Clomifene

Details

• Internal ID: 6fa5e515-77e5-4849-b181-0d552fe676cd
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: 2-[4-[(Z)-2-chloro-1,2-diphenylethenyl]phenoxy]-N,N-diethylethanamine
• SMILES (Canonical): CCN(CC)CCOC1=CC=C(C=C1)C(=C(C2=CC=CC=C2)Cl)C3=CC=CC=C3
• SMILES (Isomeric): CCN(CC)CCOC1=CC=C(C=C1)/C(=C(/C2=CC=CC=C2)\Cl)/C3=CC=CC=C3
• InChI: InChI=1S/C26H28ClNO/c1-3-28(4-2)19-20-29-24-17-15-22(16-18-24)25(21-11-7-5-8-12-21)26(27)23-13-9-6-10-14-23/h5-18H,3-4,19-20H2,1-2H3/b26-25-
• InChI Key: GKIRPKYJQBWNGO-QPLCGJKRSA-N
• Popularity: 7,859 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈ClNO
• Molecular Weight: 406.00 g/mol
• Exact Mass: 405.1859422 g/mol
• Topological Polar Surface Area (TPSA): 12.50 Ų
• XlogP: 7.20
• Atomic LogP (AlogP): 6.56
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 9

Synonyms

• Clomifene
• clomiphene
• Zuclomifene
• cis-Clomiphene
• Clomiphene B
• 15690-55-8
• Cisclomifenum
• Zuclomiphene [USAN]
• cis-Clomifene
• 911-45-5
• Cisclomiphene
• Zuclomifeno
• Zuclomifenum
• CIS-CLOMIPHENE HCL
• Zuclomifenum [INN-Latin]
• Zuclomifeno [INN-Spanish]
• Clomiphene cis-form
• Zuclomifene [INN]
• ISOMER A
• RMI-16312
• C26H28ClNO
• RMI 16,312
• Transclomiphene
• 2-[4-[(Z)-2-chloro-1,2-diphenylethenyl]phenoxy]-N,N-diethylethanamine
• Clomifeno
• UNII-3JU1DU3652
• CHEMBL167779
• Triethylamine, 2-(p-(2-chloro-1,2-diphenylvinyl)phenoxy)-
• (Z)-2-(p-(2-Chloro-1,2-diphenylvinyl)phenoxy)triethylamine
• HSDB 3039
• 3JU1DU3652
• EINECS 213-008-6
• RMI-16,312
• Zuclomiphene (USAN)
• cis-2-(p-(2-Chloro-1,2-diphenylvinyl)phenoxy)triethylamine
• Clomifene [INN:BAN]
• Clomifenum [INN-Latin]
• Clomifeno [INN-Spanish]
• cis-2-(4-(2-Chloro-1,2-diphenylethenyl)phenoxy)-N,N-diethylethanamine
• Ethanamine, 2-(4-(2-chloro-1,2-diphenylethenyl)phenoxy)-N,N-diethyl-, (Z)-
• Clomifenum
• Clostilbegit
• Enclomiphen
• Klostilbegit
• Clomifen
• En-Clomiphene
• DTXCID202843
• 2-(4-(2-Chloro-1,2-diphenylethenyl)phenoxy)-N,N-diethylethanamine
• (Z)-isomer
• Triethylamine, 2-(p-(2-chloro-1,2-diphenylvinyl)phenoxy)-, (Z)-
• CAS-911-45-5
• Clomiphene; Clomiphene B
• Ethanamine, 2-[4-(2-chloro-1,2-diphenylethenyl)phenoxy]-N,N-diethyl-
• UNII-1HRS458QU2
• 2-(p-(2-Chloro-1,2-diphenylvinyl)phenoxy)triethylamine
• 2-[p-(2-Chloro-1,2-diphenylvinyl)phenoxy]triethylamine
• DTXSID1022843
• Triethylamine, 2-[p-(2-chloro-1,2-diphenylvinyl)phenoxy]-
• 2-(p-(beta-Chloro-alpha-phenylstyryl)phenoxy)-triethylamine
• Triethylamine, 2-[p-(2-chloro-1,2-diphenylvinyl)phenoxy]-, (Z)-
• 1-(p-(beta-Diethylaminoethoxy)-phenyl)-1,2-diphenylchloroethylene
• 2-[4-(2-chloro-1,2-diphenylethenyl)phenoxy]-N,N-diethylethanamine
• Ethanamine, 2-(4-(2-chloro-1,2-diphenylethenyl)phenoxy)-N,N-diethyl-
• Clomiphene, 2
• Ethanamine, 2-[4-(2-chloro-1,2-diphenylethenyl)phenoxy]-N,N-diethyl-, (Z)-
• NCGC00179503-02
• (E)-Clomiphene;trans-Clomiphene;Enclomifene
• Clomid (Salt/Mix)
• Ardomon (Salt/Mix)
• CIS-CLOMIPHENEHCL
• Chlomaphene (Salt/Mix)
• Chloramifene (Salt/Mix)
• 2-(4-(2-Chloro-1,2-diphenylvinyl)phenoxy)-N,N-diethylethanamine
• Spectrum5_000757
• Chloramiphene (Salt/Mix)
• MRL-41 (Salt/Mix)
• SCHEMBL34894
• BSPBio_002053
• {2-[4-(2-chloro-1,2-diphenylethenyl)phenoxy]ethyl}diethylamine
• 2-(4-[2-Chloro-1,2-diphenylethenyl]phenoxy)-N,N-diethylethanamine
• 2-({4-[(Z)-2-chloro-1,2-diphenylethenyl]phenyl}oxy)-N,N-diethylethanamine
• BDBM71545
• cid_3033832
• CLOMIPHENE CIS-FORM [MI]
• CHEBI:177766
• GKIRPKYJQBWNGO-QPLCGJKRSA-N
• BDBM430640
• DTXSID601317947
• 2,2-Difluoroethylaminehydrochloride
• BCP27849
• HY-A0287
• Tox21_113110
• Tox21_113110_1
• AT36987
• IDI1_000462
• QTL1_000019
• Cisclomifenum; cis-Clomiphene;Zuclomifene
• NCGC00164385-02
• NCGC00164385-03
• NCGC00164385-05
• NCGC00164385-06
• SBI-0051318.P003
• LS-157234
• LS-157236
• BB 0262806
• CS-0019859
