Raloxifene

Details

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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 9,207 references in papers

Physical and Chemical Properties

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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

Synonyms

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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.

2D Structure

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2D Structure of Raloxifene

3D Structure

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ADMET Properties (via admetSAR 2)

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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%

Targets

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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%

Plants that contains it

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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.
Tetradium ruticarpum

Cross-Links

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PubChem 5035
NPASS NPC149571
ChEMBL CHEMBL81