{2-[4-(2-Chloro-1,2-diphenyl-vinyl)-phenoxy]-ethyl}-diethyl-amine

ID: ALA2355051

Cas Number: 911-45-5

PubChem CID: 2800

Product Number: C608596, Order Now?

Max Phase: Approved

First Approval: 1967

Molecular Formula: C26H28ClNO

Molecular Weight: 405.97

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Clomifene | Clomiphene | Clomifene|clomiphene|Clomifenum|Clomiphene B|Clomifeno|911-45-5|Mer 41|Cisclomiphene|Clomiphene free base|Clomifenum [INN-Latin]|Clomifeno [INN-Spanish]|UNII-1HRS458QU2|Chlomaphene|Chloramifene|Clomifen|2-(p-(2-Chloro-1,2-diphenylvinyl)phenoxy)triethylamine|1HRS458QU2|CHEBI:3752|911-45-5 (free base)|DTXSID1022843|HSDB 3039|2-[4-(2-chloro-1,2-diphenylethenyl)phenoxy]-N,N-diethylethanamine|EINECS 213-008-6|2-(p-(beta-chloro-alpha-phenylstyryl)phenoxy)triethylamine|2-(p-(beShow More⌵

Synonyms from Alternative Forms(15): Clomifene citrate | Clomiphene citrate | Chloramiphene | Clomid | Clomifeni citras | Clomiphene citrate (1:1) | Clostilbegyt | Ikaclomine | Pergotime | MER-41 | MRL-41 | NSC-35770 | Clophene | Milophene | Serophene

Canonical SMILES:  CCN(CC)CCOc1ccc(C(=C(Cl)c2ccccc2)c2ccccc2)cc1

Standard 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

Standard InChI Key:  GKIRPKYJQBWNGO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -2.9405   -1.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6623   -1.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2284   -1.3274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9502   -2.5627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6623   -0.4845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3793   -1.7294    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.5114   -1.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2235   -0.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0782   -0.5135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7751   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7751   -1.3274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5114   -0.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0921   -0.0872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6346   -0.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3612   -0.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9405   -0.0775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2381   -2.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6623   -2.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3744   -0.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0782   -1.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7903   -0.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7854   -1.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5024   -0.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3647    0.7363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9356    0.7363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6671   -3.8076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2381   -3.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6526    1.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9550   -4.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 10  1  0
 14 13  1  0
 15 14  1  0
 16  5  2  0
 17  4  1  0
 18  4  2  0
 19  5  1  0
 20  9  1  0
 21  9  1  0
 22 20  1  0
 23 21  1  0
 24 19  2  0
 25 16  1  0
 26 18  1  0
 27 17  2  0
 28 24  1  0
 29 26  2  0
 10 11  2  0
 29 27  1  0
 28 25  2  0
  2  1  2  3
  3  1  1  0
  4  1  1  0
  5  2  1  0
  6  2  1  0
  7  3  2  0
  8  3  1  0
  9 15  1  0
 10 12  1  0
 11  7  1  0
 12  8  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2355051

   clomiphene

2. Alternative Forms:

   

   ALA2355051

   CLOMIPHENE CITRATE

Molecule Features

Natural Product: Yes

Oral: Yes

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: Yes

Prodrug: No

Calculated Properties

Molecular Weight: 405.97

Molecular Weight (Monoisotopic): 405.1859

AlogP: 6.56

#Rotatable Bonds: 9

Polar Surface Area: 12.47

Molecular Species: BASE

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.31

CX LogP: 6.47

CX LogD: 4.57

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.37

Np Likeness Score: -0.67

References

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2. Lill MA, Winiger F, Vedani A, Ernst B..  (2005)  Impact of induced fit on ligand binding to the androgen receptor: a multidimensional QSAR study to predict endocrine-disrupting effects of environmental chemicals.,  48  (18): [PMID:16134935] [10.1021/jm050403f]

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16. Biour M, Ben Salem C, Chazouillères O, Grangé JD, Serfaty L, Poupon R..  (2004)  [Drug-induced liver injury; fourteenth updated edition of the bibliographic database of liver injuries and related drugs].,  28  (8-9): [PMID:15646539] [10.1016/s0399-8320(04)95062-2]

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Source

Source(8):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• TP-search Transporter Database
• Harvard Malaria Screening
• WHO Anatomical Therapeutic Chemical Classification
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data