• D09037
• AB00053440-08
• AB00053440_09
• AB00053440_10
• EN300-7479238
• A937583
• BRD-K29950728-048-02-6
• BRD-K29950728-048-08-3
• BRD-K91328526-048-01-4
• Q27257344
• (2-{4-[(E)-2-chloro-1,2-diphenylvinyl]phenoxy}ethyl)diethylamine
• 1-(p-(.beta.-Diethylaminoethoxy)-phenyl)-1,2-diphenylchloroethylene
• 2-(4-(2-Chloro-1,2-diphenylvinyl)-phenoxy)-N,N-diethylethanamine
• 2-(p-(.beta.-Chloro-.alpha.-phenylstyryl)phenoxy)-triethylamine
• (Z)-2-(4-(2-chloro-1,2-diphenylvinyl)phenoxy)-N,N-diethylethan-1-amine
• 2-[4-[(Z)-2-chloro-1,2-diphenyl-vinyl]phenoxy]-N,N-diethyl-ethanamine
• 2-[4-[(Z)-2-chloro-1,2-diphenyl-vinyl]phenoxy]ethyl-diethyl-amine;citric acid
• 7-TRIFLUOROMETHOXY-2,3,4,5-TETRAHYDRO-1H-BENZO[B]AZEPINEHYDROCHLORIDE
• ETHANAMINE, 2-(4-((1Z)-2-CHLORO-1,2-DIPHENYLETHENYL)PHENOXY)-N,N-DIETHYL-
• 2-[4-[(Z)-2-chloranyl-1,2-diphenyl-ethenyl]phenoxy]-N,N-diethyl-ethanamine;2-oxidanylpropane-1,2,3-tricarboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9947	99.47%
Caco-2	+	0.7120	71.20%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.8143	81.43%
Subcellular localzation	Lysosomes	0.5950	59.50%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9269	92.69%
OATP1B3 inhibitior	+	0.9443	94.43%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9573	95.73%
P-glycoprotein inhibitior	-	0.6931	69.31%
P-glycoprotein substrate	-	0.5340	53.40%
CYP3A4 substrate	+	0.5531	55.31%
CYP2C9 substrate	-	0.7713	77.13%
CYP2D6 substrate	+	0.5994	59.94%
CYP3A4 inhibition	-	0.8089	80.89%
CYP2C9 inhibition	-	0.6036	60.36%
CYP2C19 inhibition	+	0.7004	70.04%
CYP2D6 inhibition	+	0.8315	83.15%
CYP1A2 inhibition	+	0.9332	93.32%
CYP2C8 inhibition	+	0.9262	92.62%
CYP inhibitory promiscuity	+	0.9254	92.54%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7551	75.51%
Carcinogenicity (trinary)	Non-required	0.5403	54.03%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.7250	72.50%
Skin corrosion	-	0.7935	79.35%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9579	95.79%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.8000	80.00%
skin sensitisation	-	0.6915	69.15%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.6706	67.06%
Acute Oral Toxicity (c)	IV	0.6251	62.51%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.9047	90.47%
Thyroid receptor binding	+	0.7340	73.40%
Glucocorticoid receptor binding	+	0.6506	65.06%
Aromatase binding	+	0.8641	86.41%
PPAR gamma	+	0.8249	82.49%
Honey bee toxicity	-	0.9412	94.12%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.7200	72.00%
Fish aquatic toxicity	+	0.9668	96.68%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4931	Q15125	3-beta-hydroxysteroid-delta(8),delta(7)-isomerase	2 nM; 1 nM; 2 nM	Ki; Ki; Ki	via Super-PRED; via Super-PRED; PMID: 16033255
CHEMBL221	P23219	Cyclooxygenase-1	346 nM	IC50	via Super-PRED
CHEMBL240	Q12809	HERG	181.97 nM; 181.97 nM	IC50; IC50	PMID: 21185626; via Super-PRED
CHEMBL287	Q99720	Sigma opioid receptor	5 nM	Ki	PMID: 16033255

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	95.65%	94.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.08%	86.33%
CHEMBL4208	P20618	Proteasome component C5	94.97%	90.00%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	93.69%	94.97%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.24%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	87.20%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.38%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.54%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.19%	96.09%
CHEMBL3902	P09211	Glutathione S-transferase Pi	83.06%	93.81%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.39%	96.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	82.34%	94.08%

Plants that contains it

• Juncus effusus

Cross-Links

• PubChem: 1548955
• NPASS: NPC255253
• ChEMBL: CHEMBL167779