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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7) Show 7 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:41 UTC

HMDB ID

HMDB0014624

Secondary Accession Numbers

HMDB14624

Metabolite Identification

Common Name

Raloxifene

Description

Raloxifene is only found in individuals that have used or taken this drug. It is a second generation selective estrogen receptor modulator (SERM) used to prevent osteoporosis in postmenopausal women. It has estrogen agonist effects on bone and cholesterol metabolism but behaves as a complete estrogen antagonist on mammary gland and uterine tissue. [PubChem]. Raloxifene binds to estrogen receptors, resulting in differential expression of multiple estrogen-regulated genes in different tissues. Raloxifene produces estrogen-like effects on bone, reducing resorption of bone and increasing bone mineral density in postmenopausal women, thus slowing the rate of bone loss. The maintenance of bone mass by raloxifene and estrogens is, in part, through the regulation of the gene-encoding transforming growth factor-β3 (TGF-β3), which is a bone matrix protein with antiosteoclastic properties. Raloxifene activates TGF-β3 through pathways that are estrogen receptor-mediated but involve DNA sequences distinct from the estrogen response element. The drug also binds to the estrogen receptor and acts as an estrogen agonist in preosteoclastic cells, which results in the inhibtion of their proliferative capacity. This inhibition is thought to contribute to the drug's effect on bone resorption. Other mechanisms include the suppression of activity of the bone-resorbing cytokine interleukin-6 promoter activity. Raloxifene also antagonizes the effects of estrogen on mammary tissue and blocks uterotrophic responses to estrogen. By competing with estrogens for the estrogen receptors in reproductive tissue, raloxifene prevents the transcriptional activation of genes containing the estrogen response element. As well, raloxifene inhibits the estradiol-dependent proliferation of MCF-7 human mammary tumor cells in vitro. The mechansim of action of raloxifene has not been fully determined, but evidence suggests that the drug's tissue-specific estrogen agonist or antagonist activity is related to the structural differences between the raloxifene-estrogen receptor complex (specifically the surface topography of AF-2) and the estrogen-estrogen receptor complex. Also, the existence of at least 2 estrogen receptors (ERα, ERβ) may contribute to the tissue specificity of raloxifene.

Structure

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

481
  Mrv0541 02231214422D          

 34 38  0  0  0  0            999 V2000
    4.5741   -3.8233    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6265    0.7450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6378   -1.5411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.9843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3557   -3.1593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5882    2.9275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3954    3.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0371    3.5416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6517    3.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2935    4.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1007    4.4959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3318    2.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HMDB0014624
     RDKit          3D
Raloxifene
 61 65  0  0  0  0  0  0  0  0999 V2000
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   -3.4007   -0.0997   -1.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5000   -0.6971    1.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.3399    1.0214    0.8956 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1587   -1.8721   -2.1827 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6604   -1.2033    1.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2760   -1.3923    2.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4897   -2.6631    2.9738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1047   -3.7814    2.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3090   -5.0677    2.7622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5041   -3.6104    1.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
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 33 61  1  0
M  END

481
  Mrv0541 02231214422D          

 34 38  0  0  0  0            999 V2000
    4.5741   -3.8233    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6265    0.7450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6378   -1.5411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.9843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3557   -3.1593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5882    2.9275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3954    3.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0371    3.5416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0014624

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(C=C1)C1=C(C(=O)C2=CC=C(OCCN3CCCCC3)C=C2)C2=C(S1)C=C(O)C=C2

> <INCHI_IDENTIFIER>
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

> <FORMULA>
C28H27NO4S

> <MOLECULAR_WEIGHT>
473.583

> <EXACT_MASS>
473.166079047

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
52.54504114929282

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(4-hydroxyphenyl)-3-{4-[2-(piperidin-1-yl)ethoxy]benzoyl}-1-benzothiophen-6-ol

> <ALOGPS_LOGP>
5.45

> <JCHEM_LOGP>
5.6926295073730415

> <ALOGPS_LOGS>
-5.97

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
9.552212516519601

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.892227074120992

> <JCHEM_PKA_STRONGEST_BASIC>
7.953595413831779

> <JCHEM_POLAR_SURFACE_AREA>
70

> <JCHEM_REFRACTIVITY>
135.48000000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.12e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
raloxifene

