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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4)transporters (1) Show 5 proteins XML

enzymes (4)transporters (1) Show 5 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:56 UTC

HMDB ID

HMDB0015327

Secondary Accession Numbers

HMDB15327

Metabolite Identification

Common Name

Estramustine

Description

Estramustine is only found in individuals that have used or taken this drug. It is a nitrogen mustard linked to estradiol, usually as phosphate; used to treat prostatic neoplasms; also has radiation protective properties. [PubChem]Estramustine is a derivative of estradiol with a nitrogen mustard moiety. This gives it alkylating properties. In vivo, the nitrogen mustard component is active and can alklyate DNA and other cellular components (such as tubulin components) of rapidly dividing cells. This causes DNA strandbreaks or misscoding events. This leads to apoptosis and cell death. Also, due to the drugs estrogen component, it can bind more selectively to active estrogen receptors.

Structure

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


  Mrv0541 04191212172D          

 32 35  0  0  1  0            999 V2000
    1.8036   -0.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3045   -1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8036    1.2211    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3045    1.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2885    0.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1245   -0.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4100    0.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4100   -1.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1245   -1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390    0.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390   -1.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5534   -0.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3045   -0.2714    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3045    0.5536    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4100    0.1411    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4100   -0.6839    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0189    0.9661    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0189    1.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0189    0.1411    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0189   -0.6839    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2679   -1.5089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5534   -1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8036    2.0461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9824   -1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6968   -1.5089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4113   -1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4113   -0.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6968   -2.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9824   -2.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1258    0.1411    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.9824   -3.5714    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.9824   -0.2714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 19 13  1  0  0  0  0
 19 17  1  0  0  0  0
 19  1  1  0  0  0  0
 13 15  1  0  0  0  0
 13  2  1  0  0  0  0
 17  3  1  0  0  0  0
 17  4  1  0  0  0  0
  5  1  1  0  0  0  0
 15  6  1  0  0  0  0
 15  7  1  0  0  0  0
  2  8  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  2  0  0  0  0
  9 11  2  0  0  0  0
 10 12  1  0  0  0  0
 11 22  1  0  0  0  0
  3  5  1  0  0  0  0
  4  7  1  0  0  0  0
  8  9  1  0  0  0  0
 12 22  2  0  0  0  0
 13 14  1  1  0  0  0
 15 16  1  6  0  0  0
 17 18  1  1  0  0  0
 19 20  1  6  0  0  0
 22 21  1  0  0  0  0
  3 23  1  1  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 30  1  0  0  0  0
 29 31  1  0  0  0  0
 24 32  2  0  0  0  0
M  END

HMDB0015327
     RDKit          3D
Estramustine
 60 63  0  0  0  0  0  0  0  0999 V2000
    4.6328   -1.5733    1.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5628   -0.1363    0.9046 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8008    0.7151    1.8596 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3480    0.2948    1.7977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7995    0.5706    0.4239 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3691    0.2936    0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4800    0.0354    1.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8186   -0.2123    1.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3578   -0.2155   -0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6898   -0.4599   -0.4265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6500    0.5440   -0.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2649    1.7194   -0.2704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0209    0.2764   -0.7668 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9407    1.3729   -0.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5736    1.6955    0.5239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6928    3.0881    0.3395 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -6.4824   -1.0618   -1.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9045   -1.8201    0.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5637   -1.9781    1.3386 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.5115    0.0424   -1.2166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1782    0.2891   -0.9666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7535    0.5690   -2.0898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0535   -0.1865   -1.9659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5675   -0.3120   -0.5726 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9779    0.1083   -0.4828 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9571   -0.5901   -1.3443 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2794   -0.0451   -0.7850 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9849    0.3504    0.6563 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8400   -0.3935    1.4806 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6602   -1.6796    2.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8347   -2.2097    0.8995 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5978   -2.0261    0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1911    0.5157    2.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9246    1.7688    1.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8136    0.8253    2.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2566   -0.7837    1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9875    1.6243    0.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0538    0.0395    2.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4914   -0.4165    1.9519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7479    1.2395   -1.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3894    2.2959   -1.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2116    0.8625    0.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8290    1.9102    1.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3927   -0.9766   -1.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7083   -1.6674   -1.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1658   -2.8579   -0.1750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7967   -1.4568    0.6910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8843    0.0529   -2.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3094    0.3054   -3.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9959    1.6648   -2.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7759    0.3020   -2.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8648   -1.2004   -2.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3740   -1.3529   -0.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0445    1.1975   -0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9785   -1.6946   -1.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8598   -0.3824   -2.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4728    0.8976   -1.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0867   -0.7842   -0.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0763    1.4301    0.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7688   -0.4240    1.1157 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
  9 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 25  2  1  0
 28  2  1  0
 24  5  1  0
 21  6  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  6
  7 38  1  0
  8 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 20 48  1  0
 22 49  1  0
 22 50  1  0
 23 51  1  0
 23 52  1  0
 24 53  1  1
 25 54  1  6
 26 55  1  0
 26 56  1  0
 27 57  1  0
 27 58  1  0
 28 59  1  6
 29 60  1  0
M  END


