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Caffeic acid methylester
- Family: Plantae - Lamiaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Ester
| Canonical Smiles | COC(=O)/C=C/c1ccc(c(c1)O)O |
|---|---|
| InChI | InChI=1S/C10H10O4/c1-14-10(13)5-3-7-2-4-8(11)9(12)6-7/h2-6,11-12H,1H3/b5-3+ |
| InChIKey | OCNYGKNIVPVPPX-HWKANZROSA-N |
| Formula | C10H10O4 |
| HBA | 4 |
| HBD | 2 |
| MW | 194.19 |
| Rotatable Bonds | 2 |
| TPSA | 66.76 |
| LogP | 1.28 |
| Number Rings | 1 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 14 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.1 |
| Exact Mass | 194.06 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Salvia buchananii | Lamiaceae | Plantae | 2026467 |
Showing of synonyms
Caffeic acid methylester
Methyl caffeate
3843-74-1
Caffeic acid methyl ester
Caffeic acid, methyl ester
Methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
UNII-N79173B9HF
CHEBI:6856
N79173B9HF
Methyl-3,4-dihydroxy cinnamate
2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, methyl ester
Cinnamic acid, 3,4-dihydroxy-, methyl ester
67667-67-8
Methyl 3-(3,4-dihydroxyphenyl)acrylate
(E)-methyl 3-(3,4-dihydroxyphenyl)acrylate
METHYLCAFFEATE
Methyl caffeate acid
Methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Methyl (2E)-3-(3,4-dihydroxyphenyl)acrylate
CHEMBL17001
142234-81-9
Methyl (E)-3-(3,4-dihydroxyphenyl)acrylate
(E)-3,4-Dihydroxycinnamic Acid Methyl Ester
Methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate
MFCD00210468
E-Caffeic acid methyl ester
Methyl (E)-caffeate
(E)-Methyl3-(3,4-dihydroxyphenyl)acrylate
3-(3,4-Dihydroxy-phenyl)-acrylic acid methyl ester
DTXSID401030290
ALBB-024360
HY-N6005
2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, methyl ester, (2E)-
AC9787
BDBM50029209
STK523948
AKOS003263230
FM46133
AS-56651
AS-65428
DA-55392
DB-230642
DB-320084
CS-0032054
Methyl 1-(3',4'-Dihydroxyphenyl)Propenate
E80647
Methyl 1-(3'',4''-dihydroxyphenyl)propenate
A824271
Q6823935
(E)-3-(3,4-Dihydroxy-phenyl)-acrylic acid methyl ester
Methyl (E)-3-[3,4-bis(oxidanyl)phenyl]prop-2-enoate
(E)-3-(3,4-dihydroxyphenyl)-2-propenoic acid methyl ester
2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, methyl ester, (E)-
Methyl 3,4-dihydroxycinnamate
3,4-Dihydroxycinnamic acid methyl ester
Pubchem:
689075
Cas:
3843-74-1
Zinc:
ZINC000000058222
Kegg Ligand:
C10477
Chebi:
6856
Nmrshiftdb2:
60021797
Chembl:
CHEMBL17001
Bindingdb:
50029209
CPRiL:
79915
SMILES: c1ccccc1
Level: 0
Mol. Weight: 194.19 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.54
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.300
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.52
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.580
- Plasma Protein Binding
- 22.44
- 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
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 10.250
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 0.690
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.720
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.090
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Toxic
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- 4.420
- Rat (Acute)
- 2.010
- Rat (Chronic Oral)
- 2.690
- Fathead Minnow
- 4.050
- 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
- 330.940
- Hydration Free Energy
- -11.930
- Log(D) at pH=7.4
- 1.270
- Log(P)
- 1.77
- Log S
- -2.24
- Log(Vapor Pressure)
- -4.12
- Melting Point
- 129.11
- pKa Acid
- 8.67
- pKa Basic
- 3.65
| 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 | 0.9525 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9354 |
| Valacyclovir hydrolase | Q86WA6 | BPHL_HUMAN | Homo sapiens | 3 | 0.9243 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.9225 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.9123 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.9121 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.9034 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.9021 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8945 |
| Serine/threonine-protein kinase PLK1 | P53350 | PLK1_HUMAN | Homo sapiens | 4 | 0.8772 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8729 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 4 | 0.8544 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 3 | 0.8540 |
