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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-18 18:41:57 UTC

Update Date

2019-07-23 07:14:49 UTC

HMDB ID

HMDB0060666

Secondary Accession Numbers

HMDB60666

Metabolite Identification

Common Name

Endoxifen

Description

Endoxifen (EDX) is a key active metabolite of tamoxifen (TAM) with higher affinity and specificity to estrogen receptors that also inhibits aromatase activity. (PMID: 23274567 ) Tamoxifen is an antagonist of the estrogen receptor in breast tissue via its active metabolite, hydroxytamoxifen. In other tissues such as the endometrium, it behaves as an agonist, and thus may be characterized as a mixed agonist/antagonist. Tamoxifen is the usual endocrine therapy for hormone receptor-positive breast cancer in pre-menopausal women, and is also a standard in post-menopausal women although aromatase inhibitors are also frequently used in that setting. (Wikipedia ) The pharmacological activity of Tamoxifen is dependent on its conversion to its active metabolite, endoxifen, by CYP2D6. (PMID: 23711794 ) Tamoxifen is a largely inactive pro-drug, requiring metabolism into its most important metabolite endoxifen. Since the cytochrome P450 (CYP) 2D6 enzyme is primarily involved in this metabolism, genetic polymorphisms of this enzyme, but also drug-induced CYP2D6 inhibition can result in considerably reduced endoxifen formation and as a consequence may affect the efficacy of tamoxifen treatment. (PMID: 23760858 )

Structure

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

 
  Mrv0541 06181311412D          
 
 28 30  0  0  0  0            999 V2000
    9.6577  -10.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6577   -9.2435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3687  -10.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9048  -10.5403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3687   -8.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9048   -8.8671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3687  -11.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0798  -10.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9047  -11.3768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1937  -10.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3687   -7.9888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0798   -9.2435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1937   -9.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1216  -11.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8327  -10.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2355  -11.7951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4826  -10.5403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0798   -7.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7908   -8.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8327  -11.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4826  -11.3768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7908   -7.9888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5438  -11.7533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7715  -11.7951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2967  -11.2931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0077  -11.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7188  -11.2931    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4717  -11.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  4  9  1  0  0  0  0
  4 10  2  0  0  0  0
  5 11  1  0  0  0  0
  5 12  2  0  0  0  0
  6 13  1  0  0  0  0
  7 14  2  0  0  0  0
  8 15  1  0  0  0  0
  9 16  2  0  0  0  0
 10 17  1  0  0  0  0
 11 18  2  0  0  0  0
 12 19  1  0  0  0  0
 14 20  1  0  0  0  0
 16 21  1  0  0  0  0
 18 22  1  0  0  0  0
 20 23  1  0  0  0  0
 21 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 15 20  2  0  0  0  0
 17 21  2  0  0  0  0
 19 22  2  0  0  0  0
M  END

HMDB0060666
     RDKit          3D
Endoxifen
 55 57  0  0  0  0  0  0  0  0999 V2000
   -4.7725   -0.6875   -0.9514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8633   -1.0532    0.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4326   -0.8147   -0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7059   -0.0089    0.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2555    0.6741    1.7836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7082   -0.1245    2.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2595    0.4145    3.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3821    1.7919    4.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9434    2.3297    5.2717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9358    2.5668    3.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3857    2.0246    1.9214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2719    0.0905    0.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3785   -1.1097    0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7089   -1.1168   -0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4122    0.0606   -0.3894 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7586   -0.0090   -0.7187 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4818    1.1986   -0.8682 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9286    0.9262   -1.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5944    0.1477   -0.2137 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7421    0.9154    0.9830 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7369    1.2373   -0.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3748    1.2755    0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9097   -1.4681   -1.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1691   -0.7503   -2.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6734   -1.3375   -3.4296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9225   -2.6800   -3.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6627   -3.4021   -2.7511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1460   -2.7939   -1.6192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7656   -0.4144   -0.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8885   -1.5631   -1.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3948    0.1391   -1.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1989   -0.5302    1.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9745   -2.1440    0.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5982   -1.2031    2.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5987   -0.2494    4.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0154    3.3380    5.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0468    3.6362    3.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0886    2.7006    1.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1050   -2.0756    0.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2493   -2.0657   -0.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0340    1.7039   -1.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4243    1.8525   -0.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0278    0.4660   -2.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4392    1.9292   -1.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4280   -0.3638   -0.5318 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8072    1.1203    1.2295 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2278    1.9157    0.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2756    0.3900    1.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2655    2.1914   -0.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0868    2.2492    0.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9515    0.2956   -2.1666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0942   -0.7414   -4.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5124   -3.1008   -4.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8453   -4.4427   -2.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7305   -3.3303   -0.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 15 21  1  0
 21 22  2  0
  3 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 11  5  1  0
 22 12  1  0
 28 23  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  6 34  1  0
  7 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 13 39  1  0
 14 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 22 50  1  0
 24 51  1  0
 25 52  1  0
 26 53  1  0
 27 54  1  0
 28 55  1  0
M  END

 
  Mrv0541 06181311412D          
 
 28 30  0  0  0  0            999 V2000
    9.6577  -10.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6577   -9.2435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3687  -10.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9048  -10.5403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3687   -8.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9048   -8.8671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3687  -11.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0798  -10.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9047  -11.3768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1937  -10.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3687   -7.9888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0798   -9.2435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1937   -9.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1216  -11.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8327  -10.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2355  -11.7951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4826  -10.5403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0798   -7.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7908   -8.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8327  -11.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4826  -11.3768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7908   -7.9888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5438  -11.7533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7715  -11.7951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2967  -11.2931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0077  -11.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7188  -11.2931    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4717  -11.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  4  9  1  0  0  0  0
  4 10  2  0  0  0  0
  5 11  1  0  0  0  0
  5 12  2  0  0  0  0
  6 13  1  0  0  0  0
  7 14  2  0  0  0  0
  8 15  1  0  0  0  0
  9 16  2  0  0  0  0
 10 17  1  0  0  0  0
 11 18  2  0  0  0  0
 12 19  1  0  0  0  0
 14 20  1  0  0  0  0
 16 21  1  0  0  0  0
 18 22  1  0  0  0  0
 20 23  1  0  0  0  0
 21 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 15 20  2  0  0  0  0
 17 21  2  0  0  0  0
 19 22  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060666

> <DATABASE_NAME>
hmdb

> <SMILES>
CC\C(=C(/C1=CC=C(O)C=C1)C1=CC=C(OCCNC)C=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H27NO2/c1-3-24(19-7-5-4-6-8-19)25(20-9-13-22(27)14-10-20)21-11-15-23(16-12-21)28-18-17-26-2/h4-16,26-27H,3,17-18H2,1-2H3/b25-24-

> <INCHI_KEY>
MHJBZVSGOZTKRH-IZHYLOQSSA-N

> <FORMULA>
C25H27NO2

> <MOLECULAR_WEIGHT>
373.4874

> <EXACT_MASS>
373.204179113

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
43.538152744264586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(1Z)-1-{4-[2-(methylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenol

> <ALOGPS_LOGP>
5.32

> <JCHEM_LOGP>
4.919939721278035

> <ALOGPS_LOGS>
-5.61

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.122582023947947

> <JCHEM_PKA_STRONGEST_BASIC>
9.739146168566757

> <JCHEM_POLAR_SURFACE_AREA>
41.49

> <JCHEM_REFRACTIVITY>
125.11700000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.20e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
endoxifen