  Mrv0541 04191212172D          

 32 35  0  0  1  0            999 V2000
    1.8036   -0.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3045   -1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8036    1.2211    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3045    1.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2885    0.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1245   -0.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4100    0.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4100   -1.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1245   -1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390    0.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390   -1.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5534   -0.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3045   -0.2714    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3045    0.5536    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4100    0.1411    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4100   -0.6839    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0189    0.9661    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0189    1.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0189    0.1411    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0189   -0.6839    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2679   -1.5089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5534   -1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8036    2.0461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9824   -1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6968   -1.5089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4113   -1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4113   -0.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6968   -2.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9824   -2.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1258    0.1411    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.9824   -3.5714    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.9824   -0.2714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 19 13  1  0  0  0  0
 19 17  1  0  0  0  0
 19  1  1  0  0  0  0
 13 15  1  0  0  0  0
 13  2  1  0  0  0  0
 17  3  1  0  0  0  0
 17  4  1  0  0  0  0
  5  1  1  0  0  0  0
 15  6  1  0  0  0  0
 15  7  1  0  0  0  0
  2  8  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  2  0  0  0  0
  9 11  2  0  0  0  0
 10 12  1  0  0  0  0
 11 22  1  0  0  0  0
  3  5  1  0  0  0  0
  4  7  1  0  0  0  0
  8  9  1  0  0  0  0
 12 22  2  0  0  0  0
 13 14  1  1  0  0  0
 15 16  1  6  0  0  0
 17 18  1  1  0  0  0
 19 20  1  6  0  0  0
 22 21  1  0  0  0  0
  3 23  1  1  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 30  1  0  0  0  0
 29 31  1  0  0  0  0
 24 32  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015327

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=CC=C(OC(=O)N(CCCl)CCCl)C=C3CC[C@@]21[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H31Cl2NO3/c1-23-9-8-18-17-5-3-16(29-22(28)26(12-10-24)13-11-25)14-15(17)2-4-19(18)20(23)6-7-21(23)27/h3,5,14,18-21,27H,2,4,6-13H2,1H3/t18-,19-,20+,21+,23+/m1/s1

> <INCHI_KEY>
FRPJXPJMRWBBIH-RBRWEJTLSA-N

> <FORMULA>
C23H31Cl2NO3

> <MOLECULAR_WEIGHT>
440.403

> <EXACT_MASS>
439.168099277

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
48.06209161373284

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-trien-5-yl N,N-bis(2-chloroethyl)carbamate