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014624
     RDKit          3D
Raloxifene
 61 65  0  0  0  0  0  0  0  0999 V2000
   -4.2243   -0.4703   -2.2862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4007   -0.0997   -1.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9934   -0.4522   -1.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0899    0.3157   -0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2630   -0.0231   -0.7658 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7198   -1.1028   -1.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0545   -1.4080   -1.4618 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0187   -0.6513   -0.7516 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3685   -1.3114   -0.9898 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4319   -0.6669   -0.3490 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5000   -0.6971    1.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8601   -0.2320    1.5408 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3399    1.0214    0.8956 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1305    1.0613   -0.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5666   -0.2592   -1.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1587   -1.8721   -2.1827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5143   -1.5372   -2.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9426    0.7651   -0.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4689    0.1931    0.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6604   -1.2033    1.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2760   -1.3923    2.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4897   -2.6631    2.9738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1047   -3.7814    2.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3090   -5.0677    2.7622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5041   -3.6104    1.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2914   -2.3176    0.5517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9306    1.5857    1.7250 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4340    2.8157    0.6677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4700    4.2155    0.7277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9786    4.9858   -0.3006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9703    6.3659   -0.3299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4628    4.2698   -1.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4226    2.9195   -1.4367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9256    2.1274   -0.3818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4414    1.1728   -0.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9633    0.5899   -0.2006 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0648    0.3998   -1.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7566   -0.7047    0.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5295   -1.3952   -2.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2675   -2.3497   -0.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3950   -1.7591    1.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7067   -0.1339    1.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5838   -1.0681    1.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7101   -0.0049    2.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4374    1.0993    1.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9108    1.9442    1.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4711    1.9030   -0.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1040    1.2077   -1.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4190   -0.9905   -0.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3396   -0.2169   -2.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1439   -2.7461   -2.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2034   -2.1434   -2.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5793   -0.5114    3.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9618   -2.7901    3.9271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1630   -5.5701    2.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1794   -4.4413    0.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8191   -2.2270   -0.4028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8828    4.7024    1.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7485    6.8829   -0.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0609    4.8523   -2.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9938    2.4753   -2.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  6 16  1  0
 16 17  2  0
  2 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 19 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 32 33  1  0
 33 34  2  0
 17  3  1  0
 34 18  1  0
 15 10  1  0
 26 20  1  0
 34 28  1  0
  4 35  1  0
  5 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 16 51  1  0
 17 52  1  0
 21 53  1  0
 22 54  1  0
 24 55  1  0
 25 56  1  0
 26 57  1  0
 29 58  1  0
 31 59  1  0
 32 60  1  0
 33 61  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 481                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       8.538  -7.137   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       4.903   1.391   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      10.524  -2.877   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.080  -7.437   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      15.597  -5.897   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       4.831   5.465   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       6.338   5.782   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.803   6.611   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.817   7.246   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.281   8.075   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.788   8.392   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.353   4.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.381   2.855   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.931   0.244   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.538  -4.658   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081  -5.127   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.437  -5.897   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.081  -6.667   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.988  -2.048   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.017  -3.194   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.453  -1.219   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.438   0.562   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.481  -2.366   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.467  -0.584   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.977  -5.897   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.748  -4.357   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.748  -7.437   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.414  -5.127   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.414  -6.667   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.747  -4.564   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.747  -7.231   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.287  -4.564   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.287  -7.231   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.057  -5.897   0.000  0.00  0.00           C+0
CONECT    1   17   18                                                       
CONECT    2   13   14                                                       
CONECT    3   20                                                            
CONECT    4   29                                                            
CONECT    5   34                                                            
CONECT    6    7    8   12                                                  
CONECT    7    6    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   11                                                       
CONECT   11    9   10                                                       
CONECT   12    6   13                                                       
CONECT   13    2   12                                                       
CONECT   14    2   21   22                                                  
CONECT   15   16   17   20                                                  
CONECT   16   15   18   26                                                  
CONECT   17    1   15   25                                                  
CONECT   18    1   16   27                                                  
CONECT   19   20   23   24                                                  
CONECT   20    3   15   19                                                  
CONECT   21   14   23                                                       
CONECT   22   14   24                                                       
CONECT   23   19   21                                                       
CONECT   24   19   22                                                       
CONECT   25   17   30   31                                                  
CONECT   26   16   28                                                       
CONECT   27   18   29                                                       
CONECT   28   26   29                                                       
CONECT   29    4   27   28                                                  
CONECT   30   25   32                                                       
CONECT   31   25   33                                                       
CONECT   32   30   34                                                       
CONECT   33   31   34                                                       
CONECT   34    5   32   33                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

