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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-18 09:02:16 UTC

Update Date

2022-03-07 02:49:11 UTC

HMDB ID

HMDB0001937

Secondary Accession Numbers

HMDB01937

Metabolite Identification

Common Name

Salbutamol

Description

Salbutamol is a short-acting, selective beta2-adrenergic receptor agonist used in the treatment of asthma and COPD. It is 29 times more selective for beta2 receptors than beta1 receptors giving it higher specificity for pulmonary beta receptors versus beta1-adrenergic receptors located in the heart. Salbutamol is formulated as a racemic mixture of the R- and S-isomers. The R-isomer has 150 times greater affinity for the beta2-receptor than the S-isomer and the S-isomer has been associated with toxicity. This lead to the development of levalbuterol, the single R-isomer of salbutamol. However, the high cost of levalbuterol compared to salbutamol has deterred wide-spread use of this enantiomerically pure version of the drug. Salbutamol is generally used for acute episodes of bronchospasm caused by bronchial asthma, chronic bronchitis and other chronic bronchopulmonary disorders such as chronic obstructive pulmonary disorder (COPD). It is also used prophylactically for exercise-induced asthma

Structure

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

HMDB0001937
     RDKit          3D
Salbutamol
 38 38  0  0  0  0  0  0  0  0999 V2000
   -4.0128    0.6562    0.7762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9633   -0.3847    0.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2048   -1.5498    1.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2450   -0.8422   -0.9681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6337    0.0636    0.6596 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1840    1.1682   -0.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2231    1.5309    0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5567    2.6788   -0.5033 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2394    0.4980    0.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9498   -0.7908   -0.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9819   -1.7130   -0.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2956   -1.3062   -0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3573   -2.1742   -0.5797 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6014   -0.0066   -0.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139    0.4108    0.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0635    1.7628    0.4417 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5802    0.8847    0.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9814    0.1116    0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7446    1.0539    1.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1338    1.4155    0.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7952   -2.5030    0.9688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6971   -1.2814    2.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2952   -1.6773    1.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3658   -0.8615   -1.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9012   -0.1255   -1.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8865   -1.8465   -1.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4440    0.0795    1.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8551    2.0495   -0.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1459    0.8334   -1.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3233    1.8621    1.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2062    3.0249   -0.9926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0748   -1.1567   -0.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7346   -2.7289   -0.7902 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1507   -3.1158   -0.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5941    0.2800   -0.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4830   -0.1520    0.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7943    1.9362    1.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8279    1.9156    0.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
M  END

1001
  Mrv1652305271900282D          

 17 17  0  0  1  0            999 V2000
    3.5220    1.0082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -2.7044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -1.4669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    1.8332    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    2.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    1.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799    2.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2530    2.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0780    1.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -0.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -1.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -1.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2 15  1  0  0  0  0
  3 17  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 16  2  0  0  0  0
 14 15  2  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001937

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(C)NCC(O)C1=CC(CO)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H21NO3/c1-13(2,3)14-7-12(17)9-4-5-11(16)10(6-9)8-15/h4-6,12,14-17H,7-8H2,1-3H3

> <INCHI_KEY>
NDAUXUAQIAJITI-UHFFFAOYSA-N

> <FORMULA>
C13H21NO3

> <MOLECULAR_WEIGHT>
239.3107

> <EXACT_MASS>
239.152143543

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.858046828350286

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol

> <ALOGPS_LOGP>
0.44

> <JCHEM_LOGP>
0.3444161509994905

> <ALOGPS_LOGS>
-2.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.17970015088174

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.121162873207071

> <JCHEM_PKA_STRONGEST_BASIC>
9.403548944560061

> <JCHEM_POLAR_SURFACE_AREA>
72.72

> <JCHEM_REFRACTIVITY>
67.8709

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.15e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
salbutamol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001937
     RDKit          3D
Salbutamol
 38 38  0  0  0  0  0  0  0  0999 V2000
   -4.0128    0.6562    0.7762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9633   -0.3847    0.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2048   -1.5498    1.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2450   -0.8422   -0.9681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6337    0.0636    0.6596 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1840    1.1682   -0.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2231    1.5309    0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5567    2.6788   -0.5033 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2394    0.4980    0.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9498   -0.7908   -0.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9819   -1.7130   -0.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2956   -1.3062   -0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3573   -2.1742   -0.5797 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6014   -0.0066   -0.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139    0.4108    0.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0635    1.7628    0.4417 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5802    0.8847    0.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9814    0.1116    0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7446    1.0539    1.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1338    1.4155    0.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7952   -2.5030    0.9688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6971   -1.2814    2.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2952   -1.6773    1.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3658   -0.8615   -1.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9012   -0.1255   -1.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8865   -1.8465   -1.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4440    0.0795    1.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8551    2.0495   -0.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1459    0.8334   -1.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3233    1.8621    1.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2062    3.0249   -0.9926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0748   -1.1567   -0.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7346   -2.7289   -0.7902 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1507   -3.1158   -0.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5941    0.2800   -0.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4830   -0.1520    0.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7943    1.9362    1.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8279    1.9156    0.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1001                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       6.574   1.882   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       7.908  -5.048   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.907  -2.738   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       9.242   3.422   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      10.576   4.192   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.242   1.882   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.908   1.112   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.909   4.962   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.806   5.526   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.346   2.858   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.908  -0.428   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.574  -1.198   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.242  -1.198   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.574  -2.738   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.908  -3.508   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.242  -2.738   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.241  -3.508   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2   15                                                            
CONECT    3   17                                                            
CONECT    4    5    6                                                       
CONECT    5    4    8    9   10                                             
CONECT    6    4    7                                                       
CONECT    7    1    6   11                                                  
CONECT    8    5                                                            
CONECT    9    5                                                            
CONECT   10    5                                                            
CONECT   11    7   12   13                                                  
CONECT   12   11   14                                                       
CONECT   13   11   16                                                       
CONECT   14   12   15   17                                                  
CONECT   15    2   14   16                                                  
CONECT   16   13   15                                                       
CONECT   17    3   14                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0243716
HETATM    1  C1  UNL     1      -3.182   1.664  -0.902  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.293   0.395  -0.037  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.537   0.758   1.372  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.537  -0.329  -0.539  1.00  0.00           C  
HETATM    5  N1  UNL     1      -2.198  -0.444  -0.335  1.00  0.00           N  
HETATM    6  C5  UNL     1      -0.874  -0.056   0.029  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.048  -0.868  -0.928  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.426  -2.201  -0.720  1.00  0.00           O  
HETATM    9  C7  UNL     1       1.425  -0.788  -0.450  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.948  -1.952   0.179  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.212  -1.978   0.706  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.977  -0.846   0.620  1.00  0.00           C  
HETATM   13  O2  UNL     1       5.281  -0.863   1.152  1.00  0.00           O  
HETATM   14  C11 UNL     1       3.489   0.274   0.020  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.334   1.490   0.115  1.00  0.00           C  
HETATM   16  O3  UNL     1       4.921   1.777  -1.155  1.00  0.00           O  
HETATM   17  C13 UNL     1       2.216   0.311  -0.521  1.00  0.00           C  
HETATM   18  H1  UNL     1      -2.938   1.307  -1.935  1.00  0.00           H  
HETATM   19  H2  UNL     1      -4.183   2.104  -0.954  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.485   2.390  -0.513  1.00  0.00           H  
HETATM   21  H4  UNL     1      -2.772   1.416   1.796  1.00  0.00           H  
HETATM   22  H5  UNL     1      -4.534   1.333   1.356  1.00  0.00           H  
HETATM   23  H6  UNL     1      -3.705  -0.171   1.942  1.00  0.00           H  
HETATM   24  H7  UNL     1      -4.294  -1.381  -0.887  1.00  0.00           H  
HETATM   25  H8  UNL     1      -4.991   0.157  -1.426  1.00  0.00           H  
HETATM   26  H9  UNL     1      -5.267  -0.511   0.286  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.402  -1.437  -0.027  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.683   0.998  -0.076  1.00  0.00           H  
HETATM   29  H12 UNL     1      -0.578  -0.362   1.040  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.173  -0.524  -1.945  1.00  0.00           H  
HETATM   31  H14 UNL     1      -0.582  -2.304   0.252  1.00  0.00           H  
HETATM   32  H15 UNL     1       1.344  -2.883   0.199  1.00  0.00           H  
HETATM   33  H16 UNL     1       3.548  -2.889   1.152  1.00  0.00           H  
HETATM   34  H17 UNL     1       5.889  -0.024   1.079  1.00  0.00           H  
HETATM   35  H18 UNL     1       3.525   2.389   0.057  1.00  0.00           H  
HETATM   36  H19 UNL     1       4.894   1.731   0.960  1.00  0.00           H  
HETATM   37  H20 UNL     1       5.679   1.082  -1.270  1.00  0.00           H  
HETATM   38  H21 UNL     1       1.902   1.235  -0.975  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4    5
CONECT    3   21   22   23
CONECT    4   24   25   26
CONECT    5    6   27
CONECT    6    7   28   29
CONECT    7    8    9   30
CONECT    8   31
CONECT    9   10   10   17
CONECT   10   11   32
CONECT   11   12   12   33
CONECT   12   13   14
CONECT   13   34
CONECT   14   15   17   17
CONECT   15   16   35   36
CONECT   16   37
CONECT   17   38
END

HMDB0001937
     RDKit          3D
Salbutamol
 38 38  0  0  0  0  0  0  0  0999 V2000
   -4.0128    0.6562    0.7762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9633   -0.3847    0.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2048   -1.5498    1.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2450   -0.8422   -0.9681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6337    0.0636    0.6596 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1840    1.1682   -0.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2231    1.5309    0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5567    2.6788   -0.5033 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2394    0.4980    0.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9498   -0.7908   -0.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9819   -1.7130   -0.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2956   -1.3062   -0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3573   -2.1742   -0.5797 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6014   -0.0066   -0.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139    0.4108    0.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0635    1.7628    0.4417 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5802    0.8847    0.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9814    0.1116    0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7446    1.0539    1.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1338    1.4155    0.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7952   -2.5030    0.9688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6971   -1.2814    2.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2952   -1.6773    1.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3658   -0.8615   -1.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9012   -0.1255   -1.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8865   -1.8465   -1.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4440    0.0795    1.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8551    2.0495   -0.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1459    0.8334   -1.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3233    1.8621    1.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2062    3.0249   -0.9926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0748   -1.1567   -0.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7346   -2.7289   -0.7902 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1507   -3.1158   -0.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5941    0.2800   -0.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4830   -0.1520    0.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7943    1.9362    1.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8279    1.9156    0.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Proventil	ChEBI
(L)-Albuterol	HMDB
1-(Tert-butylaminomethyl)-4-hydroxy-m-xylene-alpha1,alpha3-diol	HMDB
2-(Tert-butylamino)-1-(4-hydroxy-3-hydroxymethylphenyl)ethanol	HMDB
4-Hydroxy-3-hydroxymethyl-alpha-((tert-butylamino)methyl)benzyl alcohol	HMDB
Aerolin	HMDB
Albuterol	HMDB
Almotex	HMDB
Alpha'-((tert-butylamino)methyl)-4-hydroxy-m-xylene-alpha,alpha'-diol	HMDB
Alti-salbutamol	HMDB
Anebron	HMDB
Arubendol-salbutamol	HMDB
Asmadil	HMDB
Asmanil	HMDB
Asmasal	HMDB
Asmatol	HMDB
Asmaven	HMDB
Asmidon	HMDB
Asmol	HMDB
Asmol uni-dose	HMDB
Asthalin	HMDB
Broncho-spray	HMDB
Broncovaleas	HMDB
Bronter	HMDB
Bugonol	HMDB
Bumol	HMDB
Butamol	HMDB
Buto-asma	HMDB
Butohaler	HMDB
Butotal	HMDB
Butovent	HMDB
Buventol	HMDB
Cobutolin	HMDB
Dilatamol	HMDB
DL-Albuterol	HMDB
DL-N-Tert-butyl-2-(4-hydroxy-3-hydroxymethylphenyl)-2-hydroxyethylamine	HMDB
DL-Salbutamol	HMDB
Farcolin	HMDB
Gerivent	HMDB
Grafalin	HMDB
Levalbuterol	HMDB
Libretin	HMDB
Medolin	HMDB
Mozal	HMDB
Novosalmol	HMDB
Parasma	HMDB
Pneumolat	HMDB
Proventil hfa	HMDB
Proventil inhaler	HMDB
R-Salbutamol	HMDB
Respax	HMDB
Respolin	HMDB
Sabutal	HMDB
Salamol	HMDB
Salbetol	HMDB
Salbron	HMDB
Salbu-basf	HMDB
Salbu-fatol	HMDB
Salbuhexal	HMDB
Salbulin	HMDB
Salbupur	HMDB
Salbusian	HMDB
Salbutalan	HMDB
Salbutamol free base	HMDB
Salbutamol sulfate	HMDB
Salbutamol sulphate	HMDB
Salbutamolum	HMDB
Salbutan	HMDB
Salbutol	HMDB
Salbuven	HMDB
Salbuvent	HMDB
Sallbupp	HMDB
Salmaplon	HMDB
Salomol	HMDB
Salvent	HMDB
Saventol	HMDB
Servitamol	HMDB
Spreor	HMDB
Sultanol	HMDB
Sultanol N	HMDB
Suprasma	HMDB
Suxar	HMDB
Theosal	HMDB
Tobybron	HMDB
Vencronyl	HMDB
Ventamol	HMDB
Ventilan	HMDB
Ventiloboi	HMDB
Ventodisks	HMDB
Ventolin	HMDB
Ventolin inhaler	HMDB
Ventolin rotacaps	HMDB
Ventoline	HMDB
Volare albuterol hfa	HMDB
Volare easi-breathe	HMDB
Volmax	HMDB
Zaperin	HMDB
2-t-Butylamino-1-(4-hydroxy-3-hydroxy-3-hydroxymethyl)phenylethanol	HMDB
Albuterol sulfate	HMDB

Chemical Formula

C₁₃H₂₁NO₃

Average Molecular Weight

239.3107

Monoisotopic Molecular Weight

239.152143543

IUPAC Name

4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol

Traditional Name

salbutamol

CAS Registry Number

18559-94-9

SMILES

CC(C)(C)NCC(O)C1=CC(CO)=C(O)C=C1

InChI Identifier

InChI=1S/C13H21NO3/c1-13(2,3)14-7-12(17)9-4-5-11(16)10(6-9)8-15/h4-6,12,14-17H,7-8H2,1-3H3

InChI Key

NDAUXUAQIAJITI-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
Secondary amine
Secondary aliphatic amine
Hydrocarbon derivative
Alcohol
Aromatic alcohol
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenylethanolamines (CHEBI:2549 )
phenols (CHEBI:2549 )
secondary amino compound (CHEBI:2549 )

Ontology

Not Available

Smooth muscle (HMDB: HMDB0001937)

Cellular substructure

Cytoplasm (HMDB: HMDB0001937)
Extracellular (HMDB: HMDB0001937)

Source

Exogenous

Exogenous (HMDB: HMDB0001937)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	157 - 158 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2.15 g/L	Not Available
LogP	1.4	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	160.0	30932474
[M+H]+	Not Available	158.411	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000805

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.15 g/L	ALOGPS
logP	0.44	ALOGPS
logP	0.34	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	10.12	ChemAxon
pKa (Strongest Basic)	9.4	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	72.72 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	67.87 m³·mol⁻¹	ChemAxon
Polarizability	26.86 Å³	ChemAxon
Number of Rings	1	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]+	156.58	31661259
DarkChem	[M-H]-	156.364	31661259
AllCCS	[M+H]+	155.662	32859911
AllCCS	[M-H]-	158.757	32859911
DeepCCS	[M+H]+	165.879	30932474
DeepCCS	[M-H]-	163.521	30932474
DeepCCS	[M-2H]-	196.408	30932474
DeepCCS	[M+Na]+	171.972	30932474
AllCCS	[M+H]+	155.7	32859911
AllCCS	[M+H-H2O]+	152.1	32859911
AllCCS	[M+NH4]+	159.0	32859911
AllCCS	[M+Na]+	159.9	32859911
AllCCS	[M-H]-	158.8	32859911
AllCCS	[M+Na-2H]-	159.5	32859911
AllCCS	[M+HCOO]-	160.3	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.	1.83 minutes	32390414
Predicted by Siyang on May 30, 2022	9.343 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.27 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	152.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Salbutamol	CC(C)(C)NCC(O)C1=CC(CO)=C(O)C=C1	3305.0	Standard polar	33892256
Salbutamol	CC(C)(C)NCC(O)C1=CC(CO)=C(O)C=C1	1964.3	Standard non polar	33892256
Salbutamol	CC(C)(C)NCC(O)C1=CC(CO)=C(O)C=C1	2119.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Salbutamol,1TMS,isomer #1	CC(C)(C)NCC(O[Si](C)(C)C)C1=CC=C(O)C(CO)=C1	2023.4	Semi standard non polar	33892256
Salbutamol,1TMS,isomer #2	CC(C)(C)NCC(O)C1=CC=C(O)C(CO[Si](C)(C)C)=C1	2112.8	Semi standard non polar	33892256
Salbutamol,1TMS,isomer #3	CC(C)(C)NCC(O)C1=CC=C(O[Si](C)(C)C)C(CO)=C1	2054.7	Semi standard non polar	33892256
Salbutamol,1TMS,isomer #4	CC(C)(C)N(CC(O)C1=CC=C(O)C(CO)=C1)[Si](C)(C)C	2224.3	Semi standard non polar	33892256
Salbutamol,2TMS,isomer #1	CC(C)(C)NCC(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(CO)=C1	1915.8	Semi standard non polar	33892256
Salbutamol,2TMS,isomer #2	CC(C)(C)NCC(O[Si](C)(C)C)C1=CC=C(O)C(CO[Si](C)(C)C)=C1	1981.3	Semi standard non polar	33892256
Salbutamol,2TMS,isomer #3	CC(C)(C)N(CC(O[Si](C)(C)C)C1=CC=C(O)C(CO)=C1)[Si](C)(C)C	2222.5	Semi standard non polar	33892256
Salbutamol,2TMS,isomer #4	CC(C)(C)NCC(O)C1=CC=C(O[Si](C)(C)C)C(CO[Si](C)(C)C)=C1	2031.1	Semi standard non polar	33892256
Salbutamol,2TMS,isomer #5	CC(C)(C)N(CC(O)C1=CC=C(O)C(CO[Si](C)(C)C)=C1)[Si](C)(C)C	2245.4	Semi standard non polar	33892256
Salbutamol,2TMS,isomer #6	CC(C)(C)N(CC(O)C1=CC=C(O[Si](C)(C)C)C(CO)=C1)[Si](C)(C)C	2196.9	Semi standard non polar	33892256
Salbutamol,3TMS,isomer #1	CC(C)(C)NCC(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(CO[Si](C)(C)C)=C1	1921.0	Semi standard non polar	33892256
Salbutamol,3TMS,isomer #2	CC(C)(C)N(CC(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(CO)=C1)[Si](C)(C)C	2188.6	Semi standard non polar	33892256
Salbutamol,3TMS,isomer #3	CC(C)(C)N(CC(O[Si](C)(C)C)C1=CC=C(O)C(CO[Si](C)(C)C)=C1)[Si](C)(C)C	2242.2	Semi standard non polar	33892256
Salbutamol,3TMS,isomer #4	CC(C)(C)N(CC(O)C1=CC=C(O[Si](C)(C)C)C(CO[Si](C)(C)C)=C1)[Si](C)(C)C	2232.1	Semi standard non polar	33892256
Salbutamol,4TMS,isomer #1	CC(C)(C)N(CC(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(CO[Si](C)(C)C)=C1)[Si](C)(C)C	2249.8	Semi standard non polar	33892256
Salbutamol,4TMS,isomer #1	CC(C)(C)N(CC(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(CO[Si](C)(C)C)=C1)[Si](C)(C)C	2252.4	Standard non polar	33892256
Salbutamol,4TMS,isomer #1	CC(C)(C)N(CC(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(CO[Si](C)(C)C)=C1)[Si](C)(C)C	2116.4	Standard polar	33892256
Salbutamol,1TBDMS,isomer #1	CC(C)(C)NCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(CO)=C1	2286.6	Semi standard non polar	33892256
Salbutamol,1TBDMS,isomer #2	CC(C)(C)NCC(O)C1=CC=C(O)C(CO[Si](C)(C)C(C)(C)C)=C1	2330.6	Semi standard non polar	33892256
Salbutamol,1TBDMS,isomer #3	CC(C)(C)NCC(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(CO)=C1	2308.2	Semi standard non polar	33892256
Salbutamol,1TBDMS,isomer #4	CC(C)(C)N(CC(O)C1=CC=C(O)C(CO)=C1)[Si](C)(C)C(C)(C)C	2478.9	Semi standard non polar	33892256
Salbutamol,2TBDMS,isomer #1	CC(C)(C)NCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(CO)=C1	2445.5	Semi standard non polar	33892256
Salbutamol,2TBDMS,isomer #2	CC(C)(C)NCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(CO[Si](C)(C)C(C)(C)C)=C1	2470.2	Semi standard non polar	33892256
Salbutamol,2TBDMS,isomer #3	CC(C)(C)N(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(CO)=C1)[Si](C)(C)C(C)(C)C	2730.3	Semi standard non polar	33892256
Salbutamol,2TBDMS,isomer #4	CC(C)(C)NCC(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)=C1	2537.4	Semi standard non polar	33892256
Salbutamol,2TBDMS,isomer #5	CC(C)(C)N(CC(O)C1=CC=C(O)C(CO[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2744.9	Semi standard non polar	33892256
Salbutamol,2TBDMS,isomer #6	CC(C)(C)N(CC(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(CO)=C1)[Si](C)(C)C(C)(C)C	2727.9	Semi standard non polar	33892256
Salbutamol,3TBDMS,isomer #1	CC(C)(C)NCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)=C1	2644.6	Semi standard non polar	33892256
Salbutamol,3TBDMS,isomer #2	CC(C)(C)N(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(CO)=C1)[Si](C)(C)C(C)(C)C	2926.9	Semi standard non polar	33892256
Salbutamol,3TBDMS,isomer #3	CC(C)(C)N(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(CO[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2945.8	Semi standard non polar	33892256
Salbutamol,3TBDMS,isomer #4	CC(C)(C)N(CC(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2973.8	Semi standard non polar	33892256
Salbutamol,4TBDMS,isomer #1	CC(C)(C)N(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	3136.2	Semi standard non polar	33892256
Salbutamol,4TBDMS,isomer #1	CC(C)(C)N(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2964.8	Standard non polar	33892256
Salbutamol,4TBDMS,isomer #1	CC(C)(C)N(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2549.4	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Smooth Muscle

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

DB01001

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022752

KNApSAcK ID

Not Available

Chemspider ID

1999

KEGG Compound ID

C11770

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Albuterol

METLIN ID

799

PubChem Compound

2083

PDB ID

Not Available

ChEBI ID

2549

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)

Download (PDF)

General References

Fayon M, Dumas De La Roque E, Berger P, Begueret H, Ousova O, Molimard M, Marthan R: Increased relaxation of immature airways to beta2-adrenoceptor agonists is related to attenuated expression of postjunctional smooth muscle muscarinic M2 receptors. J Appl Physiol (1985). 2005 Apr;98(4):1526-33. Epub 2004 Dec 3. [PubMed:15579574 ]
Yoshihara S, Yamada Y, Abe T, Kashimoto K, Linden A, Arisaka O: Long-lasting smooth-muscle relaxation by a novel PACAP analogue in human bronchi. Regul Pept. 2004 Dec 15;123(1-3):161-5. [PubMed:15518907 ]

Enzymes

Enzyme Details

1. 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

Enzyme Details

2. Interleukin-8

General function:: Involved in cytokine activity
Specific function:: IL-8 is a chemotactic factor that attracts neutrophils, basophils, and T-cells, but not monocytes. It is also involved in neutrophil activation. It is released from several cell types in response to an inflammatory stimulus. IL-8(6-77) has a 5-10-fold higher activity on neutrophil activation, IL-8(5-77) has increased activity on neutrophil activation and IL-8(7-77) has a higher affinity to receptors CXCR1 and CXCR2 as compared to IL-8(1-77), respectively
Gene Name:: IL8
Uniprot ID:: P10145
Molecular weight:: 11098.0

Showing metabocard for Salbutamol (HMDB0001937)

MOL for HMDB0001937 (Salbutamol)

3D MOL for HMDB0001937 (Salbutamol)

3D SDF for HMDB0001937 (Salbutamol)

3D-SDF for HMDB0001937 (Salbutamol)

PDB for HMDB0001937 (Salbutamol)

3D PDB for HMDB0001937 (Salbutamol)

SMILES for HMDB0001937 (Salbutamol)

INCHI for HMDB0001937 (Salbutamol)

Structure for HMDB0001937 (Salbutamol)

3D Structure for HMDB0001937 (Salbutamol)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes