Raloxifene
Internal ID | 10881661-827b-47e2-8dff-6561b7d08c56 |
Taxonomy | Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Phenylketones > Aryl-phenylketones |
IUPAC Name | [6-hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone |
SMILES (Canonical) | C1CCN(CC1)CCOC2=CC=C(C=C2)C(=O)C3=C(SC4=C3C=CC(=C4)O)C5=CC=C(C=C5)O |
SMILES (Isomeric) | C1CCN(CC1)CCOC2=CC=C(C=C2)C(=O)C3=C(SC4=C3C=CC(=C4)O)C5=CC=C(C=C5)O |
InChI | InChI=1S/C28H27NO4S/c30-21-8-4-20(5-9-21)28-26(24-13-10-22(31)18-25(24)34-28)27(32)19-6-11-23(12-7-19)33-17-16-29-14-2-1-3-15-29/h4-13,18,30-31H,1-3,14-17H2 |
InChI Key | GZUITABIAKMVPG-UHFFFAOYSA-N |
Popularity | 9,479 references in papers |
Molecular Formula | C28H27NO4S |
Molecular Weight | 473.60 g/mol |
Exact Mass | 473.16607952 g/mol |
Topological Polar Surface Area (TPSA) | 98.20 Ų |
XlogP | 6.10 |
Atomic LogP (AlogP) | 6.08 |
H-Bond Acceptor | 6 |
H-Bond Donor | 2 |
Rotatable Bonds | 7 |
84449-90-1 |
Keoxifene |
Raloxifenum |
Raloxifenum [Latin] |
Raloxifeno [Spanish] |
Raloxifeno |
LY 139481 |
LY-139481 |
Pharoxifene |
Raloxiphene |
There are more than 10 synonyms. If you wish to see them all click here. |

Target | Value | Probability (raw) | Probability (%) |
---|---|---|---|
Human Intestinal Absorption | + | 0.9735 | 97.35% |
Caco-2 | - | 0.9373 | 93.73% |
Blood Brain Barrier | + | 0.7000 | 70.00% |
Human oral bioavailability | - | 0.8857 | 88.57% |
Subcellular localzation | Mitochondria | 0.9006 | 90.06% |
OATP2B1 inhibitior | + | 0.5680 | 56.80% |
OATP1B1 inhibitior | + | 0.9219 | 92.19% |
OATP1B3 inhibitior | + | 0.9243 | 92.43% |
MATE1 inhibitior | - | 0.9000 | 90.00% |
OCT2 inhibitior | + | 0.7500 | 75.00% |
BSEP inhibitior | - | 0.4879 | 48.79% |
P-glycoprotein inhibitior | + | 0.7682 | 76.82% |
P-glycoprotein substrate | + | 0.9343 | 93.43% |
CYP3A4 substrate | + | 0.6210 | 62.10% |
CYP2C9 substrate | - | 1.0000 | 100.00% |
CYP2D6 substrate | + | 0.5095 | 50.95% |
CYP3A4 inhibition | + | 0.7617 | 76.17% |
CYP2C9 inhibition | - | 0.9071 | 90.71% |
CYP2C19 inhibition | + | 0.8986 | 89.86% |
CYP2D6 inhibition | + | 0.8932 | 89.32% |
CYP1A2 inhibition | - | 0.9045 | 90.45% |
CYP2C8 inhibition | + | 0.9818 | 98.18% |
CYP inhibitory promiscuity | + | 0.8222 | 82.22% |
UGT catelyzed | + | 0.6000 | 60.00% |
Carcinogenicity (binary) | - | 0.9600 | 96.00% |
Carcinogenicity (trinary) | Non-required | 0.6518 | 65.18% |
Eye corrosion | - | 0.9904 | 99.04% |
Eye irritation | - | 0.9541 | 95.41% |
Skin irritation | - | 0.7982 | 79.82% |
Skin corrosion | - | 0.9467 | 94.67% |
Ames mutagenesis | - | 0.5600 | 56.00% |
Human Ether-a-go-go-Related Gene inhibition | - | 0.4125 | 41.25% |
Micronuclear | + | 0.5300 | 53.00% |
Hepatotoxicity | - | 0.7625 | 76.25% |
skin sensitisation | - | 0.8642 | 86.42% |