COMPND    HMDB0014624
HETATM    1  O1  UNL     1      -4.224  -0.470  -2.286  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.401  -0.100  -1.434  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.993  -0.452  -1.467  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.090   0.316  -0.754  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.263  -0.023  -0.766  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.720  -1.103  -1.471  1.00  0.00           C  
HETATM    7  O2  UNL     1       2.054  -1.408  -1.462  1.00  0.00           O  
HETATM    8  C6  UNL     1       3.019  -0.651  -0.752  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.368  -1.311  -0.990  1.00  0.00           C  
HETATM   10  N1  UNL     1       5.432  -0.667  -0.349  1.00  0.00           N  
HETATM   11  C8  UNL     1       5.500  -0.697   1.056  1.00  0.00           C  
HETATM   12  C9  UNL     1       6.860  -0.232   1.541  1.00  0.00           C  
HETATM   13  C10 UNL     1       7.340   1.021   0.896  1.00  0.00           C  
HETATM   14  C11 UNL     1       7.131   1.061  -0.581  1.00  0.00           C  
HETATM   15  C12 UNL     1       6.567  -0.259  -1.075  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.159  -1.872  -2.183  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.514  -1.537  -2.174  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.943   0.765  -0.323  1.00  0.00           C  
HETATM   19  C16 UNL     1      -4.469   0.193   0.786  1.00  0.00           C  
HETATM   20  C17 UNL     1      -4.660  -1.203   1.222  1.00  0.00           C  
HETATM   21  C18 UNL     1      -5.276  -1.392   2.467  1.00  0.00           C  
HETATM   22  C19 UNL     1      -5.490  -2.663   2.974  1.00  0.00           C  
HETATM   23  C20 UNL     1      -5.105  -3.781   2.273  1.00  0.00           C  
HETATM   24  O3  UNL     1      -5.309  -5.068   2.762  1.00  0.00           O  
HETATM   25  C21 UNL     1      -4.504  -3.610   1.058  1.00  0.00           C  
HETATM   26  C22 UNL     1      -4.291  -2.318   0.552  1.00  0.00           C  
HETATM   27  S1  UNL     1      -4.931   1.586   1.725  1.00  0.00           S  
HETATM   28  C23 UNL     1      -4.434   2.816   0.668  1.00  0.00           C  
HETATM   29  C24 UNL     1      -4.470   4.215   0.728  1.00  0.00           C  
HETATM   30  C25 UNL     1      -3.979   4.986  -0.301  1.00  0.00           C  
HETATM   31  O4  UNL     1      -3.970   6.366  -0.330  1.00  0.00           O  
HETATM   32  C26 UNL     1      -3.463   4.270  -1.367  1.00  0.00           C  
HETATM   33  C27 UNL     1      -3.423   2.919  -1.437  1.00  0.00           C  
HETATM   34  C28 UNL     1      -3.926   2.127  -0.382  1.00  0.00           C  
HETATM   35  H1  UNL     1      -1.441   1.173  -0.193  1.00  0.00           H  
HETATM   36  H2  UNL     1       0.963   0.590  -0.201  1.00  0.00           H  
HETATM   37  H3  UNL     1       3.065   0.400  -1.066  1.00  0.00           H  
HETATM   38  H4  UNL     1       2.757  -0.705   0.315  1.00  0.00           H  
HETATM   39  H5  UNL     1       4.529  -1.395  -2.079  1.00  0.00           H  
HETATM   40  H6  UNL     1       4.267  -2.350  -0.553  1.00  0.00           H  
HETATM   41  H7  UNL     1       5.395  -1.759   1.424  1.00  0.00           H  
HETATM   42  H8  UNL     1       4.707  -0.134   1.590  1.00  0.00           H  
HETATM   43  H9  UNL     1       7.584  -1.068   1.483  1.00  0.00           H  
HETATM   44  H10 UNL     1       6.710  -0.005   2.637  1.00  0.00           H  
HETATM   45  H11 UNL     1       8.437   1.099   1.127  1.00  0.00           H  
HETATM   46  H12 UNL     1       6.911   1.944   1.381  1.00  0.00           H  
HETATM   47  H13 UNL     1       6.471   1.903  -0.896  1.00  0.00           H  
HETATM   48  H14 UNL     1       8.104   1.208  -1.083  1.00  0.00           H  
HETATM   49  H15 UNL     1       7.419  -0.990  -0.968  1.00  0.00           H  
HETATM   50  H16 UNL     1       6.340  -0.217  -2.148  1.00  0.00           H  
HETATM   51  H17 UNL     1       0.144  -2.746  -2.764  1.00  0.00           H  
HETATM   52  H18 UNL     1      -2.203  -2.143  -2.732  1.00  0.00           H  
HETATM   53  H19 UNL     1      -5.579  -0.511   3.018  1.00  0.00           H  
HETATM   54  H20 UNL     1      -5.962  -2.790   3.927  1.00  0.00           H  
HETATM   55  H21 UNL     1      -6.163  -5.570   2.555  1.00  0.00           H  
HETATM   56  H22 UNL     1      -4.179  -4.441   0.462  1.00  0.00           H  
HETATM   57  H23 UNL     1      -3.819  -2.227  -0.403  1.00  0.00           H  
HETATM   58  H24 UNL     1      -4.883   4.702   1.584  1.00  0.00           H  
HETATM   59  H25 UNL     1      -4.749   6.883  -0.718  1.00  0.00           H  
HETATM   60  H26 UNL     1      -3.061   4.852  -2.212  1.00  0.00           H  
HETATM   61  H27 UNL     1      -2.994   2.475  -2.325  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   18
CONECT    3    4    4   17
CONECT    4    5   35
CONECT    5    6    6   36
CONECT    6    7   16
CONECT    7    8
CONECT    8    9   37   38
CONECT    9   10   39   40
CONECT   10   11   15
CONECT   11   12   41   42
CONECT   12   13   43   44
CONECT   13   14   45   46
CONECT   14   15   47   48
CONECT   15   49   50
CONECT   16   17   17   51
CONECT   17   52
CONECT   18   19   19   34
CONECT   19   20   27
CONECT   20   21   21   26
CONECT   21   22   53
CONECT   22   23   23   54
CONECT   23   24   25
CONECT   24   55
CONECT   25   26   26   56
CONECT   26   57
CONECT   27   28
CONECT   28   29   29   34
CONECT   29   30   58
CONECT   30   31   32   32
CONECT   31   59
CONECT   32   33   60
CONECT   33   34   34   61
END

