00008438
VXX
Methyl4-hydroxy-3-methoxybenzoate
Methyl vanillate, 99%
Bmse010226
SCHEMBL275939
CHEMBL486214
Methyl vanillate, >=98%, FG
CS-D0814
NSC74385
Methyl 4-hydroxy-3-methoxy-benzoate
Methyl 4-hydroxy-3-methyoxybenzoate
S3630
Methyl (3-methoxy-4-hydroxy)benzoate
AKOS000120673
AC-9615
CCG-266450
DB08711
FV71320
PB42723
Methyl 4-hydroxy-3-(methyloxy)benzoate
AS-13512
HY-75342
SY003406
DB-007671
M1738
NS00013010
4-hydroxy-3-methoxy benzoic acid methyl ester
4-hydroxy-3-methoxy-benzoic acid methyl ester
4-hydroxy-5-methoxy-benzoic acid methyl ester
EN300-21518
3-methoxy-4-(hydroxy)benzoic acid methyl ester
4-hydroxy-5-methoxy -benzoic acid methyl ester
Q27097897
Z104500600
Methyl-4-hydroxy-3-methoxybenzoate
Pubchem:
19844
Cas:
3943-74-6
Gnps:
CCMSLIB00005883373
Zinc:
ZINC000000388238
Chebi:
46477
Nmrshiftdb2:
20044531
Metabolights:
MTBLC46477
Chembl:
CHEMBL486214
Comptox:
DTXSID5074345
Drugbank:
DB08711
Pdb Ligand:
VXX
CPRiL:
120175
SMILES: c1ccccc1
Level: 0
Mol. Weight: 182.17 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.56
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.190
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.05
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.400
- Plasma Protein Binding
- 8.86
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- 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
- 7.100
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 1.030
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.940
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.110
- Micronucleos
- Safe
- 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
- 3.420
- Rat (Acute)
- 1.970
- Rat (Chronic Oral)
- 2.390
- Fathead Minnow
- 3.930
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 287.070
- Hydration Free Energy
- -8.480
- Log(D) at pH=7.4
- 2.110
- Log(P)
- 1.87
- Log S
- -2.04
- Log(Vapor Pressure)
- -2.99
- Melting Point
- 81.22
- pKa Acid
- 7.71
- pKa Basic
- 1.46
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.9637 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.9462 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.9454 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.9390 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9250 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.9243 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.9166 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8921 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.8891 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.8784 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8763 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.8638 |
| Glycogenin-1 | P46976 | GLYG_HUMAN | Homo sapiens | 3 | 0.8525 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8502 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.8491 |
| Toxoflavin degrading enzyme | E3SET7 | E3SET7_PAEPO | Paenibacillus polymyxa | 3 | 0.8401 |
| S-norcoclaurine synthase | Q67A25 | NCS_THLFG | Thalictrum flavum subsp. glaucum | 3 | 0.8381 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.8347 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 3 | 0.8270 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.8237 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.8213 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.8152 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.8093 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.8091 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 2 | 0.7926 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.7903 |
| Tyrosine-protein kinase JAK1 | P23458 | JAK1_HUMAN | Homo sapiens | 3 | 0.7902 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7798 |
| L-methionine gamma-lyase | P13254 | MEGL_PSEPU | Pseudomonas putida | 3 | 0.7619 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.7583 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.7575 |
| Peroxidase C1A | P00433 | PER1A_ARMRU | Armoracia rusticana | 2 | 0.7510 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7507 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7498 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7490 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7487 |
| Uncharacterized protein | Q3F0V8 | Q3F0V8_BACTI | Bacillus thuringiensis serovar israelensis ATCC 35646 | 3 | 0.7476 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 3 | 0.7470 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7453 |
| 3',5'-cyclic-AMP phosphodiesterase 4B | Q07343 | PDE4B_HUMAN | Homo sapiens | 3 | 0.7449 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7439 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.7432 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 2 | 0.7422 |
