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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8)transporters (1) Show 9 proteins XML

enzymes (8)transporters (1) Show 9 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:49 UTC

HMDB ID

HMDB0015020

Secondary Accession Numbers

HMDB15020

Metabolite Identification

Common Name

Clomifene

Description

Clomifene is only found in individuals that have used or taken this drug. It is a triphenyl ethylene stilbene derivative which is an estrogen agonist or antagonist depending on the target tissue. [PubChem]Clomifene has both estrogenic and anti-estrogenic properties, but its precise mechanism of action has not been determined. Clomifene appears to stumulate the release of gonadotropins, follicle-stimulating hormone (FSH), and leuteinizing hormone (LH), which leads to the development and maturation of ovarian follicle, ovulation, and subsequent development and function of the coprus luteum, thus resulting in pregnancy. Gonadotropin release may result from direct stimulation of the hypothalamic-pituitary axis or from a decreased inhibitory influence of estrogens on the hypothalamic-pituitary axis by competing with the endogenous estrogens of the uterus, pituitary, or hypothalamus. Clomifene has no apparent progestational, androgenic, or antrandrogenic effects and does not appear to interfere with pituitary-adrenal or pituitary-thyroid function.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 04191212152D          

 29 31  0  0  0  0            999 V2000
    7.0156  -13.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0156  -13.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7179  -14.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4616  -13.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4616  -13.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7179  -12.7038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8664  -13.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8664  -13.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1640  -12.7038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6101  -14.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3125  -13.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3125  -13.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6101  -12.7038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1640  -11.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0298  -14.3537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7313  -13.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4374  -14.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1347  -13.9423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8429  -14.3474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5391  -13.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1313  -13.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8384  -12.7049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4484  -11.4643    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.8770  -11.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5737  -11.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2882  -11.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2882  -10.6306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5915  -10.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8770  -10.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  7 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  8 13  2  0  0  0  0
  9 14  2  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 14 23  1  4  0  0  0
 14 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
M  END

HMDB0260052
     RDKit          3D
Zuclomiphene
 57 59  0  0  0  0  0  0  0  0999 V2000
    5.3858    2.1644   -1.4636 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5596    0.6704   -1.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5715   -0.0401   -0.3839 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6703    0.1720    0.4718 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5501   -0.6404    1.7369 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3563   -0.5188    0.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8212   -1.6289   -0.7467 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6448   -2.1901   -0.3275 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4269   -1.6182   -0.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539   -2.3914    0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8808   -1.8472    0.4105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1640   -0.5407    0.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5115   -0.0094    0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7315    1.1669    0.7435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3663    2.1635    1.3005 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.0497    1.7456    0.8725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3944    2.3755    2.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6271    2.9586    2.2016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5572    2.9236    1.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2098    2.2927    0.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9561    1.7003   -0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6060   -0.8642   -0.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7282   -1.0629    0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7672   -1.8563    0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6799   -2.4604   -1.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5774   -2.2712   -1.8731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5282   -1.4811   -1.4637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1095    0.1963   -0.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1801   -0.3198   -0.5711 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0616    2.6192   -0.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6963    2.6028   -2.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3593    2.4932   -1.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8205    0.3418   -2.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5596    0.5039   -2.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8162    1.2426    0.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5821   -0.2409   -0.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4218   -1.7156    1.5746 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5300   -0.5602    2.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8124   -0.2308    2.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6217    0.2358    0.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5896   -1.0599    1.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417   -2.4137   -0.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7610   -1.2467   -1.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5827   -3.4233    0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7087   -2.4452    0.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6609    2.4009    2.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8883    3.4573    3.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5232    3.3766    1.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9182    2.2469   -0.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7596    1.2287   -1.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7964   -0.5879    1.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6317   -1.9970    0.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5072   -3.0918   -1.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5543   -2.7690   -2.8449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6546   -1.3315   -2.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2591    1.2182   -0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9299    0.3565   -0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 13 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 12 28  1  0
 28 29  2  0
 29  9  1  0
 21 16  1  0
 27 22  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  7 43  1  0
 10 44  1  0
 11 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  0
 23 51  1  0
 24 52  1  0
 25 53  1  0
 26 54  1  0
 27 55  1  0
 28 56  1  0
 29 57  1  0
M  END


