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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:58 UTC

HMDB ID

HMDB0015399

Secondary Accession Numbers

HMDB15399

Metabolite Identification

Common Name

Arformoterol

Description

Arformoterol is a bronchodilator. It works by relaxing muscles in the airways to improve breathing. Arformoterol inhalation is used to prevent bronchoconstriction in people with chronic obstructive pulmonary disease, including chronic bronchitis and emphysema. The use of arformoterol is pending revision due to safety concerns in regards to an increased risk of severe exacerbation of asthma symptoms, leading to hospitalization as well as death in some patients using long acting beta agonists for the treatment of asthma.

Structure

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

HMDB0015399
     RDKit          3D
Arformoterol
 49 50  0  0  0  0  0  0  0  0999 V2000
    6.9865   -2.7588   -0.4045 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6762   -1.7023    0.4720 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3852   -1.2484    0.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1404   -0.2170    1.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8500    0.2284    1.5622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8175   -0.3214    0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4624    0.1849    1.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1775    1.4050    0.1513 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2965    1.1062   -1.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0245    2.0358    0.6157 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9468    2.4874   -0.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7574    1.4432   -0.9850 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4838    2.0187   -2.1027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8878    0.9285   -0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0850    1.3286    1.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1572    0.8375    1.9108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0190   -0.0629    1.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0690   -0.5442    2.0650 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8437   -0.5048    0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7544   -1.4309   -0.5630 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7353   -1.9689   -1.8394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8576   -1.6898   -2.6879 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7763    0.0050   -0.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1041   -1.3442   -0.0256 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3929   -1.8248   -0.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5771   -3.7435   -0.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5657   -2.5556   -1.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1008   -2.8516   -0.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9422    0.2422    2.0495 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5975    1.0511    2.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7096   -0.5869    0.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2246    0.5032    2.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0355    2.1586    0.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6886    1.7621   -1.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0579    0.0615   -1.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3586    1.3383   -1.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4281    1.3976    1.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6743    3.1720    0.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4890    3.2111   -1.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2485    0.5649   -1.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6495    2.9604   -1.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4754    2.0471    1.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2828    1.1807    2.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7886   -1.1570    1.8975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5578   -1.7481    0.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4883   -2.6640   -2.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5955   -0.2955   -1.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3228   -1.7970   -0.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6054   -2.6422   -0.8501 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 19 23  2  0
  6 24  1  0
 24 25  2  0
 25  3  1  0
 23 14  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  1
  9 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  6
 13 41  1  0
 15 42  1  0
 16 43  1  0
 18 44  1  0
 20 45  1  0
 21 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  0
M  END

1274
  Mrv0541 02231215222D          

 25 26  0  0  1  0            999 V2000
    5.6655    1.8068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799   -4.3808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    3.0443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    3.8693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    0.1568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    3.8693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -0.6683    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3799   -1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    1.3943    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9509   -1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799   -1.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    1.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    2.6318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944   -2.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -2.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    3.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944   -3.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -3.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    2.6318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799   -3.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    4.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944   -4.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  1  0  0  0
  2 23  1  0  0  0  0
  2 25  1  0  0  0  0
  3 22  1  0  0  0  0
  4 24  2  0  0  0  0
  7  5  1  1  0  0  0
  5  9  1  0  0  0  0
  6 18  1  0  0  0  0
  6 24  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
 10 13  1  0  0  0  0
 12 15  2  0  0  0  0
 12 16  1  0  0  0  0
 13 14  2  0  0  0  0
 13 17  1  0  0  0  0
 14 18  1  0  0  0  0
 15 20  1  0  0  0  0
 16 21  2  0  0  0  0
 17 19  2  0  0  0  0
 18 22  2  0  0  0  0
 19 22  1  0  0  0  0
 20 23  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015399

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(C[C@@H](C)NC[C@H](O)C2=CC(NC=O)=C(O)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H24N2O4/c1-13(9-14-3-6-16(25-2)7-4-14)20-11-19(24)15-5-8-18(23)17(10-15)21-12-22/h3-8,10,12-13,19-20,23-24H,9,11H2,1-2H3,(H,21,22)/t13-,19+/m1/s1

> <INCHI_KEY>
BPZSYCZIITTYBL-YJYMSZOUSA-N

> <FORMULA>
C19H24N2O4

> <MOLECULAR_WEIGHT>
344.4049

> <EXACT_MASS>
344.173607266

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
36.55917458324811

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-{2-hydroxy-5-[(1R)-1-hydroxy-2-{[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino}ethyl]phenyl}formamide

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
1.0566727363571802

> <ALOGPS_LOGS>
-3.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.208372164637407

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.607353493587993

> <JCHEM_PKA_STRONGEST_BASIC>
9.811207541594007

> <JCHEM_POLAR_SURFACE_AREA>
90.82

> <JCHEM_REFRACTIVITY>
97.87150000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.16e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
arformoterol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015399
     RDKit          3D
Arformoterol
 49 50  0  0  0  0  0  0  0  0999 V2000
    6.9865   -2.7588   -0.4045 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6762   -1.7023    0.4720 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3852   -1.2484    0.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1404   -0.2170    1.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8500    0.2284    1.5622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8175   -0.3214    0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4624    0.1849    1.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1775    1.4050    0.1513 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2965    1.1062   -1.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0245    2.0358    0.6157 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9468    2.4874   -0.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7574    1.4432   -0.9850 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4838    2.0187   -2.1027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8878    0.9285   -0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0850    1.3286    1.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1572    0.8375    1.9108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0190   -0.0629    1.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0690   -0.5442    2.0650 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8437   -0.5048    0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7544   -1.4309   -0.5630 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7353   -1.9689   -1.8394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8576   -1.6898   -2.6879 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7763    0.0050   -0.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1041   -1.3442   -0.0256 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3929   -1.8248   -0.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5771   -3.7435   -0.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5657   -2.5556   -1.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1008   -2.8516   -0.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9422    0.2422    2.0495 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5975    1.0511    2.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7096   -0.5869    0.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2246    0.5032    2.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0355    2.1586    0.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6886    1.7621   -1.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0579    0.0615   -1.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3586    1.3383   -1.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4281    1.3976    1.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6743    3.1720    0.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4890    3.2111   -1.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2485    0.5649   -1.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6495    2.9604   -1.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4754    2.0471    1.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2828    1.1807    2.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7886   -1.1570    1.8975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5578   -1.7481    0.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4883   -2.6640   -2.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5955   -0.2955   -1.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3228   -1.7970   -0.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6054   -2.6422   -0.8501 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 19 23  2  0
  6 24  1  0
 24 25  2  0
 25  3  1  0
 23 14  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  1
  9 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  6
 13 41  1  0
 15 42  1  0
 16 43  1  0
 18 44  1  0
 20 45  1  0
 21 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1274                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      10.576   3.373   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      11.909  -8.177   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.907   5.683   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.242   7.223   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      10.576   0.293   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       6.574   7.223   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      10.576  -1.247   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.909  -2.017   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.242   1.063   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.242   2.603   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.242  -2.017   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.909  -3.557   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.908   3.373   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.908   4.913   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.243  -4.327   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.576  -4.327   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.574   2.603   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.574   5.683   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.241   3.373   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.243  -5.867   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.576  -5.867   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.241   4.913   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.909  -6.637   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.908   7.993   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.243  -8.948   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2   23   25                                                       
CONECT    3   22                                                            
CONECT    4   24                                                            
CONECT    5    7    9                                                       
CONECT    6   18   24                                                       
CONECT    7    5    8   11                                                  
CONECT    8    7   12                                                       
CONECT    9    5   10                                                       
CONECT   10    1    9   13                                                  
CONECT   11    7                                                            
CONECT   12    8   15   16                                                  
CONECT   13   10   14   17                                                  
CONECT   14   13   18                                                       
CONECT   15   12   20                                                       
CONECT   16   12   21                                                       
CONECT   17   13   19                                                       
CONECT   18    6   14   22                                                  
CONECT   19   17   22                                                       
CONECT   20   15   23                                                       
CONECT   21   16   23                                                       
CONECT   22    3   18   19                                                  
CONECT   23    2   20   21                                                  
CONECT   24    4    6                                                       
CONECT   25    2                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0015399
HETATM    1  C1  UNL     1       6.986  -2.759  -0.405  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.676  -1.702   0.472  1.00  0.00           O  
HETATM    3  C2  UNL     1       5.385  -1.248   0.583  1.00  0.00           C  
HETATM    4  C3  UNL     1       5.140  -0.217   1.456  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.850   0.228   1.562  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.817  -0.321   0.830  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.462   0.185   1.008  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.178   1.405   0.151  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.296   1.106  -1.290  1.00  0.00           C  
HETATM   10  N1  UNL     1      -0.024   2.036   0.616  1.00  0.00           N  
HETATM   11  C9  UNL     1      -0.947   2.487  -0.343  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.757   1.443  -0.985  1.00  0.00           C  
HETATM   13  O2  UNL     1      -2.484   2.019  -2.103  1.00  0.00           O  
HETATM   14  C11 UNL     1      -2.888   0.928  -0.114  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.085   1.329   1.159  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.157   0.838   1.911  1.00  0.00           C  
HETATM   17  C14 UNL     1      -5.019  -0.063   1.337  1.00  0.00           C  
HETATM   18  O3  UNL     1      -6.069  -0.544   2.065  1.00  0.00           O  
HETATM   19  C15 UNL     1      -4.844  -0.505   0.001  1.00  0.00           C  
HETATM   20  N2  UNL     1      -5.754  -1.431  -0.563  1.00  0.00           N  
HETATM   21  C16 UNL     1      -5.735  -1.969  -1.839  1.00  0.00           C  
HETATM   22  O4  UNL     1      -4.858  -1.690  -2.688  1.00  0.00           O  
HETATM   23  C17 UNL     1      -3.776   0.005  -0.694  1.00  0.00           C  
HETATM   24  C18 UNL     1       3.104  -1.344  -0.026  1.00  0.00           C  
HETATM   25  C19 UNL     1       4.393  -1.825  -0.163  1.00  0.00           C  
HETATM   26  H1  UNL     1       6.577  -3.744  -0.084  1.00  0.00           H  
HETATM   27  H2  UNL     1       6.566  -2.556  -1.428  1.00  0.00           H  
HETATM   28  H3  UNL     1       8.101  -2.852  -0.449  1.00  0.00           H  
HETATM   29  H4  UNL     1       5.942   0.242   2.049  1.00  0.00           H  
HETATM   30  H5  UNL     1       3.598   1.051   2.242  1.00  0.00           H  
HETATM   31  H6  UNL     1       0.710  -0.587   0.720  1.00  0.00           H  
HETATM   32  H7  UNL     1       1.225   0.503   2.052  1.00  0.00           H  
HETATM   33  H8  UNL     1       2.036   2.159   0.367  1.00  0.00           H  
HETATM   34  H9  UNL     1       0.689   1.762  -1.940  1.00  0.00           H  
HETATM   35  H10 UNL     1       1.058   0.062  -1.580  1.00  0.00           H  
HETATM   36  H11 UNL     1       2.359   1.338  -1.617  1.00  0.00           H  
HETATM   37  H12 UNL     1      -0.428   1.398   1.352  1.00  0.00           H  
HETATM   38  H13 UNL     1      -1.674   3.172   0.211  1.00  0.00           H  
HETATM   39  H14 UNL     1      -0.489   3.211  -1.083  1.00  0.00           H  
HETATM   40  H15 UNL     1      -1.248   0.565  -1.375  1.00  0.00           H  
HETATM   41  H16 UNL     1      -2.650   2.960  -1.842  1.00  0.00           H  
HETATM   42  H17 UNL     1      -2.475   2.047   1.658  1.00  0.00           H  
HETATM   43  H18 UNL     1      -4.283   1.181   2.928  1.00  0.00           H  
HETATM   44  H19 UNL     1      -6.789  -1.157   1.897  1.00  0.00           H  
HETATM   45  H20 UNL     1      -6.558  -1.748   0.109  1.00  0.00           H  
HETATM   46  H21 UNL     1      -6.488  -2.664  -2.166  1.00  0.00           H  
HETATM   47  H22 UNL     1      -3.595  -0.295  -1.719  1.00  0.00           H  
HETATM   48  H23 UNL     1       2.323  -1.797  -0.610  1.00  0.00           H  
HETATM   49  H24 UNL     1       4.605  -2.642  -0.850  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4   25
CONECT    4    5   29
CONECT    5    6    6   30
CONECT    6    7   24
CONECT    7    8   31   32
CONECT    8    9   10   33
CONECT    9   34   35   36
CONECT   10   11   37
CONECT   11   12   38   39
CONECT   12   13   14   40
CONECT   13   41
CONECT   14   15   15   23
CONECT   15   16   42
CONECT   16   17   17   43
CONECT   17   18   19
CONECT   18   44
CONECT   19   20   23   23
CONECT   20   21   45
CONECT   21   22   22   46
CONECT   23   47
CONECT   24   25   25   48
CONECT   25   49
END

HMDB0015399
     RDKit          3D
Arformoterol
 49 50  0  0  0  0  0  0  0  0999 V2000
    6.9865   -2.7588   -0.4045 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6762   -1.7023    0.4720 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3852   -1.2484    0.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1404   -0.2170    1.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8500    0.2284    1.5622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8175   -0.3214    0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4624    0.1849    1.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1775    1.4050    0.1513 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2965    1.1062   -1.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0245    2.0358    0.6157 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9468    2.4874   -0.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7574    1.4432   -0.9850 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4838    2.0187   -2.1027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8878    0.9285   -0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0850    1.3286    1.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1572    0.8375    1.9108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0190   -0.0629    1.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0690   -0.5442    2.0650 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8437   -0.5048    0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7544   -1.4309   -0.5630 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7353   -1.9689   -1.8394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8576   -1.6898   -2.6879 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7763    0.0050   -0.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1041   -1.3442   -0.0256 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3929   -1.8248   -0.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5771   -3.7435   -0.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5657   -2.5556   -1.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1008   -2.8516   -0.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9422    0.2422    2.0495 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5975    1.0511    2.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7096   -0.5869    0.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2246    0.5032    2.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0355    2.1586    0.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6886    1.7621   -1.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0579    0.0615   -1.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3586    1.3383   -1.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4281    1.3976    1.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6743    3.1720    0.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4890    3.2111   -1.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2485    0.5649   -1.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6495    2.9604   -1.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4754    2.0471    1.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2828    1.1807    2.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7886   -1.1570    1.8975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5578   -1.7481    0.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4883   -2.6640   -2.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5955   -0.2955   -1.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3228   -1.7970   -0.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6054   -2.6422   -0.8501 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 19 23  2  0
  6 24  1  0
 24 25  2  0
 25  3  1  0
 23 14  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  1
  9 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  6
 13 41  1  0
 15 42  1  0
 16 43  1  0
 18 44  1  0
 20 45  1  0
 21 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Formoterol	ChEBI
(R,R)-Formoterol	ChEBI
3-Formylamino-4-hydroxy-alpha-(N-1-methyl-2-p-methoxyphenethylaminomethyl)benzyl alcohol.hemifumarate	HMDB
Oxis	HMDB
Formoterol fumarate	HMDB
BD 40a	HMDB
Foradil	HMDB
Formoterol, ((r,r)-(+-))-isomer	HMDB
Eformoterol	HMDB
Formoterol	HMDB
Formoterol fumarate, ((r,r)-(+-))-isomer	HMDB

Chemical Formula

C₁₉H₂₄N₂O₄

Average Molecular Weight

344.4049

Monoisotopic Molecular Weight

344.173607266

IUPAC Name

N-{2-hydroxy-5-[(1R)-1-hydroxy-2-{[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino}ethyl]phenyl}formamide

Traditional Name

arformoterol

CAS Registry Number

67346-49-0

SMILES

COC1=CC=C(C[C@@H](C)NC[C@H](O)C2=CC(NC=O)=C(O)C=C2)C=C1

InChI Identifier

InChI=1S/C19H24N2O4/c1-13(9-14-3-6-16(25-2)7-4-14)20-11-19(24)15-5-8-18(23)17(10-15)21-12-22/h3-8,10,12-13,19-20,23-24H,9,11H2,1-2H3,(H,21,22)/t13-,19+/m1/s1

InChI Key

BPZSYCZIITTYBL-YJYMSZOUSA-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
Phenylpropane
Anilide
Phenoxy compound
Anisole
Phenol ether
N-arylamide
Methoxybenzene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Secondary carboxylic acid amide
Secondary alcohol
Amino acid or derivatives
1,2-aminoalcohol
Carboxamide group
Secondary amine
Carboxylic acid derivative
Secondary aliphatic amine
Ether
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Carbonyl group
Alcohol
Organic nitrogen compound
Organopnictogen compound
Aromatic alcohol
Organic oxide
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

N-[2-hydroxy-5-(1-hydroxy-2-\{[1-(4-methoxyphenyl)propan-2-yl]amino\}ethyl)phenyl]formamide (CHEBI:408174 )

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

Membrane (HMDB: HMDB0015399)

Source

Exogenous

Exogenous (HMDB: HMDB0015399)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.042 g/L	Not Available
LogP	2.2	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.042 g/L	ALOGPS
logP	1.91	ALOGPS
logP	1.06	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	8.61	ChemAxon
pKa (Strongest Basic)	9.81	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	90.82 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	97.87 m³·mol⁻¹	ChemAxon
Polarizability	36.56 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]+	181.58	31661259
DarkChem	[M-H]-	180.426	31661259
DeepCCS	[M+H]+	188.184	30932474
DeepCCS	[M-H]-	185.826	30932474
DeepCCS	[M-2H]-	219.56	30932474
DeepCCS	[M+Na]+	194.788	30932474
AllCCS	[M+H]+	186.5	32859911
AllCCS	[M+H-H2O]+	183.6	32859911
AllCCS	[M+NH4]+	189.3	32859911
AllCCS	[M+Na]+	190.1	32859911
AllCCS	[M-H]-	184.2	32859911
AllCCS	[M+Na-2H]-	184.6	32859911
AllCCS	[M+HCOO]-	185.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Arformoterol	COC1=CC=C(C[C@@H](C)NC[C@H](O)C2=CC(NC=O)=C(O)C=C2)C=C1	4304.2	Standard polar	33892256
Arformoterol	COC1=CC=C(C[C@@H](C)NC[C@H](O)C2=CC(NC=O)=C(O)C=C2)C=C1	3153.9	Standard non polar	33892256
Arformoterol	COC1=CC=C(C[C@@H](C)NC[C@H](O)C2=CC(NC=O)=C(O)C=C2)C=C1	3346.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Arformoterol,1TMS,isomer #1	COC1=CC=C(C[C@@H](C)NC[C@H](O[Si](C)(C)C)C2=CC=C(O)C(NC=O)=C2)C=C1	3238.9	Semi standard non polar	33892256
Arformoterol,1TMS,isomer #2	COC1=CC=C(C[C@@H](C)NC[C@H](O)C2=CC=C(O[Si](C)(C)C)C(NC=O)=C2)C=C1	3270.5	Semi standard non polar	33892256
Arformoterol,1TMS,isomer #3	COC1=CC=C(C[C@@H](C)N(C[C@H](O)C2=CC=C(O)C(NC=O)=C2)[Si](C)(C)C)C=C1	3273.9	Semi standard non polar	33892256
Arformoterol,1TMS,isomer #4	COC1=CC=C(C[C@@H](C)NC[C@H](O)C2=CC=C(O)C(N(C=O)[Si](C)(C)C)=C2)C=C1	3021.6	Semi standard non polar	33892256
Arformoterol,2TMS,isomer #1	COC1=CC=C(C[C@@H](C)NC[C@H](O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C(NC=O)=C2)C=C1	3194.4	Semi standard non polar	33892256
Arformoterol,2TMS,isomer #2	COC1=CC=C(C[C@@H](C)N(C[C@H](O[Si](C)(C)C)C2=CC=C(O)C(NC=O)=C2)[Si](C)(C)C)C=C1	3213.8	Semi standard non polar	33892256
Arformoterol,2TMS,isomer #3	COC1=CC=C(C[C@@H](C)NC[C@H](O[Si](C)(C)C)C2=CC=C(O)C(N(C=O)[Si](C)(C)C)=C2)C=C1	2920.9	Semi standard non polar	33892256
Arformoterol,2TMS,isomer #4	COC1=CC=C(C[C@@H](C)N(C[C@H](O)C2=CC=C(O[Si](C)(C)C)C(NC=O)=C2)[Si](C)(C)C)C=C1	3264.5	Semi standard non polar	33892256
Arformoterol,2TMS,isomer #5	COC1=CC=C(C[C@@H](C)NC[C@H](O)C2=CC=C(O[Si](C)(C)C)C(N(C=O)[Si](C)(C)C)=C2)C=C1	3038.4	Semi standard non polar	33892256
Arformoterol,2TMS,isomer #6	COC1=CC=C(C[C@@H](C)N(C[C@H](O)C2=CC=C(O)C(N(C=O)[Si](C)(C)C)=C2)[Si](C)(C)C)C=C1	3013.4	Semi standard non polar	33892256
Arformoterol,3TMS,isomer #1	COC1=CC=C(C[C@@H](C)N(C[C@H](O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C(NC=O)=C2)[Si](C)(C)C)C=C1	3246.8	Semi standard non polar	33892256
Arformoterol,3TMS,isomer #1	COC1=CC=C(C[C@@H](C)N(C[C@H](O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C(NC=O)=C2)[Si](C)(C)C)C=C1	2891.4	Standard non polar	33892256
Arformoterol,3TMS,isomer #1	COC1=CC=C(C[C@@H](C)N(C[C@H](O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C(NC=O)=C2)[Si](C)(C)C)C=C1	3639.8	Standard polar	33892256
Arformoterol,3TMS,isomer #2	COC1=CC=C(C[C@@H](C)NC[C@H](O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C(N(C=O)[Si](C)(C)C)=C2)C=C1	2978.4	Semi standard non polar	33892256
Arformoterol,3TMS,isomer #2	COC1=CC=C(C[C@@H](C)NC[C@H](O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C(N(C=O)[Si](C)(C)C)=C2)C=C1	2660.7	Standard non polar	33892256
Arformoterol,3TMS,isomer #2	COC1=CC=C(C[C@@H](C)NC[C@H](O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C(N(C=O)[Si](C)(C)C)=C2)C=C1	3452.6	Standard polar	33892256
Arformoterol,3TMS,isomer #3	COC1=CC=C(C[C@@H](C)N(C[C@H](O[Si](C)(C)C)C2=CC=C(O)C(N(C=O)[Si](C)(C)C)=C2)[Si](C)(C)C)C=C1	3002.4	Semi standard non polar	33892256
Arformoterol,3TMS,isomer #3	COC1=CC=C(C[C@@H](C)N(C[C@H](O[Si](C)(C)C)C2=CC=C(O)C(N(C=O)[Si](C)(C)C)=C2)[Si](C)(C)C)C=C1	2814.0	Standard non polar	33892256
Arformoterol,3TMS,isomer #3	COC1=CC=C(C[C@@H](C)N(C[C@H](O[Si](C)(C)C)C2=CC=C(O)C(N(C=O)[Si](C)(C)C)=C2)[Si](C)(C)C)C=C1	3615.3	Standard polar	33892256
Arformoterol,3TMS,isomer #4	COC1=CC=C(C[C@@H](C)N(C[C@H](O)C2=CC=C(O[Si](C)(C)C)C(N(C=O)[Si](C)(C)C)=C2)[Si](C)(C)C)C=C1	3050.6	Semi standard non polar	33892256
Arformoterol,3TMS,isomer #4	COC1=CC=C(C[C@@H](C)N(C[C@H](O)C2=CC=C(O[Si](C)(C)C)C(N(C=O)[Si](C)(C)C)=C2)[Si](C)(C)C)C=C1	2878.4	Standard non polar	33892256
Arformoterol,3TMS,isomer #4	COC1=CC=C(C[C@@H](C)N(C[C@H](O)C2=CC=C(O[Si](C)(C)C)C(N(C=O)[Si](C)(C)C)=C2)[Si](C)(C)C)C=C1	3654.3	Standard polar	33892256
Arformoterol,4TMS,isomer #1	COC1=CC=C(C[C@@H](C)N(C[C@H](O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C(N(C=O)[Si](C)(C)C)=C2)[Si](C)(C)C)C=C1	3085.9	Semi standard non polar	33892256
Arformoterol,4TMS,isomer #1	COC1=CC=C(C[C@@H](C)N(C[C@H](O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C(N(C=O)[Si](C)(C)C)=C2)[Si](C)(C)C)C=C1	2735.0	Standard non polar	33892256
Arformoterol,4TMS,isomer #1	COC1=CC=C(C[C@@H](C)N(C[C@H](O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C(N(C=O)[Si](C)(C)C)=C2)[Si](C)(C)C)C=C1	3382.4	Standard polar	33892256
Arformoterol,1TBDMS,isomer #1	COC1=CC=C(C[C@@H](C)NC[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=C(O)C(NC=O)=C2)C=C1	3498.6	Semi standard non polar	33892256
Arformoterol,1TBDMS,isomer #2	COC1=CC=C(C[C@@H](C)NC[C@H](O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C(NC=O)=C2)C=C1	3530.2	Semi standard non polar	33892256
Arformoterol,1TBDMS,isomer #3	COC1=CC=C(C[C@@H](C)N(C[C@H](O)C2=CC=C(O)C(NC=O)=C2)[Si](C)(C)C(C)(C)C)C=C1	3546.0	Semi standard non polar	33892256
Arformoterol,1TBDMS,isomer #4	COC1=CC=C(C[C@@H](C)NC[C@H](O)C2=CC=C(O)C(N(C=O)[Si](C)(C)C(C)(C)C)=C2)C=C1	3292.6	Semi standard non polar	33892256
Arformoterol,2TBDMS,isomer #1	COC1=CC=C(C[C@@H](C)NC[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C(NC=O)=C2)C=C1	3679.4	Semi standard non polar	33892256
Arformoterol,2TBDMS,isomer #2	COC1=CC=C(C[C@@H](C)N(C[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=C(O)C(NC=O)=C2)[Si](C)(C)C(C)(C)C)C=C1	3753.9	Semi standard non polar	33892256
Arformoterol,2TBDMS,isomer #3	COC1=CC=C(C[C@@H](C)NC[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=C(O)C(N(C=O)[Si](C)(C)C(C)(C)C)=C2)C=C1	3415.4	Semi standard non polar	33892256
Arformoterol,2TBDMS,isomer #4	COC1=CC=C(C[C@@H](C)N(C[C@H](O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C(NC=O)=C2)[Si](C)(C)C(C)(C)C)C=C1	3773.3	Semi standard non polar	33892256
Arformoterol,2TBDMS,isomer #5	COC1=CC=C(C[C@@H](C)NC[C@H](O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C(N(C=O)[Si](C)(C)C(C)(C)C)=C2)C=C1	3525.0	Semi standard non polar	33892256
Arformoterol,2TBDMS,isomer #6	COC1=CC=C(C[C@@H](C)N(C[C@H](O)C2=CC=C(O)C(N(C=O)[Si](C)(C)C(C)(C)C)=C2)[Si](C)(C)C(C)(C)C)C=C1	3536.9	Semi standard non polar	33892256
Arformoterol,3TBDMS,isomer #1	COC1=CC=C(C[C@@H](C)N(C[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C(NC=O)=C2)[Si](C)(C)C(C)(C)C)C=C1	3964.3	Semi standard non polar	33892256
Arformoterol,3TBDMS,isomer #1	COC1=CC=C(C[C@@H](C)N(C[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C(NC=O)=C2)[Si](C)(C)C(C)(C)C)C=C1	3498.4	Standard non polar	33892256
Arformoterol,3TBDMS,isomer #1	COC1=CC=C(C[C@@H](C)N(C[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C(NC=O)=C2)[Si](C)(C)C(C)(C)C)C=C1	3811.3	Standard polar	33892256
Arformoterol,3TBDMS,isomer #2	COC1=CC=C(C[C@@H](C)NC[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C(N(C=O)[Si](C)(C)C(C)(C)C)=C2)C=C1	3646.0	Semi standard non polar	33892256
Arformoterol,3TBDMS,isomer #2	COC1=CC=C(C[C@@H](C)NC[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C(N(C=O)[Si](C)(C)C(C)(C)C)=C2)C=C1	3155.3	Standard non polar	33892256
Arformoterol,3TBDMS,isomer #2	COC1=CC=C(C[C@@H](C)NC[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C(N(C=O)[Si](C)(C)C(C)(C)C)=C2)C=C1	3683.5	Standard polar	33892256
Arformoterol,3TBDMS,isomer #3	COC1=CC=C(C[C@@H](C)N(C[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=C(O)C(N(C=O)[Si](C)(C)C(C)(C)C)=C2)[Si](C)(C)C(C)(C)C)C=C1	3738.7	Semi standard non polar	33892256
Arformoterol,3TBDMS,isomer #3	COC1=CC=C(C[C@@H](C)N(C[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=C(O)C(N(C=O)[Si](C)(C)C(C)(C)C)=C2)[Si](C)(C)C(C)(C)C)C=C1	3331.6	Standard non polar	33892256
Arformoterol,3TBDMS,isomer #3	COC1=CC=C(C[C@@H](C)N(C[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=C(O)C(N(C=O)[Si](C)(C)C(C)(C)C)=C2)[Si](C)(C)C(C)(C)C)C=C1	3805.7	Standard polar	33892256
Arformoterol,3TBDMS,isomer #4	COC1=CC=C(C[C@@H](C)N(C[C@H](O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C(N(C=O)[Si](C)(C)C(C)(C)C)=C2)[Si](C)(C)C(C)(C)C)C=C1	3783.2	Semi standard non polar	33892256
Arformoterol,3TBDMS,isomer #4	COC1=CC=C(C[C@@H](C)N(C[C@H](O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C(N(C=O)[Si](C)(C)C(C)(C)C)=C2)[Si](C)(C)C(C)(C)C)C=C1	3343.3	Standard non polar	33892256
Arformoterol,3TBDMS,isomer #4	COC1=CC=C(C[C@@H](C)N(C[C@H](O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C(N(C=O)[Si](C)(C)C(C)(C)C)=C2)[Si](C)(C)C(C)(C)C)C=C1	3862.2	Standard polar	33892256
Arformoterol,4TBDMS,isomer #1	COC1=CC=C(C[C@@H](C)N(C[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C(N(C=O)[Si](C)(C)C(C)(C)C)=C2)[Si](C)(C)C(C)(C)C)C=C1	3976.1	Semi standard non polar	33892256
Arformoterol,4TBDMS,isomer #1	COC1=CC=C(C[C@@H](C)N(C[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C(N(C=O)[Si](C)(C)C(C)(C)C)=C2)[Si](C)(C)C(C)(C)C)C=C1	3359.3	Standard non polar	33892256
Arformoterol,4TBDMS,isomer #1	COC1=CC=C(C[C@@H](C)N(C[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C(N(C=O)[Si](C)(C)C(C)(C)C)=C2)[Si](C)(C)C(C)(C)C)C=C1	3677.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Arformoterol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00or-2902000000-10d83ebb89a446028d15	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arformoterol GC-MS (2 TMS) - 70eV, Positive	splash10-0079-1290400000-a5f812e6f46ebe2c4573	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arformoterol 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 - Arformoterol 10V, Positive-QTOF	splash10-00mk-0119000000-960431f56a40133b8573	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arformoterol 20V, Positive-QTOF	splash10-002b-0937000000-93717c858174f9fabf66	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arformoterol 40V, Positive-QTOF	splash10-0002-0900000000-d7f4b9eb1c7882357173	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arformoterol 10V, Negative-QTOF	splash10-004l-4209000000-f9910c5b8f497127e7ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arformoterol 20V, Negative-QTOF	splash10-03fu-3619000000-7dd84dcd46e229246839	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arformoterol 40V, Negative-QTOF	splash10-002f-9400000000-58f5ee81bd6c210528d7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arformoterol 10V, Positive-QTOF	splash10-002b-0059000000-c0053d7ff48e5b7bf21e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arformoterol 20V, Positive-QTOF	splash10-05bb-0797000000-ccdaa7ef72717418b1b7	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arformoterol 40V, Positive-QTOF	splash10-022c-1911000000-a90ad156589941d202e7	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arformoterol 10V, Negative-QTOF	splash10-0007-0039000000-690e9c11e66c66a1a005	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arformoterol 20V, Negative-QTOF	splash10-0007-3795000000-80c4a6628c8460481d11	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arformoterol 40V, Negative-QTOF	splash10-0017-5391000000-9e5db81cdfc6dd49e8ea	2021-10-11	Wishart Lab	View Spectrum

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 DB01274	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01274	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01274

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2340731

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Arformoterol

METLIN ID

Not Available

PubChem Compound

3083544

PDB ID

Not Available

ChEBI ID

408174

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

Cazzola M, Matera MG, Lotvall J: Ultra long-acting beta 2-agonists in development for asthma and chronic obstructive pulmonary disease. Expert Opin Investig Drugs. 2005 Jul;14(7):775-83. [PubMed:16022567 ]
Kharidia J, Fogarty CM, Laforce CF, Maier G, Hsu R, Dunnington KM, Curry L, Baumgartner RA, Hanrahan JP: A pharmacokinetic/pharmacodynamic study comparing arformoterol tartrate inhalation solution and racemic formoterol dry powder inhaler in subjects with chronic obstructive pulmonary disease. Pulm Pharmacol Ther. 2008 Aug;21(4):657-62. doi: 10.1016/j.pupt.2008.03.003. Epub 2008 Apr 7. [PubMed:18501650 ]
Baumgartner RA, Hanania NA, Calhoun WJ, Sahn SA, Sciarappa K, Hanrahan JP: Nebulized arformoterol in patients with COPD: a 12-week, multicenter, randomized, double-blind, double-dummy, placebo- and active-controlled trial. Clin Ther. 2007 Feb;29(2):261-78. [PubMed:17472819 ]
Donohue JF, Hanania NA, Sciarappa KA, Goodwin E, Grogan DR, Baumgartner RA, Hanrahan JP: Arformoterol and salmeterol in the treatment of chronic obstructive pulmonary disease: a one year evaluation of safety and tolerance. Ther Adv Respir Dis. 2008 Apr;2(2):37-48. doi: 10.1177/1753465808089455. [PubMed:19124357 ]
Panettieri RA Jr, MacIntyre N, Sims M, Kerwin E, Fogarty C, Noonan M, Claus R, Andrews WT: Comparison of the efficacy and safety of arformoterol 15 microg twice daily and arformoterol 30 microg once daily in COPD: a single-dose, multicenter, randomized, modified-blind, two-way crossover study. Clin Ther. 2009 Aug;31(8):1716-23. doi: 10.1016/j.clinthera.2009.08.012. [PubMed:19808130 ]
Hanania NA, Donohue JF, Nelson H, Sciarappa K, Goodwin E, Baumgartner RA, Hanrahan JP: The safety and efficacy of arformoterol and formoterol in COPD. COPD. 2010 Feb;7(1):17-31. doi: 10.3109/15412550903499498. [PubMed:20214460 ]

Enzymes

Enzyme Details

1. Cytochrome P450 2C9

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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Somers GI, Lindsay N, Lowdon BM, Jones AE, Freathy C, Ho S, Woodrooffe AJ, Bayliss MK, Manchee GR: A comparison of the expression and metabolizing activities of phase I and II enzymes in freshly isolated human lung parenchymal cells and cryopreserved human hepatocytes. Drug Metab Dispos. 2007 Oct;35(10):1797-805. Epub 2007 Jul 12. [PubMed:17627976 ]
Zhang M, Fawcett JP, Kennedy JM, Shaw JP: Stereoselective glucuronidation of formoterol by human liver microsomes. Br J Clin Pharmacol. 2000 Feb;49(2):152-7. [PubMed:10671910 ]

Enzyme Details

2. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Somers GI, Lindsay N, Lowdon BM, Jones AE, Freathy C, Ho S, Woodrooffe AJ, Bayliss MK, Manchee GR: A comparison of the expression and metabolizing activities of phase I and II enzymes in freshly isolated human lung parenchymal cells and cryopreserved human hepatocytes. Drug Metab Dispos. 2007 Oct;35(10):1797-805. Epub 2007 Jul 12. [PubMed:17627976 ]
Zhang M, Fawcett JP, Kennedy JM, Shaw JP: Stereoselective glucuronidation of formoterol by human liver microsomes. Br J Clin Pharmacol. 2000 Feb;49(2):152-7. [PubMed:10671910 ]

Enzyme Details

3. 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

Somers GI, Lindsay N, Lowdon BM, Jones AE, Freathy C, Ho S, Woodrooffe AJ, Bayliss MK, Manchee GR: A comparison of the expression and metabolizing activities of phase I and II enzymes in freshly isolated human lung parenchymal cells and cryopreserved human hepatocytes. Drug Metab Dispos. 2007 Oct;35(10):1797-805. Epub 2007 Jul 12. [PubMed:17627976 ]
Zhang M, Fawcett JP, Kennedy JM, Shaw JP: Stereoselective glucuronidation of formoterol by human liver microsomes. Br J Clin Pharmacol. 2000 Feb;49(2):152-7. [PubMed:10671910 ]

Enzyme Details

4. Cytochrome P450 2A6

General function:: Involved in monooxygenase activity
Specific function:: Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:: CYP2A6
Uniprot ID:: P11509
Molecular weight:: 56517.005

References

Somers GI, Lindsay N, Lowdon BM, Jones AE, Freathy C, Ho S, Woodrooffe AJ, Bayliss MK, Manchee GR: A comparison of the expression and metabolizing activities of phase I and II enzymes in freshly isolated human lung parenchymal cells and cryopreserved human hepatocytes. Drug Metab Dispos. 2007 Oct;35(10):1797-805. Epub 2007 Jul 12. [PubMed:17627976 ]
Zhang M, Fawcett JP, Kennedy JM, Shaw JP: Stereoselective glucuronidation of formoterol by human liver microsomes. Br J Clin Pharmacol. 2000 Feb;49(2):152-7. [PubMed:10671910 ]

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

Authors unspecified: Arformoterol: (R,R)-eformoterol, (R,R)-formoterol, arformoterol tartrate, eformoterol-sepracor, formoterol-sepracor, R,R-eformoterol, R,R-formoterol. Drugs R D. 2004;5(1):25-7. [PubMed:14725487 ]
Op't Holt TB: Inhaled beta agonists. Respir Care. 2007 Jul;52(7):820-32. [PubMed:17594727 ]
Matera MG, Cazzola M: ultra-long-acting beta2-adrenoceptor agonists: an emerging therapeutic option for asthma and COPD? Drugs. 2007;67(4):503-15. [PubMed:17352511 ]
Cazzola M, Hanania NA, Matera MG: Arformoterol tartrate in the treatment of COPD. Expert Rev Respir Med. 2010 Apr;4(2):155-62. doi: 10.1586/ers.10.16. [PubMed:20406080 ]
Cazzola M, Matera MG, Lotvall J: Ultra long-acting beta 2-agonists in development for asthma and chronic obstructive pulmonary disease. Expert Opin Investig Drugs. 2005 Jul;14(7):775-83. [PubMed:16022567 ]
Kharidia J, Fogarty CM, Laforce CF, Maier G, Hsu R, Dunnington KM, Curry L, Baumgartner RA, Hanrahan JP: A pharmacokinetic/pharmacodynamic study comparing arformoterol tartrate inhalation solution and racemic formoterol dry powder inhaler in subjects with chronic obstructive pulmonary disease. Pulm Pharmacol Ther. 2008 Aug;21(4):657-62. doi: 10.1016/j.pupt.2008.03.003. Epub 2008 Apr 7. [PubMed:18501650 ]
Baumgartner RA, Hanania NA, Calhoun WJ, Sahn SA, Sciarappa K, Hanrahan JP: Nebulized arformoterol in patients with COPD: a 12-week, multicenter, randomized, double-blind, double-dummy, placebo- and active-controlled trial. Clin Ther. 2007 Feb;29(2):261-78. [PubMed:17472819 ]
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 Arformoterol (HMDB0015399)

MOL for HMDB0015399 (Arformoterol)

3D MOL for HMDB0015399 (Arformoterol)

3D SDF for HMDB0015399 (Arformoterol)

3D-SDF for HMDB0015399 (Arformoterol)

PDB for HMDB0015399 (Arformoterol)

3D PDB for HMDB0015399 (Arformoterol)

SMILES for HMDB0015399 (Arformoterol)

INCHI for HMDB0015399 (Arformoterol)

Structure for HMDB0015399 (Arformoterol)

3D Structure for HMDB0015399 (Arformoterol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

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