Respiratory toxicity | + | 0.8222 | 82.22% |
Reproductive toxicity | + | 0.9778 | 97.78% |
Mitochondrial toxicity | + | 0.9375 | 93.75% |
Nephrotoxicity | - | 0.8813 | 88.13% |
Acute Oral Toxicity (c) | III | 0.5721 | 57.21% |
Estrogen receptor binding | + | 0.8940 | 89.40% |
Androgen receptor binding | + | 0.9642 | 96.42% |
Thyroid receptor binding | - | 0.5639 | 56.39% |
Glucocorticoid receptor binding | + | 0.7077 | 70.77% |
Aromatase binding | + | 0.7229 | 72.29% |
PPAR gamma | + | 0.7317 | 73.17% |
Honey bee toxicity | - | 0.9088 | 90.88% |
Biodegradation | - | 0.8250 | 82.50% |
Crustacea aquatic toxicity | - | 0.5050 | 50.50% |
Fish aquatic toxicity | + | 0.8633 | 86.33% |
Proven Targets:
CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
---|---|---|---|---|---|
CHEMBL4931 | Q15125 | 3-beta-hydroxysteroid-delta(8),delta(7)-isomerase |
1 nM 1 nM |
Ki Ki |
PMID: 16033255
via Super-PRED |
CHEMBL220 | P22303 | Acetylcholinesterase |
400 nM |
IC50 |
via CMAUP
|
CHEMBL251 | P29274 | Adenosine A2a receptor |
2111 nM |
IC50 |
via CMAUP
|
CHEMBL3577 | P00352 | Aldehyde dehydrogenase 1A1 |
501.2 nM 2511.9 nM 501.2 nM |
Potency Potency Potency |
via CMAUP
via CMAUP via Super-PRED |
CHEMBL3257 | Q06278 | Aldehyde oxidase |
3 nM 8 nM 44.5 nM |
IC50 IC50 IC50 |
PMID: 20853847
PMID: 21476569 via Super-PRED |
CHEMBL223 | P25100 | Alpha-1d adrenergic receptor |
973 nM |
IC50 |
via CMAUP
|
CHEMBL1867 | P08913 | Alpha-2a adrenergic receptor |
1664 nM |
IC50 |
via CMAUP
|
CHEMBL1942 | P18089 | Alpha-2b adrenergic receptor |
3698 nM |
IC50 |
via CMAUP
|
CHEMBL1916 | P18825 | Alpha-2c adrenergic receptor |
738 nM |
IC50 |
via CMAUP
|
CHEMBL2903 | P16050 | Arachidonate 15-lipoxygenase |
39810.7 nM |
Potency |
via CMAUP
|
CHEMBL1293236 | P46063 | ATP-dependent DNA helicase Q1 |
28183.8 nM |
Potency |
via CMAUP
|
CHEMBL2047 | Q96RI1 | Bile acid receptor FXR |
11560 nM |
IC50 |
PMID: 23688559
|
CHEMBL4096 | P04637 | Cellular tumor antigen p53 |
25118.9 nM 19952.6 nM |
Potency Potency |
via CMAUP
via CMAUP |
CHEMBL3622 | P33261 | Cytochrome P450 2C19 |
6309.57 nM 10000 nM |
AC50 AC50 |
via CMAUP
via CMAUP |
CHEMBL3397 | P11712 | Cytochrome P450 2C9 |
2000 nM |
IC50 |
via CMAUP
|
CHEMBL289 | P10635 | Cytochrome P450 2D6 |
25118.86 nM 7943.28 nM |
AC50 AC50 |
via CMAUP
via CMAUP |
CHEMBL340 | P08684 | Cytochrome P450 3A4 |
2511.9 nM 1258.9 nM 2511.9 nM 1258.9 nM |
Potency Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP via CMAUP |
CHEMBL236 | P41143 | Delta opioid receptor |
6644 nM |
IC50 |
via CMAUP
|
CHEMBL2056 | P21728 | Dopamine D1 receptor |
3864 nM |
IC50 |
via CMAUP
|
CHEMBL217 | P14416 | Dopamine D2 receptor |
1174 nM |
IC50 |
via CMAUP
|
CHEMBL234 | P35462 | Dopamine D3 receptor |
1565 nM |
IC50 |
via CMAUP
|
CHEMBL238 | Q01959 | Dopamine transporter |
1869 nM |