> <ALOGPS_LOGP>
4.97

> <JCHEM_LOGP>
5.09911391

> <ALOGPS_LOGS>
-6.06

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.37769223665565

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8839974156868172

> <JCHEM_POLAR_SURFACE_AREA>
49.77

> <JCHEM_REFRACTIVITY>
116.21289999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.85e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
estramustine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015327
     RDKit          3D
Estramustine
 60 63  0  0  0  0  0  0  0  0999 V2000
    4.6328   -1.5733    1.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5628   -0.1363    0.9046 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8008    0.7151    1.8596 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3480    0.2948    1.7977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7995    0.5706    0.4239 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3691    0.2936    0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4800    0.0354    1.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8186   -0.2123    1.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3578   -0.2155   -0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6898   -0.4599   -0.4265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6500    0.5440   -0.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2649    1.7194   -0.2704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0209    0.2764   -0.7668 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9407    1.3729   -0.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5736    1.6955    0.5239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6928    3.0881    0.3395 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -6.4824   -1.0618   -1.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9045   -1.8201    0.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5637   -1.9781    1.3386 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.5115    0.0424   -1.2166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1782    0.2891   -0.9666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7535    0.5690   -2.0898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0535   -0.1865   -1.9659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5675   -0.3120   -0.5726 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9779    0.1083   -0.4828 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9571   -0.5901   -1.3443 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2794   -0.0451   -0.7850 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9849    0.3504    0.6563 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8400   -0.3935    1.4806 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6602   -1.6796    2.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8347   -2.2097    0.8995 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5978   -2.0261    0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1911    0.5157    2.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9246    1.7688    1.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8136    0.8253    2.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2566   -0.7837    1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9875    1.6243    0.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0538    0.0395    2.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4914   -0.4165    1.9519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7479    1.2395   -1.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3894    2.2959   -1.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2116    0.8625    0.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8290    1.9102    1.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3927   -0.9766   -1.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7083   -1.6674   -1.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1658   -2.8579   -0.1750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7967   -1.4568    0.6910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8843    0.0529   -2.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3094    0.3054   -3.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9959    1.6648   -2.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7759    0.3020   -2.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8648   -1.2004   -2.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3740   -1.3529   -0.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0445    1.1975   -0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9785   -1.6946   -1.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8598   -0.3824   -2.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4728    0.8976   -1.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0867   -0.7842   -0.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0763    1.4301    0.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7688   -0.4240    1.1157 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
  9 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 25  2  1  0
 28  2  1  0
 24  5  1  0
 21  6  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  6
  7 38  1  0
  8 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 20 48  1  0
 22 49  1  0
 22 50  1  0
 23 51  1  0
 23 52  1  0
 24 53  1  1
 25 54  1  6
 26 55  1  0
 26 56  1  0
 27 57  1  0
 27 58  1  0
 28 59  1  6
 29 60  1  0
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0       3.367  -0.212   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.568  -2.047   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.367   2.279   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.568   2.573   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.272   1.033   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.099  -0.507   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.765   1.803   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.765  -2.817   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.099  -2.047   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.433   0.263   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.433  -2.817   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.766  -0.507   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.568  -0.507   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       0.568   1.033   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0      -0.765   0.263   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0      -0.765  -1.277   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0       1.902   1.803   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.902   3.343   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.902   0.263   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0       1.902  -1.277   0.000  0.00  0.00           H+0
HETATM   21  O   UNK     0      -6.100  -2.817   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.766  -2.047   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.367   3.819   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -7.434  -2.047   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      -8.767  -2.817   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0     -10.101  -2.047   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -10.101  -0.507   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.767  -4.357   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -7.434  -5.127   0.000  0.00  0.00           C+0
HETATM   30 Cl   UNK     0     -11.435   0.263   0.000  0.00  0.00          Cl+0
HETATM   31 Cl   UNK     0      -7.434  -6.667   0.000  0.00  0.00          Cl+0
HETATM   32  O   UNK     0      -7.434  -0.507   0.000  0.00  0.00           O+0
CONECT    1   19    5                                                       
CONECT    2   13    8                                                       
CONECT    3   17    5   23                                                  
CONECT    4   17    7                                                       
CONECT    5    1    3                                                       
CONECT    6   15    9   10                                                  
CONECT    7   15    4                                                       
CONECT    8    2    9                                                       
CONECT    9    6   11    8                                                  
CONECT   10    6   12                                                       
CONECT   11    9   22                                                       
CONECT   12   10   22                                                       
CONECT   13   19   15    2   14                                             
CONECT   14   13                                                            
CONECT   15   13    6    7   16                                             
CONECT   16   15                                                            
CONECT   17   19    3    4   18                                             
CONECT   18   17                                                            
CONECT   19   13   17    1   20                                             
CONECT   20   19                                                            
CONECT   21   22   24                                                       
CONECT   22   11   12   21                                                  
CONECT   23    3                                                            
CONECT   24   21   25   32                                                  
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26   30                                                       
CONECT   28   25   29                                                       
CONECT   29   28   31                                                       
CONECT   30   27                                                            
CONECT   31   29                                                            
CONECT   32   24                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

