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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:47:03 UTC

Update Date

2021-09-26 23:00:01 UTC

HMDB ID

HMDB0249279

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Bitolterol

Description

Bitolterol belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone). Bitolterol is a drug which is used to dilate air passages in the lungs that have become narrowed as a result of disease or inflammation. it is used in the treatment of asthma and chronic obstructive pulmonary disease (copd). Bitolterol is a very strong basic compound (based on its pKa). The di-4-toluate ester of (+-)-N-tert-butylnoradrenaline (colterol). This compound has been identified in human blood as reported by (PMID: 31557052 ). Bitolterol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Bitolterol is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

901
  Mrv0541 02231215052D          

 34 36  0  0  1  0            999 V2000
    8.7949   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -2.8876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6200   -3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9699   -3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2 16  1  0  0  0  0
  2 19  1  0  0  0  0
  3 18  1  0  0  0  0
  3 20  1  0  0  0  0
  4 19  2  0  0  0  0
  5 20  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7 10  1  0  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  2  0  0  0  0
 17 18  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  2  0  0  0  0
 21 24  1  0  0  0  0
 22 25  2  0  0  0  0
 22 26  1  0  0  0  0
 23 29  1  0  0  0  0
 24 30  2  0  0  0  0
 25 31  1  0  0  0  0
 26 32  2  0  0  0  0
 27 29  2  0  0  0  0
 27 30  1  0  0  0  0
 27 33  1  0  0  0  0
 28 31  2  0  0  0  0
 28 32  1  0  0  0  0
 28 34  1  0  0  0  0
M  END

HMDB0249279
     RDKit          3D
Bitolterol
 65 67  0  0  0  0  0  0  0  0999 V2000
   -7.1175   -4.5048   -0.8425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8245   -3.8838   -0.4570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5254   -3.6079    0.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3196   -3.0303    1.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4107   -2.7284    0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1182   -2.1246    0.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8257   -1.8858    1.6947 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2179   -1.8113   -0.4882 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0283   -1.2346   -0.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1402   -2.0255   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3878   -1.4630    0.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5150   -0.1208    0.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8455    0.5667    0.3058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5543    1.5565    1.2668 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8514   -0.3709    0.9126 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0741    0.2096    1.3265 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9757    0.6839    0.3470 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4766   -0.4121   -0.5822 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5188    1.8399   -0.4800 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2413    1.1526    1.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4251    0.7104   -0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1924    0.1318   -0.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9660    0.8955   -0.4792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6988    1.3949    0.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3055    1.1542    1.7366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9029    2.1837    0.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6553    2.6964    1.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7929    3.4379    1.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2165    3.6902   -0.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4311    4.4794   -0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4807    3.1885   -1.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3460    2.4495   -0.9289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7061   -3.0048   -1.1120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9138   -3.5810   -1.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9131   -4.1971   -0.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3345   -4.2057   -1.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9392   -5.6184   -0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2737   -3.8634    1.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0710   -2.8092    2.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0608   -3.1066   -0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2429   -2.1216    0.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1072    0.9634   -0.6683 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1194    1.1649    2.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3747   -0.8377    1.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9990   -1.2301    0.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4846   -0.1669    2.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4624   -0.0988   -0.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8028   -0.5166   -1.4682 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6170   -1.3681   -0.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4190    2.5147   -0.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2276    1.5507   -1.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8024    2.4871    0.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8651    1.6299    2.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7816    1.8527    0.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8729    0.2861    1.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4962    1.7848   -0.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3585    2.5225    2.4126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4008    3.8510    1.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6628    4.4377   -1.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3117    4.1186    0.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2361    5.5380   -0.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7509    3.3464   -2.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7546    2.0470   -1.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0085   -2.7772   -1.8977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1715   -3.8105   -2.4759 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
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 17 20  1  0
 12 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
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 29 30  1  0
 29 31  1  0
 31 32  2  0
  5 33  1  0
 33 34  2  0
 34  2  1  0
 22  9  1  0
 32 26  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  4 39  1  0
 10 40  1  0
 11 41  1  0
 13 42  1  0
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 30 60  1  0
 30 61  1  0
 31 62  1  0
 32 63  1  0
 33 64  1  0
 34 65  1  0
M  END

