2-(3,4-Dihydroxyphenyl)chroman-3,5,7-triol
| Internal ID | 07974617-c82a-4f9c-818c-184c90202445 |
| Taxonomy | Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins |
| IUPAC Name | 2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol |
| SMILES (Canonical) | C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)O |
| SMILES (Isomeric) | C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)O |
| InChI | InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2 |
| InChI Key | PFTAWBLQPZVEMU-UHFFFAOYSA-N |
| Popularity | 5,744 references in papers |
| Molecular Formula | C15H14O6 |
| Molecular Weight | 290.27 g/mol |
| Exact Mass | 290.07903816 g/mol |
| Topological Polar Surface Area (TPSA) | 110.00 Ų |
| XlogP | 0.40 |
| Atomic LogP (AlogP) | 1.55 |
| H-Bond Acceptor | 6 |
| H-Bond Donor | 5 |
| Rotatable Bonds | 1 |
| L-Epicatechin |
| 7295-85-4 |
| 13392-26-2 |
| (+/-)-Catechin |
| 17334-50-8 |
| CHEBI:23053 |
| 2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol |
| 2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol |
| EINECS 241-357-4 |
| cis-(+/-)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.8922 | 89.22% |
| Caco-2 | - | 0.9406 | 94.06% |
| Blood Brain Barrier | - | 0.6750 | 67.50% |
| Human oral bioavailability | - | 0.7857 | 78.57% |
| Subcellular localzation | Mitochondria | 0.4440 | 44.40% |
| OATP2B1 inhibitior | - | 0.5776 | 57.76% |
| OATP1B1 inhibitior | + | 0.8774 | 87.74% |
| OATP1B3 inhibitior | + | 0.9480 | 94.80% |
| MATE1 inhibitior | - | 0.9400 | 94.00% |
| OCT2 inhibitior | - | 0.8750 | 87.50% |
| BSEP inhibitior | - | 0.9228 | 92.28% |
| P-glycoprotein inhibitior | - | 0.9411 | 94.11% |
| P-glycoprotein substrate | - | 0.9531 | 95.31% |
| CYP3A4 substrate | - | 0.5560 | 55.60% |
| CYP2C9 substrate | - | 0.8006 | 80.06% |
| CYP2D6 substrate | + | 0.5322 | 53.22% |
| CYP3A4 inhibition | - | 0.8309 | 83.09% |
| CYP2C9 inhibition | - | 0.9071 | 90.71% |
| CYP2C19 inhibition | - | 0.9041 | 90.41% |
| CYP2D6 inhibition | - | 0.9231 | 92.31% |
| CYP1A2 inhibition | - | 0.9046 | 90.46% |
| CYP2C8 inhibition | + | 0.4599 | 45.99% |
| CYP inhibitory promiscuity | - | 0.8170 | 81.70% |
| UGT catelyzed | + | 0.7000 | 70.00% |
| Carcinogenicity (binary) | - | 0.9700 | 97.00% |
| Carcinogenicity (trinary) | Non-required | 0.5825 | 58.25% |
| Eye corrosion | - | 0.9901 | 99.01% |
| Eye irritation | + | 0.9629 | 96.29% |
| Skin irritation | - | 0.5859 | 58.59% |
| Skin corrosion | - | 0.9251 | 92.51% |
| Ames mutagenesis | + | 0.6000 | 60.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.4678 | 46.78% |
| Micronuclear | + | 0.8059 | 80.59% |
| Hepatotoxicity | - | 0.7375 | 73.75% |
| skin sensitisation | - | 0.7452 | 74.52% |
| Respiratory toxicity | + | 0.5778 | 57.78% |
| Reproductive toxicity | + | 0.8333 | 83.33% |
| Mitochondrial toxicity | + | 0.6250 | 62.50% |
| Nephrotoxicity | - | 0.6369 | 63.69% |
| Acute Oral Toxicity (c) | IV | 0.6433 | 64.33% |
| Estrogen receptor binding | - | 0.6719 | 67.19% |
| Androgen receptor binding | + | 0.6638 | 66.38% |
| Thyroid receptor binding | + | 0.7658 | 76.58% |
| Glucocorticoid receptor binding | + | 0.6993 | 69.93% |
| Aromatase binding | + | 0.6008 | 60.08% |
| PPAR gamma | + | 0.6832 | 68.32% |
| Honey bee toxicity | - | 0.8419 | 84.19% |
