Caffeic Acid
| Internal ID | 59ca48ad-9054-4775-8ee7-c49c60d518da |
| Taxonomy | Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acids |
| IUPAC Name | (E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid |
| SMILES (Canonical) | C1=CC(=C(C=C1C=CC(=O)O)O)O |
| SMILES (Isomeric) | C1=CC(=C(C=C1/C=C/C(=O)O)O)O |
| InChI | InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+ |
| InChI Key | QAIPRVGONGVQAS-DUXPYHPUSA-N |
| Popularity | 12,976 references in papers |
| Molecular Formula | C9H8O4 |
| Molecular Weight | 180.16 g/mol |
| Exact Mass | 180.04225873 g/mol |
| Topological Polar Surface Area (TPSA) | 77.80 Ų |
| XlogP | 1.20 |
| Atomic LogP (AlogP) | 1.20 |
| H-Bond Acceptor | 3 |
| H-Bond Donor | 3 |
| Rotatable Bonds | 2 |
| 3,4-Dihydroxycinnamic acid |
| 331-39-5 |
| trans-caffeic acid |
| 501-16-6 |
| 3,4-Dihydroxybenzeneacrylic acid |
| 3-(3,4-dihydroxyphenyl)acrylic acid |
| (E)-3-(3,4-dihydroxyphenyl)acrylic acid |
| Cinnamic acid, 3,4-dihydroxy- |
| (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid |
| Caffeicacid |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9739 | 97.39% |
| Caco-2 | + | 0.5000 | 50.00% |
| Blood Brain Barrier | - | 0.6500 | 65.00% |
| Human oral bioavailability | + | 0.6429 | 64.29% |
| Subcellular localzation | Mitochondria | 0.8027 | 80.27% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.9721 | 97.21% |
| OATP1B3 inhibitior | + | 0.9753 | 97.53% |
| MATE1 inhibitior | - | 0.7400 | 74.00% |
| OCT2 inhibitior | - | 1.0000 | 100.00% |
| BSEP inhibitior | - | 0.8835 | 88.35% |
| P-glycoprotein inhibitior | - | 0.9904 | 99.04% |
| P-glycoprotein substrate | - | 0.9901 | 99.01% |
| CYP3A4 substrate | - | 0.7630 | 76.30% |
| CYP2C9 substrate | - | 0.6110 | 61.10% |
| CYP2D6 substrate | - | 0.8681 | 86.81% |
| CYP3A4 inhibition | - | 0.8869 | 88.69% |
| CYP2C9 inhibition | - | 0.9071 | 90.71% |
| CYP2C19 inhibition | - | 0.9367 | 93.67% |
| CYP2D6 inhibition | - | 0.9525 | 95.25% |
| CYP1A2 inhibition | - | 0.9046 | 90.46% |
| CYP2C8 inhibition | - | 0.7546 | 75.46% |
| CYP inhibitory promiscuity | - | 0.9007 | 90.07% |
| UGT catelyzed | + | 0.5362 | 53.62% |
| Carcinogenicity (binary) | - | 0.7823 | 78.23% |
| Carcinogenicity (trinary) | Non-required | 0.5848 | 58.48% |
| Eye corrosion | - | 0.6303 | 63.03% |
| Eye irritation | + | 1.0000 | 100.00% |
| Skin irritation | + | 0.8761 | 87.61% |
| Skin corrosion | - | 0.7282 | 72.82% |
| Ames mutagenesis | - | 0.9600 | 96.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.9044 | 90.44% |
| Micronuclear | + | 0.9100 | 91.00% |
| Hepatotoxicity | - | 0.6851 | 68.51% |
| skin sensitisation | + | 0.8995 | 89.95% |
| Respiratory toxicity | - | 0.6111 | 61.11% |
| Reproductive toxicity | + | 0.7222 | 72.22% |
| Mitochondrial toxicity | - | 0.7375 | 73.75% |
| Nephrotoxicity | - | 0.7718 | 77.18% |
| Acute Oral Toxicity (c) | IV | 0.5588 | 55.88% |
| Estrogen receptor binding | - | 0.7295 | 72.95% |
| Androgen receptor binding | + | 0.7738 | 77.38% |
| Thyroid receptor binding | - | 0.5706 | 57.06% |
| Glucocorticoid receptor binding | - | 0.7055 | 70.55% |
| Aromatase binding | - | 0.8453 | 84.53% |
| PPAR gamma | + | 0.5966 | 59.66% |
| Honey bee toxicity | - | 0.9454 | 94.54% |
| Biodegradation | - | 0.5500 | 55.00% |
| Crustacea aquatic toxicity | - | 0.7400 | 74.00% |
| Fish aquatic toxicity | + | 0.9807 | 98.07% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL1293255 | P15428 | 15-hydroxyprostaglandin dehydrogenase [NAD+] |
39810.7 nM 39810.7 nM 39810.7 nM |
Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP |
| CHEMBL3577 | P00352 | Aldehyde dehydrogenase 1A1 |
39810.7 nM 39810.7 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL1900 | P15121 | Aldose reductase |
32000 nM |
IC50 |
PMID: 22236472
|
| CHEMBL215 | P09917 | Arachidonate 5-lipoxygenase |
25000 nM 8500 nM 16700 nM |
IC50 IC50 IC50 |
PMID: 19152786
PMID: 26197161 PMID: 2465410 |
| CHEMBL2487 | P05067 | Beta amyloid A4 protein |
32800 nM |
IC50 |
PMID: 22921742
|
| CHEMBL261 | P00915 | Carbonic anhydrase I |
2380 nM |
Ki |
PMID: 20185318
|
| CHEMBL205 | P00918 | Carbonic anhydrase II |
1610 nM |
Ki |
PMID: 20185318
|
| CHEMBL2885 | P07451 | Carbonic anhydrase III |
10000 nM |
Ki |
PMID: 20185318
|
| CHEMBL3729 | P22748 | Carbonic anhydrase IV |
10100 nM |
Ki |
PMID: 20185318
|
| CHEMBL3594 | Q16790 | Carbonic anhydrase IX |
7870 nM |
Ki |
PMID: 20185318
|
| CHEMBL4789 | P35218 | Carbonic anhydrase VA |
6490 nM |
Ki |
PMID: 20185318
|
| CHEMBL3969 | Q9Y2D0 | Carbonic anhydrase VB |
9080 nM |
Ki |
PMID: 20185318
|
| CHEMBL3025 | P23280 | Carbonic anhydrase VI |
7330 nM |
Ki |
PMID: 20185318
|
| CHEMBL2326 | P43166 | Carbonic anhydrase VII |
6420 nM |
Ki |
PMID: 20185318
|
| CHEMBL3242 | O43570 | Carbonic anhydrase XII |
9060 nM 9060 nM |
Ki Ki |
PMID: 26498394
PMID: 20185318 |
| CHEMBL3510 | Q9ULX7 | Carbonic anhydrase XIV |
8710 nM 8710 nM |
Ki Ki |
PMID: 20185318
PMID: 26498394 |
| CHEMBL340 | P08684 | Cytochrome P450 3A4 |
25118.9 nM 25118.9 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL2392 | P06746 | DNA polymerase beta |
15848.9 nM |
Potency |
via CMAUP
|
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase |
35481.3 nM |
Potency |
via CMAUP
|
| CHEMBL4159 | Q99714 | Endoplasmic reticulum-associated amyloid beta-peptide-binding protein |
50.1 nM 1995.3 nM 10000 nM |
Potency Potency Potency |
via Super-PRED
via CMAUP via CMAUP |
| CHEMBL1293226 | B2RXH2 | Lysine-specific demethylase 4D-like |
15848.9 nM 25118.9 nM 562.3 nM 22387.2 nM 562.3 nM 14125.4 nM |
Potency Potency Potency Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP via CMAUP via Super-PRED via CMAUP |
| CHEMBL2608 | P10253 | Lysosomal alpha-glucosidase |
7943.3 nM 39810.7 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL4040 | P28482 | MAP kinase ERK2 |
8912.5 nM 14125.4 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL321 | P14780 | Matrix metalloproteinase 9 |
10 nM 21.22 nM 10 nM |
IC50 IC50 IC50 |
PMID: 23375794
PMID: 23375794 via Super-PRED |
| CHEMBL332 | P03956 | Matrix metalloproteinase-1 |
238.91 nM 238.91 nM |
IC50 IC50 |
via Super-PRED
PMID: 23375794 |
| CHEMBL333 | P08253 | Matrix metalloproteinase-2 |
24.26 nM 24.26 nM |
IC50 IC50 |
PMID: 23375794
via Super-PRED |
| CHEMBL1293224 | P10636 | Microtubule-associated protein tau |
10000 nM 15848.9 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit |
141.3 nM 141.3 nM 141.3 nM |
Potency Potency Potency |
via Super-PRED
via CMAUP via CMAUP |
| CHEMBL1293235 | P02545 | Prelamin-A/C |
2818.4 nM |
Potency |
via CMAUP
|
| CHEMBL335 | P18031 | Protein-tyrosine phosphatase 1B |
3060 nM |
IC50 |
PMID: 19476336
|
| CHEMBL1947 | P10828 | Thyroid hormone receptor beta-1 |
12589.3 nM |
Potency |
via CMAUP
|
| CHEMBL1963 | P16473 | Thyroid stimulating hormone receptor |
794.3 nM |
Potency |
via Super-PRED
|
| CHEMBL1075138 | Q9NUW8 | Tyrosyl-DNA phosphodiesterase 1 |
794.3 nM 6309.6 nM |
Potency Potency |
via CMAUP
via CMAUP |
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 98.25% | 91.11% |
| CHEMBL1951 | P21397 | Monoamine oxidase A | 97.59% | 91.49% |
| CHEMBL3194 | P02766 | Transthyretin | 93.96% | 90.71% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 90.92% | 86.33% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 90.63% | 95.56% |
| CHEMBL1075094 | Q16236 | Nuclear factor erythroid 2-related factor 2 | 87.45% | 96.00% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 84.91% | 89.00% |
| CHEMBL1860 | P10827 | Thyroid hormone receptor alpha | 84.62% | 99.15% |
| CHEMBL4208 | P20618 | Proteasome component C5 | 80.50% | 90.00% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
To see more specific details click the taxa you are interested in.
To see more specific details click the taxa you are interested in.