HMDB0014624
     RDKit          3D
Raloxifene
 61 65  0  0  0  0  0  0  0  0999 V2000
   -4.2243   -0.4703   -2.2862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4007   -0.0997   -1.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9934   -0.4522   -1.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0899    0.3157   -0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2630   -0.0231   -0.7658 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7198   -1.1028   -1.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0545   -1.4080   -1.4618 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0187   -0.6513   -0.7516 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3685   -1.3114   -0.9898 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4319   -0.6669   -0.3490 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5000   -0.6971    1.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8601   -0.2320    1.5408 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3399    1.0214    0.8956 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1305    1.0613   -0.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5666   -0.2592   -1.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1587   -1.8721   -2.1827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5143   -1.5372   -2.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9426    0.7651   -0.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4689    0.1931    0.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6604   -1.2033    1.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2760   -1.3923    2.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4897   -2.6631    2.9738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1047   -3.7814    2.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3090   -5.0677    2.7622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5041   -3.6104    1.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2914   -2.3176    0.5517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9306    1.5857    1.7250 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4340    2.8157    0.6677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4700    4.2155    0.7277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9786    4.9858   -0.3006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9703    6.3659   -0.3299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4628    4.2698   -1.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4226    2.9195   -1.4367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9256    2.1274   -0.3818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4414    1.1728   -0.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9633    0.5899   -0.2006 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0648    0.3998   -1.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7566   -0.7047    0.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5295   -1.3952   -2.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2675   -2.3497   -0.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3950   -1.7591    1.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7067   -0.1339    1.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5838   -1.0681    1.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7101   -0.0049    2.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4374    1.0993    1.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9108    1.9442    1.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4711    1.9030   -0.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1040    1.2077   -1.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4190   -0.9905   -0.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3396   -0.2169   -2.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1439   -2.7461   -2.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2034   -2.1434   -2.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5793   -0.5114    3.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9618   -2.7901    3.9271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1630   -5.5701    2.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1794   -4.4413    0.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8191   -2.2270   -0.4028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8828    4.7024    1.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7485    6.8829   -0.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0609    4.8523   -2.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9938    2.4753   -2.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  6 16  1  0
 16 17  2  0
  2 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 19 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 32 33  1  0
 33 34  2  0
 17  3  1  0
 34 18  1  0
 15 10  1  0
 26 20  1  0
 34 28  1  0
  4 35  1  0
  5 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 16 51  1  0
 17 52  1  0
 21 53  1  0
 22 54  1  0
 24 55  1  0
 25 56  1  0
 26 57  1  0
 29 58  1  0
 31 59  1  0
 32 60  1  0
 33 61  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2-(4-Hydroxyphenyl)-6-hydroxybenzo(b)thien-3-yl)(4-(2-(1-piperidinyl)ethoxy)phenyl)methanone	ChEBI
Keoxifene	ChEBI
LY 139481	ChEBI
Raloxifeno	ChEBI
Raloxifenum	ChEBI
Eviden	Kegg
Raxeto	Kegg
LY-139481	HMDB
RAL	HMDB
Raloxifene hydrochloride	HMDB
Evista	HMDB
Keoxifene hydrochloride	HMDB
Raloxifene HCL	HMDB

