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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:51 UTC

HMDB ID

HMDB0015073

Secondary Accession Numbers

HMDB15073

Metabolite Identification

Common Name

Salmeterol

Description

Salmeterol is only found in individuals that have used or taken this drug. It is a long-acting beta2-adrenergic receptor agonist drug that is currently prescribed for the treatment of asthma and chronic obstructive pulmonary disease COPD. Salmeterol's long, lipophilic side chain binds to exosites near beta(2)-receptors in the lungs and on bronchiolar smooth muscle, allowing the active portion of the molecule to remain at the receptor site, continually binding and releasing. Beta(2)-receptor stimulation in the lung causes relaxation of bronchial smooth muscle, bronchodilation, and increased bronchial airflow.

Structure

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

938
  Mrv0541 02231215072D          

 30 31  0  0  1  0            999 V2000
    7.8089    1.9842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.9659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -6.6785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -5.4410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -2.1409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799   -0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799    0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944    0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -2.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944    1.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -3.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5234    3.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5234    4.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8089    2.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -4.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2379    4.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -4.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2379    5.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -4.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -5.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -5.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -5.8535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5234    5.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9524    5.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -5.8535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5234    6.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9524    6.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2379    6.9343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  1 16  1  0  0  0  0
  2 13  1  0  0  0  0
  3 24  1  0  0  0  0
  4 27  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 18  1  0  0  0  0
 17 19  2  0  0  0  0
 17 21  1  0  0  0  0
 18 20  1  0  0  0  0
 19 22  1  0  0  0  0
 20 25  2  0  0  0  0
 20 26  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  2  0  0  0  0
 22 27  1  0  0  0  0
 23 24  1  0  0  0  0
 25 28  1  0  0  0  0
 26 29  2  0  0  0  0
 28 30  2  0  0  0  0
 29 30  1  0  0  0  0
M  END

HMDB0015073
     RDKit          3D
Salmeterol
 67 68  0  0  0  0  0  0  0  0999 V2000
   -9.9663   -0.0963   -1.0973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5652    1.2196   -1.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1215    1.3066   -0.8031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4058    0.1513   -0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0702    0.2121   -0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2704   -0.9671    0.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4716   -0.7266    1.3537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4693   -1.5159   -0.9348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4248   -0.6973   -1.4136 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3013   -0.4796   -0.5827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4331   -1.6989   -0.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3014   -1.2094    0.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6533   -2.3084    0.8886 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7681   -1.8513    1.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5576   -0.7491    1.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5938   -0.2957    1.9308 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5443   -1.2430    2.2538 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1806   -1.8095    1.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8333   -0.7227    0.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9063   -0.0048    0.9819 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5453    1.0601    0.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0612    2.3382    0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7204    3.2573   -0.6734 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8055    2.9275   -1.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2721    1.6495   -1.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6356    0.6949   -0.6089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4741    1.4544   -0.1447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1795    2.6050   -0.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4960    2.5365   -0.7996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2613    3.6502   -1.1370 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0223   -0.4333   -0.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1608    1.8717   -0.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7167    1.5713   -2.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9161   -0.7950   -0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9739   -1.7727    0.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9602   -0.0055    1.8507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0858   -2.5083   -0.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1788   -1.7112   -1.7550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2695   -0.6970   -2.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6269    0.2367   -1.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5139    0.0303    0.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0390   -2.1077   -1.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9592   -2.4978    0.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2227   -0.4020   -0.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7473   -0.7221    1.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1260   -2.6576   -0.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1289   -3.1418    1.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3800   -1.4832    2.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4379   -2.7384    1.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8782    0.1408    1.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8469   -1.0503    0.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3114   -0.7687    2.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0874   -2.0397    2.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8991   -2.6112    1.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4273   -2.3124    0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3336   -1.1787   -0.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0790    0.0139   -0.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4449    0.4951    1.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6990   -0.6879    1.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2133    2.5737    0.7362 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3506    4.2597   -0.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2713    3.6793   -2.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1200    1.3870   -2.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9933   -0.3233   -0.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4484    1.5576    0.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6827    3.5691   -0.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8149    4.5722   -1.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
  5 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 29  3  1  0
 26 21  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  4 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 12 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  0
 15 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 20 58  1  0
 20 59  1  0
 22 60  1  0
 23 61  1  0
 24 62  1  0
 25 63  1  0
 26 64  1  0
 27 65  1  0
 28 66  1  0
 30 67  1  0
M  END