| Caffeic acid O-methyltransferase | Q9ZTU2 | Q9ZTU2_LOLPR | Lolium perenne | 4 | 0.8538 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.8449 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8361 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8346 |
| DNA gyrase subunit A | P0AES5 | GYRA_SHIFL | Shigella flexneri | 3 | 0.8265 |
| DNA polymerase III subunit epsilon | P03007 | DPO3E_ECOLI | Escherichia coli | 3 | 0.8254 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8190 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8180 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.8072 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8057 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8028 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.8000 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.7935 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7925 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7924 |
| 2-aminohexano-6-lactam racemase | Q7M181 | ACLR_ACHOB | Achromobacter obae | 3 | 0.7868 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7856 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7776 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.7718 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.7677 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7665 |
| Ras-related protein Rap-1b | P61224 | RAP1B_HUMAN | Homo sapiens | 4 | 0.7607 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7595 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7592 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7540 |
| Nucleoside diphosphate kinase A 2 | P52175 | NDKA2_BOVIN | Bos taurus | 3 | 0.7532 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7505 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7500 |
| Threonine--tRNA ligase | P0A8M3 | SYT_ECOLI | Escherichia coli | 3 | 0.7419 |
| Cyclic nucleotide-binding domain-containing protein | E0RR11 | E0RR11_SPITD | Spirochaeta thermophila | 2 | 0.7405 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7357 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7345 |
| Thymidylate synthase | Q4JQW2 | TYSY_VZVO | Varicella-zoster virus | 3 | 0.7328 |
| DNA-binding transcriptional dual regulator CRP | P0ACJ8 | CRP_ECOLI | Escherichia coli | 3 | 0.7326 |
| Cyclic nucleotide-gated potassium channel mll3241 | Q98GN8 | CNGK1_RHILO | Mesorhizobium japonicum) | 3 | 0.7324 |
| N-terminal acetyltransferase A complex subunit NAT1 | P12945 | NAT1_YEAST | Saccharomyces cerevisiae | 2 | 0.7306 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7301 |
| Ribosomal RNA small subunit methyltransferase Nep1 | Q57977 | NEP1_METJA | Methanocaldococcus jannaschii | 3 | 0.7299 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7247 |
| Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 | Q9Y3Z3 | SAMH1_HUMAN | Homo sapiens | 3 | 0.7212 |
| 3',5'-cyclic-AMP phosphodiesterase 4B | Q07343 | PDE4B_HUMAN | Homo sapiens | 3 | 0.7212 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7203 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7198 |
| DNA-binding transcriptional dual regulator CRP | P0ACJ8 | CRP_ECOLI | Escherichia coli | 3 | 0.7193 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 2 | 0.7186 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7186 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 3 | 0.7178 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7148 |
| Cyclic AMP receptor protein | Q5SID7 | CRP_THET8 | Thermus thermophilus | 2 | 0.7139 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7124 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7114 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7113 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7109 |
| Guanylate kinase | P15454 | KGUA_YEAST | Saccharomyces cerevisiae | 3 | 0.7104 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 4 | 0.7101 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 2 | 0.7088 |
| Tryptophan--tRNA ligase | Q9PIB4 | SYW_CAMJE | Campylobacter jejuni subsp. jejuni serotype O:2 | 4 | 0.7085 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7067 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7065 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7041 |
| Serine/threonine-protein kinase PLK1 | P53350 | PLK1_HUMAN | Homo sapiens | 4 | 0.7026 |
| LD-carboxypeptidase | A0A6L8PVW7 | A0A1Q4LWC0_BACAN | Bacillus anthracis | 3 | 0.7026 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.7024 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7022 |