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Methyl-3,4,5-trimethoxycinnamate
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
- Class: Phenolic
| Canonical Smiles | COC(=O)/C=C/c1cc(OC)c(c(c1)OC)OC |
|---|---|
| InChI | InChI=1S/C13H16O5/c1-15-10-7-9(5-6-12(14)17-3)8-11(16-2)13(10)18-4/h5-8H,1-4H3/b6-5+ |
| InChIKey | KLXHCGFNNUQTEY-AATRIKPKSA-N |
| Formula | C13H16O5 |
| HBA | 5 |
| HBD | 0 |
| MW | 252.27 |
| Rotatable Bonds | 5 |
| TPSA | 53.99 |
| LogP | 1.9 |
| Number Rings | 1 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 18 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.31 |
| Exact Mass | 252.1 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Rauvolfia macrophylla | Apocynaceae | Plantae | 4059 |
Showing of synonyms
Methyl-3,4,5-trimethoxycinnamate
Methyl 3,4,5-trimethoxycinnamate
DTXSID001289631
Methyl (E)-3,4,5-trimethoxycinnamate
DTXCID501720252
672-252-5
20329-96-8
7560-49-8
Methyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate
2-Propenoic acid, 3-(3,4,5-trimethoxyphenyl)-, methyl ester, (2E)-
3,4,5-Trimethoxybenzeneacrylic acid methyl ester
Methyl (E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate
Methyl trans-3,4,5-trimethoxycinnamate
CHEBI:86898
Cinnamic acid, 3,4,5-trimethoxy-, methyl ester
Methyl trans-3-(3,4,5-trimethoxyphenyl)acrylate
Methyl-3,4,5-trimethoxy cinnamate
NSC648088
Methyl 3-(3,4,5-trimethoxyphenyl)acrylate
Methyl 3,4,5-Trimethoxycinnamate (>85%)
(E)-Methyl 3-(3,4,5-trimethoxyphenyl)acrylate
Methyl 3,4,5-trimethyoxycinnamate
MFCD03614740
(E)-Methyl 3,4,5-trimethoxycinnamate
2-Propenoic acid, 3-(3,4,5-trimethoxyphenyl)-, methyl ester
Bmse010223
Methyl 3-(3,4,5-trimethoxyphenyl)-2-propenoate
NSC 648088
SCHEMBL2433925
CHEMBL1991500
HY-N3289A
HY-N3289
Methyl (3,4,5-trimethoxy)cinnamate
AKOS003307574
CCG-214455
FM70502
MS-8964
NSC-648088
DA-65395
3,4,5-trimethoxycinnamic acid methyl ester
CS-0023816
PK04_181140
(E)-Methyl3-(3,4,5-trimethoxyphenyl)acrylate
H10856
Methyl ester of 3,4,5-Trimethoxycinnamic acid
EN300-1588614
(E)-methyl 3-(3,4,5-trimethoxyphenyl)prop-2-enoate
Q27159282
Methyl (2E)-3-(3,4,5-trimethoxyphenyl)-2-propenoate #
2-Propenoic acid,3-(3,4,5-trimethoxyphenyl)-,methyl ester,(2E)-
2-Propenoic acid, 3-(3,4,5-trimethoxyphenyl)-, methyl ester, trans
Methyl (2E)-3-(3,4,5-trimethoxyphenyl)acrylate
- Kaoke MD, Sema DK, et al. (2020). A new cytotoxic glycocerebroside from Rauvolfia macrophylla Stapf. Natural products chemistry & research,2020, 8, 1-5. [View]
Pubchem:
735846
Cas:
20329-96-8
Gnps:
CCMSLIB00004695444
Zinc:
ZINC000000153660
Chebi:
86898
Nmrshiftdb2:
60030081
Chembl:
CHEMBL1991500
CPRiL:
430896
SMILES: c1ccccc1
Level: 0
Mol. Weight: 252.27 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.4
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.110
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.06
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.540
- Plasma Protein Binding
- 6.7
- 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
- 3.300
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.370
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.350
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.660
- 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
- 3.330
- Rat (Acute)
- 2.350
- Rat (Chronic Oral)
- 2.330
- Fathead Minnow
- 4.540
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 323.770
- Hydration Free Energy
- -6.600
- Log(D) at pH=7.4
- 2.390
- Log(P)
- 2.12
- Log S
- -2.28
- Log(Vapor Pressure)
- -4.02
- Melting Point
- 89.22
- pKa Acid
- 9.2
- pKa Basic
- 0.66
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.9630 |
| Toxoflavin degrading enzyme | E3SET7 | E3SET7_PAEPO | Paenibacillus polymyxa | 3 | 0.9565 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.9492 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8847 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.8576 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8489 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7893 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7765 |
| Caffeic acid O-methyltransferase | Q9ZTU2 | Q9ZTU2_LOLPR | Lolium perenne | 3 | 0.7742 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7725 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7679 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.7547 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7376 |
| Thymidylate synthase | Q4JQW2 | TYSY_VZVO | Varicella-zoster virus | 3 | 0.7312 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7287 |
| Orotidine 5'-phosphate decarboxylase | O26232 | PYRF_METTH | Methanothermobacter thermautotrophicus | 3 | 0.7282 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 2 | 0.7273 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7217 |
| Serine/threonine-protein kinase toxin HipA | P23874 | HIPA_ECOLI | Escherichia coli | 2 | 0.7214 |
| WxcM-like protein | Q12KT8 | Q12KT8_SHEDO | Shewanella denitrificans | 3 | 0.7209 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 2 | 0.7205 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 2 | 0.7199 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7179 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 2 | 0.7174 |
| DNA gyrase subunit A | P0AES5 | GYRA_SHIFL | Shigella flexneri | 3 | 0.7163 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 2 | 0.7157 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7129 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7120 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7117 |
| 2-phospho-L-lactate transferase | Q8PVT6 | COFD_METMA | Methanosarcina mazei | 3 | 0.7093 |
| Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 | O88703 | HCN2_MOUSE | Mus musculus | 2 | 0.7083 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 2 | 0.7075 |
| Nucleoside diphosphate kinase | A5J299 | A5J299_PENVA | Penaeus vannamei | 2 | 0.7050 |
| GMP synthase [glutamine-hydrolyzing] | Q8IJR9 | Q8IJR9_PLAF7 | Plasmodium falciparum | 4 | 0.7047 |
| 5-methylthioadenosine/S-adenosylhomocysteine deaminase | Q7NZ90 | Q7NZ90_CHRVO | Chromobacterium violaceum | 2 | 0.7043 |
| Serine/threonine-protein kinase PLK1 | P53350 | PLK1_HUMAN | Homo sapiens | 3 | 0.7016 |
| N-terminal acetyltransferase A complex subunit NAT1 | P12945 | NAT1_YEAST | Saccharomyces cerevisiae | 2 | 0.7008 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7005 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7001 |