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060666
     RDKit          3D
Endoxifen
 55 57  0  0  0  0  0  0  0  0999 V2000
   -4.7725   -0.6875   -0.9514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8633   -1.0532    0.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4326   -0.8147   -0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7059   -0.0089    0.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2555    0.6741    1.7836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7082   -0.1245    2.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2595    0.4145    3.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3821    1.7919    4.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9434    2.3297    5.2717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9358    2.5668    3.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3857    2.0246    1.9214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2719    0.0905    0.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3785   -1.1097    0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7089   -1.1168   -0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4122    0.0606   -0.3894 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7586   -0.0090   -0.7187 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4818    1.1986   -0.8682 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9286    0.9262   -1.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5944    0.1477   -0.2137 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7421    0.9154    0.9830 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7369    1.2373   -0.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3748    1.2755    0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9097   -1.4681   -1.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1691   -0.7503   -2.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6734   -1.3375   -3.4296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9225   -2.6800   -3.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6627   -3.4021   -2.7511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1460   -2.7939   -1.6192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7656   -0.4144   -0.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8885   -1.5631   -1.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3948    0.1391   -1.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1989   -0.5302    1.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9745   -2.1440    0.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5982   -1.2031    2.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5987   -0.2494    4.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0154    3.3380    5.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0468    3.6362    3.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0886    2.7006    1.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1050   -2.0756    0.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2493   -2.0657   -0.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0340    1.7039   -1.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4243    1.8525   -0.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0278    0.4660   -2.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4392    1.9292   -1.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4280   -0.3638   -0.5318 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8072    1.1203    1.2295 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2278    1.9157    0.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2756    0.3900    1.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2655    2.1914   -0.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0868    2.2492    0.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9515    0.2956   -2.1666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0942   -0.7414   -4.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5124   -3.1008   -4.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8453   -4.4427   -2.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7305   -3.3303   -0.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 15 21  1  0
 21 22  2  0
  3 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 11  5  1  0
 22 12  1  0
 28 23  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  6 34  1  0
  7 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 13 39  1  0
 14 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 22 50  1  0
 24 51  1  0
 25 52  1  0
 26 53  1  0
 27 54  1  0
 28 55  1  0
M  END

HEADER    PROTEIN                                 18-JUN-13   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-JUN-13         0                                  
HETATM    1  C   UNK     0      18.028 -18.816   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.028 -17.255   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.355 -19.597   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.622 -19.675   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.355 -16.474   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.622 -16.552   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.355 -21.159   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.682 -18.816   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.622 -21.237   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.295 -18.894   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.355 -14.912   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.682 -17.255   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.295 -17.333   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.760 -21.939   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.088 -19.597   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.373 -22.018   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.967 -19.675   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.682 -14.132   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.010 -16.474   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.088 -21.159   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.967 -21.237   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      22.010 -14.912   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      23.415 -21.939   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      12.640 -22.018   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      24.820 -21.081   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      26.148 -21.861   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      27.475 -21.081   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      28.880 -21.861   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9   10                                                  
CONECT    5    2   11   12                                                  
CONECT    6    2   13                                                       
CONECT    7    3   14                                                       
CONECT    8    3   15                                                       
CONECT    9    4   16                                                       
CONECT   10    4   17                                                       
CONECT   11    5   18                                                       
CONECT   12    5   19                                                       
CONECT   13    6                                                            
CONECT   14    7   20                                                       
CONECT   15    8   20                                                       
CONECT   16    9   21                                                       
CONECT   17   10   21                                                       
CONECT   18   11   22                                                       
CONECT   19   12   22                                                       
CONECT   20   14   23   15                                                  
CONECT   21   16   24   17                                                  
CONECT   22   18   19                                                       
CONECT   23   20   25                                                       
CONECT   24   21                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