  Mrv0541 04191212152D          

 29 31  0  0  0  0            999 V2000
    7.0156  -13.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0156  -13.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7179  -14.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4616  -13.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4616  -13.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7179  -12.7038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8664  -13.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8664  -13.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1640  -12.7038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6101  -14.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3125  -13.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3125  -13.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6101  -12.7038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1640  -11.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0298  -14.3537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7313  -13.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4374  -14.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1347  -13.9423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8429  -14.3474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5391  -13.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1313  -13.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8384  -12.7049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4484  -11.4643    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.8770  -11.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5737  -11.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2882  -11.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2882  -10.6306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5915  -10.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8770  -10.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  7 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  8 13  2  0  0  0  0
  9 14  2  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 14 23  1  4  0  0  0
 14 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015020

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN(CC)CCOC1=CC=C(C=C1)C(=C(Cl)C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
GKIRPKYJQBWNGO-UHFFFAOYSA-N

> <FORMULA>
C26H28ClNO

> <MOLECULAR_WEIGHT>
405.96

> <EXACT_MASS>
405.18594223

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
46.6999499313048

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{2-[4-(2-chloro-1,2-diphenylethenyl)phenoxy]ethyl}diethylamine

> <ALOGPS_LOGP>
6.08

> <JCHEM_LOGP>
6.474937693999999

> <ALOGPS_LOGS>
-5.99

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.306697064734209

> <JCHEM_POLAR_SURFACE_AREA>
12.47

> <JCHEM_REFRACTIVITY>
133.76119999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.14e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pioner

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0260052
     RDKit          3D
Zuclomiphene
 57 59  0  0  0  0  0  0  0  0999 V2000
    5.3858    2.1644   -1.4636 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5596    0.6704   -1.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5715   -0.0401   -0.3839 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6703    0.1720    0.4718 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5501   -0.6404    1.7369 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3563   -0.5188    0.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8212   -1.6289   -0.7467 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6448   -2.1901   -0.3275 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4269   -1.6182   -0.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539   -2.3914    0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8808   -1.8472    0.4105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1640   -0.5407    0.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5115   -0.0094    0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7315    1.1669    0.7435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3663    2.1635    1.3005 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.0497    1.7456    0.8725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3944    2.3755    2.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6271    2.9586    2.2016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5572    2.9236    1.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2098    2.2927    0.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9561    1.7003   -0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6060   -0.8642   -0.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7282   -1.0629    0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7672   -1.8563    0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6799   -2.4604   -1.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5774   -2.2712   -1.8731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5282   -1.4811   -1.4637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1095    0.1963   -0.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1801   -0.3198   -0.5711 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0616    2.6192   -0.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6963    2.6028   -2.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3593    2.4932   -1.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8205    0.3418   -2.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5596    0.5039   -2.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8162    1.2426    0.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5821   -0.2409   -0.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4218   -1.7156    1.5746 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5300   -0.5602    2.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8124   -0.2308    2.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6217    0.2358    0.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5896   -1.0599    1.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417   -2.4137   -0.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7610   -1.2467   -1.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5827   -3.4233    0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7087   -2.4452    0.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6609    2.4009    2.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8883    3.4573    3.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5232    3.3766    1.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9182    2.2469   -0.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7596    1.2287   -1.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7964   -0.5879    1.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6317   -1.9970    0.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5072   -3.0918   -1.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5543   -2.7690   -2.8449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6546   -1.3315   -2.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2591    1.2182   -0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9299    0.3565   -0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 13 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 12 28  1  0
 28 29  2  0
 29  9  1  0
 21 16  1  0
 27 22  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  7 43  1  0
 10 44  1  0
 11 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  0
 23 51  1  0
 24 52  1  0
 25 53  1  0
 26 54  1  0
 27 55  1  0
 28 56  1  0
 29 57  1  0
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      13.096 -24.485   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.096 -26.028   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.407 -26.799   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.795 -26.028   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.795 -24.485   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.407 -23.714   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.417 -26.028   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.417 -24.485   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.106 -23.714   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.806 -26.799   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.117 -26.028   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.117 -24.485   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.806 -23.714   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.106 -22.171   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      22.456 -26.794   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      23.765 -26.030   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.083 -26.784   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      26.385 -26.026   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      27.707 -26.782   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      29.006 -26.024   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      26.378 -24.485   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      27.698 -23.716   0.000  0.00  0.00           C+0
HETATM   23 Cl   UNK     0      15.770 -21.400   0.000  0.00  0.00          Cl+0
HETATM   24  C   UNK     0      18.437 -21.403   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.738 -22.154   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      21.071 -21.384   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      21.071 -19.844   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      19.771 -19.093   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      18.437 -19.863   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    1                                                       
CONECT    7    8   10                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8    5   14                                                  
CONECT   10    7   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    9   23   24                                                  
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22                                                       
CONECT   22   21                                                            
CONECT   23   14                                                            
CONECT   24   14   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   24                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