938
  Mrv0541 02231215072D          

 30 31  0  0  1  0            999 V2000
    7.8089    1.9842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.9659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -6.6785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -5.4410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -2.1409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799   -0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799    0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944    0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -2.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944    1.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -3.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5234    3.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5234    4.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8089    2.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -4.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2379    4.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -4.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2379    5.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -4.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -5.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -5.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -5.8535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5234    5.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9524    5.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -5.8535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5234    6.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9524    6.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2379    6.9343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  1 16  1  0  0  0  0
  2 13  1  0  0  0  0
  3 24  1  0  0  0  0
  4 27  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 18  1  0  0  0  0
 17 19  2  0  0  0  0
 17 21  1  0  0  0  0
 18 20  1  0  0  0  0
 19 22  1  0  0  0  0
 20 25  2  0  0  0  0
 20 26  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  2  0  0  0  0
 22 27  1  0  0  0  0
 23 24  1  0  0  0  0
 25 28  1  0  0  0  0
 26 29  2  0  0  0  0
 28 30  2  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015073

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC1=C(O)C=CC(=C1)C(O)CNCCCCCCOCCCCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H37NO4/c27-20-23-18-22(13-14-24(23)28)25(29)19-26-15-7-1-2-8-16-30-17-9-6-12-21-10-4-3-5-11-21/h3-5,10-11,13-14,18,25-29H,1-2,6-9,12,15-17,19-20H2

> <INCHI_KEY>
GIIZNNXWQWCKIB-UHFFFAOYSA-N

> <FORMULA>
C25H37NO4

> <MOLECULAR_WEIGHT>
415.5656

> <EXACT_MASS>
415.272258677

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
50.59519997365934

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(1-hydroxy-2-{[6-(4-phenylbutoxy)hexyl]amino}ethyl)-2-(hydroxymethyl)phenol

> <ALOGPS_LOGP>
3.82

> <JCHEM_LOGP>
3.6146962067229897

> <ALOGPS_LOGS>
-5.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.18049423738092