COMPND    HMDB0015327
HETATM    1  C1  UNL     1       4.633  -1.573   1.270  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.563  -0.136   0.905  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.801   0.715   1.860  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.348   0.295   1.798  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.799   0.571   0.424  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.369   0.294   0.304  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.480   0.035   1.366  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.819  -0.212   1.115  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.358  -0.215  -0.152  1.00  0.00           C  
HETATM   10  O1  UNL     1      -3.690  -0.460  -0.427  1.00  0.00           O  
HETATM   11  C10 UNL     1      -4.650   0.544  -0.482  1.00  0.00           C  
HETATM   12  O2  UNL     1      -4.265   1.719  -0.270  1.00  0.00           O  
HETATM   13  N1  UNL     1      -6.021   0.276  -0.767  1.00  0.00           N  
HETATM   14  C11 UNL     1      -6.941   1.373  -0.804  1.00  0.00           C  
HETATM   15  C12 UNL     1      -7.574   1.696   0.524  1.00  0.00           C  
HETATM   16 CL1  UNL     1      -8.693   3.088   0.339  1.00  0.00          CL  
HETATM   17  C13 UNL     1      -6.482  -1.062  -1.033  1.00  0.00           C  
HETATM   18  C14 UNL     1      -6.905  -1.820   0.180  1.00  0.00           C  
HETATM   19 CL2  UNL     1      -5.564  -1.978   1.339  1.00  0.00          CL  
HETATM   20  C15 UNL     1      -1.512   0.042  -1.217  1.00  0.00           C  
HETATM   21  C16 UNL     1      -0.178   0.289  -0.967  1.00  0.00           C  
HETATM   22  C17 UNL     1       0.753   0.569  -2.090  1.00  0.00           C  
HETATM   23  C18 UNL     1       2.053  -0.186  -1.966  1.00  0.00           C  
HETATM   24  C19 UNL     1       2.568  -0.312  -0.573  1.00  0.00           C  
HETATM   25  C20 UNL     1       3.978   0.108  -0.483  1.00  0.00           C  
HETATM   26  C21 UNL     1       4.957  -0.590  -1.344  1.00  0.00           C  
HETATM   27  C22 UNL     1       6.279  -0.045  -0.785  1.00  0.00           C  
HETATM   28  C23 UNL     1       5.985   0.350   0.656  1.00  0.00           C  
HETATM   29  O3  UNL     1       6.840  -0.394   1.481  1.00  0.00           O  
HETATM   30  H1  UNL     1       4.660  -1.680   2.375  1.00  0.00           H  
HETATM   31  H2  UNL     1       3.835  -2.210   0.900  1.00  0.00           H  
HETATM   32  H3  UNL     1       5.598  -2.026   0.898  1.00  0.00           H  
HETATM   33  H4  UNL     1       4.191   0.516   2.885  1.00  0.00           H  
HETATM   34  H5  UNL     1       3.925   1.769   1.586  1.00  0.00           H  
HETATM   35  H6  UNL     1       1.814   0.825   2.584  1.00  0.00           H  
HETATM   36  H7  UNL     1       2.257  -0.784   1.987  1.00  0.00           H  
HETATM   37  H8  UNL     1       1.988   1.624   0.154  1.00  0.00           H  
HETATM   38  H9  UNL     1      -0.054   0.040   2.350  1.00  0.00           H  
HETATM   39  H10 UNL     1      -2.491  -0.416   1.952  1.00  0.00           H  
HETATM   40  H11 UNL     1      -7.748   1.240  -1.556  1.00  0.00           H  
HETATM   41  H12 UNL     1      -6.389   2.296  -1.135  1.00  0.00           H  
HETATM   42  H13 UNL     1      -8.212   0.862   0.868  1.00  0.00           H  
HETATM   43  H14 UNL     1      -6.829   1.910   1.302  1.00  0.00           H  
HETATM   44  H15 UNL     1      -7.393  -0.977  -1.696  1.00  0.00           H  
HETATM   45  H16 UNL     1      -5.708  -1.667  -1.556  1.00  0.00           H  
HETATM   46  H17 UNL     1      -7.166  -2.858  -0.175  1.00  0.00           H  
HETATM   47  H18 UNL     1      -7.797  -1.457   0.691  1.00  0.00           H  
HETATM   48  H19 UNL     1      -1.884   0.053  -2.247  1.00  0.00           H  
HETATM   49  H20 UNL     1       0.309   0.305  -3.072  1.00  0.00           H  
HETATM   50  H21 UNL     1       0.996   1.665  -2.079  1.00  0.00           H  
HETATM   51  H22 UNL     1       2.776   0.302  -2.655  1.00  0.00           H  
HETATM   52  H23 UNL     1       1.865  -1.200  -2.426  1.00  0.00           H  
HETATM   53  H24 UNL     1       2.374  -1.353  -0.235  1.00  0.00           H  
HETATM   54  H25 UNL     1       4.045   1.197  -0.652  1.00  0.00           H  
HETATM   55  H26 UNL     1       4.978  -1.695  -1.125  1.00  0.00           H  
HETATM   56  H27 UNL     1       4.860  -0.382  -2.423  1.00  0.00           H  
HETATM   57  H28 UNL     1       6.473   0.898  -1.330  1.00  0.00           H  
HETATM   58  H29 UNL     1       7.087  -0.784  -0.856  1.00  0.00           H  
HETATM   59  H30 UNL     1       6.076   1.430   0.825  1.00  0.00           H  
HETATM   60  H31 UNL     1       7.769  -0.424   1.116  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3   25   28
CONECT    3    4   33   34
CONECT    4    5   35   36
CONECT    5    6   24   37
CONECT    6    7    7   21
CONECT    7    8   38
CONECT    8    9    9   39
CONECT    9   10   20
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14   17
CONECT   14   15   40   41
CONECT   15   16   42   43
CONECT   17   18   44   45
CONECT   18   19   46   47
CONECT   20   21   21   48
CONECT   21   22
CONECT   22   23   49   50
CONECT   23   24   51   52
CONECT   24   25   53
CONECT   25   26   54
CONECT   26   27   55   56
CONECT   27   28   57   58
CONECT   28   29   59
CONECT   29   60
END

HMDB0015327
     RDKit          3D
Estramustine
 60 63  0  0  0  0  0  0  0  0999 V2000
    4.6328   -1.5733    1.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5628   -0.1363    0.9046 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8008    0.7151    1.8596 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3480    0.2948    1.7977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7995    0.5706    0.4239 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3691    0.2936    0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4800    0.0354    1.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8186   -0.2123    1.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3578   -0.2155   -0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6898   -0.4599   -0.4265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6500    0.5440   -0.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2649    1.7194   -0.2704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0209    0.2764   -0.7668 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9407    1.3729   -0.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5736    1.6955    0.5239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6928    3.0881    0.3395 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -6.4824   -1.0618   -1.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9045   -1.8201    0.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5637   -1.9781    1.3386 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.5115    0.0424   -1.2166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1782    0.2891   -0.9666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7535    0.5690   -2.0898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0535   -0.1865   -1.9659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5675   -0.3120   -0.5726 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9779    0.1083   -0.4828 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9571   -0.5901   -1.3443 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2794   -0.0451   -0.7850 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9849    0.3504    0.6563 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8400   -0.3935    1.4806 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6602   -1.6796    2.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8347   -2.2097    0.8995 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5978   -2.0261    0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1911    0.5157    2.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9246    1.7688    1.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8136    0.8253    2.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2566   -0.7837    1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9875    1.6243    0.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0538    0.0395    2.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4914   -0.4165    1.9519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7479    1.2395   -1.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3894    2.2959   -1.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2116    0.8625    0.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8290    1.9102    1.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3927   -0.9766   -1.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7083   -1.6674   -1.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1658   -2.8579   -0.1750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7967   -1.4568    0.6910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8843    0.0529   -2.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3094    0.3054   -3.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9959    1.6648   -2.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7759    0.3020   -2.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8648   -1.2004   -2.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3740   -1.3529   -0.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0445    1.1975   -0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9785   -1.6946   -1.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8598   -0.3824   -2.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4728    0.8976   -1.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0867   -0.7842   -0.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0763    1.4301    0.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7688   -0.4240    1.1157 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
  9 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 25  2  1  0
 28  2  1  0
 24  5  1  0
 21  6  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  6
  7 38  1  0
  8 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 20 48  1  0
 22 49  1  0
 22 50  1  0
 23 51  1  0
 23 52  1  0
 24 53  1  1
 25 54  1  6
 26 55  1  0
 26 56  1  0
 27 57  1  0
 27 58  1  0
 28 59  1  6
 29 60  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
17beta-Estradiol 3-(bis(2-chloroethyl)carbamate)	ChEBI
Estradiol 3-(N,N-bis(2-chloroethyl)carbamate)	ChEBI
Estramustina	ChEBI
Estramustinum	ChEBI
17b-Estradiol 3-(bis(2-chloroethyl)carbamate)	Generator
17b-Estradiol 3-(bis(2-chloroethyl)carbamic acid)	Generator
17beta-Estradiol 3-(bis(2-chloroethyl)carbamic acid)	Generator
17Β-estradiol 3-(bis(2-chloroethyl)carbamate)	Generator
17Β-estradiol 3-(bis(2-chloroethyl)carbamic acid)	Generator
Estradiol 3-(N,N-bis(2-chloroethyl)carbamic acid)	Generator
Estramustin sodium phosphate	HMDB
Estramustine sodium phosphate	HMDB
Estracyt	HMDB
Estramustine phosphate sodium	HMDB
Phosphate, estramustin	HMDB
Leo 275	HMDB
Emcyt	HMDB
Estramustinphosphate	HMDB
Estramustin phosphate	HMDB
Leo-275	HMDB
Phosphate sodium, estramustine	HMDB

Chemical Formula

C₂₃H₃₁Cl₂NO₃

Average Molecular Weight

440.403

Monoisotopic Molecular Weight

439.168099277

IUPAC Name

(1S,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-trien-5-yl N,N-bis(2-chloroethyl)carbamate

Traditional Name

estramustine

CAS Registry Number

2998-57-4

SMILES

[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=CC=C(OC(=O)N(CCCl)CCCl)C=C3CC[C@@]21[H]

InChI Identifier

InChI=1S/C23H31Cl2NO3/c1-23-9-8-18-17-5-3-16(29-22(28)26(12-10-24)13-11-25)14-15(17)2-4-19(18)20(23)6-7-21(23)27/h3,5,14,18-21,27H,2,4,6-13H2,1H3/t18-,19-,20+,21+,23+/m1/s1

InChI Key

FRPJXPJMRWBBIH-RBRWEJTLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrane steroids

Alternative Parents

Substituents

Estrane-skeleton
Hydroxysteroid
17-hydroxysteroid
Phenanthrene
Tetralin
Nitrogen mustard
Benzenoid
Cyclic alcohol
Carbamic acid ester
Secondary alcohol
Carbonic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxide
Alkyl chloride
Alcohol
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Alkyl halide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

carbamate ester (CHEBI:4868 )
organochlorine compound (CHEBI:4868 )
17beta-hydroxy steroid (CHEBI:4868 )
C18 steroids (estrogens) and derivatives (C11228 )
Estrane and derivatives (C11228 )
C18 steroids (estrogens) and derivatives (LMST02010038 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0015327)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	104.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.00038 g/L	Not Available
LogP	5.7	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00038 g/L	ALOGPS
logP	4.97	ALOGPS
logP	5.1	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	19.38	ChemAxon
pKa (Strongest Basic)	-0.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	116.21 m³·mol⁻¹	ChemAxon
Polarizability	48.06 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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
DeepCCS	[M-2H]-	234.069	30932474
DeepCCS	[M+Na]+	209.129	30932474
AllCCS	[M+H]+	201.2	32859911
AllCCS	[M+H-H2O]+	199.3	32859911
AllCCS	[M+NH4]+	203.0	32859911
AllCCS	[M+Na]+	203.5	32859911
AllCCS	[M-H]-	199.9	32859911
AllCCS	[M+Na-2H]-	200.7	32859911
AllCCS	[M+HCOO]-	201.8	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.	8.99 minutes	32390414
Predicted by Siyang on May 30, 2022	21.1311 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.35 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	31.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2932.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	592.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	254.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	253.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	556.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	941.5 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	907.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	86.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1701.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	660.7 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	2039.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	567.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	570.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	270.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	473.0 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	8.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Estramustine	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=CC=C(OC(=O)N(CCCl)CCCl)C=C3CC[C@@]21[H]	4074.1	Standard polar	33892256
Estramustine	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=CC=C(OC(=O)N(CCCl)CCCl)C=C3CC[C@@]21[H]	3252.7	Standard non polar	33892256
Estramustine	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=CC=C(OC(=O)N(CCCl)CCCl)C=C3CC[C@@]21[H]	3597.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Estramustine,1TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(OC(=O)N(CCCl)CCCl)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O[Si](C)(C)C	3542.0	Semi standard non polar	33892256
Estramustine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(OC(=O)N(CCCl)CCCl)=CC=C4[C@H]3CC[C@]12C	3809.9	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 - Estramustine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-7427900000-b87366cc1573c4f6c93a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Estramustine GC-MS (1 TMS) - 70eV, Positive	splash10-0006-8704900000-9a612e46f22fe81c874c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Estramustine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Estramustine 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 - Estramustine 10V, Positive-QTOF	splash10-006x-0720900000-7d95b1bd74a3e1ae6ae2	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estramustine 20V, Positive-QTOF	splash10-0a4l-2971100000-a6f224fc389435653942	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estramustine 40V, Positive-QTOF	splash10-03fu-9510000000-032d08f0be5c8b065fa7	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estramustine 10V, Negative-QTOF	splash10-000i-0522900000-a880e700fad8ec3373b9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estramustine 20V, Negative-QTOF	splash10-0v4i-0962500000-ffc041fb7d64ff64e5e8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estramustine 40V, Negative-QTOF	splash10-0h4o-7980000000-eef6a5c5a61126ea9699	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estramustine 10V, Positive-QTOF	splash10-0006-0020900000-c6017d6c0b19d376975c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estramustine 20V, Positive-QTOF	splash10-01vo-0216900000-e073983c6de9895bcdc7	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estramustine 40V, Positive-QTOF	splash10-0bt9-5910000000-1c6900d7579dfbd1cc68	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estramustine 10V, Negative-QTOF	splash10-0019-4002900000-5c59bbd62d2862fbf52d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estramustine 20V, Negative-QTOF	splash10-001i-9050000000-f5313068b0db56036aa5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estramustine 40V, Negative-QTOF	splash10-001i-9000000000-c2fa753da65a4bac80a1	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
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 DB01196	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01196	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01196

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

227635

KEGG Compound ID

C11228

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Estramustine

METLIN ID

Not Available

PubChem Compound

259331

PDB ID

Not Available

ChEBI ID

4868

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. 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

Ho SM: Estrogens and anti-estrogens: key mediators of prostate carcinogenesis and new therapeutic candidates. J Cell Biochem. 2004 Feb 15;91(3):491-503. [PubMed:14755680 ]

Enzyme Details

2. Cytochrome P450 3A4

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

References

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

Enzyme Details

3. Microtubule-associated protein 2

General function:: Involved in negative regulation of microtubule depolymerization
Specific function:: The exact function of MAP2 is unknown but MAPs may stabilize the microtubules against depolymerization. They also seem to have a stiffening effect on microtubules
Gene Name:: MAP2
Uniprot ID:: P11137
Molecular weight:: 199524.5

