Luteolin
| Internal ID | 1fc456b8-89ee-41db-a889-aa2b630e0077 |
| Taxonomy | Phenylpropanoids and polyketides > Flavonoids > Flavones |
| IUPAC Name | 2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one |
| SMILES (Canonical) | C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O)O |
| SMILES (Isomeric) | C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O)O |
| InChI | InChI=1S/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H |
| InChI Key | IQPNAANSBPBGFQ-UHFFFAOYSA-N |
| Popularity | 9,534 references in papers |
| Molecular Formula | C15H10O6 |
| Molecular Weight | 286.24 g/mol |
| Exact Mass | 286.04773803 g/mol |
| Topological Polar Surface Area (TPSA) | 107.00 Ų |
| XlogP | 1.40 |
| Atomic LogP (AlogP) | 2.28 |
| H-Bond Acceptor | 6 |
| H-Bond Donor | 4 |
| Rotatable Bonds | 1 |
| 491-70-3 |
| Digitoflavone |
| Luteolol |
| 3',4',5,7-Tetrahydroxyflavone |
| 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one |
| Flacitran |
| Luteoline |
| Salifazide |
| Weld Lake |
| Yama kariyasu |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9071 | 90.71% |
| Caco-2 | + | 0.7457 | 74.57% |
| Blood Brain Barrier | - | 0.7750 | 77.50% |
| Human oral bioavailability | - | 0.5714 | 57.14% |
| Subcellular localzation | Mitochondria | 0.5892 | 58.92% |
| OATP2B1 inhibitior | + | 0.5053 | 50.53% |
| OATP1B1 inhibitior | + | 0.9662 | 96.62% |
| OATP1B3 inhibitior | + | 0.9480 | 94.80% |
| MATE1 inhibitior | + | 0.6600 | 66.00% |
| OCT2 inhibitior | - | 0.9750 | 97.50% |
| BSEP inhibitior | - | 0.8342 | 83.42% |
| P-glycoprotein inhibitior | - | 0.9249 | 92.49% |
| P-glycoprotein substrate | - | 0.9343 | 93.43% |
| CYP3A4 substrate | - | 0.5353 | 53.53% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.8553 | 85.53% |
| CYP3A4 inhibition | + | 0.6951 | 69.51% |
| CYP2C9 inhibition | - | 0.5823 | 58.23% |
| CYP2C19 inhibition | - | 0.9025 | 90.25% |
| CYP2D6 inhibition | - | 0.9287 | 92.87% |
| CYP1A2 inhibition | + | 0.9106 | 91.06% |
| CYP2C8 inhibition | + | 0.8230 | 82.30% |
| CYP inhibitory promiscuity | + | 0.5822 | 58.22% |
| UGT catelyzed | + | 0.8000 | 80.00% |
| Carcinogenicity (binary) | - | 1.0000 | 100.00% |
| Carcinogenicity (trinary) | Non-required | 0.6750 | 67.50% |
| Eye corrosion | - | 0.9905 | 99.05% |
| Eye irritation | + | 0.9781 | 97.81% |
| Skin irritation | + | 0.5835 | 58.35% |
| Skin corrosion | - | 0.9397 | 93.97% |
| Ames mutagenesis | + | 0.6600 | 66.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.8797 | 87.97% |
| Micronuclear | + | 0.9300 | 93.00% |
| Hepatotoxicity | - | 0.5125 | 51.25% |
| skin sensitisation | - | 0.7447 | 74.47% |
| Respiratory toxicity | + | 0.5778 | 57.78% |
| Reproductive toxicity | + | 0.7667 | 76.67% |
| Mitochondrial toxicity | + | 0.5875 | 58.75% |
| Nephrotoxicity | - | 0.6902 | 69.02% |
| Acute Oral Toxicity (c) | II | 0.7348 | 73.48% |
| Estrogen receptor binding | + | 0.8691 | 86.91% |
| Androgen receptor binding | + | 0.9020 | 90.20% |
| Thyroid receptor binding | + | 0.6411 | 64.11% |
| Glucocorticoid receptor binding | + | 0.9141 | 91.41% |
| Aromatase binding | + | 0.8547 | 85.47% |
| PPAR gamma | + | 0.9000 | 90.00% |
| Honey bee toxicity | - | 0.7975 | 79.75% |
| Biodegradation | - | 0.9500 | 95.00% |
| Crustacea aquatic toxicity | - | 0.5700 | 57.00% |
| Fish aquatic toxicity | + | 0.9124 | 91.24% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL1293255 | P15428 | 15-hydroxyprostaglandin dehydrogenase [NAD+] |
11220.2 nM |
Potency |
via CMAUP
|
| CHEMBL3577 | P00352 | Aldehyde dehydrogenase 1A1 |
19952.6 nM 8912.5 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL5983 | O60218 | Aldo-keto reductase family 1 member B10 |
107800 nM 9200 nM |
IC50 IC50 |
PMID: 26529431
PMID: 26529431 |
| CHEMBL1900 | P15121 | Aldose reductase |
600 nM 3200 nM 600 nM |
IC50 IC50 IC50 |
PMID: 23683835
PMID: 26529431 via Super-PRED |
| CHEMBL3687 | P18054 | Arachidonate 12-lipoxygenase |
15848.9 nM 2511.9 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL2903 | P16050 | Arachidonate 15-lipoxygenase |
2511.9 nM 1584.9 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL215 | P09917 | Arachidonate 5-lipoxygenase |
1600 nM |
IC50 |
PMID: 24368208
|
| CHEMBL5393 | Q9UNQ0 | ATP-binding cassette sub-family G member 2 |
8900 nM |
IC50 |
PMID: 21275386
|
| CHEMBL1293236 | P46063 | ATP-dependent DNA helicase Q1 |
7943.3 nM 6309.6 nM 8912.5 nM 12589.3 nM |
Potency Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP via CMAUP |
| CHEMBL2487 | P05067 | Beta amyloid A4 protein |
6400 nM |
IC50 |
PMID: 24878198
|
| CHEMBL1293237 | P54132 | Bloom syndrome protein |
19952.6 nM 15848.9 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL205 | P00918 | Carbonic anhydrase II |
3691.6 nM |
Ki |
PMID: 26498393
|
| CHEMBL3729 | P22748 | Carbonic anhydrase IV |
293 nM 293 nM |
Ki Ki |
PMID: 26498393
via Super-PRED |
| CHEMBL2326 | P43166 | Carbonic anhydrase VII |
4.7 nM 4.7 nM |
Ki Ki |
PMID: 26498393
via Super-PRED |
| CHEMBL3242 | O43570 | Carbonic anhydrase XII |
60.3 nM 60.3 nM |
Ki Ki |
PMID: 26498393
via Super-PRED |
| CHEMBL4096 | P04637 | Cellular tumor antigen p53 |
3162.3 nM 5011.9 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL301 | P24941 | Cyclin-dependent kinase 2 |
20000 nM |
IC50 |
PMID: 17178224
|
| CHEMBL2231 | P04798 | Cytochrome P450 1A1 |
1249 nM |
IC50 |
PMID: 20696580
|
| CHEMBL3356 | P05177 | Cytochrome P450 1A2 |
3370 nM |
IC50 |
PMID: 20696580
|
| CHEMBL4878 | Q16678 | Cytochrome P450 1B1 |
79 nM 79 nM |
IC50 IC50 |
PMID: 20696580
via Super-PRED |
| CHEMBL3622 | P33261 | Cytochrome P450 2C19 |
15848.9 nM |
Potency |
via CMAUP
|
| CHEMBL3397 | P11712 | Cytochrome P450 2C9 |
31622.8 nM |
Potency |
via CMAUP
|
| CHEMBL289 | P10635 | Cytochrome P450 2D6 |
31622.8 nM |
Potency |
via CMAUP
|
| CHEMBL340 | P08684 | Cytochrome P450 3A4 |
15848.9 nM 5011.9 nM 15848.9 nM 5011.9 nM |
Potency Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP via CMAUP |
| CHEMBL2558 | P53355 | Death-associated protein kinase 1 |
21000 nM |
IC50 |
PMID: 26322379
|
| CHEMBL284 | P27487 | Dipeptidyl peptidase IV |
120 nM |
IC50 |
via Super-PRED
|
| CHEMBL2392 | P06746 | DNA polymerase beta |
7079.5 nM |
Potency |
via CMAUP
|
| CHEMBL4159 | Q99714 | Endoplasmic reticulum-associated amyloid beta-peptide-binding protein |
10000 nM 10000 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL1293267 | Q9HC97 | G-protein coupled receptor 35 |
18600 nM |
IC50 |
PMID: 24900447
|
| CHEMBL1293257 | P51570 | Galactokinase |
47269 nM |
Potency |
via CMAUP
|
| CHEMBL262 | P49841 | Glycogen synthase kinase-3 beta |
1500 nM |
IC50 |
DOI: 10.1007/s00044-012-0353-y
|
| CHEMBL2424 | Q04760 | Glyoxalase I |
7700 nM |
IC50 |
PMID: 18258440
|
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha |
398.1 nM 398.1 nM 398.1 nM |
Potency Potency Potency |
via CMAUP
via CMAUP via Super-PRED |
| CHEMBL4660 | P28907 | Lymphocyte differentiation antigen CD38 |
8200 nM |
IC50 |
PMID: 21641214
|
| CHEMBL1293226 | B2RXH2 | Lysine-specific demethylase 4D-like |
8912.5 nM 8912.5 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL2608 | P10253 | Lysosomal alpha-glucosidase |
25118.9 nM |
Potency |
via CMAUP
|
| CHEMBL4393 | P39900 | Matrix metalloproteinase 12 |
980 nM 980 nM |
IC50 IC50 |
PMID: 22658537
via Super-PRED |
| CHEMBL280 | P45452 | Matrix metalloproteinase 13 |
10050 nM |
IC50 |
PMID: 22658537
|
| CHEMBL283 | P08254 | Matrix metalloproteinase 3 |
16200 nM |
IC50 |
PMID: 22658537
|
| CHEMBL321 | P14780 | Matrix metalloproteinase 9 |
5620 nM |
IC50 |
PMID: 22658537
|
| CHEMBL333 | P08253 | Matrix metalloproteinase-2 |
3610 nM |
IC50 |
PMID: 22658537
|
| CHEMBL1293224 | P10636 | Microtubule-associated protein tau |
17782.8 nM 12589.3 nM 12589.3 nM |
Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP |
| CHEMBL1951 | P21397 | Monoamine oxidase A |
4900 nM |
IC50 |
PMID: 20045650
|
| CHEMBL1250375 | Q9NPH5 | NADPH oxidase 4 |
850 nM |
IC50 |
PMID: 20731357
|
| CHEMBL4302 | P08183 | P-glycoprotein 1 |
19600 nM |
IC50 |
PMID: 15240100
|
| CHEMBL3105 | P09874 | Poly [ADP-ribose] polymerase-1 |
4265.8 nM 4200 nM |
IC50 IC50 |
PMID: 23574272
PMID: 23574272 |
| CHEMBL1293235 | P02545 | Prelamin-A/C |
3162.3 nM |
Potency |
via CMAUP
|
| CHEMBL2478 | P04745 | Salivary alpha-amylase |
18400 nM |
IC50 |
PMID: 18507367
|
| CHEMBL1293232 | Q16637 | Survival motor neuron protein |
8912.5 nM |
Potency |
via CMAUP
|
| CHEMBL6164 | O95271 | Tankyrase-1 |
2398.83 nM 2400 nM |
IC50 IC50 |
PMID: 23574272
PMID: 23574272 |
| CHEMBL6154 | Q9H2K2 | Tankyrase-2 |
1071.52 nM 1100 nM |
IC50 IC50 |
PMID: 23574272
PMID: 23574272 |
| CHEMBL1947 | P10828 | Thyroid hormone receptor beta-1 |
44668.4 nM |
Potency |
via CMAUP
|
| CHEMBL1963 | P16473 | Thyroid stimulating hormone receptor |
39810.7 nM |
Potency |
via CMAUP
|
| CHEMBL3194 | P02766 | Transthyretin |
7000 nM 70 nM |
IC50 Kd |
PMID: 26214366
via Super-PRED |
| CHEMBL1974 | P36888 | Tyrosine-protein kinase receptor FLT3 |
830 nM 830 nM |
IC50 IC50 |
PMID: 23411073
via Super-PRED |
| CHEMBL2599 | P43405 | Tyrosine-protein kinase SYK |
12000 nM |
IC50 |
PMID: 22257213
|
| CHEMBL1075138 | Q9NUW8 | Tyrosyl-DNA phosphodiesterase 1 |
19952.6 nM 39810.7 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL1929 | P47989 | Xanthine dehydrogenase |
550 nM 11540 nM 7800 nM |
IC50 IC50 IC50 |
PMID: 9461655
PMID: 19476336 PMID: 26096677 |
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 98.84% | 91.11% |
| CHEMBL1951 | P21397 | Monoamine oxidase A | 96.41% | 91.49% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 94.32% | 89.00% |
| CHEMBL1860 | P10827 | Thyroid hormone receptor alpha | 93.92% | 99.15% |
| CHEMBL2581 | P07339 | Cathepsin D | 92.02% | 98.95% |
| CHEMBL1929 | P47989 | Xanthine dehydrogenase | 89.61% | 96.12% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 88.17% | 94.00% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 87.56% | 95.56% |
| CHEMBL5845 | P23415 | Glycine receptor subunit alpha-1 | 85.89% | 90.71% |
| CHEMBL3401 | O75469 | Pregnane X receptor | 85.41% | 94.73% |
| CHEMBL5697 | Q9GZT9 | Egl nine homolog 1 | 84.02% | 93.40% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 83.64% | 86.33% |
| CHEMBL1978 | P11511 | Cytochrome P450 19A1 | 82.37% | 91.76% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 81.41% | 99.23% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 80.81% | 94.45% |
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.