| ATP-dependent protease subunit HslV | P0A7B8 | HSLV_ECOLI | Escherichia coli | 3 | 0.7397 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7380 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7362 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7356 |
| Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial | Q8N5Z0 | AADAT_HUMAN | Homo sapiens | 2 | 0.7338 |
| Tannase | B3Y018 | B3Y018_LACPN | Lactiplantibacillus plantarum | 3 | 0.7336 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7327 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 2 | 0.7324 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 2 | 0.7317 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7313 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7309 |
| Metallo-beta-lactamase type 2 | P26918 | BLAB_AERHY | Aeromonas hydrophila | 2 | 0.7303 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 2 | 0.7298 |
| Ceramide transfer protein | Q9Y5P4 | CERT_HUMAN | Homo sapiens | 2 | 0.7277 |
| Histone-lysine N-methyltransferase SETD7 | Q8WTS6 | SETD7_HUMAN | Homo sapiens | 3 | 0.7276 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.7256 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7252 |
| Ribosomal RNA small subunit methyltransferase Nep1 | Q57977 | NEP1_METJA | Methanocaldococcus jannaschii | 3 | 0.7211 |
| Adenylosuccinate synthetase isozyme 1 | P28650 | PURA1_MOUSE | Mus musculus | 4 | 0.7203 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7197 |
| chitinase | B0Y2Y2 | B0Y2Y2_ASPFC | Aspergillus fumigatus | 3 | 0.7190 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7179 |
| Histone-lysine N-methyltransferase EHMT2 | Q96KQ7 | EHMT2_HUMAN | Homo sapiens | 3 | 0.7178 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7177 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7162 |
| Histone-lysine N-methyltransferase 2A | Q03164 | KMT2A_HUMAN | Homo sapiens | 3 | 0.7152 |
| Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 | Q8GZB6 | SUVH4_ARATH | Arabidopsis thaliana | 3 | 0.7150 |
| Mitogen-activated protein kinase kinase kinase 5 | Q99683 | M3K5_HUMAN | Homo sapiens | 2 | 0.7140 |
| Tannase | B3Y018 | B3Y018_LACPN | Lactiplantibacillus plantarum | 3 | 0.7138 |
| Transitional endoplasmic reticulum ATPase | P55072 | TERA_HUMAN | Homo sapiens | 3 | 0.7123 |
| Catalase-peroxidase | Q3JNW6 | KATG_BURP1 | Burkholderia pseudomallei | 2 | 0.7121 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.7118 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7115 |
| N-acetyltransferase domain-containing protein | Q9HV14 | Q9HV14_PSEAE | Pseudomonas aeruginosa | 3 | 0.7114 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7112 |
| Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 3 | 0.7107 |
| Histone-lysine N-methyltransferase 2C | Q8NEZ4 | KMT2C_HUMAN | Homo sapiens | 3 | 0.7102 |
| tRNA (guanine-N(1)-)-methyltransferase | Q2GIL5 | TRMD_ANAPZ | Anaplasma phagocytophilum | 3 | 0.7099 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7097 |
| 16S rRNA (adenine(1408)-N(1))-methyltransferase | A8C927 | NPMA_ECOLX | Escherichia coli | 3 | 0.7084 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7079 |
| dTDP-4-dehydrorhamnose 3,5-epimerase | A0A6L7H6N0 | A0A1S0QLH9_BACAN | Bacillus anthracis | 3 | 0.7076 |
| Inosine-5'-monophosphate dehydrogenase | P50097 | IMDH_TRIFO | Tritrichomonas foetus | 2 | 0.7074 |
| Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 3 | 0.7064 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 2 | 0.7061 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 3 | 0.7060 |
| Tyrosine-protein kinase JAK1 | P23458 | JAK1_HUMAN | Homo sapiens | 3 | 0.7058 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7055 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7054 |
| SKP1-like protein 1A | Q39255 | SKP1A_ARATH | Arabidopsis thaliana | 3 | 0.7050 |
| Rho family GTPase | C4M4W4 | C4M4W4_ENTHI | Entamoeba histolytica | 4 | 0.7049 |
| Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 3 | 0.7047 |
| Beta-galactoside alpha-2,6-sialyltransferase 1 | P15907 | SIAT1_HUMAN | Homo sapiens | 3 | 0.7040 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7031 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7029 |
| Uridine phosphorylase | P0A1F6 | UDP_SALTY | Salmonella typhimurium | 3 | 0.7025 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7007 |
| dTDP-4-dehydro-6-deoxyglucose 3-epimerase | Q5SFD1 | CHMJ_STRBI | Streptomyces bikiniensis | 3 | 0.7007 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7006 |