References

Moraga D, Rivas-Berrios A, Farias G, Wallin M, Maccioni RB: Estramustine-phosphate binds to a tubulin binding domain on microtubule-associated proteins MAP-2 and tau. Biochim Biophys Acta. 1992 May 22;1121(1-2):97-103. [PubMed:1599956 ]
Stearns ME, Wang M, Sousa O: Evidence that estramustine binds MAP-1A to inhibit type IV collagenase secretion. J Cell Sci. 1991 Jan;98 ( Pt 1):55-63. [PubMed:1647395 ]
Friden B, Rutberg M, Deinum J, Wallin M: The effect of estramustine derivatives on microtubule assembly in vitro depends on the charge of the substituent. Biochem Pharmacol. 1991 Aug 8;42(5):997-1006. [PubMed:1908244 ]
Burns RG: Stoichiometry of estramustine phosphate binding to MAP2 measured by the disassembly of chick brain MAP2:tubulin microtubules. Cell Motil Cytoskeleton. 1990;17(3):167-73. [PubMed:2125244 ]
Falconer MM, Vielkind U, Brown DL: Association of acetylated microtubules, vimentin intermediate filaments, and MAP 2 during early neural differentiation in EC cell culture. Biochem Cell Biol. 1989 Sep;67(9):537-44. [PubMed:2679799 ]
Tew KD: The mechanism of action of estramustine. Semin Oncol. 1983 Sep;10(3 Suppl 3):21-6. [PubMed:6364362 ]

Enzyme Details

4. 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

Ferno M, Borg A, Ingvar C, Jonsson PE: Estrogen receptor and binding site for estramustine in metastatic malignant melanoma. Anticancer Res. 1987 Jul-Aug;7(4B):741-3. [PubMed:3314674 ]
Yoshizumi N: [The effects of site-directed chemotherapy due to E2 as a drug carrier to the human endometrial adenocarcinoma cells in vitro]. Nihon Sanka Fujinka Gakkai Zasshi. 1985 Apr;37(4):637-45. [PubMed:3989343 ]
von Schoultz E, Carlstrom K, Henriksson R, Lagerlof B, Hansson J: Estramustine binding protein in primary tumours and metastases of malignant melanoma. Melanoma Res. 1994 Dec;4(6):401-5. [PubMed:7703721 ]
Tew KD: The mechanism of action of estramustine. Semin Oncol. 1983 Sep;10(3 Suppl 3):21-6. [PubMed:6364362 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

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

References

Yang CP, Shen HJ, Horwitz SB: Modulation of the function of P-glycoprotein by estramustine. J Natl Cancer Inst. 1994 May 4;86(9):723-5. [PubMed:7908991 ]
Tiersten AD, Nelsen C, Talbot S, Vahdat L, Fine R, Troxel A, Brafman L, Shriberg L, Antman K, Petrylak DP: A phase II trial of docetaxel and estramustine in patients with refractory metastatic breast carcinoma. Cancer. 2003 Feb 1;97(3):537-44. [PubMed:12548594 ]
Smith CD, Zilfou JT, Zhang X, Hudes GR, Tew KD: Modulation of P-glycoprotein activity by estramustine is limited by binding to plasma proteins. Cancer. 1995 May 15;75(10):2597-604. [PubMed:7736407 ]
Speicher LA, Barone LR, Chapman AE, Hudes GR, Laing N, Smith CD, Tew KD: P-glycoprotein binding and modulation of the multidrug-resistant phenotype by estramustine. J Natl Cancer Inst. 1994 May 4;86(9):688-94. [PubMed:7908988 ]

Showing metabocard for Estramustine (HMDB0015327)

MOL for HMDB0015327 (Estramustine)

3D MOL for HMDB0015327 (Estramustine)

3D SDF for HMDB0015327 (Estramustine)

3D-SDF for HMDB0015327 (Estramustine)

PDB for HMDB0015327 (Estramustine)

3D PDB for HMDB0015327 (Estramustine)

SMILES for HMDB0015327 (Estramustine)

INCHI for HMDB0015327 (Estramustine)

Structure for HMDB0015327 (Estramustine)

3D Structure for HMDB0015327 (Estramustine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

Transporters

References