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P-methoxycinnamic acid
- Family: Plantae - Caryophyllaceae
- Kingdom: Plantae
- Class: Phenolic
| Canonical Smiles | COc1ccc(cc1)/C=C/C(=O)O |
|---|---|
| InChI | InChI=1S/C10H10O3/c1-13-9-5-2-8(3-6-9)4-7-10(11)12/h2-7H,1H3,(H,11,12)/b7-4+ |
| InChIKey | AFDXODALSZRGIH-QPJJXVBHSA-N |
| Formula | C10H10O3 |
| HBA | 2 |
| HBD | 1 |
| MW | 178.19 |
| Rotatable Bonds | 3 |
| TPSA | 46.53 |
| LogP | 1.79 |
| Number Rings | 1 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 13 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.1 |
| Exact Mass | 178.06 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Vaccaria pyramidata | Caryophyllaceae | Plantae | 39387 |
Showing of synonyms
P-methoxycinnamic acid
4-Methoxycinnamic acid
830-09-1
943-89-5
(E)-3-(4-Methoxyphenyl)acrylic acid
3-(4-methoxyphenyl)acrylic acid
Trans-4-Methoxycinnamic acid
(E)-3-(4-methoxyphenyl)prop-2-enoic acid
(2E)-3-(4-methoxyphenyl)prop-2-enoic acid
Para-methoxycinnamic acid
2-Propenoic acid, 3-(4-methoxyphenyl)-
Cinnamic acid, p-methoxy-
3-(4-Methoxyphenyl)-2-propenoic acid
4-Methoxycinnamate
MFCD00004398
O-Methyl-p-coumaric acid
2-Propenoic acid, 3-(4-methoxyphenyl)-, (2E)-
Cinnamic acid, 4-methoxy-
4-Methoxycinnamic acid, predominantly trans
(E)-3-(4-methoxyphenyl)-2-propenoic acid
Bernel hydro
METHOXYCINNAMIC ACID, PARA
(E)-p-Methoxycinnamic acid
P-methoxycinnamate
NSC-5303
NSC-623437
CHEMBL95770
4-Methoxy-(2E)-cinnamic acid
DTXSID1046059
Trans-2-Propenoic acid, 3-(4-methoxyphenyl)-
6G4ML8401A
NCGC00159448-02
(E)-3-(4-Methoxy-phenyl)-acrylic acid
4-Methoxycinnamicacid
4-Methoxy cinnamic acid
PMCA
P-Methoxy ciannamic acid
Trans-3-(4-Methoxyphenyl)acrylic acid
P-MeOCinnamicAcid
K3Z
EINECS 213-405-4
Para-methoxycinnamate
4-Methoxy cinnamate
P-Methoxy ciannamate
O-Methyl-p-coumarate
P-MCA
Trans-4-Methoxycinnamate
O-Methyl-p-cumaric Acid
Bmse010212
Trans-4-methoxycinnamic-acid
2-Propenoic acid, 3-(4-methoxyphenyl)-, (E)-
SCHEMBL58699
(E)-p-Methoxy-cinnamic acid
30-09-1
MLS002473129
Trans-4-methoxy-cinnamic acid
4-Methoxycinnamic acid, trans-
3-(4-Methoxy-phenyl)-acrylate
DTXCID9026059
AFDXODALSZRGIH-QPJJXVBHSA-
NSC5303
CHEBI:143736
HMS1783A08
HMS2267B19
(E)-3-(4-Methoxyphenyl)acrylate
3-(4-methoxyphenyl)-2-Propenoate
AAA94389
ALBB-011726
BCP21420
HY-N1387
STR01310
Tox21_111674
BBL012085
BDBM50146453
NSC623437
STK005095
AKOS000118882
FM38609
PS-5777
(E)-3-(4-methoxyphenyl)-acrylic acid
NCGC00159448-03
NCGC00159448-04
AC-10371
CAS-943-89-5
DA-59571
SMR000112200
4-Methoxycinnamic acid, >=98.0% (GC)
P-Methoxycinnamic acid, predominantly trans
CS-0016807
M0576
NS00013547
A10220
EN300-312690
G60885
SBI-0635112.0002
(2E)-3-(4-Methoxyphenyl)-2-propenoic acid #
4-Methoxycinnamic acid, predominantly trans, 99%
A837404
AE-641/00135031
BRD-K26273521-001-07-3
Q63391599
Z56931888
F1638-0067
0C546A89-9721-4B4E-89EE-7EC28A9A3391
InChI=1/C10H10O3/c1-13-9-5-2-8(3-6-9)4-7-10(11)12/h2-7H,1H3,(H,11,12)/b7-4+
- Said R, Hamed A, et al. (2019). Flavone C-glycosides from Vaccaria pyramidata: Structure elucidation by spectroscopy and theoretical calculations. Phytochemistry Letters, 2019, 29, 119-124. [View]
Pubchem:
699414
Cas:
830-09-1
Gnps:
CCMSLIB00000426426
Zinc:
ZINC000000077999
Chebi:
143736
Nmrshiftdb2:
20073795
Chembl:
CHEMBL95770
Comptox:
DTXSID1046059
Pdb Ligand:
K3Z
Bindingdb:
50146453
CPRiL:
248377
SMILES: c1ccccc1
Level: 0
Mol. Weight: 178.19 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.7
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.290
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.82
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.930
- Plasma Protein Binding
- 40.86
- 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
- 5.160
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 0.470
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.110
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.460
- 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
- 2.600
- Rat (Acute)
- 1.740
- Rat (Chronic Oral)
- 2.520
- Fathead Minnow
- 4.000
- 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
- 290.240
- Hydration Free Energy
- -9.020
- Log(D) at pH=7.4
- -0.910
- Log(P)
- 2.41
- Log S
- -3.56
- Log(Vapor Pressure)
- -4.76
- Melting Point
- 182.45
- pKa Acid
- 4.25
- pKa Basic
- 2.28
| 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 | 0.9714 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.9414 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.9324 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.9112 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.8985 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.8816 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 2 | 0.8478 |
| DNA gyrase subunit A | P0AES5 | GYRA_SHIFL | Shigella flexneri | 3 | 0.8237 |
| Malate synthase G | P9WK17 | MASZ_MYCTU | Mycobacterium tuberculosis | 3 | 0.7910 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7901 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7870 |
| Replication factor C subunit 1 | P38630 | RFC1_YEAST | Saccharomyces cerevisiae | 4 | 0.7859 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 3 | 0.7788 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7608 |
| Thymidylate synthase | Q4JQW2 | TYSY_VZVO | Varicella-zoster virus | 3 | 0.7580 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7525 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7491 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7473 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7473 |
| Cytosolic IMP-GMP specific 5'-nucleotidase | Q5ZZB6 | Q5ZZB6_LEGPH | Legionella pneumophila subsp. pneumophila | 3 | 0.7463 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7451 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7449 |
| Major NAD(P)H-flavin oxidoreductase | P46072 | FRA1_ALIFS | Aliivibrio fischeri | 2 | 0.7435 |
| Serine/threonine-protein kinase RIO1 | Q9BRS2 | RIOK1_HUMAN | Homo sapiens | 3 | 0.7423 |
| Biotin carboxylase | P43873 | ACCC_HAEIN | Haemophilus influenzae | 3 | 0.7406 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7393 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7381 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7380 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7379 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7364 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7360 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 2 | 0.7350 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7343 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 2 | 0.7323 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7313 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7310 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | Q81LL4 | MTNN_BACAN | Bacillus anthracis | 2 | 0.7309 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7309 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7298 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7296 |
| ATP-dependent helicase/nuclease subunit A | P23478 | ADDA_BACSU | Bacillus subtilis | 2 | 0.7285 |
| Nucleoside 2-deoxyribosyltransferase | Q8RLY5 | Q8RLY5_LACHE | Lactobacillus helveticus | 2 | 0.7276 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7273 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7267 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 2 | 0.7258 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7240 |
| Pantothenate synthetase | P9WIL4 | PANC_MYCTO | Mycobacterium tuberculosis | 2 | 0.7239 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 2 | 0.7235 |
| BMP-2-inducible protein kinase | Q9NSY1 | BMP2K_HUMAN | Homo sapiens | 2 | 0.7235 |
| Myosin heavy chain kinase A | P42527 | MHCKA_DICDI | Dictyostelium discoideum | 2 | 0.7226 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 2 | 0.7221 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7215 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7214 |
| 5-formyltetrahydrofolate cyclo-ligase | P75430 | MTHFS_MYCPN | Mycoplasma pneumoniae | 2 | 0.7209 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7209 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7199 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 2 | 0.7168 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7151 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7148 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 2 | 0.7147 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7144 |
| Protein kinase C iota type | Q62074 | KPCI_MOUSE | Mus musculus | 2 | 0.7142 |
| Adenosylmethionine-8-amino-7-oxononanoate aminotransferase | P12995 | BIOA_ECOLI | Escherichia coli | 2 | 0.7132 |
| Nucleoside diphosphate kinase | Q5UQL3 | NDK_MIMIV | Acanthamoeba polyphaga mimivirus | 2 | 0.7132 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7129 |
| 2-aminohexano-6-lactam racemase | Q7M181 | ACLR_ACHOB | Achromobacter obae | 2 | 0.7125 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7122 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 2 | 0.7107 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 2 | 0.7100 |
| Tyrosine-protein kinase JAK1 | P23458 | JAK1_HUMAN | Homo sapiens | 2 | 0.7097 |
| 1-deoxy-D-xylulose 5-phosphate reductoisomerase | P45568 | DXR_ECOLI | Escherichia coli | 2 | 0.7095 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 2 | 0.7093 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 2 | 0.7089 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7082 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 2 | 0.7077 |
| Focal adhesion kinase 1 | Q05397 | FAK1_HUMAN | Homo sapiens | 2 | 0.7075 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 2 | 0.7072 |
| Beta-glucosidase 12 | B8AVF0 | BGL12_ORYSI | Oryza sativa subsp. indica | 2 | 0.7070 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 2 | 0.7059 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 2 | 0.7057 |
| Aminoglycoside N(3)-acetyltransferase | A0A3P1UCA6 | Q81P86_BACAN | Bacillus anthracis | 2 | 0.7056 |
| Biotin carboxylase | P24182 | ACCC_ECOLI | Escherichia coli | 2 | 0.7055 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 2 | 0.7051 |
| 3-dehydroquinate dehydratase | Q48255 | AROQ_HELPY | Helicobacter pylori | 3 | 0.7041 |
| cGMP-dependent protein kinase 2 | Q13237 | KGP2_HUMAN | Homo sapiens | 2 | 0.7040 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 2 | 0.7025 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 2 | 0.7002 |