IC50 |
via CMAUP
|
CHEMBL4159 | Q99714 | Endoplasmic reticulum-associated amyloid beta-peptide-binding protein |
7943.3 nM 2511.9 nM |
Potency Potency |
via CMAUP
via CMAUP |
CHEMBL206 | P03372 | Estrogen receptor alpha |
4 nM 0.72 nM 0.7 nM 1.8 nM 1.8 nM 1.8 nM 1.8 nM 1.8 nM 1.8 nM 1.8 nM 1.8 nM 2.4 nM 0.73 nM 0.89 nM 1.8 nM 0.46 nM 1.8 nM 1.8 nM 0.3 nM 0.47 nM 0.553 nM 0.03 nM |
IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 Ki |
PMID: 11356100
PMID: 11356100 PMID: 12459017 PMID: 12565955 PMID: 15006374 PMID: 15084115 PMID: 15109649 PMID: 15125925 PMID: 15225685 PMID: 15225686 PMID: 15582421 PMID: 15658851 PMID: 15713417 PMID: 15911274 PMID: 16203138 PMID: 16499324 PMID: 16722623 PMID: 19366247 PMID: 20659801 PMID: 27185013 via CMAUP via Super-PRED |
CHEMBL242 | Q92731 | Estrogen receptor beta |
15 nM 12 nM 12 nM 12 nM 12 nM 12 nM 12 nM 12 nM 12 nM 18.9 nM 1.6 nM 1.9 nM 12 nM 8.2 nM 8.2 nM 6.9 nM 1.6 nM |
IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 |
PMID: 12459017
PMID: 12565955 PMID: 15006374 PMID: 15084115 PMID: 15109649 PMID: 15125925 PMID: 15225685 PMID: 15225686 PMID: 15582421 PMID: 15713417 PMID: 15911274 PMID: 15993065 PMID: 16203138 PMID: 16722623 PMID: 19366247 PMID: 20659801 via Super-PRED |
CHEMBL237 | P41145 | Kappa opioid receptor |
1602 nM |
IC50 |
via CMAUP
|
CHEMBL1293224 | P10636 | Microtubule-associated protein tau |
14125.4 nM 12589.3 nM |
Potency Potency |
via CMAUP
via CMAUP |
CHEMBL233 | P35372 | Mu opioid receptor |
1176 nM |
IC50 |
via CMAUP
|
CHEMBL2327 | P21452 | Neurokinin 2 receptor |
3989 nM |
IC50 |
via CMAUP
|
CHEMBL222 | P23975 | Norepinephrine transporter |
282 nM |
IC50 |
via CMAUP
|
CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit |
12589.3 nM 12589.3 nM |
Potency Potency |
via CMAUP
via CMAUP |
CHEMBL2536 | Q13393 | Phospholipase D1 |
4300 nM 4000 nM |
IC50 IC50 |
PMID: 19136975
PMID: 19136975 |
CHEMBL2734 | O14939 | Phospholipase D2 |
3400 nM 10000 nM |
IC50 IC50 |
PMID: 19136975
PMID: 19136975 |
CHEMBL3401 | O75469 | Pregnane X receptor |
11710 nM |
EC50 |
PMID: 23688559
|
CHEMBL1293235 | P02545 | Prelamin-A/C |
354.8 nM 354.8 nM |
Potency Potency |
via CMAUP
via Super-PRED |
CHEMBL2842 | P42345 | Serine/threonine-protein kinase mTOR |
23280.9 nM 26121.6 nM |
Potency Potency |
via CMAUP
via CMAUP |
CHEMBL224 | P28223 | Serotonin 2a (5-HT2a) receptor |
1450 nM |
IC50 |
via CMAUP
|
CHEMBL1833 | P41595 | Serotonin 2b (5-HT2b) receptor |
355 nM 69 nM |
IC50 Ki |
via CMAUP
via Super-PRED |
CHEMBL225 | P28335 | Serotonin 2c (5-HT2c) receptor |
1178 nM |
IC50 |
via CMAUP
|
CHEMBL3371 | P50406 | Serotonin 6 (5-HT6) receptor |
750 nM 750 nM |
Ki Ki |
PMID: 22537153
via Super-PRED |
CHEMBL228 | P31645 | Serotonin transporter |
3576 nM |
IC50 |
via CMAUP
|
CHEMBL287 | Q99720 | Sigma opioid receptor |
681 nM |
IC50 |
via CMAUP
|
CHEMBL1293256 | P40225 | Thrombopoietin |
15848.9 nM 15848.9 nM |
Potency Potency |
via CMAUP
via CMAUP |
CHEMBL1963 | P16473 | Thyroid stimulating hormone receptor |
31622.8 nM 31622.8 nM |
Potency Potency |
via CMAUP
via CMAUP |
CHEMBL1841 | P06241 | Tyrosine-protein kinase FYN |
3666 nM |
IC50 |
via CMAUP
|
CHEMBL1075138 | Q9NUW8 | Tyrosyl-DNA phosphodiesterase 1 |
12589.3 nM 19952.6 nM |
Potency Potency |
via CMAUP
via CMAUP |
CHEMBL1293227 | O75604 | Ubiquitin carboxyl-terminal hydrolase 2 |
5011.9 nM |
Potency |
via CMAUP
|
Predicted Targets (via Super-PRED):
CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
---|---|---|---|---|
CHEMBL2107 | P61073 | C-X-C chemokine receptor type 4 | 97.42% | 93.10% |
CHEMBL4208 | P20618 | Proteasome component C5 | 97.12% | 90.00% |
CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 95.22% | 96.09% |
CHEMBL2581 | P07339 | Cathepsin D | 95.06% | 98.95% |
CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 94.93% | 86.33% |
CHEMBL6175 | Q9H3R0 | Lysine-specific demethylase 4C | 93.00% | 96.69% |
CHEMBL220 | P22303 | Acetylcholinesterase | 92.69% | 94.45% |
CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 92.35% | 99.17% |
CHEMBL1860 | P10827 | Thyroid hormone receptor alpha | 90.10% | 99.15% |
CHEMBL2288 | Q13526 | Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 | 89.77% | 91.71% |
CHEMBL335 | P18031 | Protein-tyrosine phosphatase 1B | 89.54% | 95.17% |
CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 89.44% | 94.00% |
CHEMBL1293255 | P15428 | 15-hydroxyprostaglandin dehydrogenase [NAD+] | 89.34% | 83.57% |
CHEMBL2243 | O00519 | Anandamide amidohydrolase | 88.11% | 97.53% |
CHEMBL5845 | P23415 | Glycine receptor subunit alpha-1 | 87.94% | 90.71% |
CHEMBL1075162 | Q13304 | Uracil nucleotide/cysteinyl leukotriene receptor | 86.59% | 80.33% |
CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 85.76% | 91.11% |
CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 85.63% | 89.00% |
CHEMBL2095172 | P14867 | GABA-A receptor; alpha-1/beta-2/gamma-2 | 83.86% | 92.67% |
CHEMBL1744525 | P43490 | Nicotinamide phosphoribosyltransferase | 83.67% | 96.25% |
CHEMBL3891 | P07384 | Calpain 1 | 83.30% | 93.04% |
CHEMBL5608 | Q16288 | NT-3 growth factor receptor | 82.94% | 95.89% |
CHEMBL2007 | P16234 | Platelet-derived growth factor receptor alpha | 81.43% | 91.07% |
CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 81.43% | 95.56% |
CHEMBL344 | Q99705 | Melanin-concentrating hormone receptor 1 | 80.78% | 92.50% |
CHEMBL3091268 | Q92753 | Nuclear receptor ROR-beta | 80.75% | 95.50% |
CHEMBL4330 | Q9NS75 | Cysteinyl leukotriene receptor 2 | 80.64% | 98.00% |
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.
Tetradium ruticarpum |