(-)-xylariamide A
| Internal ID | 50a9aae7-3c99-40a8-af14-7dadf987e1e2 |
| Taxonomy | Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Tyrosine and derivatives |
| IUPAC Name | (2R)-3-(3-chloro-4-hydroxyphenyl)-2-[[(E)-4-methoxy-4-oxobut-2-enoyl]amino]propanoic acid |
| SMILES (Canonical) | COC(=O)C=CC(=O)NC(CC1=CC(=C(C=C1)O)Cl)C(=O)O |
| SMILES (Isomeric) | COC(=O)/C=C/C(=O)N[C@H](CC1=CC(=C(C=C1)O)Cl)C(=O)O |
| InChI | InChI=1S/C14H14ClNO6/c1-22-13(19)5-4-12(18)16-10(14(20)21)7-8-2-3-11(17)9(15)6-8/h2-6,10,17H,7H2,1H3,(H,16,18)(H,20,21)/b5-4+/t10-/m1/s1 |
| InChI Key | KCOKHEIACSQLBQ-ORAHPGNNSA-N |
| Popularity | 10 references in papers |
| Molecular Formula | C14H14ClNO6 |
| Molecular Weight | 327.71 g/mol |
| Exact Mass | 327.0509649 g/mol |
| Topological Polar Surface Area (TPSA) | 113.00 Ų |
| XlogP | 1.50 |
| Atomic LogP (AlogP) | 0.89 |
| H-Bond Acceptor | 5 |
| H-Bond Donor | 3 |
| Rotatable Bonds | 6 |
| CHEMBL463133 |
| cxl017 |
| BDBM50339590 |
| (R)-3-(3-chloro-4-hydroxyphenyl)-2-(4-methoxy-4-oxobut-2-enamido)propanoic acid |
| (2R)-3-(3-chloro-4-hydroxy-phenyl)-2-[[(E)-4-methoxy-4-oxo-but-2-enoyl]amino]propanoic acid |
| (2R)-3-(3-chloro-4-hydroxyphenyl)-2-[[(E)-4-methoxy-4-oxobut-2-enoyl]amino]propanoic acid |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9581 | 95.81% |
| Caco-2 | - | 0.7367 | 73.67% |
| Blood Brain Barrier | + | 0.5250 | 52.50% |
| Human oral bioavailability | - | 0.7000 | 70.00% |
| Subcellular localzation | Mitochondria | 0.8032 | 80.32% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.8707 | 87.07% |
| OATP1B3 inhibitior | + | 0.9455 | 94.55% |
| MATE1 inhibitior | - | 0.8200 | 82.00% |
| OCT2 inhibitior | - | 0.8750 | 87.50% |
| BSEP inhibitior | - | 0.7810 | 78.10% |
| P-glycoprotein inhibitior | - | 0.9566 | 95.66% |
| P-glycoprotein substrate | - | 0.8945 | 89.45% |
| CYP3A4 substrate | + | 0.5468 | 54.68% |
| CYP2C9 substrate | - | 0.6062 | 60.62% |
| CYP2D6 substrate | - | 0.8541 | 85.41% |
| CYP3A4 inhibition | - | 0.6874 | 68.74% |
| CYP2C9 inhibition | - | 0.7952 | 79.52% |
| CYP2C19 inhibition | - | 0.7535 | 75.35% |
| CYP2D6 inhibition | - | 0.9262 | 92.62% |
| CYP1A2 inhibition | - | 0.7185 | 71.85% |
| CYP2C8 inhibition | + | 0.5366 | 53.66% |
| CYP inhibitory promiscuity | - | 0.9172 | 91.72% |
| UGT catelyzed | + | 0.8000 | 80.00% |
| Carcinogenicity (binary) | - | 0.6338 | 63.38% |
| Carcinogenicity (trinary) | Non-required | 0.5439 | 54.39% |
| Eye corrosion | - | 0.9915 | 99.15% |
| Eye irritation | - | 0.9160 | 91.60% |
| Skin irritation | - | 0.8057 | 80.57% |
| Skin corrosion | - | 0.9570 | 95.70% |
| Ames mutagenesis | - | 0.7054 | 70.54% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.4725 | 47.25% |
| Micronuclear | + | 0.7059 | 70.59% |
| Hepatotoxicity | - | 0.5557 | 55.57% |
| skin sensitisation | - | 0.8421 | 84.21% |
| Respiratory toxicity | + | 0.5556 | 55.56% |
| Reproductive toxicity | + | 0.8778 | 87.78% |
| Mitochondrial toxicity | + | 0.7500 | 75.00% |
| Nephrotoxicity | - | 0.5836 | 58.36% |
| Acute Oral Toxicity (c) | III | 0.8108 | 81.08% |
| Estrogen receptor binding | - | 0.5523 | 55.23% |
| Androgen receptor binding | + | 0.6580 | 65.80% |
| Thyroid receptor binding | - | 0.5551 | 55.51% |
| Glucocorticoid receptor binding | - | 0.5276 | 52.76% |
| Aromatase binding | - | 0.7283 | 72.83% |
| PPAR gamma | + | 0.5222 | 52.22% |
| Honey bee toxicity | - | 0.8795 | 87.95% |
| Biodegradation | - | 0.7750 | 77.50% |
| Crustacea aquatic toxicity | - | 0.5675 | 56.75% |
| Fish aquatic toxicity | + | 0.9476 | 94.76% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| No proven targets yet! | |||||
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 96.81% | 94.45% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 96.78% | 91.11% |
| CHEMBL2581 | P07339 | Cathepsin D | 96.62% | 98.95% |
| CHEMBL4040 | P28482 | MAP kinase ERK2 | 95.18% | 83.82% |
| CHEMBL221 | P23219 | Cyclooxygenase-1 | 94.04% | 90.17% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 91.74% | 99.17% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 91.59% | 96.09% |
| CHEMBL3976 | Q9UHL4 | Dipeptidyl peptidase II | 91.39% | 92.29% |
| CHEMBL3091268 | Q92753 | Nuclear receptor ROR-beta | 90.72% | 95.50% |
| CHEMBL1255126 | O15151 | Protein Mdm4 | 88.23% | 90.20% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 88.11% | 95.56% |
| CHEMBL1860 | P10827 | Thyroid hormone receptor alpha | 87.24% | 99.15% |
| CHEMBL4208 | P20618 | Proteasome component C5 | 87.19% | 90.00% |
| CHEMBL1075094 | Q16236 | Nuclear factor erythroid 2-related factor 2 | 87.16% | 96.00% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 86.91% | 86.33% |
| CHEMBL3401 | O75469 | Pregnane X receptor | 85.12% | 94.73% |
| CHEMBL1907591 | P30926 | Neuronal acetylcholine receptor; alpha4/beta4 | 84.64% | 100.00% |
| CHEMBL4793 | Q86TI2 | Dipeptidyl peptidase IX | 84.23% | 96.95% |
| CHEMBL340 | P08684 | Cytochrome P450 3A4 | 83.56% | 91.19% |
| CHEMBL3492 | P49721 | Proteasome Macropain subunit | 83.36% | 90.24% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
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| PubChem | 11290362 |
| LOTUS | LTS0251970 |
| wikiData | Q75070275 |