Raloxifene

Details

• 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

Physical and Chemical Properties

• 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

• 84449-90-1
• Keoxifene
• Raloxifenum
• Raloxifenum [Latin]
• Raloxifeno [Spanish]
• Raloxifeno
• LY 139481
• LY-139481
• Pharoxifene
• Raloxiphene
• Eviden
• Raxeto
• Raloxifene [INN:BAN]
• CCRIS 7129
• HSDB 7460
• CHEMBL81
• (6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophen-3-yl)(4-(2-(piperidin-1-yl)ethoxy)phenyl)methanone
• NSC-747974
• UNII-YX9162EO3I
• (2-(4-Hydroxyphenyl)-6-hydroxybenzo(b)thien-3-yl)(4-(2-(1-piperidinyl)ethoxy)phenyl)methanone
• [6-hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone
• Keoxifene; LY 139481;
• C28H27NO4S
• CHEBI:8772
• YX9162EO3I
• DTXSID3023550
• Raloxifene (INN)
• 2-(4-hydroxyphenyl)-3-{4-[2-(piperidin-1-yl)ethoxy]benzoyl}-1-benzothiophen-6-ol
• Methanone, (6-hydroxy-2-(4-hydroxyphenyl)benzo(b)thien-3-yl)(4-(2-(1-piperidinyl)ethoxy)phenyl)-
• J22.982B
• LY139481
• RALOXIFENE [INN]
• 2-(4-hydroxyphenyl)-3-({4-[2-(piperidin-1-yl)ethoxy]phenyl}carbonyl)-1-benzothiophen-6-ol
• [6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone
• Methanone, [6-Hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]-
• NCGC00015889-05
• CAS-82640-04-8
• Raloxifene, 6
• [2-(4-Hydroxyphenyl)-6-hydroxybenzo[b]thien-3-yl][4-(2-(1-piperidinyl)ethoxy)phenyl]methanone
• [2-(4-hydroxyphenyl)-6-hydroxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone
• [6-hydroxy-2-(4-hydroxyphenyl)-1-benzothien-3-yl]{4-[(2-piperidin-1-ylethyl)oxy]phenyl}methanone
• Eviden (TN)
• Raxeto (TN)
• RALOXIFENE [MI]
• Prestwick0_000862
• Prestwick1_000862
• Prestwick2_000862
• Prestwick3_000862
• Lopac-R-1402
• RALOXIFENE [HSDB]
• RALOXIFENE [VANDF]
• D01XBA
• SCHEMBL6144
• RALOXIFENE [WHO-DD]
• Lopac0_001051
• BSPBio_000903
• KBioGR_002361
• KBioSS_002364
• BIDD:ER0216
• BIDD:GT0795
• SPBio_002824
• BPBio1_000995
• DTXCID803550
• GTPL2820
• BDBM19441
• KBio2_002361
• KBio2_004929
• KBio2_007497
• KBio3_002840
• cid_11071264
• cMAP_000032
• HMS2089F06
• HMS3742O11
• BCP09772
• Raloxifene (extended-release, CDT)
• C28-H27-N-O4-S
• Tox21_202603
• MFCD00866415
• NSC747974
• NSC761389
• s5781
• AKOS015896267
• AC-8399
• CCG-205128
• CS-T-61050
• DB00481
• NSC 747974
• NSC-761389
• SDCCGSBI-0051021.P003
• [6-hydroxy-2-(4-hydroxyphenyl)benzothiophen-3-yl]-[4-[2-(1-piperidyl)ethoxy]phenyl]methanone
• MRF-0000684
• SMP2_000095
• NCGC00015889-01
• NCGC00015889-02
• NCGC00015889-04
• NCGC00015889-06
• NCGC00015889-07
• NCGC00015889-08
• NCGC00015889-10
• NCGC00015889-22
• NCGC00092353-02
• NCGC00092353-04
• NCGC00260151-01
• AS-35086
• HY-13738
• SBI-0051021.P002
• CAS-84449-90-1
• LS-177821
• CS-0007764
• FT-0674305
• EN300-58333
• VU0155042-3
• C07228
• D08465
• A916152
• Q425223
• BRD-K63828191-003-11-5
• 6-hydroxy-2-(4-hydoxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene
• 6-hydroxy-2-(4-hydoxyphenyl)-3[-4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene
• 6-Hydroxy-2-(4-Hydroxyphenyl)-3-[4(2-Piperidinoethoxy)benzoyl]benzo[b]thiophene
• 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]-thiophene
• 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene
• 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2piperidinoethoxy)-benzoyl]benzo[b]thiophene
• 6-hydroxy-2-(4-hydroxyphenyl)-3[-4-(2-piperidinoethoxy)benzoyl]benzo [b]thiophene
• 6-hydroxy-2-(4-hydroxyphenyl)-3[-4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene
• 6-hydroxy-2-(4-hydroxyphenyl)-3[-4-(2piperidinoethoxy)benzoyl]benzo[b]thiophene
• 6-hydroxy-2-(4-hyroxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene
• [2-(4-Hydroxyphenyl)-6-hydroxybenzo[b]thien-3-yl] [4-[2-(1-piperidinyl)ethoxy]phenyl]methanone; Raloxifeno
• [6-Hydroxy-2-(4-hydroxy-phenyl)-benzo[b]thiophen-3-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone
• [6-hydroxy-2-(4-hydroxyphenyl)-1-benzothien-3-yl][4-(2-piperidin-1-ylethoxy)phenyl]methanone
• [6-hydroxy-2-(4-hydroxyphenyl)benzo-[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone
• [6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl]-[4-[2-(1-piperidinyl)ethoxy]phenyl]methanone
• [6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl]-[4-[2-(1piperidinyl)ethoxy]phenyl]methanone
• 6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl 4-[2-(1-piperidinyl)ethoxy]phenyl methanone

2D Structure

ADMET Properties (via admetSAR 2)

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

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

• Tetradium ruticarpum

Cross-Links

• PubChem: 5035
• NPASS: NPC149571
• ChEMBL: CHEMBL81