COMPND    HMDB0015020
HETATM    1  C1  UNL     1       7.055  -1.553  -0.367  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.635  -0.432  -1.236  1.00  0.00           C  
HETATM    3  N1  UNL     1       5.554   0.379  -0.858  1.00  0.00           N  
HETATM    4  C3  UNL     1       5.777   1.207   0.295  1.00  0.00           C  
HETATM    5  C4  UNL     1       6.782   2.293   0.023  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.231  -0.131  -0.962  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.869  -1.194   0.048  1.00  0.00           C  
HETATM    8  O1  UNL     1       2.623  -1.714  -0.018  1.00  0.00           O  
HETATM    9  C7  UNL     1       1.345  -1.340   0.066  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.340  -2.310  -0.076  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.979  -1.987  -0.003  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.416  -0.686   0.217  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.834  -0.372   0.314  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.624  -1.034   1.114  1.00  0.00           C  
HETATM   15 CL1  UNL     1      -2.889  -2.334   2.087  1.00  0.00          CL  
HETATM   16  C13 UNL     1      -5.058  -0.850   1.259  1.00  0.00           C  
HETATM   17  C14 UNL     1      -5.890  -0.713   0.198  1.00  0.00           C  
HETATM   18  C15 UNL     1      -7.256  -0.530   0.367  1.00  0.00           C  
HETATM   19  C16 UNL     1      -7.765  -0.489   1.624  1.00  0.00           C  
HETATM   20  C17 UNL     1      -6.918  -0.629   2.705  1.00  0.00           C  
HETATM   21  C18 UNL     1      -5.564  -0.809   2.538  1.00  0.00           C  
HETATM   22  C19 UNL     1      -3.363   0.705  -0.503  1.00  0.00           C  
HETATM   23  C20 UNL     1      -4.218   1.638   0.043  1.00  0.00           C  
HETATM   24  C21 UNL     1      -4.748   2.643  -0.712  1.00  0.00           C  
HETATM   25  C22 UNL     1      -4.437   2.739  -2.031  1.00  0.00           C  
HETATM   26  C23 UNL     1      -3.584   1.814  -2.586  1.00  0.00           C  
HETATM   27  C24 UNL     1      -3.044   0.805  -1.852  1.00  0.00           C  
HETATM   28  C25 UNL     1      -0.426   0.252   0.356  1.00  0.00           C  
HETATM   29  C26 UNL     1       0.933  -0.067   0.282  1.00  0.00           C  
HETATM   30  H1  UNL     1       6.770  -1.392   0.689  1.00  0.00           H  
HETATM   31  H2  UNL     1       8.193  -1.618  -0.351  1.00  0.00           H  
HETATM   32  H3  UNL     1       6.753  -2.570  -0.698  1.00  0.00           H  
HETATM   33  H4  UNL     1       6.403  -0.845  -2.260  1.00  0.00           H  