901
  Mrv0541 02231215052D          

 34 36  0  0  1  0            999 V2000
    8.7949   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -2.8876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6200   -3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9699   -3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2 16  1  0  0  0  0
  2 19  1  0  0  0  0
  3 18  1  0  0  0  0
  3 20  1  0  0  0  0
  4 19  2  0  0  0  0
  5 20  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
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  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  2  0  0  0  0
 17 18  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  2  0  0  0  0
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 27 33  1  0  0  0  0
 28 31  2  0  0  0  0
 28 32  1  0  0  0  0
 28 34  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249279

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC=C(C=C1)C(=O)OC1=C(OC(=O)C2=CC=C(C)C=C2)C=C(C=C1)C(O)CNC(C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H31NO5/c1-18-6-10-20(11-7-18)26(31)33-24-15-14-22(23(30)17-29-28(3,4)5)16-25(24)34-27(32)21-12-8-19(2)9-13-21/h6-16,23,29-30H,17H2,1-5H3

> <INCHI_KEY>
FZGVEKPRDOIXJY-UHFFFAOYSA-N

> <FORMULA>
C28H31NO5

> <MOLECULAR_WEIGHT>
461.5494

> <EXACT_MASS>
461.220223107

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
50.90765366205686

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(4-methylbenzoyloxy)phenyl 4-methylbenzoate

> <ALOGPS_LOGP>
4.69

> <JCHEM_LOGP>
6.304932955333332

> <ALOGPS_LOGS>
-5.98

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.996353628469908

> <JCHEM_PKA_STRONGEST_BASIC>
9.58701074563407

> <JCHEM_POLAR_SURFACE_AREA>
84.86

> <JCHEM_REFRACTIVITY>
132.7623

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.80e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bitolterol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249279
     RDKit          3D
Bitolterol
 65 67  0  0  0  0  0  0  0  0999 V2000
   -7.1175   -4.5048   -0.8425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8245   -3.8838   -0.4570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5254   -3.6079    0.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3196   -3.0303    1.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4107   -2.7284    0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1182   -2.1246    0.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8257   -1.8858    1.6947 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2179   -1.8113   -0.4882 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0283   -1.2346   -0.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1402   -2.0255   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3878   -1.4630    0.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5150   -0.1208    0.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8455    0.5667    0.3058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5543    1.5565    1.2668 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8514   -0.3709    0.9126 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0741    0.2096    1.3265 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9757    0.6839    0.3470 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4766   -0.4121   -0.5822 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5188    1.8399   -0.4800 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2413    1.1526    1.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4251    0.7104   -0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1924    0.1318   -0.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9660    0.8955   -0.4792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6988    1.3949    0.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3055    1.1542    1.7366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9029    2.1837    0.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6553    2.6964    1.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7929    3.4379    1.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2165    3.6902   -0.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4311    4.4794   -0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4807    3.1885   -1.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3460    2.4495   -0.9289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7061   -3.0048   -1.1120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9138   -3.5810   -1.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9131   -4.1971   -0.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3345   -4.2057   -1.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9392   -5.6184   -0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2737   -3.8634    1.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0710   -2.8092    2.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0608   -3.1066   -0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2429   -2.1216    0.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1072    0.9634   -0.6683 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1194    1.1649    2.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3747   -0.8377    1.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9990   -1.2301    0.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4846   -0.1669    2.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4624   -0.0988   -0.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8028   -0.5166   -1.4682 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6170   -1.3681   -0.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4190    2.5147   -0.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2276    1.5507   -1.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8024    2.4871    0.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8651    1.6299    2.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7816    1.8527    0.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8729    0.2861    1.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4962    1.7848   -0.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3585    2.5225    2.4126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4008    3.8510    1.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6628    4.4377   -1.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3117    4.1186    0.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2361    5.5380   -0.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7509    3.3464   -2.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7546    2.0470   -1.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0085   -2.7772   -1.8977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1715   -3.8105   -2.4759 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 12 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  2  0
  5 33  1  0
 33 34  2  0
 34  2  1  0
 22  9  1  0
 32 26  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  4 39  1  0
 10 40  1  0
 11 41  1  0
 13 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 18 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 27 57  1  0
 28 58  1  0
 30 59  1  0
 30 60  1  0
 30 61  1  0
 31 62  1  0
 32 63  1  0
 33 64  1  0
 34 65  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 901                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      16.417  -2.310   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      12.416   1.540   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.748   0.000   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      15.083   1.540   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       8.415  -2.310   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      16.417  -5.390   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      16.417  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.083  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.083  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.417  -8.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.957  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.877  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.750  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.750  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.416  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.416   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.082  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.082  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.750   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.415  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.750   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.081   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.083   4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.416   4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.081   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.748  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.750   6.930   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.414   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.083   6.160   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.416   6.160   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.748   2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.414   0.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.750   8.470   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.080   2.310   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   16   19                                                       
CONECT    3   18   20                                                       
CONECT    4   19                                                            
CONECT    5   20                                                            
CONECT    6    7    8                                                       
CONECT    7    6   10   11   12                                             
CONECT    8    6    9                                                       
CONECT    9    1    8   13                                                  
CONECT   10    7                                                            
CONECT   11    7                                                            
CONECT   12    7                                                            
CONECT   13    9   14   15                                                  
CONECT   14   13   16                                                       
CONECT   15   13   17                                                       
CONECT   16    2   14   18                                                  
CONECT   17   15   18                                                       
CONECT   18    3   16   17                                                  
CONECT   19    2    4   21                                                  
CONECT   20    3    5   22                                                  
CONECT   21   19   23   24                                                  
CONECT   22   20   25   26                                                  
CONECT   23   21   29                                                       
CONECT   24   21   30                                                       
CONECT   25   22   31                                                       
CONECT   26   22   32                                                       
CONECT   27   29   30   33                                                  
CONECT   28   31   32   34                                                  
CONECT   29   23   27                                                       
CONECT   30   24   27                                                       
CONECT   31   25   28                                                       
CONECT   32   26   28                                                       
CONECT   33   27                                                            
CONECT   34   28                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

COMPND    HMDB0249279
HETATM    1  C1  UNL     1      -7.117  -4.505  -0.842  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.824  -3.884  -0.457  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.525  -3.608   0.858  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.320  -3.030   1.205  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.411  -2.728   0.225  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.118  -2.125   0.504  1.00  0.00           C  
HETATM    7  O1  UNL     1      -1.826  -1.886   1.695  1.00  0.00           O  
HETATM    8  O2  UNL     1      -1.218  -1.811  -0.488  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.028  -1.235  -0.290  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.140  -2.025  -0.098  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.388  -1.463   0.099  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.515  -0.121   0.103  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.845   0.567   0.306  1.00  0.00           C  
HETATM   14  O3  UNL     1       3.554   1.556   1.267  1.00  0.00           O  
HETATM   15  C12 UNL     1       4.851  -0.371   0.913  1.00  0.00           C  
HETATM   16  N1  UNL     1       6.074   0.210   1.327  1.00  0.00           N  
HETATM   17  C13 UNL     1       6.976   0.684   0.347  1.00  0.00           C  
HETATM   18  C14 UNL     1       7.477  -0.412  -0.582  1.00  0.00           C  
HETATM   19  C15 UNL     1       6.519   1.840  -0.480  1.00  0.00           C  
HETATM   20  C16 UNL     1       8.241   1.153   1.105  1.00  0.00           C  
HETATM   21  C17 UNL     1       1.425   0.710  -0.085  1.00  0.00           C  
HETATM   22  C18 UNL     1       0.192   0.132  -0.280  1.00  0.00           C  
HETATM   23  O4  UNL     1      -0.966   0.895  -0.479  1.00  0.00           O  
HETATM   24  C19 UNL     1      -1.699   1.395   0.575  1.00  0.00           C  
HETATM   25  O5  UNL     1      -1.305   1.154   1.737  1.00  0.00           O  
HETATM   26  C20 UNL     1      -2.903   2.184   0.356  1.00  0.00           C  
HETATM   27  C21 UNL     1      -3.655   2.696   1.387  1.00  0.00           C  
HETATM   28  C22 UNL     1      -4.793   3.438   1.188  1.00  0.00           C  
HETATM   29  C23 UNL     1      -5.217   3.690  -0.115  1.00  0.00           C  
HETATM   30  C24 UNL     1      -6.431   4.479  -0.385  1.00  0.00           C  
HETATM   31  C25 UNL     1      -4.481   3.189  -1.150  1.00  0.00           C  
HETATM   32  C26 UNL     1      -3.346   2.450  -0.929  1.00  0.00           C  
HETATM   33  C27 UNL     1      -3.706  -3.005  -1.112  1.00  0.00           C  
HETATM   34  C28 UNL     1      -4.914  -3.581  -1.434  1.00  0.00           C  
HETATM   35  H1  UNL     1      -7.913  -4.197  -0.132  1.00  0.00           H  
HETATM   36  H2  UNL     1      -7.335  -4.206  -1.886  1.00  0.00           H  
HETATM   37  H3  UNL     1      -6.939  -5.618  -0.801  1.00  0.00           H  
HETATM   38  H4  UNL     1      -6.274  -3.863   1.600  1.00  0.00           H  
HETATM   39  H5  UNL     1      -4.071  -2.809   2.227  1.00  0.00           H  
HETATM   40  H6  UNL     1       1.061  -3.107  -0.098  1.00  0.00           H  
HETATM   41  H7  UNL     1       3.243  -2.122   0.250  1.00  0.00           H  
HETATM   42  H8  UNL     1       4.107   0.963  -0.668  1.00  0.00           H  
HETATM   43  H9  UNL     1       3.119   1.165   2.042  1.00  0.00           H  
HETATM   44  H10 UNL     1       4.375  -0.838   1.809  1.00  0.00           H  
HETATM   45  H11 UNL     1       4.999  -1.230   0.204  1.00  0.00           H  
HETATM   46  H12 UNL     1       6.485  -0.167   2.187  1.00  0.00           H  
HETATM   47  H13 UNL     1       8.462  -0.099  -0.978  1.00  0.00           H  
HETATM   48  H14 UNL     1       6.803  -0.517  -1.468  1.00  0.00           H  
HETATM   49  H15 UNL     1       7.617  -1.368  -0.057  1.00  0.00           H  
HETATM   50  H16 UNL     1       7.419   2.515  -0.646  1.00  0.00           H  
HETATM   51  H17 UNL     1       6.228   1.551  -1.515  1.00  0.00           H  
HETATM   52  H18 UNL     1       5.802   2.487   0.039  1.00  0.00           H  
HETATM   53  H19 UNL     1       7.865   1.630   2.032  1.00  0.00           H  
HETATM   54  H20 UNL     1       8.782   1.853   0.439  1.00  0.00           H  
HETATM   55  H21 UNL     1       8.873   0.286   1.339  1.00  0.00           H  
HETATM   56  H22 UNL     1       1.496   1.785  -0.087  1.00  0.00           H  
HETATM   57  H23 UNL     1      -3.359   2.522   2.413  1.00  0.00           H  
HETATM   58  H24 UNL     1      -5.401   3.851   1.968  1.00  0.00           H  
HETATM   59  H25 UNL     1      -6.663   4.438  -1.458  1.00  0.00           H  
HETATM   60  H26 UNL     1      -7.312   4.119   0.186  1.00  0.00           H  
HETATM   61  H27 UNL     1      -6.236   5.538  -0.085  1.00  0.00           H  
HETATM   62  H28 UNL     1      -4.751   3.346  -2.200  1.00  0.00           H  
HETATM   63  H29 UNL     1      -2.755   2.047  -1.740  1.00  0.00           H  
HETATM   64  H30 UNL     1      -3.008  -2.777  -1.898  1.00  0.00           H  
HETATM   65  H31 UNL     1      -5.171  -3.811  -2.476  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3    3   34
CONECT    3    4   38
CONECT    4    5    5   39
CONECT    5    6   33
CONECT    6    7    7    8
CONECT    8    9
CONECT    9   10   10   22
CONECT   10   11   40
CONECT   11   12   12   41
CONECT   12   13   21
CONECT   13   14   15   42
CONECT   14   43
CONECT   15   16   44   45
CONECT   16   17   46
CONECT   17   18   19   20
CONECT   18   47   48   49
CONECT   19   50   51   52
CONECT   20   53   54   55
CONECT   21   22   22   56
CONECT   22   23
CONECT   23   24
CONECT   24   25   25   26
CONECT   26   27   27   32
CONECT   27   28   57
CONECT   28   29   29   58
CONECT   29   30   31
CONECT   30   59   60   61
CONECT   31   32   32   62
CONECT   32   63
CONECT   33   34   34   64
CONECT   34   65
END

HMDB0249279
     RDKit          3D
Bitolterol
 65 67  0  0  0  0  0  0  0  0999 V2000
   -7.1175   -4.5048   -0.8425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8245   -3.8838   -0.4570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5254   -3.6079    0.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3196   -3.0303    1.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4107   -2.7284    0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1182   -2.1246    0.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8257   -1.8858    1.6947 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2179   -1.8113   -0.4882 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0283   -1.2346   -0.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1402   -2.0255   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3878   -1.4630    0.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5150   -0.1208    0.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8455    0.5667    0.3058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5543    1.5565    1.2668 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8514   -0.3709    0.9126 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0741    0.2096    1.3265 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9757    0.6839    0.3470 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4766   -0.4121   -0.5822 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5188    1.8399   -0.4800 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2413    1.1526    1.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4251    0.7104   -0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1924    0.1318   -0.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9660    0.8955   -0.4792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6988    1.3949    0.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3055    1.1542    1.7366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9029    2.1837    0.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6553    2.6964    1.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7929    3.4379    1.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2165    3.6902   -0.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4311    4.4794   -0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4807    3.1885   -1.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3460    2.4495   -0.9289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7061   -3.0048   -1.1120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9138   -3.5810   -1.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9131   -4.1971   -0.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3345   -4.2057   -1.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9392   -5.6184   -0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2737   -3.8634    1.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0710   -2.8092    2.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0608   -3.1066   -0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2429   -2.1216    0.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1072    0.9634   -0.6683 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1194    1.1649    2.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3747   -0.8377    1.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9990   -1.2301    0.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4846   -0.1669    2.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4624   -0.0988   -0.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8028   -0.5166   -1.4682 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6170   -1.3681   -0.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4190    2.5147   -0.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2276    1.5507   -1.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8024    2.4871    0.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8651    1.6299    2.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7816    1.8527    0.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8729    0.2861    1.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4962    1.7848   -0.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3585    2.5225    2.4126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4008    3.8510    1.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6628    4.4377   -1.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3117    4.1186    0.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2361    5.5380   -0.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7509    3.3464   -2.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7546    2.0470   -1.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0085   -2.7772   -1.8977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1715   -3.8105   -2.4759 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 12 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  2  0
  5 33  1  0
 33 34  2  0
 34  2  1  0
 22  9  1  0
 32 26  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  4 39  1  0
 10 40  1  0
 11 41  1  0
 13 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 18 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 27 57  1  0
 28 58  1  0
 30 59  1  0
 30 60  1  0
 30 61  1  0
 31 62  1  0
 32 63  1  0
 33 64  1  0
 34 65  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(2-(Tert-butylamino)-1-hydroxyethyl)-O-phenylene di-p-toluate	ChEBI
4-[2-(Tert-butylamino)-1-hydroxyethyl]-O-phenylene di-p-toluate	ChEBI
Bis(4-methylbenzoic acid) 4-[2-(tert-butylamino)-1-hydroxyethyl]-1,2-phenylene ester	ChEBI
Bitolterolum	ChEBI
4-(2-(Tert-butylamino)-1-hydroxyethyl)-O-phenylene di-p-toluic acid	Generator
4-[2-(Tert-butylamino)-1-hydroxyethyl]-O-phenylene di-p-toluic acid	Generator
Bis(4-methylbenzoate) 4-[2-(tert-butylamino)-1-hydroxyethyl]-1,2-phenylene ester	Generator
Dura brand OF bitolterol methanesulfonate	MeSH
Bitolterol mesylate	MeSH
Tornalate	MeSH
Bitolterol methanesulfonate	MeSH

Chemical Formula

C₂₈H₃₁NO₅

Average Molecular Weight

461.5494

Monoisotopic Molecular Weight

461.220223107

IUPAC Name

4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(4-methylbenzoyloxy)phenyl 4-methylbenzoate

Traditional Name

bitolterol

CAS Registry Number

Not Available

SMILES

CC1=CC=C(C=C1)C(=O)OC1=C(OC(=O)C2=CC=C(C)C=C2)C=C(C=C1)C(O)CNC(C)(C)C

InChI Identifier

InChI=1S/C28H31NO5/c1-18-6-10-20(11-7-18)26(31)33-24-15-14-22(23(30)17-29-28(3,4)5)16-25(24)34-27(32)21-12-8-19(2)9-13-21/h6-16,23,29-30H,17H2,1-5H3

InChI Key

FZGVEKPRDOIXJY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Depsides and depsidones

Sub Class

Not Available

Direct Parent

Depsides and depsidones

Alternative Parents

Substituents

Depside backbone
Benzoate ester
Phenol ester
Benzoic acid or derivatives
Phenoxy compound
Benzoyl
Aralkylamine
Toluene
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Secondary alcohol
Amino acid or derivatives
1,2-aminoalcohol
Carboxylic acid ester
Secondary amine
Carboxylic acid derivative
Secondary aliphatic amine
Aromatic alcohol
Organic oxide
Alcohol
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

diester (CHEBI:3133 )
carboxylic ester (CHEBI:3133 )
secondary alcohol (CHEBI:3133 )
secondary amino compound (CHEBI:3133 )
ethanolamines (CHEBI:3133 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0249279)

