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M-coumaric acid
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
- Class: Phenolic
| Canonical Smiles | OC(=O)/C=C/c1cccc(c1)O |
|---|---|
| InChI | InChI=1S/C9H8O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-6,10H,(H,11,12)/b5-4+ |
| InChIKey | KKSDGJDHHZEWEP-SNAWJCMRSA-N |
| Formula | C9H8O3 |
| HBA | 2 |
| HBD | 2 |
| MW | 164.16 |
| Rotatable Bonds | 2 |
| TPSA | 57.53 |
| LogP | 1.49 |
| Number Rings | 1 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 12 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.0 |
| Exact Mass | 164.05 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Phoenix dactylifera | Arecaceae | Plantae | 42345 |
| 2 | Cassia absus | Leguminosae/Fabaceae | Plantae | 592576 |
Showing of synonyms
M-coumaric acid
(2E)-3-(3-hydroxyphenyl)acrylic acid
(2E)-3-(3-hydroxyphenyl)prop-2-enoic acid
Trans-3-coumaric acid
3'-Hydroxycinnamic acid
KWJ2DDJ34H
(2E)-3-(3-Hydroxyphenyl)-2-propenoic acid
CHEBI:32357
NSC-28956
NSC-50308
HYDROXYCINNAMIC ACID, TRANS-3-
209-615-0
3-Hydroxycinnamic acid
14755-02-3
588-30-7
3-Coumaric acid
M-Hydroxycinnamic acid
(E)-3-(3-Hydroxyphenyl)acrylic acid
Trans-3-Hydroxycinnamic acid
3-(3-Hydroxyphenyl)acrylic acid
Trans-m-Coumaric Acid
2-propenoic acid, 3-(3-hydroxyphenyl)-, (2E)-
Trans-3-Hydroxycinnamate
Cinnamic acid, m-hydroxy-
(E)-3-(3-hydroxyphenyl)prop-2-enoic acid
2-Propenoic acid, 3-(3-hydroxyphenyl)-
MFCD00004390
3-(3-hydroxyphenyl)prop-2-enoic acid
(E)-3-(3-Hydroxyphenyl)-2-propenoic acid
NSC 28956
NSC 50308
2-Propenoic acid, 3-(3-hydroxyphenyl)-, (E)-
CHEMBL98521
3-(3-Hydroxyphenyl)acrylsaeure
3-(3-hydroxyphenyl)-2-propenoic acid
M-Coumarate
3-hydroxycinnamate
(2E)-3-(3-hydroxyphenyl)prop-2-enoate
3-(3-hydroxyphenyl)acrylate
3-(3-hydroxyphenyl)prop-2-enoate
Trans-m-Cumaric Acid
UNII-KWJ2DDJ34H
M-Hydroxycinnamate
M-hydroxy-Cinnamate
EINECS 209-615-0
3'-Hydroxycinnamate
(E)-m-Coumaric acid
M-hydroxy-Cinnamic acid
AI3-32389
Bmse000093
Cinnamic acid, 3-hydroxy-
M-Coumaric acid (Standard)
SCHEMBL442408
CHEBI:47925
HY-N7127R
(E)-m-Coumaric acid (Standard)
DTXSID001336224
3-(3-hydroxyphenyl)-2-Propenoate
ALBB-006261
MSK40362
NSC28956
NSC50308
M-Coumaric acid, analytical standard
Trans-3-Hydroxycinnamic acid, 99%
BBL013143
BDBM50146456
S5586
STK400397
AKOS000146568
CCG-266308
FH37075
HY-113357R
(E)-3-(3-hydroxyphenyl)-acrylic acid
(E)-3-(3-hydroxy-phenyl)-acrylic acid
(E)-3-(3-hydroxyphenyl)-2-propenoate
(2E)-3-(3-hydroxyphenyl)-2-propenoate
1ST40362
AC-16619
AS-12450
LS-13594
HY-113357
CS-0062284
NS00076981
EN300-103182
EN300-345689
F15419
G60884
Q6712039
Z247613734
358818FD-674F-4656-96AF-40F17C30F2EE
InChI=1/C9H8O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-6,10H,(H,11,12)/b5-4
- Zribi I, Sbai H, et al. (2017). Phytotoxic activity and chemical composition of Cassia absus seeds and aerial parts. Natural product research, 2017, 31(24), 2918-2922. [View] [PubMed]
- Guesmi A, Ben Hamadi N. (2018). Study on optimizing dyeing of cotton using date pits extract as a combined source of coloring matter and bio-mordant. Natural product research, 2018, 32(7), 810-814. [View] [PubMed]
Pubchem:
637541
Cas:
14755-02-3
Gnps:
CCMSLIB00012176088
Zinc:
ZINC000000155996
Kegg Ligand:
C12621
Chebi:
32357
Nmrshiftdb2:
10024831
Metabolights:
MTBLC32357
Chembl:
CHEMBL98521
Comptox:
DTXSID00891551
Bindingdb:
50146456
CPRiL:
32178
SMILES: c1ccccc1
Level: 0
Mol. Weight: 164.16 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.89
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.18
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.48
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.75
- Plasma Protein Binding
- 41.95
- 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
- 5.79
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 0.09
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.7
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.14
- Micronucleos
- Toxic
- 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
- 2.61
- Rat (Acute)
- 1.94
- Rat (Chronic Oral)
- 2.51
- Fathead Minnow
- 3.97
- 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
- 322.43
- Hydration Free Energy
- -9.36
- Log(D) at pH=7.4
- -1.03
- Log(P)
- 1.88
- Log S
- -2.38
- Log(Vapor Pressure)
- -5.42
- Melting Point
- 216.09
- pKa Acid
- 4.55
- pKa Basic
- 3.08
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.9450 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.9415 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.9322 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.9207 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 3 | 0.9052 |
| Threonine synthase 1, chloroplastic | Q9S7B5 | THRC1_ARATH | Arabidopsis thaliana | 3 | 0.8977 |
| 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase | O67060 | ISPE_AQUAE | Aquifex aeolicus | 3 | 0.8975 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8781 |
| Aspartate aminotransferase | P00509 | AAT_ECOLI | Escherichia coli | 3 | 0.8774 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.8621 |
| Glycogen phosphorylase, liver form | P06737 | PYGL_HUMAN | Homo sapiens | 3 | 0.8560 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.8520 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.8500 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.8166 |
| Valacyclovir hydrolase | Q86WA6 | BPHL_HUMAN | Homo sapiens | 3 | 0.7766 |
| Malate synthase G | P9WK17 | MASZ_MYCTU | Mycobacterium tuberculosis | 3 | 0.7734 |
| DNA polymerase III subunit epsilon | P03007 | DPO3E_ECOLI | Escherichia coli | 3 | 0.7726 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 3 | 0.7669 |
| Orotidine 5'-phosphate decarboxylase | Q5L0U0 | PYRF_GEOKA | Geobacillus kaustophilus | 3 | 0.7648 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7619 |
| Cysteine desulfurase IscS 2 | O29689 | ISCS2_ARCFU | Archaeoglobus fulgidus | 3 | 0.7549 |
| Orotidine 5'-phosphate decarboxylase | O26232 | PYRF_METTH | Methanothermobacter thermautotrophicus | 3 | 0.7513 |
| Ribonuclease TTHA0252 | Q5SLP1 | RNSE_THET8 | Thermus thermophilus | 3 | 0.7506 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7479 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7420 |
| CalS13 | Q8KND8 | Q8KND8_MICEC | Micromonospora echinospora | 3 | 0.7402 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7385 |
| Nucleoside diphosphate kinase A 2 | P52175 | NDKA2_BOVIN | Bos taurus | 3 | 0.7355 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7349 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7322 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | Q81LL4 | MTNN_BACAN | Bacillus anthracis | 2 | 0.7292 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7278 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7258 |
| Nucleoside 2-deoxyribosyltransferase | Q8RLY5 | Q8RLY5_LACHE | Lactobacillus helveticus | 2 | 0.7219 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 2 | 0.7215 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7212 |
| Uncharacterized protein YML079W | Q03629 | YMH9_YEAST | Saccharomyces cerevisiae | 2 | 0.7201 |
| Class 10 plant pathogenesis-related protein 2B | Q9LLQ2 | P102B_LUPLU | Lupinus luteus | 2 | 0.7190 |
| 3',5'-cyclic-AMP phosphodiesterase 4B | Q07343 | PDE4B_HUMAN | Homo sapiens | 3 | 0.7185 |
| rRNA methylase | Q8DSS3 | Q8DSS3_STRMU | Streptococcus mutans serotype c | 2 | 0.7183 |
| Cyclic GMP-AMP phosphodiesterase SMPDL3A | Q92484 | ASM3A_HUMAN | Homo sapiens | 2 | 0.7178 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7173 |
| 3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase | P19992 | HSD_STREX | Streptomyces exfoliatus | 2 | 0.7164 |
| Gentisate 1,2-dioxygenase | Q67FT0 | Q67FT0_PSESE | Pseudaminobacter salicylatoxidans | 2 | 0.7158 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7158 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 2 | 0.7149 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 2 | 0.7147 |
| 5-aminolevulinate synthase | P18079 | HEM1_RHOCB | Rhodobacter capsulatus | 3 | 0.7132 |
| N-acetyltransferase domain-containing protein | Q9HV14 | Q9HV14_PSEAE | Pseudomonas aeruginosa | 2 | 0.7124 |
| Aspartate aminotransferase, mitochondrial | P00508 | AATM_CHICK | Gallus gallus | 3 | 0.7121 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7118 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | P0AF12 | MTNN_ECOLI | Escherichia coli | 2 | 0.7106 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7090 |
| Thymidine kinase | P0DTH5 | KITH_HHV11 | Human herpesvirus 1 | 2 | 0.7085 |
| D-alanyl-D-alanine carboxypeptidase | P15555 | DAC_STRSR | Streptomyces sp | 2 | 0.7071 |
| Pyridoxal kinase | O00764 | PDXK_HUMAN | Homo sapiens | 2 | 0.7065 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7059 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 2 | 0.7054 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7050 |
| Adenosine monophosphate-protein transferase | Q8ZVF7 | Q8ZVF7_PYRAE | Pyrobaculum aerophilum | 3 | 0.7049 |
| Holliday junction branch migration complex subunit RuvB | Q9PMT7 | RUVB_CAMJE | Campylobacter jejuni subsp. jejuni serotype O:2 | 2 | 0.7045 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 2 | 0.7043 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 2 | 0.7035 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 2 | 0.7022 |
| 5-methylthioadenosine/S-adenosylhomocysteine deaminase | Q7NZ90 | Q7NZ90_CHRVO | Chromobacterium violaceum | 2 | 0.7018 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7007 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 2 | 0.7003 |
| N-terminal acetyltransferase A complex subunit NAT1 | P12945 | NAT1_YEAST | Saccharomyces cerevisiae | 2 | 0.7002 |