| Biodegradation | - | 0.8000 | 80.00% |
| Crustacea aquatic toxicity | + | 0.5600 | 56.00% |
| Fish aquatic toxicity | + | 0.7342 | 73.42% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL1293255 | P15428 | 15-hydroxyprostaglandin dehydrogenase [NAD+] |
19952.6 nM |
Potency |
via CMAUP
|
| CHEMBL3577 | P00352 | Aldehyde dehydrogenase 1A1 |
10000 nM |
Potency |
via CMAUP
|
| CHEMBL5979 | P05186 | Alkaline phosphatase, tissue-nonspecific isozyme |
407 nM |
IC50 |
via Super-PRED
|
| CHEMBL2903 | P16050 | Arachidonate 15-lipoxygenase |
12589.3 nM |
Potency |
via CMAUP
|
| CHEMBL1293236 | P46063 | ATP-dependent DNA helicase Q1 |
141253.8 nM 14125.4 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL261 | P00915 | Carbonic anhydrase I |
2420 nM |
Ki |
PMID: 20674354
|
| CHEMBL205 | P00918 | Carbonic anhydrase II |
1840 nM |
Ki |
PMID: 20674354
|
| CHEMBL2885 | P07451 | Carbonic anhydrase III |
3580 nM |
Ki |
PMID: 20674354
|
| CHEMBL3729 | P22748 | Carbonic anhydrase IV |
4900 nM |
Ki |
PMID: 20674354
|
| CHEMBL3594 | Q16790 | Carbonic anhydrase IX |
5030 nM |
Ki |
PMID: 20674354
|
| CHEMBL4789 | P35218 | Carbonic anhydrase VA |
4210 nM |
Ki |
PMID: 20674354
|
| CHEMBL3969 | Q9Y2D0 | Carbonic anhydrase VB |
4020 nM |
Ki |
PMID: 20674354
|
| CHEMBL3025 | P23280 | Carbonic anhydrase VI |
4910 nM |
Ki |
PMID: 20674354
|
| CHEMBL2326 | P43166 | Carbonic anhydrase VII |
450 nM 450 nM |
Ki Ki |
PMID: 20674354
via Super-PRED |
| CHEMBL3242 | O43570 | Carbonic anhydrase XII |
4720 nM |
Ki |
PMID: 20674354
|
| CHEMBL3912 | Q8N1Q1 | Carbonic anhydrase XIII |
10510 nM |
Ki |
PMID: 20674354
|
| CHEMBL3510 | Q9ULX7 | Carbonic anhydrase XIV |
11550 nM |
Ki |
PMID: 20674354
|
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase |
2511.9 nM |
Potency |
via CMAUP
|
| CHEMBL1293226 | B2RXH2 | Lysine-specific demethylase 4D-like |
11220.2 nM |
Potency |
via CMAUP
|
| CHEMBL4040 | P28482 | MAP kinase ERK2 |
15848.9 nM |
Potency |
via CMAUP
|
| CHEMBL1293224 | P10636 | Microtubule-associated protein tau |
14125.4 nM 14125.4 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit |
28.2 nM |
Potency |
via Super-PRED
|
| CHEMBL1075138 | Q9NUW8 | Tyrosyl-DNA phosphodiesterase 1 |
3162.3 nM |
Potency |
via CMAUP
|
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 99.36% | 91.11% |
| CHEMBL1951 | P21397 | Monoamine oxidase A | 98.34% | 91.49% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 90.87% | 97.09% |
| CHEMBL1860 | P10827 | Thyroid hormone receptor alpha | 86.65% | 99.15% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 86.55% | 89.00% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 86.27% | 95.56% |
| CHEMBL1929 | P47989 | Xanthine dehydrogenase | 85.19% | 96.12% |
| CHEMBL5697 | Q9GZT9 | Egl nine homolog 1 | 84.40% | 93.40% |
| CHEMBL3194 | P02766 | Transthyretin | 84.35% | 90.71% |
| CHEMBL3401 | O75469 | Pregnane X receptor | 81.47% | 94.73% |
| CHEMBL3438 | Q05513 | Protein kinase C zeta | 81.02% | 88.48% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 80.01% | 94.45% |
| CHEMBL4208 | P20618 | Proteasome component C5 | 80.01% | 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.
| PubChem | 1203 |
| NPASS | NPC61477 |
| ChEMBL | CHEMBL206452 |
| LOTUS | LTS0090912 |
| wikiData | Q51617472 |