COMPND    HMDB0060666
HETATM    1  C1  UNL     1      -4.772  -0.688  -0.951  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.863  -1.053   0.212  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.433  -0.815  -0.146  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.706  -0.009   0.599  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.255   0.674   1.784  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.708  -0.125   2.850  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.260   0.415   3.989  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.382   1.792   4.109  1.00  0.00           C  
HETATM    9  O1  UNL     1      -3.943   2.330   5.272  1.00  0.00           O  
HETATM   10  C9  UNL     1      -2.936   2.567   3.058  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.386   2.025   1.921  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.272   0.091   0.264  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.378  -1.110   0.082  1.00  0.00           C  
HETATM   14  C13 UNL     1       1.709  -1.117  -0.242  1.00  0.00           C  
HETATM   15  C14 UNL     1       2.412   0.061  -0.389  1.00  0.00           C  
HETATM   16  O2  UNL     1       3.759  -0.009  -0.719  1.00  0.00           O  
HETATM   17  C15 UNL     1       4.482   1.199  -0.868  1.00  0.00           C  
HETATM   18  C16 UNL     1       5.929   0.926  -1.226  1.00  0.00           C  
HETATM   19  N1  UNL     1       6.594   0.148  -0.214  1.00  0.00           N  
HETATM   20  C17 UNL     1       6.742   0.915   0.983  1.00  0.00           C  
HETATM   21  C18 UNL     1       1.737   1.237  -0.201  1.00  0.00           C  
HETATM   22  C19 UNL     1       0.375   1.275   0.132  1.00  0.00           C  
HETATM   23  C20 UNL     1      -1.910  -1.468  -1.369  1.00  0.00           C  
HETATM   24  C21 UNL     1      -1.169  -0.750  -2.287  1.00  0.00           C  
HETATM   25  C22 UNL     1      -0.673  -1.338  -3.430  1.00  0.00           C  
HETATM   26  C23 UNL     1      -0.923  -2.680  -3.666  1.00  0.00           C  
HETATM   27  C24 UNL     1      -1.663  -3.402  -2.751  1.00  0.00           C  
HETATM   28  C25 UNL     1      -2.146  -2.794  -1.619  1.00  0.00           C  
HETATM   29  H1  UNL     1      -5.766  -0.414  -0.544  1.00  0.00           H  
HETATM   30  H2  UNL     1      -4.889  -1.563  -1.639  1.00  0.00           H  
HETATM   31  H3  UNL     1      -4.395   0.139  -1.550  1.00  0.00           H  
HETATM   32  H4  UNL     1      -4.199  -0.530   1.094  1.00  0.00           H  
HETATM   33  H5  UNL     1      -3.975  -2.144   0.369  1.00  0.00           H  
HETATM   34  H6  UNL     1      -2.598  -1.203   2.730  1.00  0.00           H  
HETATM   35  H7  UNL     1      -3.599  -0.249   4.792  1.00  0.00           H  
HETATM   36  H8  UNL     1      -4.015   3.338   5.322  1.00  0.00           H  
HETATM   37  H9  UNL     1      -3.047   3.636   3.184  1.00  0.00           H  
HETATM   38  H10 UNL     1      -2.089   2.701   1.152  1.00  0.00           H  
HETATM   39  H11 UNL     1      -0.105  -2.076   0.192  1.00  0.00           H  
HETATM   40  H12 UNL     1       2.249  -2.066  -0.394  1.00  0.00           H  
HETATM   41  H13 UNL     1       4.034   1.704  -1.774  1.00  0.00           H  
HETATM   42  H14 UNL     1       4.424   1.853  -0.000  1.00  0.00           H  
HETATM   43  H15 UNL     1       6.028   0.466  -2.236  1.00  0.00           H  
HETATM   44  H16 UNL     1       6.439   1.929  -1.275  1.00  0.00           H  
HETATM   45  H17 UNL     1       7.428  -0.364  -0.532  1.00  0.00           H  
HETATM   46  H18 UNL     1       7.807   1.120   1.229  1.00  0.00           H  
HETATM   47  H19 UNL     1       6.228   1.916   0.932  1.00  0.00           H  
HETATM   48  H20 UNL     1       6.276   0.390   1.823  1.00  0.00           H  
HETATM   49  H21 UNL     1       2.266   2.191  -0.309  1.00  0.00           H  
HETATM   50  H22 UNL     1      -0.087   2.249   0.258  1.00  0.00           H  
HETATM   51  H23 UNL     1      -0.951   0.296  -2.167  1.00  0.00           H  
HETATM   52  H24 UNL     1      -0.094  -0.741  -4.135  1.00  0.00           H  
HETATM   53  H25 UNL     1      -0.512  -3.101  -4.580  1.00  0.00           H  
HETATM   54  H26 UNL     1      -1.845  -4.443  -2.953  1.00  0.00           H  
HETATM   55  H27 UNL     1      -2.730  -3.330  -0.880  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3   32   33
CONECT    3    4    4   23
CONECT    4    5   12
CONECT    5    6    6   11
CONECT    6    7   34
CONECT    7    8    8   35
CONECT    8    9   10
CONECT    9   36
CONECT   10   11   11   37
CONECT   11   38
CONECT   12   13   13   22
CONECT   13   14   39
CONECT   14   15   15   40
CONECT   15   16   21
CONECT   16   17
CONECT   17   18   41   42
CONECT   18   19   43   44
CONECT   19   20   45
CONECT   20   46   47   48
CONECT   21   22   22   49
CONECT   22   50
CONECT   23   24   24   28
CONECT   24   25   51
CONECT   25   26   26   52
CONECT   26   27   53
CONECT   27   28   28   54
CONECT   28   55
END

