3,4-Dihydroxybenzoic acid
| Internal ID | c9e45047-e295-436d-8ced-d2827c145e67 |
| Taxonomy | Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Hydroxybenzoic acid derivatives |
| IUPAC Name | 3,4-dihydroxybenzoic acid |
| SMILES (Canonical) | C1=CC(=C(C=C1C(=O)O)O)O |
| SMILES (Isomeric) | C1=CC(=C(C=C1C(=O)O)O)O |
| InChI | InChI=1S/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11) |
| InChI Key | YQUVCSBJEUQKSH-UHFFFAOYSA-N |
| Popularity | 7,020 references in papers |
| Molecular Formula | C7H6O4 |
| Molecular Weight | 154.12 g/mol |
| Exact Mass | 154.02660867 g/mol |
| Topological Polar Surface Area (TPSA) | 77.80 Ų |
| XlogP | 1.10 |
| Atomic LogP (AlogP) | 0.80 |
| H-Bond Acceptor | 3 |
| H-Bond Donor | 3 |
| Rotatable Bonds | 1 |
| protocatechuic acid |
| 99-50-3 |
| Protocatehuic acid |
| 4-Carboxy-1,2-dihydroxybenzene |
| protocatechuate |
| 4,5-Dihydroxybenzoic acid |
| Benzoic acid, 3,4-dihydroxy- |
| CCRIS 6291 |
| protocatechuicacid |
| EINECS 202-760-0 |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9598 | 95.98% |
| Caco-2 | - | 0.5935 | 59.35% |
| Blood Brain Barrier | - | 0.6750 | 67.50% |
| Human oral bioavailability | + | 0.6571 | 65.71% |
| Subcellular localzation | Mitochondria | 0.8732 | 87.32% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.9779 | 97.79% |
| OATP1B3 inhibitior | + | 0.9647 | 96.47% |
| MATE1 inhibitior | - | 0.8200 | 82.00% |
| OCT2 inhibitior | - | 1.0000 | 100.00% |
| BSEP inhibitior | - | 0.9867 | 98.67% |
| P-glycoprotein inhibitior | - | 0.9824 | 98.24% |
| P-glycoprotein substrate | - | 0.9942 | 99.42% |
| CYP3A4 substrate | - | 0.8317 | 83.17% |
| CYP2C9 substrate | - | 0.8120 | 81.20% |
| CYP2D6 substrate | - | 0.8735 | 87.35% |
| CYP3A4 inhibition | - | 0.9535 | 95.35% |
| CYP2C9 inhibition | - | 0.9568 | 95.68% |
| CYP2C19 inhibition | - | 0.9707 | 97.07% |
| CYP2D6 inhibition | - | 0.9636 | 96.36% |
| CYP1A2 inhibition | - | 0.9545 | 95.45% |
| CYP2C8 inhibition | - | 0.8081 | 80.81% |
| CYP inhibitory promiscuity | - | 0.9564 | 95.64% |
| UGT catelyzed | + | 0.9000 | 90.00% |
| Carcinogenicity (binary) | - | 0.7623 | 76.23% |
| Carcinogenicity (trinary) | Non-required | 0.6219 | 62.19% |
| Eye corrosion | + | 0.5165 | 51.65% |
| Eye irritation | + | 1.0000 | 100.00% |
| Skin irritation | + | 0.9070 | 90.70% |
| Skin corrosion | - | 0.6894 | 68.94% |
| Ames mutagenesis | - | 0.7200 | 72.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.9038 | 90.38% |
| Micronuclear | + | 0.8700 | 87.00% |
| Hepatotoxicity | + | 0.6375 | 63.75% |
| skin sensitisation | + | 0.8452 | 84.52% |
| Respiratory toxicity | - | 0.6111 | 61.11% |
| Reproductive toxicity | + | 0.7222 | 72.22% |
| Mitochondrial toxicity | - | 0.6750 | 67.50% |
| Nephrotoxicity | - | 0.5543 | 55.43% |
| Acute Oral Toxicity (c) | III | 0.5059 | 50.59% |
| Estrogen receptor binding | - | 0.8269 | 82.69% |
| Androgen receptor binding | - | 0.5658 | 56.58% |
| Thyroid receptor binding | - | 0.8454 | 84.54% |
| Glucocorticoid receptor binding | - | 0.6615 | 66.15% |
| Aromatase binding | - | 0.7999 | 79.99% |
| PPAR gamma | - | 0.7772 | 77.72% |
| Honey bee toxicity | - | 0.9686 | 96.86% |
| Biodegradation | + | 0.9500 | 95.00% |
| Crustacea aquatic toxicity | - | 0.9200 | 92.00% |
| Fish aquatic toxicity | + | 0.9494 | 94.94% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL261 | P00915 | Carbonic anhydrase I |
1080 nM |
Ki |
PMID: 21282059
|
| CHEMBL205 | P00918 | Carbonic anhydrase II |
470 nM 470 nM |
Ki Ki |
PMID: 21282059
via Super-PRED |
| CHEMBL3729 | P22748 | Carbonic anhydrase IV |
2450 nM |
Ki |
PMID: 22687439
|
| CHEMBL3594 | Q16790 | Carbonic anhydrase IX |
4450 nM |
Ki |
PMID: 21282059
|
| CHEMBL3025 | P23280 | Carbonic anhydrase VI |
4720 nM 4720 nM |
Ki Ki |
PMID: 21669522
PMID: 22687439 |
| CHEMBL2326 | P43166 | Carbonic anhydrase VII |
7870 nM |
Ki |
PMID: 22668600
|
| CHEMBL3242 | O43570 | Carbonic anhydrase XII |
4090 nM |
Ki |
PMID: 21282059
|
| CHEMBL3510 | Q9ULX7 | Carbonic anhydrase XIV |
690 nM 690 nM |
Ki Ki |
PMID: 22668600
via Super-PRED |
| CHEMBL2392 | P06746 | DNA polymerase beta |
25118.9 nM |
Potency |
via CMAUP
|
| CHEMBL1287622 | Q9Y468 | Lethal(3)malignant brain tumor-like protein 1 |
39810.7 nM |
Potency |
via CMAUP
|
| CHEMBL1293226 | B2RXH2 | Lysine-specific demethylase 4D-like |
35481.3 nM |
Potency |
via CMAUP
|
| CHEMBL2608 | P10253 | Lysosomal alpha-glucosidase |
5011.9 nM |
Potency |
via CMAUP
|
| CHEMBL1293224 | P10636 | Microtubule-associated protein tau |
2818.4 nM |
Potency |
via CMAUP
|
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL3194 | P02766 | Transthyretin | 96.11% | 90.71% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 93.22% | 91.11% |
| CHEMBL1951 | P21397 | Monoamine oxidase A | 88.53% | 91.49% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 87.13% | 86.33% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 85.81% | 95.56% |
| CHEMBL4208 | P20618 | Proteasome component C5 | 83.81% | 90.00% |
| CHEMBL1811 | P34995 | Prostanoid EP1 receptor | 83.11% | 95.71% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 82.76% | 99.17% |
| CHEMBL3864 | Q06124 | Protein-tyrosine phosphatase 2C | 82.13% | 94.42% |
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.
| PubChem | 72 |
| NPASS | NPC156654 |
| ChEMBL | CHEMBL37537 |
| LOTUS | LTS0018765 |
| wikiData | Q418599 |