HETATM   34  H5  UNL     1       7.521   0.254  -1.435  1.00  0.00           H  
HETATM   35  H6  UNL     1       6.114   0.623   1.171  1.00  0.00           H  
HETATM   36  H7  UNL     1       4.811   1.707   0.538  1.00  0.00           H  
HETATM   37  H8  UNL     1       6.530   2.858  -0.913  1.00  0.00           H  
HETATM   38  H9  UNL     1       6.717   3.075   0.833  1.00  0.00           H  
HETATM   39  H10 UNL     1       7.811   1.939   0.030  1.00  0.00           H  
HETATM   40  H11 UNL     1       4.050  -0.517  -2.011  1.00  0.00           H  
HETATM   41  H12 UNL     1       3.528   0.718  -0.867  1.00  0.00           H  
HETATM   42  H13 UNL     1       4.593  -2.072  -0.079  1.00  0.00           H  
HETATM   43  H14 UNL     1       4.131  -0.816   1.081  1.00  0.00           H  
HETATM   44  H15 UNL     1       0.682  -3.319  -0.245  1.00  0.00           H  
HETATM   45  H16 UNL     1      -1.757  -2.747  -0.119  1.00  0.00           H  
HETATM   46  H17 UNL     1      -5.512  -0.750  -0.818  1.00  0.00           H  
HETATM   47  H18 UNL     1      -7.866  -0.429  -0.518  1.00  0.00           H  
HETATM   48  H19 UNL     1      -8.811  -0.348   1.787  1.00  0.00           H  
HETATM   49  H20 UNL     1      -7.331  -0.595   3.695  1.00  0.00           H  
HETATM   50  H21 UNL     1      -4.915  -0.914   3.418  1.00  0.00           H  
HETATM   51  H22 UNL     1      -4.480   1.591   1.104  1.00  0.00           H  
HETATM   52  H23 UNL     1      -5.432   3.402  -0.301  1.00  0.00           H  
HETATM   53  H24 UNL     1      -4.844   3.523  -2.651  1.00  0.00           H  
HETATM   54  H25 UNL     1      -3.337   1.890  -3.635  1.00  0.00           H  
HETATM   55  H26 UNL     1      -2.364   0.047  -2.231  1.00  0.00           H  
HETATM   56  H27 UNL     1      -0.726   1.263   0.526  1.00  0.00           H  
HETATM   57  H28 UNL     1       1.636   0.739   0.419  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3   33   34
CONECT    3    4    6
CONECT    4    5   35   36
CONECT    5   37   38   39
CONECT    6    7   40   41
CONECT    7    8   42   43
CONECT    8    9
CONECT    9   10   10   29
CONECT   10   11   44
CONECT   11   12   12   45
CONECT   12   13   28
CONECT   13   14   14   22
CONECT   14   15   16
CONECT   16   17   17   21
CONECT   17   18   46
CONECT   18   19   19   47
CONECT   19   20   48
CONECT   20   21   21   49
CONECT   21   50
CONECT   22   23   23   27
CONECT   23   24   51
CONECT   24   25   25   52
CONECT   25   26   53
CONECT   26   27   27   54
CONECT   27   55
CONECT   28   29   29   56
CONECT   29   57
END

HMDB0260052
     RDKit          3D
Zuclomiphene
 57 59  0  0  0  0  0  0  0  0999 V2000
    5.3858    2.1644   -1.4636 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5596    0.6704   -1.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5715   -0.0401   -0.3839 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6703    0.1720    0.4718 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5501   -0.6404    1.7369 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3563   -0.5188    0.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8212   -1.6289   -0.7467 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6448   -2.1901   -0.3275 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4269   -1.6182   -0.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539   -2.3914    0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8808   -1.8472    0.4105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1640   -0.5407    0.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5115   -0.0094    0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7315    1.1669    0.7435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3663    2.1635    1.3005 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.0497    1.7456    0.8725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3944    2.3755    2.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6271    2.9586    2.2016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5572    2.9236    1.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2098    2.2927    0.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9561    1.7003   -0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6060   -0.8642   -0.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7282   -1.0629    0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7672   -1.8563    0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6799   -2.4604   -1.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5774   -2.2712   -1.8731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5282   -1.4811   -1.4637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1095    0.1963   -0.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1801   -0.3198   -0.5711 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0616    2.6192   -0.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6963    2.6028   -2.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3593    2.4932   -1.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8205    0.3418   -2.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5596    0.5039   -2.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8162    1.2426    0.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5821   -0.2409   -0.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4218   -1.7156    1.5746 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5300   -0.5602    2.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8124   -0.2308    2.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6217    0.2358    0.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5896   -1.0599    1.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417   -2.4137   -0.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7610   -1.2467   -1.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5827   -3.4233    0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7087   -2.4452    0.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6609    2.4009    2.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8883    3.4573    3.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5232    3.3766    1.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9182    2.2469   -0.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7596    1.2287   -1.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7964   -0.5879    1.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6317   -1.9970    0.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5072   -3.0918   -1.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5543   -2.7690   -2.8449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6546   -1.3315   -2.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2591    1.2182   -0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9299    0.3565   -0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 13 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 12 28  1  0
 28 29  2  0
 29  9  1  0
 21 16  1  0
 27 22  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  7 43  1  0
 10 44  1  0
 11 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  0
 23 51  1  0
 24 52  1  0
 25 53  1  0
 26 54  1  0
 27 55  1  0
 28 56  1  0
 29 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(4-(2-Chloro-1,2-diphenylethenyl)phenoxy)-N,N-diethylethanamine	ChEBI
2-(p-(2-Chloro-1,2-diphenylvinyl)phenoxy)triethylamine	ChEBI
2-(p-(beta-Chloro-alpha-phenylstyryl)phenoxy)triethylamine	ChEBI
Clomifeno	ChEBI
Clomifenum	ChEBI
2-(p-(b-Chloro-a-phenylstyryl)phenoxy)triethylamine	Generator
2-(p-(Β-chloro-α-phenylstyryl)phenoxy)triethylamine	Generator
Chlomaphene	HMDB
Chloramifene	HMDB
Chloramiphene	HMDB
Cisclomiphene	HMDB
Clomifene citrate	HMDB
Clomiphene	HMDB
Clomiphene citrate	HMDB
Clomiphene citrate (Z,e)	HMDB
Racemic clomiphene citrate	HMDB
Zuclomiphene citrate	HMDB
Clostilbegit	MeSH, HMDB
Gravosan	MeSH, HMDB
Klostilbegit	MeSH, HMDB
Serophene	MeSH, HMDB
Clomid	MeSH, HMDB
Clomifen	MeSH, HMDB
Citrate, clomiphene	MeSH, HMDB
Clomide	MeSH, HMDB
Dyneric	MeSH, HMDB
Clomiphene hydrochloride	MeSH, HMDB
Hydrochloride, clomiphene	MeSH, HMDB
Clomifene	ChEBI

Chemical Formula

C₂₆H₂₈ClNO

Average Molecular Weight

405.96

Monoisotopic Molecular Weight

405.18594223

IUPAC Name

{2-[4-(2-chloro-1,2-diphenylethenyl)phenoxy]ethyl}diethylamine

Traditional Name

pioner

CAS Registry Number

911-45-5

SMILES

CCN(CC)CCOC1=CC=C(C=C1)C(=C(Cl)C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

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

InChI Key

GKIRPKYJQBWNGO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Diphenylmethane
Phenoxy compound
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Ether
Chloroalkene
Haloalkene
Vinyl halide
Vinyl chloride
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Organic oxygen compound
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tertiary amine (CHEBI:3752 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.00041 g/L	Not Available
LogP	7.2	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00041 g/L	ALOGPS
logP	6.08	ALOGPS
logP	6.47	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.47 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	133.76 m³·mol⁻¹	ChemAxon
Polarizability	46.7 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	197.614	30932474
DeepCCS	[M-H]-	195.256	30932474
DeepCCS	[M-2H]-	229.521	30932474
DeepCCS	[M+Na]+	205.461	30932474
AllCCS	[M+H]+	200.6	32859911
AllCCS	[M+H-H2O]+	197.9	32859911
AllCCS	[M+NH4]+	203.1	32859911
AllCCS	[M+Na]+	203.8	32859911
AllCCS	[M-H]-	195.5	32859911
AllCCS	[M+Na-2H]-	195.1	32859911
AllCCS	[M+HCOO]-	194.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Clomifene	CCN(CC)CCOC1=CC=C(C=C1)C(=C(Cl)C1=CC=CC=C1)C1=CC=CC=C1	4170.8	Standard polar	33892256
Clomifene	CCN(CC)CCOC1=CC=C(C=C1)C(=C(Cl)C1=CC=CC=C1)C1=CC=CC=C1	2985.7	Standard non polar	33892256
Clomifene	CCN(CC)CCOC1=CC=C(C=C1)C(=C(Cl)C1=CC=CC=C1)C1=CC=CC=C1	2959.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Clomifene GC-MS (Non-derivatized) - 70eV, Positive	splash10-052r-9012000000-45df4fe468787edb6d89	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Clomifene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Clomifene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clomifene LC-ESI-qTof , Positive-QTOF	splash10-0a4i-0000900000-6e563271338e3449b9f0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clomifene , positive-QTOF	splash10-0a4i-0000900000-6e563271338e3449b9f0	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clomifene 10V, Positive-QTOF	splash10-0a4i-1312900000-ca9aa2374db80c007b5f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clomifene 20V, Positive-QTOF	splash10-0udr-4933200000-164fa87cdbe23cc72977	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clomifene 40V, Positive-QTOF	splash10-0fi9-9451000000-5927a010de880212b24f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clomifene 10V, Negative-QTOF	splash10-0udi-1323900000-270e95f39bc9c23eae50	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clomifene 20V, Negative-QTOF	splash10-0pb9-4129400000-86f55d0b88e5983df5a4	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clomifene 40V, Negative-QTOF	splash10-05i0-9454000000-848ee095f1842299cd00	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clomifene 10V, Positive-QTOF	splash10-0a4i-0000900000-ff68a542dc5bb5928f03	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clomifene 20V, Positive-QTOF	splash10-0pb9-0801900000-ebdadab4e693385de318	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clomifene 40V, Positive-QTOF	splash10-0uk9-9710000000-e2c0a936a58120fde734	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clomifene 10V, Negative-QTOF	splash10-0udi-1000900000-551503881b71c4f9f47c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clomifene 20V, Negative-QTOF	splash10-0ue9-7035900000-c45916b720c3b1c8bb5d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clomifene 40V, Negative-QTOF	splash10-0a4i-0019000000-2f31a2afd1fc50c9b823	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00882	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00882	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00882

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2698

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Clomifene

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

3752

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Hughes E, Brown J, Collins JJ, Vanderkerchove P: Clomiphene citrate for unexplained subfertility in women. Cochrane Database Syst Rev. 2010 Jan 20;(1):CD000057. doi: 10.1002/14651858.CD000057.pub2. [PubMed:20091498 ]
Brown J, Farquhar C, Beck J, Boothroyd C, Hughes E: Clomiphene and anti-oestrogens for ovulation induction in PCOS. Cochrane Database Syst Rev. 2009 Oct 7;(4):CD002249. doi: 10.1002/14651858.CD002249.pub4. [PubMed:19821295 ]
Authors unspecified: Use of clomiphene citrate in women. Fertil Steril. 2006 Nov;86(5 Suppl 1):S187-93. [PubMed:17055820 ]
Homburg R: Oral agents for ovulation induction--clomiphene citrate versus aromatase inhibitors. Hum Fertil (Camb). 2008 Mar;11(1):17-22. doi: 10.1080/14647270701689670. [PubMed:18320435 ]
Homburg R: Clomiphene citrate--end of an era? A mini-review. Hum Reprod. 2005 Aug;20(8):2043-51. Epub 2005 May 5. [PubMed:15878925 ]
Purvin VA: Visual disturbance secondary to clomiphene citrate. Arch Ophthalmol. 1995 Apr;113(4):482-4. [PubMed:7710399 ]
Fritz MA, Holmes RT, Keenan EJ: Effect of clomiphene citrate treatment on endometrial estrogen and progesterone receptor induction in women. Am J Obstet Gynecol. 1991 Jul;165(1):177-85. [PubMed:1906682 ]
Hayon T, Atlas L, Levy E, Dvilansky A, Shpilberg O, Nathan I: Multifactorial activities of nonsteroidal antiestrogens against leukemia. Cancer Detect Prev. 2003;27(5):389-96. [PubMed:14585326 ]

Enzymes

Enzyme Details

1. Cholesterol side-chain cleavage enzyme, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name:: CYP11A1
Uniprot ID:: P05108
Molecular weight:: 60101.87

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 1A1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP1A1
Uniprot ID:: P04798
Molecular weight:: 58164.815

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

6. Cytochrome P450 19A1

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:: CYP19A1
Uniprot ID:: P11511
Molecular weight:: 57882.48

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

7. Cytochrome P450 2A6

General function:: Involved in monooxygenase activity
Specific function:: Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:: CYP2A6
Uniprot ID:: P11509
Molecular weight:: 56517.005

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

8. Estrogen receptor

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Can activate the transcriptional activity of TFF1
Gene Name:: ESR1
Uniprot ID:: P03372
Molecular weight:: 66215.4

References

Sasson S: Equilibrium binding analysis of estrogen agonists and antagonists: relation to the activation of the estrogen receptor. Pathol Biol (Paris). 1991 Jan;39(1):59-69. [PubMed:2011412 ]
Kurosawa T, Hiroi H, Momoeda M, Inoue S, Taketani Y: Clomiphene citrate elicits estrogen agonistic/antagonistic effects differentially via estrogen receptors alpha and beta. Endocr J. 2010;57(6):517-21. Epub 2010 Apr 6. [PubMed:20379036 ]
Hughes E, Brown J, Collins JJ, Vanderkerchove P: Clomiphene citrate for unexplained subfertility in women. Cochrane Database Syst Rev. 2010 Jan 20;(1):CD000057. doi: 10.1002/14651858.CD000057.pub2. [PubMed:20091498 ]
Brown J, Farquhar C, Beck J, Boothroyd C, Hughes E: Clomiphene and anti-oestrogens for ovulation induction in PCOS. Cochrane Database Syst Rev. 2009 Oct 7;(4):CD002249. doi: 10.1002/14651858.CD002249.pub4. [PubMed:19821295 ]
Authors unspecified: Use of clomiphene citrate in women. Fertil Steril. 2006 Nov;86(5 Suppl 1):S187-93. [PubMed:17055820 ]
Overbeek A, Lambalk N: Pharmacogenomics of ovulation induction: facilitating decisions on who, when and how to treat. Pharmacogenomics. 2009 Sep;10(9):1377-9. doi: 10.2217/pgs.09.110. [PubMed:19761360 ]
Homburg R: Oral agents for ovulation induction--clomiphene citrate versus aromatase inhibitors. Hum Fertil (Camb). 2008 Mar;11(1):17-22. doi: 10.1080/14647270701689670. [PubMed:18320435 ]
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Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Rao US, Fine RL, Scarborough GA: Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Biochem Pharmacol. 1994 Jul 19;48(2):287-92. [PubMed:7914405 ]

Showing metabocard for Clomifene (HMDB0015020)

MOL for HMDB0015020 (Clomifene)

3D MOL for HMDB0015020 (Clomifene)

3D SDF for HMDB0015020 (Clomifene)

3D-SDF for HMDB0015020 (Clomifene)

PDB for HMDB0015020 (Clomifene)

3D PDB for HMDB0015020 (Clomifene)

SMILES for HMDB0015020 (Clomifene)

INCHI for HMDB0015020 (Clomifene)

Structure for HMDB0015020 (Clomifene)

3D Structure for HMDB0015020 (Clomifene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

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Transporters

References