HMDB0060666
     RDKit          3D
Endoxifen
 55 57  0  0  0  0  0  0  0  0999 V2000
   -4.7725   -0.6875   -0.9514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8633   -1.0532    0.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4326   -0.8147   -0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7059   -0.0089    0.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2555    0.6741    1.7836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7082   -0.1245    2.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2595    0.4145    3.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3821    1.7919    4.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9434    2.3297    5.2717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9358    2.5668    3.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3857    2.0246    1.9214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2719    0.0905    0.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3785   -1.1097    0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7089   -1.1168   -0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4122    0.0606   -0.3894 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7586   -0.0090   -0.7187 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4818    1.1986   -0.8682 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9286    0.9262   -1.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5944    0.1477   -0.2137 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7421    0.9154    0.9830 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7369    1.2373   -0.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3748    1.2755    0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9097   -1.4681   -1.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1691   -0.7503   -2.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6734   -1.3375   -3.4296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9225   -2.6800   -3.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6627   -3.4021   -2.7511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1460   -2.7939   -1.6192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7656   -0.4144   -0.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8885   -1.5631   -1.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3948    0.1391   -1.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1989   -0.5302    1.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9745   -2.1440    0.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5982   -1.2031    2.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5987   -0.2494    4.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0154    3.3380    5.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0468    3.6362    3.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0886    2.7006    1.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1050   -2.0756    0.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2493   -2.0657   -0.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0340    1.7039   -1.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4243    1.8525   -0.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0278    0.4660   -2.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4392    1.9292   -1.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4280   -0.3638   -0.5318 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8072    1.1203    1.2295 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2278    1.9157    0.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2756    0.3900    1.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2655    2.1914   -0.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0868    2.2492    0.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9515    0.2956   -2.1666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0942   -0.7414   -4.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5124   -3.1008   -4.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8453   -4.4427   -2.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7305   -3.3303   -0.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 15 21  1  0
 21 22  2  0
  3 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 11  5  1  0
 22 12  1  0
 28 23  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  6 34  1  0
  7 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 13 39  1  0
 14 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 22 50  1  0
 24 51  1  0
 25 52  1  0
 26 53  1  0
 27 54  1  0
 28 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Hydroxy-N-desmethyltamoxifen	Kegg
4-Hydroxy-N-demethyltamoxifen	HMDB
4-Hydroxy-N-desmethyltamoxifen, (Z)-isomer	HMDB
Z-Endoxifen	MeSH

Chemical Formula

C₂₅H₂₇NO₂

Average Molecular Weight

373.4874

Monoisotopic Molecular Weight

373.204179113

IUPAC Name

4-[(1Z)-1-{4-[2-(methylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenol

Traditional Name

endoxifen

CAS Registry Number

Not Available

SMILES

CC\C(=C(/C1=CC=C(O)C=C1)C1=CC=C(OCCNC)C=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C25H27NO2/c1-3-24(19-7-5-4-6-8-19)25(20-9-13-22(27)14-10-20)21-11-15-23(16-12-21)28-18-17-26-2/h4-16,26-27H,3,17-18H2,1-2H3/b25-24-

InChI Key

MHJBZVSGOZTKRH-IZHYLOQSSA-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
Phenylpropane
Phenoxy compound
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Secondary amine
Ether
Secondary aliphatic amine
Organic oxygen compound
Amine
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

stilbenoid (CHEBI:80555 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060666)

Organ

Liver (HMDB: HMDB0060666)
Kidney (HMDB: HMDB0060666)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060666)