Process

Not Available

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
logP	4.69	ALOGPS
logP	6.3	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	14	ChemAxon
pKa (Strongest Basic)	9.59	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	84.86 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	132.76 m³·mol⁻¹	ChemAxon
Polarizability	50.91 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	209.21	30932474
DeepCCS	[M-H]-	206.814	30932474
DeepCCS	[M-2H]-	239.698	30932474
DeepCCS	[M+Na]+	215.122	30932474
AllCCS	[M+H]+	215.8	32859911
AllCCS	[M+H-H2O]+	213.7	32859911
AllCCS	[M+NH4]+	217.7	32859911
AllCCS	[M+Na]+	218.3	32859911
AllCCS	[M-H]-	211.8	32859911
AllCCS	[M+Na-2H]-	212.0	32859911
AllCCS	[M+HCOO]-	212.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bitolterol	CC1=CC=C(C=C1)C(=O)OC1=C(OC(=O)C2=CC=C(C)C=C2)C=C(C=C1)C(O)CNC(C)(C)C	4470.4	Standard polar	33892256
Bitolterol	CC1=CC=C(C=C1)C(=O)OC1=C(OC(=O)C2=CC=C(C)C=C2)C=C(C=C1)C(O)CNC(C)(C)C	3498.5	Standard non polar	33892256
Bitolterol	CC1=CC=C(C=C1)C(=O)OC1=C(OC(=O)C2=CC=C(C)C=C2)C=C(C=C1)C(O)CNC(C)(C)C	3493.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bitolterol,2TMS,isomer #1	CC1=CC=C(C(=O)OC2=CC=C(C(CN(C(C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C2OC(=O)C2=CC=C(C)C=C2)C=C1	3564.2	Semi standard non polar	33892256
Bitolterol,2TMS,isomer #1	CC1=CC=C(C(=O)OC2=CC=C(C(CN(C(C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C2OC(=O)C2=CC=C(C)C=C2)C=C1	3372.7	Standard non polar	33892256
Bitolterol,2TMS,isomer #1	CC1=CC=C(C(=O)OC2=CC=C(C(CN(C(C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C2OC(=O)C2=CC=C(C)C=C2)C=C1	4199.1	Standard polar	33892256
Bitolterol,2TBDMS,isomer #1	CC1=CC=C(C(=O)OC2=CC=C(C(CN(C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C2OC(=O)C2=CC=C(C)C=C2)C=C1	4008.9	Semi standard non polar	33892256
Bitolterol,2TBDMS,isomer #1	CC1=CC=C(C(=O)OC2=CC=C(C(CN(C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C2OC(=O)C2=CC=C(C)C=C2)C=C1	3658.5	Standard non polar	33892256
Bitolterol,2TBDMS,isomer #1	CC1=CC=C(C(=O)OC2=CC=C(C(CN(C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C2OC(=O)C2=CC=C(C)C=C2)C=C1	4268.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bitolterol GC-MS (Non-derivatized) - 70eV, Positive	splash10-06dr-9515300000-9183ab463ea023a403bf	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bitolterol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bitolterol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bitolterol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bitolterol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bitolterol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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 - Bitolterol 10V, Positive-QTOF	splash10-07bf-0206900000-0d2add6387daa82a668a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bitolterol 20V, Positive-QTOF	splash10-06du-0409400000-bb41c3be88071d157bd2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bitolterol 40V, Positive-QTOF	splash10-014i-5931000000-5bf735cde96a513326c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bitolterol 10V, Negative-QTOF	splash10-03dl-2203900000-2ae4baeac004d904db77	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bitolterol 20V, Negative-QTOF	splash10-0076-8519700000-66927241cb18ed810572	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bitolterol 40V, Negative-QTOF	splash10-000l-7931000000-151a6828e2b9760ef552	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bitolterol 10V, Positive-QTOF	splash10-05n0-0406900000-3abf7d0e232423e8dc9f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bitolterol 20V, Positive-QTOF	splash10-00kr-3409400000-5ffcffe98e28c353480b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bitolterol 40V, Positive-QTOF	splash10-0006-9100000000-e6b66fd8168c15691318	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bitolterol 10V, Negative-QTOF	splash10-03di-0002900000-898b8130cb2475df346a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bitolterol 20V, Negative-QTOF	splash10-01vo-0029500000-546df6039034f820cc04	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bitolterol 40V, Negative-QTOF	splash10-0006-8379500000-a31b75ebcff135547850	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00901

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C06853

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bitolterol

METLIN ID

Not Available

PubChem Compound

35330

PDB ID

Not Available

ChEBI ID

3133

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Bitolterol (HMDB0249279)

MOL for HMDB0249279 (Bitolterol)

3D MOL for HMDB0249279 (Bitolterol)

3D SDF for HMDB0249279 (Bitolterol)

3D-SDF for HMDB0249279 (Bitolterol)

PDB for HMDB0249279 (Bitolterol)

3D PDB for HMDB0249279 (Bitolterol)

SMILES for HMDB0249279 (Bitolterol)

INCHI for HMDB0249279 (Bitolterol)

Structure for HMDB0249279 (Bitolterol)

3D Structure for HMDB0249279 (Bitolterol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra