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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:45 UTC

HMDB ID

HMDB0014844

Secondary Accession Numbers

HMDB14844

Metabolite Identification

Common Name

Tamsulosin

Description

Tamsulosin is a selective antagonist at alpha-1A and alpha-1B-adrenoceptors in the prostate, prostatic capsule, prostatic urethra, and bladder neck. At least three discrete alpha1-adrenoceptor subtypes have been identified: alpha-1A, alpha-1B and alpha-1D; their distribution differs between human organs and tissue. Approximately 70% of the alpha1-receptors in human prostate are of the alpha-1A subtype. Blockage of these receptors causes relaxation of smooth muscles in the bladder neck and prostate.

Structure

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

706
  Mrv0541 02231214562D          

 28 29  0  0  1  0            999 V2000
    3.7935    3.7910    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -1.9842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.9659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9685    3.7910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    3.7910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -3.6342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.0784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    4.6160    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.4909    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2224    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -1.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -2.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -3.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -1.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -3.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -2.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -3.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -4.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -4.8717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  2  0  0  0  0
  1  5  2  0  0  0  0
  1  8  1  0  0  0  0
  1 15  1  0  0  0  0
  2 17  1  0  0  0  0
  2 20  1  0  0  0  0
  3 18  1  0  0  0  0
  3 23  1  0  0  0  0
  6 21  1  0  0  0  0
  6 27  1  0  0  0  0
  9  7  1  6  0  0  0
  7 13  1  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 11 14  2  0  0  0  0
 11 16  1  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 15 18  2  0  0  0  0
 16 19  2  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 21 24  2  0  0  0  0
 22 25  1  0  0  0  0
 24 26  1  0  0  0  0
 25 26  2  0  0  0  0
 27 28  1  0  0  0  0
M  END

HMDB0014844
     RDKit          3D
Tamsulosin
 56 57  0  0  0  0  0  0  0  0999 V2000
   -8.2755   -0.4188   -0.7255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1573   -1.2930   -0.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8841   -0.9072   -0.6849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3153    0.3373   -0.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9851    1.2550    0.3935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4042    2.4665    0.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1436    2.7547    0.2345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4824    1.7941   -0.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0147    0.5739   -0.8660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3952   -0.3565   -1.5997 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2679   -0.6515   -2.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9759   -0.7899   -1.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4664    0.3102   -0.8105 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7667   -0.0598   -0.1471 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1425    0.9647    0.9082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9234   -0.1296   -1.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1864   -0.5043   -0.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4939   -1.8446   -0.3210 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6714   -2.1819    0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5232   -1.2218    0.8321 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6954   -1.6113    1.4593 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0000   -2.9827    1.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2132    0.1379    0.7314 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3101    1.2943    1.3970 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.7402    2.8920    1.1619 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6476    1.1113    0.7031 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5175    1.1076    2.8844 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0324    0.4546    0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9535    0.4546   -1.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9359   -1.0191   -1.4136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9436   -0.1468    0.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3083   -2.3454   -0.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1475   -1.2972    0.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9817    1.0660    0.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9061    3.2234    1.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6488    3.7076    0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4855    2.0650   -0.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4127   -1.6658   -2.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1342    0.0248   -3.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2126   -1.0527   -2.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9950   -1.6864   -0.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3393    1.1704   -1.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6195   -1.0615    0.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2116    1.2587    1.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9161    0.6017    1.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4771    1.8986    0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1048    0.8464   -1.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7344   -0.8765   -1.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8166   -2.5724   -0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8874   -3.2426    0.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0401   -3.0847    1.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9138   -3.4308    0.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2960   -3.5300    2.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5082    3.5906    1.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9735    3.0790    1.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8092    1.5242    0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 24 27  2  0
 23 28  2  0
  9  4  1  0
 28 17  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  1
 15 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 18 49  1  0
 19 50  1  0
 22 51  1  0
 22 52  1  0
 22 53  1  0
 25 54  1  0
 25 55  1  0
 28 56  1  0
M  END

706
  Mrv0541 02231214562D          

 28 29  0  0  1  0            999 V2000
    3.7935    3.7910    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -1.9842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.9659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9685    3.7910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    3.7910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -3.6342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.0784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    4.6160    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.4909    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2224    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -1.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -2.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -3.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -1.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -3.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -2.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -3.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -4.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -4.8717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  2  0  0  0  0
  1  5  2  0  0  0  0
  1  8  1  0  0  0  0
  1 15  1  0  0  0  0
  2 17  1  0  0  0  0
  2 20  1  0  0  0  0
  3 18  1  0  0  0  0
  3 23  1  0  0  0  0
  6 21  1  0  0  0  0
  6 27  1  0  0  0  0
  9  7  1  6  0  0  0
  7 13  1  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 11 14  2  0  0  0  0
 11 16  1  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 15 18  2  0  0  0  0
 16 19  2  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 21 24  2  0  0  0  0
 22 25  1  0  0  0  0
 24 26  1  0  0  0  0
 25 26  2  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014844

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC(=C(OC)C=C1)S(N)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28N2O5S/c1-4-26-17-7-5-6-8-18(17)27-12-11-22-15(2)13-16-9-10-19(25-3)20(14-16)28(21,23)24/h5-10,14-15,22H,4,11-13H2,1-3H3,(H2,21,23,24)/t15-/m1/s1

> <INCHI_KEY>
DRHKJLXJIQTDTD-OAHLLOKOSA-N

> <FORMULA>
C20H28N2O5S

> <MOLECULAR_WEIGHT>
408.512

> <EXACT_MASS>
408.171892706

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
43.95205639905195

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(2R)-2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl]-2-methoxybenzene-1-sulfonamide

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
2.038114116278142

> <ALOGPS_LOGS>
-4.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.932656072654002

> <JCHEM_PKA_STRONGEST_BASIC>
9.284809828172845

> <JCHEM_POLAR_SURFACE_AREA>
99.88

> <JCHEM_REFRACTIVITY>
108.8649

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.55e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tamsulosin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014844
     RDKit          3D
Tamsulosin
 56 57  0  0  0  0  0  0  0  0999 V2000
   -8.2755   -0.4188   -0.7255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1573   -1.2930   -0.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8841   -0.9072   -0.6849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3153    0.3373   -0.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9851    1.2550    0.3935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4042    2.4665    0.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1436    2.7547    0.2345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4824    1.7941   -0.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0147    0.5739   -0.8660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3952   -0.3565   -1.5997 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2679   -0.6515   -2.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9759   -0.7899   -1.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4664    0.3102   -0.8105 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7667   -0.0598   -0.1471 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1425    0.9647    0.9082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9234   -0.1296   -1.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1864   -0.5043   -0.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4939   -1.8446   -0.3210 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6714   -2.1819    0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5232   -1.2218    0.8321 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6954   -1.6113    1.4593 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0000   -2.9827    1.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2132    0.1379    0.7314 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3101    1.2943    1.3970 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.7402    2.8920    1.1619 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6476    1.1113    0.7031 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5175    1.1076    2.8844 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0324    0.4546    0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9535    0.4546   -1.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9359   -1.0191   -1.4136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9436   -0.1468    0.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3083   -2.3454   -0.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1475   -1.2972    0.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9817    1.0660    0.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9061    3.2234    1.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6488    3.7076    0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4855    2.0650   -0.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4127   -1.6658   -2.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1342    0.0248   -3.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2126   -1.0527   -2.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9950   -1.6864   -0.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3393    1.1704   -1.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6195   -1.0615    0.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2116    1.2587    1.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9161    0.6017    1.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4771    1.8986    0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1048    0.8464   -1.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7344   -0.8765   -1.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8166   -2.5724   -0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8874   -3.2426    0.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0401   -3.0847    1.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9138   -3.4308    0.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2960   -3.5300    2.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5082    3.5906    1.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9735    3.0790    1.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8092    1.5242    0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 24 27  2  0
 23 28  2  0
  9  4  1  0
 28 17  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  1
 15 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 18 49  1  0
 19 50  1  0
 22 51  1  0
 22 52  1  0
 22 53  1  0
 25 54  1  0
 25 55  1  0
 28 56  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 706                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       7.081   7.077   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      12.416  -3.704   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       4.414   5.536   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.541   7.077   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       8.621   7.077   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      12.416  -6.784   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      11.082   0.146   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       7.081   8.617   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       9.748   0.916   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.748   2.456   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415   3.226   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415   0.146   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.082  -1.394   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.415   4.766   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081   5.536   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081   2.456   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.416  -2.164   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.748   4.766   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.748   3.226   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.750  -4.474   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.750  -6.014   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.083  -3.704   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.080   4.766   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.083  -6.784   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.417  -4.474   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.417  -6.014   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.416  -8.324   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.082  -9.094   0.000  0.00  0.00           C+0
CONECT    1    4    5    8   15                                             
CONECT    2   17   20                                                       
CONECT    3   18   23                                                       
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6   21   27                                                       
CONECT    7    9   13                                                       
CONECT    8    1                                                            
CONECT    9    7   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10   14   16                                                  
CONECT   12    9                                                            
CONECT   13    7   17                                                       
CONECT   14   11   15                                                       
CONECT   15    1   14   18                                                  
CONECT   16   11   19                                                       
CONECT   17    2   13                                                       
CONECT   18    3   15   19                                                  
CONECT   19   16   18                                                       
CONECT   20    2   21   22                                                  
CONECT   21    6   20   24                                                  
CONECT   22   20   25                                                       
CONECT   23    3                                                            
CONECT   24   21   26                                                       
CONECT   25   22   26                                                       
CONECT   26   24   25                                                       
CONECT   27    6   28                                                       
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

COMPND    HMDB0014844
HETATM    1  C1  UNL     1      -8.275  -0.419  -0.726  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.157  -1.293  -0.264  1.00  0.00           C  
HETATM    3  O1  UNL     1      -5.884  -0.907  -0.685  1.00  0.00           O  
HETATM    4  C3  UNL     1      -5.315   0.337  -0.362  1.00  0.00           C  
HETATM    5  C4  UNL     1      -5.985   1.255   0.394  1.00  0.00           C  
HETATM    6  C5  UNL     1      -5.404   2.467   0.696  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.144   2.755   0.234  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.482   1.794  -0.538  1.00  0.00           C  
HETATM    9  C8  UNL     1      -4.015   0.574  -0.866  1.00  0.00           C  
HETATM   10  O2  UNL     1      -3.395  -0.357  -1.600  1.00  0.00           O  
HETATM   11  C9  UNL     1      -2.268  -0.652  -2.243  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.976  -0.790  -1.526  1.00  0.00           C  
HETATM   13  N1  UNL     1      -0.466   0.310  -0.811  1.00  0.00           N  
HETATM   14  C11 UNL     1       0.767  -0.060  -0.147  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.142   0.965   0.908  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.923  -0.130  -1.098  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.186  -0.504  -0.421  1.00  0.00           C  
HETATM   18  C15 UNL     1       3.494  -1.845  -0.321  1.00  0.00           C  
HETATM   19  C16 UNL     1       4.671  -2.182   0.312  1.00  0.00           C  
HETATM   20  C17 UNL     1       5.523  -1.222   0.832  1.00  0.00           C  
HETATM   21  O3  UNL     1       6.695  -1.611   1.459  1.00  0.00           O  
HETATM   22  C18 UNL     1       7.000  -2.983   1.557  1.00  0.00           C  
HETATM   23  C19 UNL     1       5.213   0.138   0.731  1.00  0.00           C  
HETATM   24  S1  UNL     1       6.310   1.294   1.397  1.00  0.00           S  
HETATM   25  N2  UNL     1       5.740   2.892   1.162  1.00  0.00           N  
HETATM   26  O4  UNL     1       7.648   1.111   0.703  1.00  0.00           O  
HETATM   27  O5  UNL     1       6.518   1.108   2.884  1.00  0.00           O  
HETATM   28  C20 UNL     1       4.032   0.455   0.096  1.00  0.00           C  
HETATM   29  H1  UNL     1      -7.953   0.455  -1.328  1.00  0.00           H  
HETATM   30  H2  UNL     1      -8.936  -1.019  -1.414  1.00  0.00           H  
HETATM   31  H3  UNL     1      -8.944  -0.147   0.119  1.00  0.00           H  
HETATM   32  H4  UNL     1      -7.308  -2.345  -0.598  1.00  0.00           H  
HETATM   33  H5  UNL     1      -7.147  -1.297   0.849  1.00  0.00           H  
HETATM   34  H6  UNL     1      -6.982   1.066   0.776  1.00  0.00           H  
HETATM   35  H7  UNL     1      -5.906   3.223   1.295  1.00  0.00           H  
HETATM   36  H8  UNL     1      -3.649   3.708   0.454  1.00  0.00           H  
HETATM   37  H9  UNL     1      -2.485   2.065  -0.904  1.00  0.00           H  
HETATM   38  H10 UNL     1      -2.413  -1.666  -2.764  1.00  0.00           H  
HETATM   39  H11 UNL     1      -2.134   0.025  -3.142  1.00  0.00           H  
HETATM   40  H12 UNL     1      -0.213  -1.053  -2.322  1.00  0.00           H  
HETATM   41  H13 UNL     1      -0.995  -1.686  -0.865  1.00  0.00           H  
HETATM   42  H14 UNL     1      -0.339   1.170  -1.400  1.00  0.00           H  
HETATM   43  H15 UNL     1       0.620  -1.062   0.279  1.00  0.00           H  
HETATM   44  H16 UNL     1       0.212   1.259   1.476  1.00  0.00           H  
HETATM   45  H17 UNL     1       1.916   0.602   1.583  1.00  0.00           H  
HETATM   46  H18 UNL     1       1.477   1.899   0.414  1.00  0.00           H  
HETATM   47  H19 UNL     1       2.105   0.846  -1.592  1.00  0.00           H  
HETATM   48  H20 UNL     1       1.734  -0.877  -1.892  1.00  0.00           H  
HETATM   49  H21 UNL     1       2.817  -2.572  -0.733  1.00  0.00           H  
HETATM   50  H22 UNL     1       4.887  -3.243   0.376  1.00  0.00           H  
HETATM   51  H23 UNL     1       8.040  -3.085   1.961  1.00  0.00           H  
HETATM   52  H24 UNL     1       6.914  -3.431   0.536  1.00  0.00           H  
HETATM   53  H25 UNL     1       6.296  -3.530   2.220  1.00  0.00           H  
HETATM   54  H26 UNL     1       6.508   3.591   1.306  1.00  0.00           H  
HETATM   55  H27 UNL     1       4.973   3.079   1.867  1.00  0.00           H  
HETATM   56  H28 UNL     1       3.809   1.524   0.027  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3   32   33
CONECT    3    4
CONECT    4    5    5    9
CONECT    5    6   34
CONECT    6    7    7   35
CONECT    7    8   36
CONECT    8    9    9   37
CONECT    9   10
CONECT   10   11
CONECT   11   12   38   39
CONECT   12   13   40   41
CONECT   13   14   42
CONECT   14   15   16   43
CONECT   15   44   45   46
CONECT   16   17   47   48
CONECT   17   18   18   28
CONECT   18   19   49
CONECT   19   20   20   50
CONECT   20   21   23
CONECT   21   22
CONECT   22   51   52   53
CONECT   23   24   28   28
CONECT   24   25   26   26   27
CONECT   24   27
CONECT   25   54   55
CONECT   28   56
END

HMDB0014844
     RDKit          3D
Tamsulosin
 56 57  0  0  0  0  0  0  0  0999 V2000
   -8.2755   -0.4188   -0.7255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1573   -1.2930   -0.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8841   -0.9072   -0.6849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3153    0.3373   -0.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9851    1.2550    0.3935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4042    2.4665    0.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1436    2.7547    0.2345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4824    1.7941   -0.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0147    0.5739   -0.8660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3952   -0.3565   -1.5997 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2679   -0.6515   -2.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9759   -0.7899   -1.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4664    0.3102   -0.8105 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7667   -0.0598   -0.1471 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1425    0.9647    0.9082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9234   -0.1296   -1.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1864   -0.5043   -0.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4939   -1.8446   -0.3210 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6714   -2.1819    0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5232   -1.2218    0.8321 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6954   -1.6113    1.4593 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0000   -2.9827    1.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2132    0.1379    0.7314 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3101    1.2943    1.3970 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.7402    2.8920    1.1619 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6476    1.1113    0.7031 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5175    1.1076    2.8844 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0324    0.4546    0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9535    0.4546   -1.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9359   -1.0191   -1.4136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9436   -0.1468    0.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3083   -2.3454   -0.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1475   -1.2972    0.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9817    1.0660    0.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9061    3.2234    1.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6488    3.7076    0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4855    2.0650   -0.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4127   -1.6658   -2.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1342    0.0248   -3.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2126   -1.0527   -2.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9950   -1.6864   -0.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3393    1.1704   -1.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6195   -1.0615    0.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2116    1.2587    1.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9161    0.6017    1.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4771    1.8986    0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1048    0.8464   -1.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7344   -0.8765   -1.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8166   -2.5724   -0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8874   -3.2426    0.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0401   -3.0847    1.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9138   -3.4308    0.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2960   -3.5300    2.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5082    3.5906    1.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9735    3.0790    1.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8092    1.5242    0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 24 27  2  0
 23 28  2  0
  9  4  1  0
 28 17  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  1
 15 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 18 49  1  0
 19 50  1  0
 22 51  1  0
 22 52  1  0
 22 53  1  0
 25 54  1  0
 25 55  1  0
 28 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Tamsulosin	ChEBI
(R)-(-)-Tamsulosin	ChEBI
(R)-5-(2-((2-(2-Ethoxyphenoxy)ethyl)amino)propyl)-2-methoxybenzenesulfonamide	ChEBI
Tamsulosina	ChEBI
Tamsulosine	ChEBI
Tamsulosinum	ChEBI
Flomax	Kegg
Tamsulon	Kegg
(R)-5-(2-((2-(2-Ethoxyphenoxy)ethyl)amino)propyl)-2-methoxybenzenesulphonamide	Generator
5-[2-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxy-benzenesulfonamide	HMDB
5-[2-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxy-benzenesulphonamide	HMDB
YM-617	HMDB
5-(2-((2-(2-Ethoxyphenoxy)ethyl)amino)propyl)-2-methoxybenzenesulfonamide	HMDB
Tamsulosin hydrochloride	HMDB

Chemical Formula

C₂₀H₂₈N₂O₅S

Average Molecular Weight

408.512

Monoisotopic Molecular Weight

408.171892706

IUPAC Name

5-[(2R)-2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl]-2-methoxybenzene-1-sulfonamide

Traditional Name

tamsulosin

CAS Registry Number

106133-20-4

SMILES

CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC(=C(OC)C=C1)S(N)(=O)=O

InChI Identifier

InChI=1S/C20H28N2O5S/c1-4-26-17-7-5-6-8-18(17)27-12-11-22-15(2)13-16-9-10-19(25-3)20(14-16)28(21,23)24/h5-10,14-15,22H,4,11-13H2,1-3H3,(H2,21,23,24)/t15-/m1/s1

InChI Key

DRHKJLXJIQTDTD-OAHLLOKOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenethylamines

Direct Parent

Amphetamines and derivatives

Alternative Parents

Substituents

Amphetamine or derivatives
Benzenesulfonamide
Benzenesulfonyl group
Phenylpropane
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
Aralkylamine
Organosulfonic acid amide
Aminosulfonyl compound
Sulfonyl
Organosulfonic acid or derivatives
Organic sulfonic acid or derivatives
Secondary aliphatic amine
Ether
Secondary amine
Organooxygen compound
Organonitrogen compound
Amine
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Organosulfur compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

sulfonamide (CHEBI:9398 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0014844)
Membrane (HMDB: HMDB0014844)

Source

Exogenous

Exogenous (HMDB: HMDB0014844)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	226 - 228 °C (hydrochloride salt)	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0066 g/L	Not Available
LogP	2.3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0066 g/L	ALOGPS
logP	3.05	ALOGPS
logP	2.04	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	9.93	ChemAxon
pKa (Strongest Basic)	9.28	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	99.88 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	108.86 m³·mol⁻¹	ChemAxon
Polarizability	43.95 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]+	195.849	31661259
DarkChem	[M-H]-	195.534	31661259
DeepCCS	[M+H]+	194.287	30932474
DeepCCS	[M-H]-	191.929	30932474
DeepCCS	[M-2H]-	225.873	30932474
DeepCCS	[M+Na]+	201.101	30932474
AllCCS	[M+H]+	199.2	32859911
AllCCS	[M+H-H2O]+	196.6	32859911
AllCCS	[M+NH4]+	201.6	32859911
AllCCS	[M+Na]+	202.2	32859911
AllCCS	[M-H]-	194.6	32859911
AllCCS	[M+Na-2H]-	195.4	32859911
AllCCS	[M+HCOO]-	196.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tamsulosin	CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC(=C(OC)C=C1)S(N)(=O)=O	5068.6	Standard polar	33892256
Tamsulosin	CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC(=C(OC)C=C1)S(N)(=O)=O	3472.7	Standard non polar	33892256
Tamsulosin	CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC(=C(OC)C=C1)S(N)(=O)=O	3370.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tamsulosin,1TMS,isomer #1	CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(=O)(=O)N[Si](C)(C)C)=C1	3296.5	Semi standard non polar	33892256
Tamsulosin,1TMS,isomer #1	CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(=O)(=O)N[Si](C)(C)C)=C1	3259.3	Standard non polar	33892256
Tamsulosin,1TMS,isomer #1	CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(=O)(=O)N[Si](C)(C)C)=C1	4372.5	Standard polar	33892256
Tamsulosin,1TMS,isomer #2	CCOC1=CC=CC=C1OCCN([C@H](C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1)[Si](C)(C)C	3380.0	Semi standard non polar	33892256
Tamsulosin,1TMS,isomer #2	CCOC1=CC=CC=C1OCCN([C@H](C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1)[Si](C)(C)C	3309.3	Standard non polar	33892256
Tamsulosin,1TMS,isomer #2	CCOC1=CC=CC=C1OCCN([C@H](C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1)[Si](C)(C)C	5035.5	Standard polar	33892256
Tamsulosin,2TMS,isomer #1	CCOC1=CC=CC=C1OCCN([C@H](C)CC1=CC=C(OC)C(S(=O)(=O)N[Si](C)(C)C)=C1)[Si](C)(C)C	3385.9	Semi standard non polar	33892256
Tamsulosin,2TMS,isomer #1	CCOC1=CC=CC=C1OCCN([C@H](C)CC1=CC=C(OC)C(S(=O)(=O)N[Si](C)(C)C)=C1)[Si](C)(C)C	3430.9	Standard non polar	33892256
Tamsulosin,2TMS,isomer #1	CCOC1=CC=CC=C1OCCN([C@H](C)CC1=CC=C(OC)C(S(=O)(=O)N[Si](C)(C)C)=C1)[Si](C)(C)C	4242.7	Standard polar	33892256
Tamsulosin,2TMS,isomer #2	CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1	3259.1	Semi standard non polar	33892256
Tamsulosin,2TMS,isomer #2	CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1	3436.6	Standard non polar	33892256
Tamsulosin,2TMS,isomer #2	CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1	4246.2	Standard polar	33892256
Tamsulosin,3TMS,isomer #1	CCOC1=CC=CC=C1OCCN([C@H](C)CC1=CC=C(OC)C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1)[Si](C)(C)C	3392.9	Semi standard non polar	33892256
Tamsulosin,3TMS,isomer #1	CCOC1=CC=CC=C1OCCN([C@H](C)CC1=CC=C(OC)C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1)[Si](C)(C)C	3609.5	Standard non polar	33892256
Tamsulosin,3TMS,isomer #1	CCOC1=CC=CC=C1OCCN([C@H](C)CC1=CC=C(OC)C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1)[Si](C)(C)C	4127.4	Standard polar	33892256
Tamsulosin,1TBDMS,isomer #1	CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=C1	3503.5	Semi standard non polar	33892256
Tamsulosin,1TBDMS,isomer #1	CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=C1	3511.8	Standard non polar	33892256
Tamsulosin,1TBDMS,isomer #1	CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=C1	4327.4	Standard polar	33892256
Tamsulosin,1TBDMS,isomer #2	CCOC1=CC=CC=C1OCCN([C@H](C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1)[Si](C)(C)C(C)(C)C	3622.7	Semi standard non polar	33892256
Tamsulosin,1TBDMS,isomer #2	CCOC1=CC=CC=C1OCCN([C@H](C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1)[Si](C)(C)C(C)(C)C	3513.8	Standard non polar	33892256
Tamsulosin,1TBDMS,isomer #2	CCOC1=CC=CC=C1OCCN([C@H](C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1)[Si](C)(C)C(C)(C)C	5004.3	Standard polar	33892256
Tamsulosin,2TBDMS,isomer #1	CCOC1=CC=CC=C1OCCN([C@H](C)CC1=CC=C(OC)C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	3831.1	Semi standard non polar	33892256
Tamsulosin,2TBDMS,isomer #1	CCOC1=CC=CC=C1OCCN([C@H](C)CC1=CC=C(OC)C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	3909.1	Standard non polar	33892256
Tamsulosin,2TBDMS,isomer #1	CCOC1=CC=CC=C1OCCN([C@H](C)CC1=CC=C(OC)C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	4247.3	Standard polar	33892256
Tamsulosin,2TBDMS,isomer #2	CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3689.8	Semi standard non polar	33892256
Tamsulosin,2TBDMS,isomer #2	CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3884.7	Standard non polar	33892256
Tamsulosin,2TBDMS,isomer #2	CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	4220.2	Standard polar	33892256
Tamsulosin,3TBDMS,isomer #1	CCOC1=CC=CC=C1OCCN([C@H](C)CC1=CC=C(OC)C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	4048.7	Semi standard non polar	33892256
Tamsulosin,3TBDMS,isomer #1	CCOC1=CC=CC=C1OCCN([C@H](C)CC1=CC=C(OC)C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	4262.2	Standard non polar	33892256
Tamsulosin,3TBDMS,isomer #1	CCOC1=CC=CC=C1OCCN([C@H](C)CC1=CC=C(OC)C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	4149.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tamsulosin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fc0-1696000000-feeed148e3d1a2085e88	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tamsulosin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tamsulosin 10V, Positive-QTOF	splash10-0a4i-0234900000-bc2e2b9eaaaeda3fce7e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tamsulosin 20V, Positive-QTOF	splash10-05i0-1593100000-b0b9b35ee520544357c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tamsulosin 40V, Positive-QTOF	splash10-01b9-5931000000-a01082b9fcdb3d11e596	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tamsulosin 10V, Negative-QTOF	splash10-0a4i-2322900000-a47a51f53354ebc1348d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tamsulosin 20V, Negative-QTOF	splash10-0550-3907200000-6c1b7cdc5c84f0dccbf3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tamsulosin 40V, Negative-QTOF	splash10-06vj-9513000000-b91e35440806c5c374f9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tamsulosin 10V, Positive-QTOF	splash10-05fr-0090500000-1c851350cf0ebcbae96b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tamsulosin 20V, Positive-QTOF	splash10-05i1-0090100000-b587f2fee8a0ea015942	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tamsulosin 40V, Positive-QTOF	splash10-0udl-0190000000-e302ff6e9ab7b1839d49	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tamsulosin 10V, Negative-QTOF	splash10-0a4i-0011900000-843109d3cddf29aa626d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tamsulosin 20V, Negative-QTOF	splash10-0a6r-3496200000-c3ebf3e04317201646fb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tamsulosin 40V, Negative-QTOF	splash10-0a4i-7975000000-15eea5b5d8ae22b42b13	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00706	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00706	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00706

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

114457

KEGG Compound ID

C07124

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tamsulosin

METLIN ID

Not Available

PubChem Compound

129211

PDB ID

Not Available

ChEBI ID

9398

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

Lyseng-Williamson KA, Jarvis B, Wagstaff AJ: Tamsulosin: an update of its role in the management of lower urinary tract symptoms. Drugs. 2002;62(1):135-67. [PubMed:11790159 ]
Dunn CJ, Matheson A, Faulds DM: Tamsulosin: a review of its pharmacology and therapeutic efficacy in the management of lower urinary tract symptoms. Drugs Aging. 2002;19(2):135-61. [PubMed:11950378 ]
Wilt TJ, Mac Donald R, Rutks I: Tamsulosin for benign prostatic hyperplasia. Cochrane Database Syst Rev. 2003;(1):CD002081. [PubMed:12535426 ]

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 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

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

Enzyme Details

3. Alpha-1A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:: ADRA1A
Uniprot ID:: P35348
Molecular weight:: 51486.0

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Abrams P, Speakman M, Stott M, Arkell D, Pocock R: A dose-ranging study of the efficacy and safety of tamsulosin, the first prostate-selective alpha 1A-adrenoceptor antagonist, in patients with benign prostatic obstruction (symptomatic benign prostatic hyperplasia). Br J Urol. 1997 Oct;80(4):587-96. [PubMed:9352698 ]
Na YJ, Guo YL, Gu FL: Clinical comparison of selective and non-selective alpha 1A-adrenoceptor antagonists for bladder outlet obstruction associated with benign prostatic hyperplasia: studies on tamsulosin and terazosin in Chinese patients. The Chinese Tamsulosin Study Group. J Med. 1998;29(5-6):289-304. [PubMed:10503165 ]
Lee E, Lee C: Clinical comparison of selective and non-selective alpha 1A-adrenoreceptor antagonists in benign prostatic hyperplasia: studies on tamsulosin in a fixed dose and terazosin in increasing doses. Br J Urol. 1997 Oct;80(4):606-11. [PubMed:9352700 ]
Chapple CR, Wyndaele JJ, Nordling J, Boeminghaus F, Ypma AF, Abrams P: Tamsulosin, the first prostate-selective alpha 1A-adrenoceptor antagonist. A meta-analysis of two randomized, placebo-controlled, multicentre studies in patients with benign prostatic obstruction (symptomatic BPH). European Tamsulosin Study Group. Eur Urol. 1996;29(2):155-67. [PubMed:8647141 ]
Schulman CC, Cortvriend J, Jonas U, Lock TM, Vaage S, Speakman MJ: Tamsulosin, the first prostate-selective alpha 1A-adrenoceptor antagonist. Analysis of a multinational, multicentre, open-label study assessing the long-term efficacy and safety in patients with benign prostatic obstruction (symptomatic BPH). European Tamsulosin Study Group. Eur Urol. 1996;29(2):145-54. [PubMed:8647140 ]
Chen Y, Li H, Dong Q, Wang KJ: Blockade of alpha 1A-adrenoceptor: a novel possible strategy for male contraception. Med Hypotheses. 2009 Aug;73(2):140-1. doi: 10.1016/j.mehy.2009.02.022. Epub 2009 May 8. [PubMed:19427736 ]
Michel MC, de la Rosette JJ: Efficacy and safety of tamsulosin in the treatment of urological diseases. Expert Opin Pharmacother. 2004 Jan;5(1):151-60. [PubMed:14680444 ]

Enzyme Details

4. Alpha-1B adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
Gene Name:: ADRA1B
Uniprot ID:: P35368
Molecular weight:: 56835.4

References

Ishiguro M, Futabayashi Y, Ohnuki T, Ahmed M, Muramatsu I, Nagatomo T: Identification of binding sites of prazosin, tamsulosin and KMD-3213 with alpha(1)-adrenergic receptor subtypes by molecular modeling. Life Sci. 2002 Oct 11;71(21):2531-41. [PubMed:12270758 ]
Michel MC, Hanft G, Gross G: Functional studies on alpha 1-adrenoceptor subtypes mediating inotropic effects in rat right ventricle. Br J Pharmacol. 1994 Feb;111(2):539-46. [PubMed:7911719 ]
Taguchi K, Saitoh M, Sato S, Asano M, Michel MC: Effects of tamsulosin metabolites at alpha-1 adrenoceptor subtypes. J Pharmacol Exp Ther. 1997 Jan;280(1):1-5. [PubMed:8996174 ]
Richardson CD, Donatucci CF, Page SO, Wilson KH, Schwinn DA: Pharmacology of tamsulosin: saturation-binding isotherms and competition analysis using cloned alpha 1-adrenergic receptor subtypes. Prostate. 1997 Sep 15;33(1):55-9. [PubMed:9294627 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Michel MC, de la Rosette JJ: Efficacy and safety of tamsulosin in the treatment of urological diseases. Expert Opin Pharmacother. 2004 Jan;5(1):151-60. [PubMed:14680444 ]

Enzyme Details

5. Alpha-1D adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium
Gene Name:: ADRA1D
Uniprot ID:: P25100
Molecular weight:: 60462.2

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Noble AJ, Chess-Williams R, Couldwell C, Furukawa K, Uchyiuma T, Korstanje C, Chapple CR: The effects of tamsulosin, a high affinity antagonist at functional alpha 1A- and alpha 1D-adrenoceptor subtypes. Br J Pharmacol. 1997 Jan;120(2):231-8. [PubMed:9117115 ]
Lowe FC: Summary of clinical experiences with tamsulosin for the treatment of benign prostatic hyperplasia. Rev Urol. 2005;7 Suppl 4:S13-21. [PubMed:16986050 ]
Tomiyama Y, Tatemichi S, Tadachi M, Kobayashi S, Hayashi M, Kobayashi M, Yamazaki Y, Shibata N: [Effect of silodosin on intraurethral pressure increase induced by hypogastric nerve stimulation in dogs with benign prostatic hyperplasia]. Yakugaku Zasshi. 2006 Mar;126 Spec no.:225-30. [PubMed:16518087 ]
Ishiguro M, Futabayashi Y, Ohnuki T, Ahmed M, Muramatsu I, Nagatomo T: Identification of binding sites of prazosin, tamsulosin and KMD-3213 with alpha(1)-adrenergic receptor subtypes by molecular modeling. Life Sci. 2002 Oct 11;71(21):2531-41. [PubMed:12270758 ]
Taguchi K, Saitoh M, Sato S, Asano M, Michel MC: Effects of tamsulosin metabolites at alpha-1 adrenoceptor subtypes. J Pharmacol Exp Ther. 1997 Jan;280(1):1-5. [PubMed:8996174 ]
Michel MC, de la Rosette JJ: Efficacy and safety of tamsulosin in the treatment of urological diseases. Expert Opin Pharmacother. 2004 Jan;5(1):151-60. [PubMed:14680444 ]

Showing metabocard for Tamsulosin (HMDB0014844)

MOL for HMDB0014844 (Tamsulosin)

3D MOL for HMDB0014844 (Tamsulosin)

3D SDF for HMDB0014844 (Tamsulosin)

3D-SDF for HMDB0014844 (Tamsulosin)

PDB for HMDB0014844 (Tamsulosin)

3D PDB for HMDB0014844 (Tamsulosin)

SMILES for HMDB0014844 (Tamsulosin)

INCHI for HMDB0014844 (Tamsulosin)

Structure for HMDB0014844 (Tamsulosin)

3D Structure for HMDB0014844 (Tamsulosin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

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