Cellular substructure

Cytoplasm (HMDB: HMDB0060666)
Membrane (HMDB: HMDB0060666)

Source

Endogenous

Endogenous (HMDB: HMDB0060666)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Tamoxifen Action Pathway (PathBank: SMP0000471)

Metabolic pathway

Tamoxifen Metabolism Pathway (PathBank: SMP0000606)

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00092 g/L	ALOGPS
logP	5.32	ALOGPS
logP	4.92	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	9.12	ChemAxon
pKa (Strongest Basic)	9.74	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	41.49 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	125.12 m³·mol⁻¹	ChemAxon
Polarizability	43.54 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	192.824	31661259
DarkChem	[M-H]-	191.209	31661259
DeepCCS	[M+H]+	194.92	30932474
DeepCCS	[M-H]-	192.562	30932474
DeepCCS	[M-2H]-	226.705	30932474
DeepCCS	[M+Na]+	201.933	30932474
AllCCS	[M+H]+	194.9	32859911
AllCCS	[M+H-H2O]+	192.0	32859911
AllCCS	[M+NH4]+	197.7	32859911
AllCCS	[M+Na]+	198.4	32859911
AllCCS	[M-H]-	196.9	32859911
AllCCS	[M+Na-2H]-	196.8	32859911
AllCCS	[M+HCOO]-	196.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.58 minutes	32390414
Predicted by Siyang on May 30, 2022	15.0529 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.29 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2468.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	308.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	223.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	198.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	332.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	712.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	622.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	154.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1401.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	586.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1500.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	449.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	419.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	239.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	220.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Endoxifen	CC\C(=C(/C1=CC=C(O)C=C1)C1=CC=C(OCCNC)C=C1)C1=CC=CC=C1	4035.4	Standard polar	33892256
Endoxifen	CC\C(=C(/C1=CC=C(O)C=C1)C1=CC=C(OCCNC)C=C1)C1=CC=CC=C1	2890.9	Standard non polar	33892256
Endoxifen	CC\C(=C(/C1=CC=C(O)C=C1)C1=CC=C(OCCNC)C=C1)C1=CC=CC=C1	3064.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Endoxifen,1TMS,isomer #1	CC/C(=C(/C1=CC=C(OCCNC)C=C1)C1=CC=C(O[Si](C)(C)C)C=C1)C1=CC=CC=C1	3311.9	Semi standard non polar	33892256
Endoxifen,1TMS,isomer #2	CC/C(=C(\C1=CC=C(O)C=C1)C1=CC=C(OCCN(C)[Si](C)(C)C)C=C1)C1=CC=CC=C1	3531.5	Semi standard non polar	33892256
Endoxifen,2TMS,isomer #1	CC/C(=C(/C1=CC=C(OCCN(C)[Si](C)(C)C)C=C1)C1=CC=C(O[Si](C)(C)C)C=C1)C1=CC=CC=C1	3472.9	Semi standard non polar	33892256
Endoxifen,2TMS,isomer #1	CC/C(=C(/C1=CC=C(OCCN(C)[Si](C)(C)C)C=C1)C1=CC=C(O[Si](C)(C)C)C=C1)C1=CC=CC=C1	3160.9	Standard non polar	33892256
Endoxifen,2TMS,isomer #1	CC/C(=C(/C1=CC=C(OCCN(C)[Si](C)(C)C)C=C1)C1=CC=C(O[Si](C)(C)C)C=C1)C1=CC=CC=C1	3707.9	Standard polar	33892256
Endoxifen,1TBDMS,isomer #1	CC/C(=C(/C1=CC=C(OCCNC)C=C1)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C1	3541.4	Semi standard non polar	33892256
Endoxifen,1TBDMS,isomer #2	CC/C(=C(\C1=CC=C(O)C=C1)C1=CC=C(OCCN(C)[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C1	3744.9	Semi standard non polar	33892256
Endoxifen,2TBDMS,isomer #1	CC/C(=C(/C1=CC=C(OCCN(C)[Si](C)(C)C(C)(C)C)C=C1)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C1	3896.8	Semi standard non polar	33892256
Endoxifen,2TBDMS,isomer #1	CC/C(=C(/C1=CC=C(OCCN(C)[Si](C)(C)C(C)(C)C)C=C1)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C1	3568.0	Standard non polar	33892256
Endoxifen,2TBDMS,isomer #1	CC/C(=C(/C1=CC=C(OCCN(C)[Si](C)(C)C(C)(C)C)C=C1)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C1	3850.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Endoxifen GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9133000000-c2161354cdf77d434e99	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Endoxifen GC-MS (1 TMS) - 70eV, Positive	splash10-0006-9004200000-3d59e8fe230516e4b37b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Endoxifen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Endoxifen 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Endoxifen 10V, Positive-QTOF	splash10-00di-2249000000-8346297433ff370f4efc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Endoxifen 20V, Positive-QTOF	splash10-0a4i-9353000000-c4a46698f9bb9d64a6a3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Endoxifen 40V, Positive-QTOF	splash10-0a4l-9251000000-f988f5670acac5e08df6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Endoxifen 10V, Negative-QTOF	splash10-00di-1009000000-62ed97feda2a9f20b6ac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Endoxifen 20V, Negative-QTOF	splash10-01b9-1019000000-b6b443507b9eb725195a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Endoxifen 40V, Negative-QTOF	splash10-014i-6297000000-442332a961e6bb4bfde8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Endoxifen 10V, Positive-QTOF	splash10-00di-0019000000-d78eeafe19daa54ddac9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Endoxifen 20V, Positive-QTOF	splash10-05fr-1149000000-e1df0c6d8dfb9b328713	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Endoxifen 40V, Positive-QTOF	splash10-066u-9823000000-06951b7a731996b904ce	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Endoxifen 10V, Negative-QTOF	splash10-00di-0009000000-b38f885c98c9697e45e8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Endoxifen 20V, Negative-QTOF	splash10-00xr-0019000000-bbed0c38c9db23b2f1cd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Endoxifen 40V, Negative-QTOF	splash10-02ta-0089000000-32d3e92619afbb528e2a	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Tamoxifen Action Pathway		Not Available
Tamoxifen Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C16547

