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Methyl (E)-3-(4‐hydroxy‐3-methoxyphenyl)acrylate
- Family: Plantae - Chenopodiaceae
- Kingdom: Plantae
-
Class: Phenolic
- Subclass: Hydroxycinnamic Acid
| Canonical Smiles | COC(=O)/C=C/c1ccc(c(c1)OC)O |
|---|---|
| InChI | InChI=1S/C11H12O4/c1-14-10-7-8(3-5-9(10)12)4-6-11(13)15-2/h3-7,12H,1-2H3/b6-4+ |
| InChIKey | AUJXJFHANFIVKH-GQCTYLIASA-N |
| Formula | C11H12O4 |
| HBA | 4 |
| HBD | 1 |
| MW | 208.21 |
| Rotatable Bonds | 3 |
| TPSA | 55.76 |
| LogP | 1.59 |
| Number Rings | 1 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 15 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.18 |
| Exact Mass | 208.07 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Haloxylon scoparium | Chenopodiaceae | Plantae | 1665493 |
| 2 | Suaeda maritima | Chenopodiaceae | Plantae | 126913 |
Showing of synonyms
Methyl (E)-3-(4‐hydroxy‐3-methoxyphenyl)acrylate
Methyl ferulate
Ferulic acid methyl ester
2309-07-1
2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, methyl ester
Trans-Ferulic acid methyl ester
Methyl trans-ferulate
Methyl ferulate, (E)-
Y98BUA66RX
CINNAMIC ACID, 4-HYDROXY-3-METHOXY-, METHYL ESTER
Methyl (E)-4-hydroxy-3-methoxycinnamate
NSC 74548
NSC-74548
UNII-Y98BUA66RX
Methyl 4'-hydroxy-3'-methoxycinnamate
BRN 2731141
AI3-23713
4-10-00-01779 (Beilstein Handbook Reference)
Methyl 3-(4-hydroxy-3-methoxyphenyl)acrylate
22329-76-6
Methyl 4-hydroxy-3-methoxycinnamate
Trans-methylferulate
Ferulic acid methylester
CHEBI:67379
Methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
CHEMBL32969
Methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
2-propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, methyl ester, (2E)-
(E)-Methyl 3-(4-hydroxy-3-methoxyphenyl)acrylate
Methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)acrylate
MFCD00017208
Methyl (E)-3-(4-hydroxy-3-methoxyphenyl)acrylate
Bmse000609
Bmse010229
(E)-Ferulic acid methyl ester
ALBB-026142
NSC74548
BDBM50236705
S5451
STK665368
AKOS003404666
AKOS025310509
CCG-266639
CS-W019429
FM33217
GS-3694
HY-W018643
BS-48861
DA-55389
FM133555
EN300-28623
4-hydroxy-3-methoxy-cinnamic acid methyl ester
O11884
(E)-4-hydroxy-3-methoxycinnamic acid methyl ester
(E)4-hydroxy-3-methoxycinnamic acid methyl ester
Methyl(E)-3-(4-hydroxy-3-methoxyphenyl)acrylate
Q27135838
Z18704892
Methyl (E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoate
Methyl(2e)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoate
Methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoate
Methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoate #
Methyl (E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoate
2-Propenoic acid, (2E)-hydroxy-3-methoxyphenyl)-methyl ester
3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid methyl ester
Methyl (~{E})-3-(3-methoxy-4-oxidanyl-phenyl)prop-2-enoate
- Lachkar N, Lamchouri F, et al. (2021). Chemical composition, phenolic content and antioxidant capacity of Haloxylon scoparium extracts. Evidence-based complementary and alternative medicine : eCAM, 2021, 2021, 9011168. [View] [PubMed]
- Abd El-Latif R.R, Mansour R.M, et al. (2014). Three new flavonol glycosides from Suaeda maritima. Journal of Asian natural products research, 2014, 16(5), 434-9. [View] [PubMed]
Pubchem:
5357283
Cas:
2309-07-1
Zinc:
ZINC000001621053
Chebi:
67379
Nmrshiftdb2:
60021798
Metabolights:
MTBLC67379
Chembl:
CHEMBL32969
Pdb Ligand:
SZQ
Bindingdb:
50236705
CPRiL:
106896
SMILES: c1ccccc1
Level: 0
Mol. Weight: 208.21 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.54
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.240
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.86
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.530
- Plasma Protein Binding
- 17.75
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-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
- 7.010
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 0.950
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.710
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.700
- 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
- 3.910
- Rat (Acute)
- 2.060
- Rat (Chronic Oral)
- 2.360
- Fathead Minnow
- 4.210
- 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
- 317.790
- Hydration Free Energy
- -8.860
- Log(D) at pH=7.4
- 1.960
- Log(P)
- 1.97
- Log S
- -2.5
- Log(Vapor Pressure)
- -3.82
- Melting Point
- 98.28
- pKa Acid
- 8.84
- pKa Basic
- 2.64
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.9644 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9517 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.9461 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.9312 |
| Valacyclovir hydrolase | Q86WA6 | BPHL_HUMAN | Homo sapiens | 3 | 0.9258 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.9119 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.9069 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8977 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8861 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8812 |
| Caffeic acid O-methyltransferase | Q9ZTU2 | Q9ZTU2_LOLPR | Lolium perenne | 4 | 0.8760 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.8748 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 4 | 0.8702 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8691 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.8656 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.8633 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 3 | 0.8576 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.8531 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8309 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.8270 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.8265 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8208 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8109 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.8102 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.8099 |
| 2-aminohexano-6-lactam racemase | Q7M181 | ACLR_ACHOB | Achromobacter obae | 3 | 0.8063 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8020 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7874 |
| Tyrosine-protein kinase JAK1 | P23458 | JAK1_HUMAN | Homo sapiens | 3 | 0.7865 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7861 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7811 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7770 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.7743 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7699 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.7653 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7648 |
| Ras-related protein Rap-1b | P61224 | RAP1B_HUMAN | Homo sapiens | 4 | 0.7639 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7635 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7623 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.7596 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7540 |
| 3',5'-cyclic-AMP phosphodiesterase 4B | Q07343 | PDE4B_HUMAN | Homo sapiens | 3 | 0.7534 |
| 16S rRNA (adenine(1408)-N(1))-methyltransferase | A8C927 | NPMA_ECOLX | Escherichia coli | 3 | 0.7512 |
| Deoxycytidine kinase | P27707 | DCK_HUMAN | Homo sapiens | 3 | 0.7470 |
| Deoxycytidine kinase | P27707 | DCK_HUMAN | Homo sapiens | 3 | 0.7470 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7450 |
| Threonine--tRNA ligase | P0A8M3 | SYT_ECOLI | Escherichia coli | 3 | 0.7445 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7408 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7398 |
| Histone-lysine N-methyltransferase SETD7 | Q8WTS6 | SETD7_HUMAN | Homo sapiens | 3 | 0.7325 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7316 |
| Thymidylate synthase | Q4JQW2 | TYSY_VZVO | Varicella-zoster virus | 3 | 0.7306 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7305 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7303 |
| Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 | Q8GZB6 | SUVH4_ARATH | Arabidopsis thaliana | 3 | 0.7295 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7295 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7280 |
| Beta-glucosidase 12 | B8AVF0 | BGL12_ORYSI | Oryza sativa subsp. indica | 2 | 0.7274 |
| Histone-lysine N-methyltransferase EHMT2 | Q96KQ7 | EHMT2_HUMAN | Homo sapiens | 3 | 0.7270 |
| Histone-lysine N-methyltransferase 2A | Q03164 | KMT2A_HUMAN | Homo sapiens | 3 | 0.7246 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7246 |
| DNA gyrase subunit A | P0AES5 | GYRA_SHIFL | Shigella flexneri | 3 | 0.7236 |
| BMP-2-inducible protein kinase | Q9NSY1 | BMP2K_HUMAN | Homo sapiens | 2 | 0.7236 |
| Histone-lysine N-methyltransferase 2C | Q8NEZ4 | KMT2C_HUMAN | Homo sapiens | 3 | 0.7224 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7221 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 4 | 0.7217 |
| L-methionine gamma-lyase | Q84AR1 | Q84AR1_CITFR | Citrobacter freundii | 3 | 0.7217 |
| Adenosine monophosphate-protein transferase | Q8ZVF7 | Q8ZVF7_PYRAE | Pyrobaculum aerophilum | 3 | 0.7203 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7187 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7184 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 2 | 0.7163 |
| DNA (cytosine-5)-methyltransferase 3A | O88508 | DNM3A_MOUSE | Mus musculus | 3 | 0.7162 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7159 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7154 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7151 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7127 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 4 | 0.7121 |
| Histone-lysine N-methyltransferase 2A | Q03164 | KMT2A_HUMAN | Homo sapiens | 3 | 0.7120 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 3 | 0.7112 |
| Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 3 | 0.7111 |
| 2-phospho-L-lactate transferase | Q8PVT6 | COFD_METMA | Methanosarcina mazei | 3 | 0.7103 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7097 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7093 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7085 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7084 |
| dTDP-4-dehydrorhamnose 3,5-epimerase | A0A6L7H6N0 | A0A1S0QLH9_BACAN | Bacillus anthracis | 3 | 0.7082 |
| Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 3 | 0.7075 |
| Tyrosine-protein kinase JAK1 | P23458 | JAK1_HUMAN | Homo sapiens | 3 | 0.7066 |
| DNA polymerase III subunit epsilon | P03007 | DPO3E_ECOLI | Escherichia coli | 2 | 0.7056 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7043 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 2 | 0.7037 |
| N-terminal acetyltransferase A complex subunit NAT1 | P12945 | NAT1_YEAST | Saccharomyces cerevisiae | 2 | 0.7031 |
| Uridine phosphorylase | P0A1F6 | UDP_SALTY | Salmonella typhimurium | 3 | 0.7026 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7021 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 2 | 0.7016 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7014 |
| Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial | Q8N5Z0 | AADAT_HUMAN | Homo sapiens | 2 | 0.7010 |
| WxcM-like protein | Q12KT8 | Q12KT8_SHEDO | Shewanella denitrificans | 3 | 0.7008 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7004 |