Chemical Formula

C₂₈H₂₇NO₄S

Average Molecular Weight

473.583

Monoisotopic Molecular Weight

473.166079047

IUPAC Name

2-(4-hydroxyphenyl)-3-{4-[2-(piperidin-1-yl)ethoxy]benzoyl}-1-benzothiophen-6-ol

Traditional Name

raloxifene

CAS Registry Number

84449-90-1

SMILES

OC1=CC=C(C=C1)C1=C(C(=O)C2=CC=C(OCCN3CCCCC3)C=C2)C2=C(S1)C=C(O)C=C2

InChI Identifier

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

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl-phenylketones

Alternative Parents

Substituents

Aryl-phenylketone
3-aroylthiophene
Benzothiophene
1-benzothiophene
Phenoxy compound
Benzoyl
Phenol ether
Thiophene carboxylic acid or derivatives
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Piperidine
Heteroaromatic compound
Thiophene
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Ether
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

1-benzothiophenes (CHEBI:45355 )
N-oxyethylpiperidine (CHEBI:45355 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	143 - 147 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.00051 g/L	Not Available
LogP	5.2	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00051 g/L	ALOGPS
logP	5.45	ALOGPS
logP	5.69	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	8.89	ChemAxon
pKa (Strongest Basic)	7.95	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	135.48 m³·mol⁻¹	ChemAxon
Polarizability	52.55 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	207.571	31661259
DarkChem	[M-H]-	199.175	31661259
DeepCCS	[M+H]+	212.591	30932474
DeepCCS	[M-H]-	210.233	30932474
DeepCCS	[M-2H]-	243.207	30932474
DeepCCS	[M+Na]+	218.684	30932474
AllCCS	[M+H]+	215.1	32859911
AllCCS	[M+H-H2O]+	213.1	32859911
AllCCS	[M+NH4]+	217.0	32859911
AllCCS	[M+Na]+	217.5	32859911
AllCCS	[M-H]-	207.1	32859911
AllCCS	[M+Na-2H]-	207.6	32859911
AllCCS	[M+HCOO]-	208.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Raloxifene	OC1=CC=C(C=C1)C1=C(C(=O)C2=CC=C(OCCN3CCCCC3)C=C2)C2=C(S1)C=C(O)C=C2	5124.8	Standard polar	33892256
Raloxifene	OC1=CC=C(C=C1)C1=C(C(=O)C2=CC=C(OCCN3CCCCC3)C=C2)C2=C(S1)C=C(O)C=C2	3980.2	Standard non polar	33892256
Raloxifene	OC1=CC=C(C=C1)C1=C(C(=O)C2=CC=C(OCCN3CCCCC3)C=C2)C2=C(S1)C=C(O)C=C2	4656.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Raloxifene,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=C(C(=O)C3=CC=C(OCCN4CCCCC4)C=C3)C3=CC=C(O)C=C3S2)C=C1	4441.7	Semi standard non polar	33892256
Raloxifene,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C2C(C(=O)C3=CC=C(OCCN4CCCCC4)C=C3)=C(C3=CC=C(O)C=C3)SC2=C1	4452.5	Semi standard non polar	33892256
Raloxifene,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=C(C(=O)C3=CC=C(OCCN4CCCCC4)C=C3)C3=CC=C(O[Si](C)(C)C)C=C3S2)C=C1	4320.6	Semi standard non polar	33892256
Raloxifene,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(C(=O)C3=CC=C(OCCN4CCCCC4)C=C3)C3=CC=C(O)C=C3S2)C=C1	4702.9	Semi standard non polar	33892256
Raloxifene,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C2C(C(=O)C3=CC=C(OCCN4CCCCC4)C=C3)=C(C3=CC=C(O)C=C3)SC2=C1	4701.5	Semi standard non polar	33892256
Raloxifene,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(C(=O)C3=CC=C(OCCN4CCCCC4)C=C3)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3S2)C=C1	4793.4	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 - Raloxifene GC-MS (Non-derivatized) - 70eV, Positive	splash10-006t-9112200000-194dfc7c577ba3e76b98	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Raloxifene GC-MS (2 TMS) - 70eV, Positive	splash10-0udj-9010136000-3bb502413414534da20b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Raloxifene 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 - Raloxifene LC-ESI-QFT , negative-QTOF	splash10-0229-0035900000-dcf0b4afb1abd2691c7c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Raloxifene LC-ESI-QFT , positive-QTOF	splash10-0229-6600900000-ea14790ae9aed263379b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Raloxifene 10V, Positive-QTOF	splash10-00di-0000900000-f184aabcb2eb146ebe92	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Raloxifene 20V, Positive-QTOF	splash10-00di-0000900000-3d3c761b7ff900186d5f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Raloxifene 40V, Positive-QTOF	splash10-00di-0231900000-0fc53037915f41184d0b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Raloxifene 30V, Positive-QTOF	splash10-00di-0000900000-6e89a56db5f01a157640	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Raloxifene 30V, Positive-QTOF	splash10-0229-1800900000-cfc74f58ad18897ca1be	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Raloxifene 45V, Positive-QTOF	splash10-03di-8900000000-6cbb38555e813af5fa9c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Raloxifene 15V, Positive-QTOF	splash10-00di-0000900000-76a62cda029e256d3f18	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Raloxifene 50V, Positive-QTOF	splash10-014j-0494000000-d01ec5346aa038f5719a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Raloxifene 40V, Positive-QTOF	splash10-00di-0230900000-0fc53037915f41184d0b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Raloxifene 30V, Positive-QTOF	splash10-0229-0007900000-9eb122a555c8e7444904	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Raloxifene 50V, Positive-QTOF	splash10-014j-0494000000-6cde9fd49faae3fb307d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Raloxifene 15V, Negative-QTOF	splash10-00di-0000900000-3015478097ea6bee8d7a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Raloxifene 90V, Positive-QTOF	splash10-001i-9000000000-f3e7a5afa55ea1305028	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Raloxifene 30V, Negative-QTOF	splash10-0229-0007900000-2bda40c3103c3604b7c1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Raloxifene 45V, Negative-QTOF	splash10-03di-0059000000-1bf6aa63d8858df8932f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Raloxifene 90V, Negative-QTOF	splash10-03dr-0190000000-7ee2becffb54ed42c6e2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Raloxifene 60V, Negative-QTOF	splash10-01p6-0092000000-86616f94829b2c365c93	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Raloxifene 10V, Positive-QTOF	splash10-00di-0114900000-e8c217b2f20574044c33	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Raloxifene 20V, Positive-QTOF	splash10-03xs-4984400000-a2731ab247793dc0402e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Raloxifene 40V, Positive-QTOF	splash10-014u-7296000000-82a010336a5451ab7f97	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Raloxifene 10V, Negative-QTOF	splash10-00di-1012900000-c3bc16da6ed53c190cf7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Raloxifene 20V, Negative-QTOF	splash10-03kc-2149500000-8a3b4929414c1ff5dc90	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Raloxifene 40V, Negative-QTOF	splash10-00l6-5596000000-26179eaf5995f4a2067b	2016-08-03	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 DB00481	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00481	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00481

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4859

KEGG Compound ID

C07228

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Raloxifene

METLIN ID

Not Available

PubChem Compound

5035

PDB ID

Not Available

ChEBI ID

8772

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

Khovidhunkit W, Shoback DM: Clinical effects of raloxifene hydrochloride in women. Ann Intern Med. 1999 Mar 2;130(5):431-9. [PubMed:10068418 ]
Cummings SR, Eckert S, Krueger KA, Grady D, Powles TJ, Cauley JA, Norton L, Nickelsen T, Bjarnason NH, Morrow M, Lippman ME, Black D, Glusman JE, Costa A, Jordan VC: The effect of raloxifene on risk of breast cancer in postmenopausal women: results from the MORE randomized trial. Multiple Outcomes of Raloxifene Evaluation. JAMA. 1999 Jun 16;281(23):2189-97. [PubMed:10376571 ]
Bryant HU, Glasebrook AL, Yang NN, Sato M: An estrogen receptor basis for raloxifene action in bone. J Steroid Biochem Mol Biol. 1999 Apr-Jun;69(1-6):37-44. [PubMed:10418979 ]
Balfour JA, Goa KL: Raloxifene. Drugs Aging. 1998 Apr;12(4):335-41; discussion 342. [PubMed:9571395 ]
Clemett D, Spencer CM: Raloxifene: a review of its use in postmenopausal osteoporosis. Drugs. 2000 Aug;60(2):379-411. [PubMed:10983739 ]
Barrett-Connor E: Raloxifene: risks and benefits. Ann N Y Acad Sci. 2001 Dec;949:295-303. [PubMed:11795366 ]
Heringa M: Review on raloxifene: profile of a selective estrogen receptor modulator. Int J Clin Pharmacol Ther. 2003 Aug;41(8):331-45. [PubMed:12940590 ]
Authors unspecified: A STARring role for raloxifene? Lancet Oncol. 2006 Jun;7(6):443. [PubMed:16750489 ]
Diez-Perez A: Selective estrogen receptor modulators (SERMS). Arq Bras Endocrinol Metabol. 2006 Aug;50(4):720-34. [PubMed:17117297 ]
Silverman SL: New selective estrogen receptor modulators (SERMs) in development. Curr Osteoporos Rep. 2010 Sep;8(3):151-3. doi: 10.1007/s11914-010-0025-0. [PubMed:20603714 ]

Enzymes

Enzyme Details

1. Aldehyde oxidase

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: AOX1
Uniprot ID:: Q06278
Molecular weight:: 147916.735

References

Obach RS: Potent inhibition of human liver aldehyde oxidase by raloxifene. Drug Metab Dispos. 2004 Jan;32(1):89-97. [PubMed:14709625 ]
Obach RS, Huynh P, Allen MC, Beedham C: Human liver aldehyde oxidase: inhibition by 239 drugs. J Clin Pharmacol. 2004 Jan;44(1):7-19. [PubMed:14681337 ]
Sahi J, Khan KK, Black CB: Aldehyde oxidase activity and inhibition in hepatocytes and cytosolic fractions from mouse, rat, monkey and human. Drug Metab Lett. 2008 Aug;2(3):176-83. [PubMed:19356090 ]

Enzyme Details

2. Estrogen receptor beta

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner. Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA- binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual
Gene Name:: ESR2
Uniprot ID:: Q92731
Molecular weight:: 59215.8

References

Bryant HU, Glasebrook AL, Yang NN, Sato M: An estrogen receptor basis for raloxifene action in bone. J Steroid Biochem Mol Biol. 1999 Apr-Jun;69(1-6):37-44. [PubMed:10418979 ]
Iannone MA, Consler TG, Pearce KH, Stimmel JB, Parks DJ, Gray JG: Multiplexed molecular interactions of nuclear receptors using fluorescent microspheres. Cytometry. 2001 Aug 1;44(4):326-37. [PubMed:11500849 ]
Zhou W, Koldzic-Zivanovic N, Clarke CH, de Beun R, Wassermann K, Bury PS, Cunningham KA, Thomas ML: Selective estrogen receptor modulator effects in the rat brain. Neuroendocrinology. 2002 Jan;75(1):24-33. [PubMed:11810032 ]
Sun J, Huang YR, Harrington WR, Sheng S, Katzenellenbogen JA, Katzenellenbogen BS: Antagonists selective for estrogen receptor alpha. Endocrinology. 2002 Mar;143(3):941-7. [PubMed:11861516 ]
Kim IY, Seong DH, Kim BC, Lee DK, Remaley AT, Leach F, Morton RA, Kim SJ: Raloxifene, a selective estrogen receptor modulator, induces apoptosis in androgen-responsive human prostate cancer cell line LNCaP through an androgen-independent pathway. Cancer Res. 2002 Jul 1;62(13):3649-53. [PubMed:12097269 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

3. 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

4. Cytochrome P450 2B6

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. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

References

Walsky RL, Astuccio AV, Obach RS: Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J Clin Pharmacol. 2006 Dec;46(12):1426-38. [PubMed:17101742 ]

Enzyme Details

5. 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

6. Cytochrome P450 2C8

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. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

References

Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [PubMed:15601807 ]
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. 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

Khovidhunkit W, Shoback DM: Clinical effects of raloxifene hydrochloride in women. Ann Intern Med. 1999 Mar 2;130(5):431-9. [PubMed:10068418 ]
Cummings SR, Eckert S, Krueger KA, Grady D, Powles TJ, Cauley JA, Norton L, Nickelsen T, Bjarnason NH, Morrow M, Lippman ME, Black D, Glusman JE, Costa A, Jordan VC: The effect of raloxifene on risk of breast cancer in postmenopausal women: results from the MORE randomized trial. Multiple Outcomes of Raloxifene Evaluation. JAMA. 1999 Jun 16;281(23):2189-97. [PubMed:10376571 ]
Bryant HU, Glasebrook AL, Yang NN, Sato M: An estrogen receptor basis for raloxifene action in bone. J Steroid Biochem Mol Biol. 1999 Apr-Jun;69(1-6):37-44. [PubMed:10418979 ]
Figtree GA, Lu Y, Webb CM, Collins P: Raloxifene acutely relaxes rabbit coronary arteries in vitro by an estrogen receptor-dependent and nitric oxide-dependent mechanism. Circulation. 1999 Sep 7;100(10):1095-101. [PubMed:10477535 ]
Schafer JI, Liu H, Tonetti DA, Jordan VC: The interaction of raloxifene and the active metabolite of the antiestrogen EM-800 (SC 5705) with the human estrogen receptor. Cancer Res. 1999 Sep 1;59(17):4308-13. [PubMed:10485477 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Scott JA, Da Camara CC, Early JE: Raloxifene: a selective estrogen receptor modulator. Am Fam Physician. 1999 Sep 15;60(4):1131-9. [PubMed:10507743 ]
Matsumoto T: [Selective estrogen receptor modulators (SERMs)]. Clin Calcium. 2006 Sep;16(9):1520-25. [PubMed:16951478 ]
Moen MD, Keating GM: Raloxifene: a review of its use in the prevention of invasive breast cancer. Drugs. 2008;68(14):2059-83. [PubMed:18778124 ]

Showing metabocard for Raloxifene (HMDB0014624)

MOL for HMDB0014624 (Raloxifene)

3D MOL for HMDB0014624 (Raloxifene)

3D SDF for HMDB0014624 (Raloxifene)

3D-SDF for HMDB0014624 (Raloxifene)

PDB for HMDB0014624 (Raloxifene)

3D PDB for HMDB0014624 (Raloxifene)

SMILES for HMDB0014624 (Raloxifene)

INCHI for HMDB0014624 (Raloxifene)

Structure for HMDB0014624 (Raloxifene)

3D Structure for HMDB0014624 (Raloxifene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

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References