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.116023889198962

> <JCHEM_PKA_STRONGEST_BASIC>
9.404292511622396

> <JCHEM_POLAR_SURFACE_AREA>
81.95

> <JCHEM_REFRACTIVITY>
122.39040000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.26e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
salmeterol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015073
     RDKit          3D
Salmeterol
 67 68  0  0  0  0  0  0  0  0999 V2000
   -9.9663   -0.0963   -1.0973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5652    1.2196   -1.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1215    1.3066   -0.8031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4058    0.1513   -0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0702    0.2121   -0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2704   -0.9671    0.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4716   -0.7266    1.3537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4693   -1.5159   -0.9348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4248   -0.6973   -1.4136 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3013   -0.4796   -0.5827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4331   -1.6989   -0.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3014   -1.2094    0.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6533   -2.3084    0.8886 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7681   -1.8513    1.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5576   -0.7491    1.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5938   -0.2957    1.9308 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5443   -1.2430    2.2538 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1806   -1.8095    1.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8333   -0.7227    0.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9063   -0.0048    0.9819 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5453    1.0601    0.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0612    2.3382    0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7204    3.2573   -0.6734 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8055    2.9275   -1.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2721    1.6495   -1.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6356    0.6949   -0.6089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4741    1.4544   -0.1447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1795    2.6050   -0.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4960    2.5365   -0.7996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2613    3.6502   -1.1370 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0223   -0.4333   -0.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1608    1.8717   -0.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7167    1.5713   -2.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9161   -0.7950   -0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9739   -1.7727    0.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9602   -0.0055    1.8507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0858   -2.5083   -0.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1788   -1.7112   -1.7550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2695   -0.6970   -2.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6269    0.2367   -1.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5139    0.0303    0.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0390   -2.1077   -1.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9592   -2.4978    0.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2227   -0.4020   -0.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7473   -0.7221    1.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1260   -2.6576   -0.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1289   -3.1418    1.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3800   -1.4832    2.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4379   -2.7384    1.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8782    0.1408    1.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8469   -1.0503    0.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3114   -0.7687    2.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0874   -2.0397    2.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8991   -2.6112    1.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4273   -2.3124    0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3336   -1.1787   -0.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0790    0.0139   -0.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4449    0.4951    1.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6990   -0.6879    1.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2133    2.5737    0.7362 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3506    4.2597   -0.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2713    3.6793   -2.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1200    1.3870   -2.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9933   -0.3233   -0.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4484    1.5576    0.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6827    3.5691   -0.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8149    4.5722   -1.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
  5 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 29  3  1  0
 26 21  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  4 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 12 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  0
 15 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 20 58  1  0
 20 59  1  0
 22 60  1  0
 23 61  1  0
 24 62  1  0
 25 63  1  0
 26 64  1  0
 27 65  1  0
 28 66  1  0
 30 67  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 938                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      14.577   3.704   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       6.574  -5.536   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.908 -12.467   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.907 -10.157   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       9.242  -3.996   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      11.909  -0.916   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.909   0.624   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.576  -1.686   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.243   1.394   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.576  -3.226   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.242  -5.536   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.243   2.934   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.908  -6.306   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.910   6.014   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.910   7.554   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.577   5.244   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.908  -7.847   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.244   8.324   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.574  -8.617   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.244   9.864   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.242  -8.617   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.574 -10.157   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.242 -10.157   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.908 -10.927   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.910  10.634   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.578  10.634   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.241 -10.927   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.910  12.174   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      18.578  12.174   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.244  12.944   0.000  0.00  0.00           C+0
CONECT    1   12   16                                                       
CONECT    2   13                                                            
CONECT    3   24                                                            
CONECT    4   27                                                            
CONECT    5   10   11                                                       
CONECT    6    7    8                                                       
CONECT    7    6    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   12                                                       
CONECT   10    5    8                                                       
CONECT   11    5   13                                                       
CONECT   12    1    9                                                       
CONECT   13    2   11   17                                                  
CONECT   14   15   16                                                       
CONECT   15   14   18                                                       
CONECT   16    1   14                                                       
CONECT   17   13   19   21                                                  
CONECT   18   15   20                                                       
CONECT   19   17   22                                                       
CONECT   20   18   25   26                                                  
CONECT   21   17   23                                                       
CONECT   22   19   24   27                                                  
CONECT   23   21   24                                                       
CONECT   24    3   22   23                                                  
CONECT   25   20   28                                                       
CONECT   26   20   29                                                       
CONECT   27    4   22                                                       
CONECT   28   25   30                                                       
CONECT   29   26   30                                                       
CONECT   30   28   29                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

COMPND    HMDB0015073
HETATM    1  O1  UNL     1      -9.966  -0.096  -1.097  1.00  0.00           O  
HETATM    2  C1  UNL     1      -9.565   1.220  -1.162  1.00  0.00           C  
HETATM    3  C2  UNL     1      -8.122   1.307  -0.803  1.00  0.00           C  
HETATM    4  C3  UNL     1      -7.406   0.151  -0.473  1.00  0.00           C  
HETATM    5  C4  UNL     1      -6.070   0.212  -0.139  1.00  0.00           C  
HETATM    6  C5  UNL     1      -5.270  -0.967   0.215  1.00  0.00           C  
HETATM    7  O2  UNL     1      -4.472  -0.727   1.354  1.00  0.00           O  
HETATM    8  C6  UNL     1      -4.469  -1.516  -0.935  1.00  0.00           C  
HETATM    9  N1  UNL     1      -3.425  -0.697  -1.414  1.00  0.00           N  
HETATM   10  C7  UNL     1      -2.301  -0.480  -0.583  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.433  -1.699  -0.349  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.301  -1.209   0.567  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.653  -2.308   0.889  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.768  -1.851   1.789  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.558  -0.749   1.153  1.00  0.00           C  
HETATM   16  O3  UNL     1       3.594  -0.296   1.931  1.00  0.00           O  
HETATM   17  C13 UNL     1       4.544  -1.243   2.254  1.00  0.00           C  
HETATM   18  C14 UNL     1       5.181  -1.809   1.028  1.00  0.00           C  
HETATM   19  C15 UNL     1       5.833  -0.723   0.229  1.00  0.00           C  
HETATM   20  C16 UNL     1       6.906  -0.005   0.982  1.00  0.00           C  
HETATM   21  C17 UNL     1       7.545   1.060   0.145  1.00  0.00           C  
HETATM   22  C18 UNL     1       7.061   2.338   0.135  1.00  0.00           C  
HETATM   23  C19 UNL     1       7.720   3.257  -0.673  1.00  0.00           C  
HETATM   24  C20 UNL     1       8.805   2.928  -1.434  1.00  0.00           C  
HETATM   25  C21 UNL     1       9.272   1.650  -1.410  1.00  0.00           C  
HETATM   26  C22 UNL     1       8.636   0.695  -0.609  1.00  0.00           C  
HETATM   27  C23 UNL     1      -5.474   1.454  -0.145  1.00  0.00           C  
HETATM   28  C24 UNL     1      -6.179   2.605  -0.471  1.00  0.00           C  
HETATM   29  C25 UNL     1      -7.496   2.537  -0.800  1.00  0.00           C  
HETATM   30  O4  UNL     1      -8.261   3.650  -1.137  1.00  0.00           O  
HETATM   31  H1  UNL     1     -10.022  -0.433  -0.166  1.00  0.00           H  
HETATM   32  H2  UNL     1     -10.161   1.872  -0.462  1.00  0.00           H  
HETATM   33  H3  UNL     1      -9.717   1.571  -2.196  1.00  0.00           H  
HETATM   34  H4  UNL     1      -7.916  -0.795  -0.483  1.00  0.00           H  
HETATM   35  H5  UNL     1      -5.974  -1.773   0.526  1.00  0.00           H  
HETATM   36  H6  UNL     1      -4.960  -0.005   1.851  1.00  0.00           H  
HETATM   37  H7  UNL     1      -4.086  -2.508  -0.616  1.00  0.00           H  
HETATM   38  H8  UNL     1      -5.179  -1.711  -1.755  1.00  0.00           H  
HETATM   39  H9  UNL     1      -3.269  -0.697  -2.421  1.00  0.00           H  
HETATM   40  H10 UNL     1      -1.627   0.237  -1.145  1.00  0.00           H  
HETATM   41  H11 UNL     1      -2.514   0.030   0.359  1.00  0.00           H  
HETATM   42  H12 UNL     1      -1.039  -2.108  -1.278  1.00  0.00           H  
HETATM   43  H13 UNL     1      -1.959  -2.498   0.210  1.00  0.00           H  
HETATM   44  H14 UNL     1       0.223  -0.402  -0.023  1.00  0.00           H  
HETATM   45  H15 UNL     1      -0.747  -0.722   1.435  1.00  0.00           H  
HETATM   46  H16 UNL     1       1.126  -2.658  -0.057  1.00  0.00           H  
HETATM   47  H17 UNL     1       0.129  -3.142   1.378  1.00  0.00           H  
HETATM   48  H18 UNL     1       1.380  -1.483   2.762  1.00  0.00           H  
HETATM   49  H19 UNL     1       2.438  -2.738   1.929  1.00  0.00           H  
HETATM   50  H20 UNL     1       1.878   0.141   1.003  1.00  0.00           H  
HETATM   51  H21 UNL     1       2.847  -1.050   0.128  1.00  0.00           H  
HETATM   52  H22 UNL     1       5.311  -0.769   2.890  1.00  0.00           H  
HETATM   53  H23 UNL     1       4.087  -2.040   2.896  1.00  0.00           H  
HETATM   54  H24 UNL     1       5.899  -2.611   1.308  1.00  0.00           H  
HETATM   55  H25 UNL     1       4.427  -2.312   0.370  1.00  0.00           H  
HETATM   56  H26 UNL     1       6.334  -1.179  -0.673  1.00  0.00           H  
HETATM   57  H27 UNL     1       5.079   0.014  -0.139  1.00  0.00           H  
HETATM   58  H28 UNL     1       6.445   0.495   1.877  1.00  0.00           H  
HETATM   59  H29 UNL     1       7.699  -0.688   1.329  1.00  0.00           H  
HETATM   60  H30 UNL     1       6.213   2.574   0.736  1.00  0.00           H  
HETATM   61  H31 UNL     1       7.351   4.260  -0.689  1.00  0.00           H  
HETATM   62  H32 UNL     1       9.271   3.679  -2.037  1.00  0.00           H  
HETATM   63  H33 UNL     1      10.120   1.387  -2.004  1.00  0.00           H  
HETATM   64  H34 UNL     1       8.993  -0.323  -0.578  1.00  0.00           H  
HETATM   65  H35 UNL     1      -4.448   1.558   0.105  1.00  0.00           H  
HETATM   66  H36 UNL     1      -5.683   3.569  -0.467  1.00  0.00           H  
HETATM   67  H37 UNL     1      -7.815   4.572  -1.140  1.00  0.00           H  
CONECT    1    2   31
CONECT    2    3   32   33
CONECT    3    4    4   29
CONECT    4    5   34
CONECT    5    6   27   27
CONECT    6    7    8   35
CONECT    7   36
CONECT    8    9   37   38
CONECT    9   10   39
CONECT   10   11   40   41
CONECT   11   12   42   43
CONECT   12   13   44   45
CONECT   13   14   46   47
CONECT   14   15   48   49
CONECT   15   16   50   51
CONECT   16   17
CONECT   17   18   52   53
CONECT   18   19   54   55
CONECT   19   20   56   57
CONECT   20   21   58   59
CONECT   21   22   22   26
CONECT   22   23   60
CONECT   23   24   24   61
CONECT   24   25   62
CONECT   25   26   26   63
CONECT   26   64
CONECT   27   28   65
CONECT   28   29   29   66
CONECT   29   30
CONECT   30   67
END

HMDB0015073
     RDKit          3D
Salmeterol
 67 68  0  0  0  0  0  0  0  0999 V2000
   -9.9663   -0.0963   -1.0973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5652    1.2196   -1.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1215    1.3066   -0.8031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4058    0.1513   -0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0702    0.2121   -0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2704   -0.9671    0.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4716   -0.7266    1.3537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4693   -1.5159   -0.9348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4248   -0.6973   -1.4136 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3013   -0.4796   -0.5827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4331   -1.6989   -0.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3014   -1.2094    0.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6533   -2.3084    0.8886 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7681   -1.8513    1.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5576   -0.7491    1.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5938   -0.2957    1.9308 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5443   -1.2430    2.2538 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1806   -1.8095    1.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8333   -0.7227    0.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9063   -0.0048    0.9819 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5453    1.0601    0.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0612    2.3382    0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7204    3.2573   -0.6734 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8055    2.9275   -1.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2721    1.6495   -1.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6356    0.6949   -0.6089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4741    1.4544   -0.1447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1795    2.6050   -0.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4960    2.5365   -0.7996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2613    3.6502   -1.1370 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0223   -0.4333   -0.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1608    1.8717   -0.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7167    1.5713   -2.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9161   -0.7950   -0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9739   -1.7727    0.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9602   -0.0055    1.8507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0858   -2.5083   -0.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1788   -1.7112   -1.7550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2695   -0.6970   -2.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6269    0.2367   -1.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5139    0.0303    0.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0390   -2.1077   -1.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9592   -2.4978    0.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2227   -0.4020   -0.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7473   -0.7221    1.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1260   -2.6576   -0.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1289   -3.1418    1.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3800   -1.4832    2.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4379   -2.7384    1.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8782    0.1408    1.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8469   -1.0503    0.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3114   -0.7687    2.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0874   -2.0397    2.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8991   -2.6112    1.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4273   -2.3124    0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3336   -1.1787   -0.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0790    0.0139   -0.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4449    0.4951    1.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6990   -0.6879    1.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2133    2.5737    0.7362 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3506    4.2597   -0.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2713    3.6793   -2.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1200    1.3870   -2.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9933   -0.3233   -0.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4484    1.5576    0.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6827    3.5691   -0.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8149    4.5722   -1.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
  5 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 29  3  1  0
 26 21  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  4 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 12 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  0
 15 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 20 58  1  0
 20 59  1  0
 22 60  1  0
 23 61  1  0
 24 62  1  0
 25 63  1  0
 26 64  1  0
 27 65  1  0
 28 66  1  0
 30 67  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Serevent	HMDB
GR-33343X	HMDB
Salmaterol	HMDB
GR-33343-X	HMDB
Salmeterol xinafoate	HMDB
Xinafoate, salmeterol	HMDB
Salmeterol	MeSH

Chemical Formula

C₂₅H₃₇NO₄

Average Molecular Weight

415.5656

Monoisotopic Molecular Weight

415.272258677

IUPAC Name

4-(1-hydroxy-2-{[6-(4-phenylbutoxy)hexyl]amino}ethyl)-2-(hydroxymethyl)phenol

Traditional Name

salmeterol

CAS Registry Number

89365-50-4

SMILES

OCC1=C(O)C=CC(=C1)C(O)CNCCCCCCOCCCCC1=CC=CC=C1

InChI Identifier

InChI=1S/C25H37NO4/c27-20-23-18-22(13-14-24(23)28)25(29)19-26-15-7-1-2-8-16-30-17-9-6-12-21-10-4-3-5-11-21/h3-5,10-11,13-14,18,25-29H,1-2,6-9,12,15-17,19-20H2

InChI Key

GIIZNNXWQWCKIB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzyl alcohols. These are organic compounds containing the phenylmethanol substructure.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzyl alcohols

Direct Parent

Benzyl alcohols

Alternative Parents

Substituents

Benzyl alcohol
Phenol
Aralkylamine
1-hydroxy-2-unsubstituted benzenoid
Secondary alcohol
1,2-aminoalcohol
Dialkyl ether
Secondary aliphatic amine
Ether
Secondary amine
Amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Aromatic alcohol
Alcohol
Hydrocarbon derivative
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

secondary alcohol (CHEBI:64064 )
phenols (CHEBI:64064 )
secondary amino compound (CHEBI:64064 )
ether (CHEBI:64064 )
primary alcohol (CHEBI:64064 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	75.5 - 76.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0023 g/L	Not Available
LogP	4.2	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	202.9	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0023 g/L	ALOGPS
logP	3.82	ALOGPS
logP	3.61	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	10.12	ChemAxon
pKa (Strongest Basic)	9.4	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	81.95 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	122.39 m³·mol⁻¹	ChemAxon
Polarizability	50.6 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	198.134	31661259
DarkChem	[M-H]-	193.897	31661259
DeepCCS	[M+H]+	201.501	30932474
DeepCCS	[M-H]-	199.086	30932474
DeepCCS	[M-2H]-	233.436	30932474
DeepCCS	[M+Na]+	208.662	30932474
AllCCS	[M+H]+	202.2	32859911
AllCCS	[M+H-H2O]+	200.0	32859911
AllCCS	[M+NH4]+	204.2	32859911
AllCCS	[M+Na]+	204.7	32859911
AllCCS	[M-H]-	194.5	32859911
AllCCS	[M+Na-2H]-	196.2	32859911
AllCCS	[M+HCOO]-	198.1	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.	7.44 minutes	32390414
Predicted by Siyang on May 30, 2022	12.5045 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.62 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	58.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Salmeterol	OCC1=C(O)C=CC(=C1)C(O)CNCCCCCCOCCCCC1=CC=CC=C1	4103.6	Standard polar	33892256
Salmeterol	OCC1=C(O)C=CC(=C1)C(O)CNCCCCCCOCCCCC1=CC=CC=C1	3112.3	Standard non polar	33892256
Salmeterol	OCC1=C(O)C=CC(=C1)C(O)CNCCCCCCOCCCCC1=CC=CC=C1	3605.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Salmeterol,1TMS,isomer #1	C[Si](C)(C)OCC1=CC(C(O)CNCCCCCCOCCCCC2=CC=CC=C2)=CC=C1O	3641.2	Semi standard non polar	33892256
Salmeterol,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C(O)CNCCCCCCOCCCCC2=CC=CC=C2)C=C1CO	3597.3	Semi standard non polar	33892256
Salmeterol,1TMS,isomer #3	C[Si](C)(C)OC(CNCCCCCCOCCCCC1=CC=CC=C1)C1=CC=C(O)C(CO)=C1	3572.2	Semi standard non polar	33892256
Salmeterol,1TMS,isomer #4	C[Si](C)(C)N(CCCCCCOCCCCC1=CC=CC=C1)CC(O)C1=CC=C(O)C(CO)=C1	3632.9	Semi standard non polar	33892256
Salmeterol,2TMS,isomer #1	C[Si](C)(C)OCC1=CC(C(CNCCCCCCOCCCCC2=CC=CC=C2)O[Si](C)(C)C)=CC=C1O	3511.2	Semi standard non polar	33892256
Salmeterol,2TMS,isomer #2	C[Si](C)(C)OCC1=CC(C(O)CNCCCCCCOCCCCC2=CC=CC=C2)=CC=C1O[Si](C)(C)C	3586.6	Semi standard non polar	33892256
Salmeterol,2TMS,isomer #3	C[Si](C)(C)OCC1=CC(C(O)CN(CCCCCCOCCCCC2=CC=CC=C2)[Si](C)(C)C)=CC=C1O	3610.8	Semi standard non polar	33892256
Salmeterol,2TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C(CNCCCCCCOCCCCC2=CC=CC=C2)O[Si](C)(C)C)C=C1CO	3443.3	Semi standard non polar	33892256
Salmeterol,2TMS,isomer #5	C[Si](C)(C)OC1=CC=C(C(O)CN(CCCCCCOCCCCC2=CC=CC=C2)[Si](C)(C)C)C=C1CO	3588.7	Semi standard non polar	33892256
Salmeterol,2TMS,isomer #6	C[Si](C)(C)OC(CN(CCCCCCOCCCCC1=CC=CC=C1)[Si](C)(C)C)C1=CC=C(O)C(CO)=C1	3587.9	Semi standard non polar	33892256
Salmeterol,3TMS,isomer #1	C[Si](C)(C)OCC1=CC(C(CNCCCCCCOCCCCC2=CC=CC=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3385.1	Semi standard non polar	33892256
Salmeterol,3TMS,isomer #2	C[Si](C)(C)OCC1=CC(C(CN(CCCCCCOCCCCC2=CC=CC=C2)[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O	3583.3	Semi standard non polar	33892256
Salmeterol,3TMS,isomer #3	C[Si](C)(C)OCC1=CC(C(O)CN(CCCCCCOCCCCC2=CC=CC=C2)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3602.6	Semi standard non polar	33892256
Salmeterol,3TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C(CN(CCCCCCOCCCCC2=CC=CC=C2)[Si](C)(C)C)O[Si](C)(C)C)C=C1CO	3557.9	Semi standard non polar	33892256
Salmeterol,4TMS,isomer #1	C[Si](C)(C)OCC1=CC(C(CN(CCCCCCOCCCCC2=CC=CC=C2)[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3570.1	Semi standard non polar	33892256
Salmeterol,4TMS,isomer #1	C[Si](C)(C)OCC1=CC(C(CN(CCCCCCOCCCCC2=CC=CC=C2)[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3255.7	Standard non polar	33892256
Salmeterol,4TMS,isomer #1	C[Si](C)(C)OCC1=CC(C(CN(CCCCCCOCCCCC2=CC=CC=C2)[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3702.3	Standard polar	33892256
Salmeterol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC(C(O)CNCCCCCCOCCCCC2=CC=CC=C2)=CC=C1O	3871.3	Semi standard non polar	33892256
Salmeterol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C(O)CNCCCCCCOCCCCC2=CC=CC=C2)C=C1CO	3843.5	Semi standard non polar	33892256
Salmeterol,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(CNCCCCCCOCCCCC1=CC=CC=C1)C1=CC=C(O)C(CO)=C1	3795.8	Semi standard non polar	33892256
Salmeterol,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(CCCCCCOCCCCC1=CC=CC=C1)CC(O)C1=CC=C(O)C(CO)=C1	3857.5	Semi standard non polar	33892256
Salmeterol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC(C(CNCCCCCCOCCCCC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O	3941.7	Semi standard non polar	33892256
Salmeterol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1=CC(C(O)CNCCCCCCOCCCCC2=CC=CC=C2)=CC=C1O[Si](C)(C)C(C)(C)C	4028.0	Semi standard non polar	33892256
Salmeterol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC1=CC(C(O)CN(CCCCCCOCCCCC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)=CC=C1O	4087.1	Semi standard non polar	33892256
Salmeterol,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C(CNCCCCCCOCCCCC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)C=C1CO	3894.9	Semi standard non polar	33892256
Salmeterol,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C(C(O)CN(CCCCCCOCCCCC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1CO	4084.5	Semi standard non polar	33892256
Salmeterol,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(CN(CCCCCCOCCCCC1=CC=CC=C1)[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(CO)=C1	4066.0	Semi standard non polar	33892256
Salmeterol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC(C(CNCCCCCCOCCCCC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4046.7	Semi standard non polar	33892256
Salmeterol,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1=CC(C(CN(CCCCCCOCCCCC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O	4288.3	Semi standard non polar	33892256
Salmeterol,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC1=CC(C(O)CN(CCCCCCOCCCCC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4304.9	Semi standard non polar	33892256
Salmeterol,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C(CN(CCCCCCOCCCCC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1CO	4272.5	Semi standard non polar	33892256
Salmeterol,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC(C(CN(CCCCCCOCCCCC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4470.4	Semi standard non polar	33892256
Salmeterol,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC(C(CN(CCCCCCOCCCCC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3864.7	Standard non polar	33892256
Salmeterol,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC(C(CN(CCCCCCOCCCCC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3923.9	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

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 DB00938	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00938	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00938

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4968

KEGG Compound ID

C07241

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Salmeterol

METLIN ID

Not Available

PubChem Compound

5152

PDB ID

Not Available

ChEBI ID

64064

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

Salpeter SR, Buckley NS, Ormiston TM, Salpeter EE: Meta-analysis: effect of long-acting beta-agonists on severe asthma exacerbations and asthma-related deaths. Ann Intern Med. 2006 Jun 20;144(12):904-12. Epub 2006 Jun 5. [PubMed:16754916 ]

Enzymes

Enzyme Details

1. 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

2. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

Enzyme Details

3. Cytochrome P450 3A7

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A7
Uniprot ID:: P24462
Molecular weight:: 57525.03

Enzyme Details

4. Cytochrome P450 2C8

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

References

Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [PubMed:15601807 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Beta-2 adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
Gene Name:: ADRB2
Uniprot ID:: P07550
Molecular weight:: 46458.3

References

Rong Y, Arbabian M, Thiriot DS, Seibold A, Clark RB, Ruoho AE: Probing the salmeterol binding site on the beta 2-adrenergic receptor using a novel photoaffinity ligand, [(125)I]iodoazidosalmeterol. Biochemistry. 1999 Aug 31;38(35):11278-86. [PubMed:10471277 ]
Finney PA, Donnelly LE, Belvisi MG, Chuang TT, Birrell M, Harris A, Mak JC, Scorer C, Barnes PJ, Adcock IM, Giembycz MA: Chronic systemic administration of salmeterol to rats promotes pulmonary beta(2)-adrenoceptor desensitization and down-regulation of G(s alpha). Br J Pharmacol. 2001 Mar;132(6):1261-70. [PubMed:11250877 ]
Green SA, Rathz DA, Schuster AJ, Liggett SB: The Ile164 beta(2)-adrenoceptor polymorphism alters salmeterol exosite binding and conventional agonist coupling to G(s). Eur J Pharmacol. 2001 Jun 15;421(3):141-7. [PubMed:11516429 ]
Meliton AY, Munoz NM, Liu J, Lambertino AT, Boetticher E, Myo S, Myou S, Zhu X, Johnson M, Leff AR: Blockade of LTC4 synthesis caused by additive inhibition of gIV-PLA2 phosphorylation: Effect of salmeterol and PDE4 inhibition in human eosinophils. J Allergy Clin Immunol. 2003 Aug;112(2):404-10. [PubMed:12897749 ]
Brogden RN, Faulds D: Salmeterol xinafoate: a review of its pharmacological properties and therapeutic potential in reversible obstructive airways disease. Allergol Immunopathol (Madr). 1992 Mar-Apr;20(2):72-84. [PubMed:1359777 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Salmeterol (HMDB0015073)

MOL for HMDB0015073 (Salmeterol)

3D MOL for HMDB0015073 (Salmeterol)

3D SDF for HMDB0015073 (Salmeterol)

3D-SDF for HMDB0015073 (Salmeterol)

PDB for HMDB0015073 (Salmeterol)

3D PDB for HMDB0015073 (Salmeterol)

SMILES for HMDB0015073 (Salmeterol)

INCHI for HMDB0015073 (Salmeterol)

Structure for HMDB0015073 (Salmeterol)

3D Structure for HMDB0015073 (Salmeterol)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

References

References

References