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Endoxifen

METLIN ID

Not Available

PubChem Compound

10090750

PDB ID

Not Available

ChEBI ID

Not Available

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

Ribeiro MP, Silva FS, Santos AE, Santos MS, Custodio JB: The antiestrogen endoxifen protects rat liver mitochondria from permeability transition pore opening and oxidative stress at concentrations that do not affect the phosphorylation efficiency. Toxicol Appl Pharmacol. 2013 Feb 15;267(1):104-12. doi: 10.1016/j.taap.2012.12.012. Epub 2012 Dec 27. [PubMed:23274567 ]
Yang G, Nowsheen S, Aziz K, Georgakilas AG: Toxicity and adverse effects of Tamoxifen and other anti-estrogen drugs. Pharmacol Ther. 2013 Sep;139(3):392-404. doi: 10.1016/j.pharmthera.2013.05.005. Epub 2013 May 24. [PubMed:23711794 ]
Binkhorst L, Mathijssen RH, van Herk-Sukel MP, Bannink M, Jager A, Wiemer EA, van Gelder T: Unjustified prescribing of CYP2D6 inhibiting SSRIs in women treated with tamoxifen. Breast Cancer Res Treat. 2013 Jun;139(3):923-9. doi: 10.1007/s10549-013-2585-z. Epub 2013 Jun 13. [PubMed:23760858 ]

Showing metabocard for Endoxifen (HMDB0060666)

MOL for HMDB0060666 (Endoxifen)

3D MOL for HMDB0060666 (Endoxifen)

3D SDF for HMDB0060666 (Endoxifen)

3D-SDF for HMDB0060666 (Endoxifen)

PDB for HMDB0060666 (Endoxifen)

3D PDB for HMDB0060666 (Endoxifen)

SMILES for HMDB0060666 (Endoxifen)

INCHI for HMDB0060666 (Endoxifen)

Structure for HMDB0060666 (Endoxifen)

3D Structure for HMDB0060666 (Endoxifen)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra