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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:54 UTC

HMDB ID

HMDB0015234

Secondary Accession Numbers

HMDB15234

Metabolite Identification

Common Name

Arbutamine

Description

Arbutamine, also known as genesa, belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine. Arbutamine is a drug which is used to elicit acute cardiovascular responses (cardiac stumulant), similar to those produced by exercise, in order to aid in diagnosing the presence or absence of coronary artery disease (cad) in patients who cannot exercise adequately. Arbutamine is a very strong basic compound (based on its pKa). In humans, arbutamine is involved in arbutamine action pathway.

Structure

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

HMDB0015234
     RDKit          3D
Arbutamine
 46 47  0  0  0  0  0  0  0  0999 V2000
    7.5066   -1.9087    0.9041 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3481   -1.1355    0.8239 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3085    0.0305    0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1758    0.8115   -0.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0105    0.4488    0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8003    1.3062    0.5258 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9891    0.7937   -0.6412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7346    1.6210   -0.8518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0095    1.0299   -2.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3916   -0.3069   -1.8087 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3715   -0.6036   -0.8491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7598   -0.1507   -1.1718 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7488    1.2497   -1.3227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7300   -0.4397   -0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5625   -1.2886    0.9427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5557   -1.4872    1.8829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7504   -0.8129    1.7521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7808   -0.9785    2.6717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9747    0.0572    0.7002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1926    0.7164    0.6059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9603    0.2199   -0.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0383   -0.7058    1.3896 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1796   -1.4748    1.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1422   -1.6731    1.6666 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2128    0.3197   -0.4409 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1706    1.7319   -0.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2416    1.2845    1.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1572    2.3531    0.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7102   -0.2640   -0.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6304    0.7371   -1.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0390    2.6590   -1.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1550    1.5997    0.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7758    0.9991   -2.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7704    1.7148   -2.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4344   -0.9334   -1.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3716   -1.7279   -0.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0931   -0.1706    0.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1447   -0.6329   -2.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5533    1.6604   -0.4486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6317   -1.7991    1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4297   -2.1619    2.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7521   -1.5729    3.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3334    1.3542   -0.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1599    0.9139   -1.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1255   -1.0065    1.9191 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1422   -2.3768    2.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 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
 19 21  2  0
  5 22  1  0
 22 23  2  0
 23  2  1  0
 21 14  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  6
 13 39  1  0
 15 40  1  0
 16 41  1  0
 18 42  1  0
 20 43  1  0
 21 44  1  0
 22 45  1  0
 23 46  1  0
M  END

1102
  Mrv0541 02231215152D          

 23 24  0  0  1  0            999 V2000
    2.8075   -0.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -3.6342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -4.4592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5234    4.2035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.0784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    2.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.1592    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3799    2.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -2.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -2.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799    3.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944    2.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -3.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -3.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944    4.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8089    2.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -3.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8089    3.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11  1  1  1  0  0  0
  2 18  1  0  0  0  0
  3 22  1  0  0  0  0
  4 23  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 16  2  0  0  0  0
 12 17  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 14 18  1  0  0  0  0
 15 19  2  0  0  0  0
 16 20  1  0  0  0  0
 17 21  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>
HMDB0015234

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@@H](CNCCCCC1=CC=C(O)C=C1)C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H23NO4/c20-15-7-4-13(5-8-15)3-1-2-10-19-12-18(23)14-6-9-16(21)17(22)11-14/h4-9,11,18-23H,1-3,10,12H2/t18-/m0/s1

> <INCHI_KEY>
IIRWWTKISYTTBL-SFHVURJKSA-N

> <FORMULA>
C18H23NO4

> <MOLECULAR_WEIGHT>
317.3795

> <EXACT_MASS>
317.162708229

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
35.5440906533178

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(1R)-1-hydroxy-2-{[4-(4-hydroxyphenyl)butyl]amino}ethyl]benzene-1,2-diol

> <ALOGPS_LOGP>
2.08

> <JCHEM_LOGP>
1.9953032245022408

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.442234462502894

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.96653532193289

> <JCHEM_PKA_STRONGEST_BASIC>
9.759931277265373

> <JCHEM_POLAR_SURFACE_AREA>
92.95

> <JCHEM_REFRACTIVITY>
89.78080000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
arbutamine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015234
     RDKit          3D
Arbutamine
 46 47  0  0  0  0  0  0  0  0999 V2000
    7.5066   -1.9087    0.9041 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3481   -1.1355    0.8239 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3085    0.0305    0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1758    0.8115   -0.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0105    0.4488    0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8003    1.3062    0.5258 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9891    0.7937   -0.6412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7346    1.6210   -0.8518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0095    1.0299   -2.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3916   -0.3069   -1.8087 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3715   -0.6036   -0.8491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7598   -0.1507   -1.1718 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7488    1.2497   -1.3227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7300   -0.4397   -0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5625   -1.2886    0.9427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5557   -1.4872    1.8829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7504   -0.8129    1.7521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7808   -0.9785    2.6717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9747    0.0572    0.7002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1926    0.7164    0.6059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9603    0.2199   -0.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0383   -0.7058    1.3896 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1796   -1.4748    1.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1422   -1.6731    1.6666 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2128    0.3197   -0.4409 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1706    1.7319   -0.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2416    1.2845    1.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1572    2.3531    0.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7102   -0.2640   -0.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6304    0.7371   -1.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0390    2.6590   -1.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1550    1.5997    0.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7758    0.9991   -2.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7704    1.7148   -2.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4344   -0.9334   -1.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3716   -1.7279   -0.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0931   -0.1706    0.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1447   -0.6329   -2.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5533    1.6604   -0.4486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6317   -1.7991    1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4297   -2.1619    2.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7521   -1.5729    3.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3334    1.3542   -0.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1599    0.9139   -1.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1255   -1.0065    1.9191 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1422   -2.3768    2.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 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
 19 21  2  0
  5 22  1  0
 22 23  2  0
 23  2  1  0
 21 14  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  6
 13 39  1  0
 15 40  1  0
 16 41  1  0
 18 42  1  0
 20 43  1  0
 21 44  1  0
 22 45  1  0
 23 46  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1102                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       5.241  -1.394   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.907  -6.784   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       6.574  -8.324   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      15.910   7.847   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       7.908   0.146   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       9.242   2.456   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.576   3.226   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.242   0.916   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.908  -1.394   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.576   4.766   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.574  -2.164   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.909   5.536   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.574  -3.704   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.241  -4.474   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.908  -4.474   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.909   7.077   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.243   4.766   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.241  -6.014   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.908  -6.014   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.243   7.847   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.577   5.536   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.574  -6.784   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.577   7.077   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   18                                                            
CONECT    3   22                                                            
CONECT    4   23                                                            
CONECT    5    8    9                                                       
CONECT    6    7    8                                                       
CONECT    7    6   10                                                       
CONECT    8    5    6                                                       
CONECT    9    5   11                                                       
CONECT   10    7   12                                                       
CONECT   11    1    9   13                                                  
CONECT   12   10   16   17                                                  
CONECT   13   11   14   15                                                  
CONECT   14   13   18                                                       
CONECT   15   13   19                                                       
CONECT   16   12   20                                                       
CONECT   17   12   21                                                       
CONECT   18    2   14   22                                                  
CONECT   19   15   22                                                       
CONECT   20   16   23                                                       
CONECT   21   17   23                                                       
CONECT   22    3   18   19                                                  
CONECT   23    4   20   21                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0015234
HETATM    1  O1  UNL     1       7.507  -1.909   0.904  1.00  0.00           O  
HETATM    2  C1  UNL     1       6.348  -1.136   0.824  1.00  0.00           C  
HETATM    3  C2  UNL     1       6.308   0.031   0.078  1.00  0.00           C  
HETATM    4  C3  UNL     1       5.176   0.812  -0.017  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.010   0.449   0.646  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.800   1.306   0.526  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.989   0.794  -0.641  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.735   1.621  -0.852  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.010   1.030  -2.032  1.00  0.00           C  
HETATM   10  N1  UNL     1      -0.392  -0.307  -1.809  1.00  0.00           N  
HETATM   11  C9  UNL     1      -1.372  -0.604  -0.849  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.760  -0.151  -1.172  1.00  0.00           C  
HETATM   13  O2  UNL     1      -2.749   1.250  -1.323  1.00  0.00           O  
HETATM   14  C11 UNL     1      -3.730  -0.440  -0.118  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.563  -1.289   0.943  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.556  -1.487   1.883  1.00  0.00           C  
HETATM   17  C14 UNL     1      -5.750  -0.813   1.752  1.00  0.00           C  
HETATM   18  O3  UNL     1      -6.781  -0.978   2.672  1.00  0.00           O  
HETATM   19  C15 UNL     1      -5.975   0.057   0.700  1.00  0.00           C  
HETATM   20  O4  UNL     1      -7.193   0.716   0.606  1.00  0.00           O  
HETATM   21  C16 UNL     1      -4.960   0.220  -0.205  1.00  0.00           C  
HETATM   22  C17 UNL     1       4.038  -0.706   1.390  1.00  0.00           C  
HETATM   23  C18 UNL     1       5.180  -1.475   1.473  1.00  0.00           C  
HETATM   24  H1  UNL     1       8.142  -1.673   1.667  1.00  0.00           H  
HETATM   25  H2  UNL     1       7.213   0.320  -0.441  1.00  0.00           H  
HETATM   26  H3  UNL     1       5.171   1.732  -0.615  1.00  0.00           H  
HETATM   27  H4  UNL     1       2.242   1.285   1.470  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.157   2.353   0.307  1.00  0.00           H  
HETATM   29  H6  UNL     1       1.710  -0.264  -0.387  1.00  0.00           H  
HETATM   30  H7  UNL     1       2.630   0.737  -1.536  1.00  0.00           H  
HETATM   31  H8  UNL     1       1.039   2.659  -1.074  1.00  0.00           H  
HETATM   32  H9  UNL     1       0.155   1.600   0.074  1.00  0.00           H  
HETATM   33  H10 UNL     1       0.776   0.999  -2.852  1.00  0.00           H  
HETATM   34  H11 UNL     1      -0.770   1.715  -2.442  1.00  0.00           H  
HETATM   35  H12 UNL     1       0.434  -0.933  -1.815  1.00  0.00           H  
HETATM   36  H13 UNL     1      -1.372  -1.728  -0.715  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.093  -0.171   0.131  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.145  -0.633  -2.116  1.00  0.00           H  
HETATM   39  H16 UNL     1      -2.553   1.660  -0.449  1.00  0.00           H  
HETATM   40  H17 UNL     1      -2.632  -1.799   1.024  1.00  0.00           H  
HETATM   41  H18 UNL     1      -4.430  -2.162   2.732  1.00  0.00           H  
HETATM   42  H19 UNL     1      -6.752  -1.573   3.474  1.00  0.00           H  
HETATM   43  H20 UNL     1      -7.333   1.354  -0.182  1.00  0.00           H  
HETATM   44  H21 UNL     1      -5.160   0.914  -1.029  1.00  0.00           H  
HETATM   45  H22 UNL     1       3.126  -1.007   1.919  1.00  0.00           H  
HETATM   46  H23 UNL     1       5.142  -2.377   2.076  1.00  0.00           H  
CONECT    1    2   24
CONECT    2    3    3   23
CONECT    3    4   25
CONECT    4    5    5   26
CONECT    5    6   22
CONECT    6    7   27   28
CONECT    7    8   29   30
CONECT    8    9   31   32
CONECT    9   10   33   34
CONECT   10   11   35
CONECT   11   12   36   37
CONECT   12   13   14   38
CONECT   13   39
CONECT   14   15   15   21
CONECT   15   16   40
CONECT   16   17   17   41
CONECT   17   18   19
CONECT   18   42
CONECT   19   20   21   21
CONECT   20   43
CONECT   21   44
CONECT   22   23   23   45
CONECT   23   46
END

HMDB0015234
     RDKit          3D
Arbutamine
 46 47  0  0  0  0  0  0  0  0999 V2000
    7.5066   -1.9087    0.9041 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3481   -1.1355    0.8239 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3085    0.0305    0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1758    0.8115   -0.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0105    0.4488    0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8003    1.3062    0.5258 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9891    0.7937   -0.6412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7346    1.6210   -0.8518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0095    1.0299   -2.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3916   -0.3069   -1.8087 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3715   -0.6036   -0.8491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7598   -0.1507   -1.1718 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7488    1.2497   -1.3227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7300   -0.4397   -0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5625   -1.2886    0.9427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5557   -1.4872    1.8829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7504   -0.8129    1.7521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7808   -0.9785    2.6717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9747    0.0572    0.7002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1926    0.7164    0.6059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9603    0.2199   -0.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0383   -0.7058    1.3896 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1796   -1.4748    1.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1422   -1.6731    1.6666 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2128    0.3197   -0.4409 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1706    1.7319   -0.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2416    1.2845    1.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1572    2.3531    0.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7102   -0.2640   -0.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6304    0.7371   -1.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0390    2.6590   -1.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1550    1.5997    0.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7758    0.9991   -2.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7704    1.7148   -2.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4344   -0.9334   -1.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3716   -1.7279   -0.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0931   -0.1706    0.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1447   -0.6329   -2.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5533    1.6604   -0.4486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6317   -1.7991    1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4297   -2.1619    2.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7521   -1.5729    3.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3334    1.3542   -0.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1599    0.9139   -1.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1255   -1.0065    1.9191 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1422   -2.3768    2.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 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
 19 21  2  0
  5 22  1  0
 22 23  2  0
 23  2  1  0
 21 14  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  6
 13 39  1  0
 15 40  1  0
 16 41  1  0
 18 42  1  0
 20 43  1  0
 21 44  1  0
 22 45  1  0
 23 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Arbutamina	ChEBI
Arbutaminum	ChEBI
Arbutamine hydrochloride	HMDB
Arbutamine hydrochloride, (R)-isomer	HMDB
GenESA	HMDB

Chemical Formula

C₁₈H₂₃NO₄

Average Molecular Weight

317.3795

Monoisotopic Molecular Weight

317.162708229

IUPAC Name

4-[(1R)-1-hydroxy-2-{[4-(4-hydroxyphenyl)butyl]amino}ethyl]benzene-1,2-diol

Traditional Name

arbutamine

CAS Registry Number

128470-16-6

SMILES

O[C@@H](CNCCCCC1=CC=C(O)C=C1)C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C18H23NO4/c20-15-7-4-13(5-8-15)3-1-2-10-19-12-18(23)14-6-9-16(21)17(22)11-14/h4-9,11,18-23H,1-3,10,12H2/t18-/m0/s1

InChI Key

IIRWWTKISYTTBL-SFHVURJKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylbutylamines

Direct Parent

Phenylbutylamines

Alternative Parents

Substituents

Phenylbutylamine
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
1,2-aminoalcohol
Secondary alcohol
Secondary aliphatic amine
Secondary amine
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Amine
Aromatic alcohol
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

catecholamine (CHEBI:50580 )

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: HMDB0015234)

Source

Exogenous

Exogenous (HMDB: HMDB0015234)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Arbutamine Action Pathway (PathBank: SMP0000664)

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	0.084 g/L	Not Available
LogP	2.9	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.084 g/L	ALOGPS
logP	2.08	ALOGPS
logP	2	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.97	ChemAxon
pKa (Strongest Basic)	9.76	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	92.95 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	89.78 m³·mol⁻¹	ChemAxon
Polarizability	35.54 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]+	177.148	31661259
DarkChem	[M-H]-	177.209	31661259
DeepCCS	[M+H]+	180.883	30932474
DeepCCS	[M-H]-	178.333	30932474
DeepCCS	[M-2H]-	212.557	30932474
DeepCCS	[M+Na]+	188.803	30932474
AllCCS	[M+H]+	177.4	32859911
AllCCS	[M+H-H2O]+	174.3	32859911
AllCCS	[M+NH4]+	180.4	32859911
AllCCS	[M+Na]+	181.2	32859911
AllCCS	[M-H]-	178.0	32859911
AllCCS	[M+Na-2H]-	178.3	32859911
AllCCS	[M+HCOO]-	178.7	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.	3.34 minutes	32390414
Predicted by Siyang on May 30, 2022	10.078 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.72 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	117.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	755.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	180.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	134.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	152.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	91.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	361.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	321.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	719.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	684.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	293.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	955.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	193.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	250.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	603.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	400.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	130.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Arbutamine	O[C@@H](CNCCCCC1=CC=C(O)C=C1)C1=CC(O)=C(O)C=C1	4464.5	Standard polar	33892256
Arbutamine	O[C@@H](CNCCCCC1=CC=C(O)C=C1)C1=CC(O)=C(O)C=C1	3129.7	Standard non polar	33892256
Arbutamine	O[C@@H](CNCCCCC1=CC=C(O)C=C1)C1=CC(O)=C(O)C=C1	3206.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Arbutamine,1TMS,isomer #1	C[Si](C)(C)O[C@@H](CNCCCCC1=CC=C(O)C=C1)C1=CC=C(O)C(O)=C1	3208.3	Semi standard non polar	33892256
Arbutamine,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(CCCCNC[C@H](O)C2=CC=C(O)C(O)=C2)C=C1	3122.8	Semi standard non polar	33892256
Arbutamine,1TMS,isomer #3	C[Si](C)(C)OC1=CC([C@@H](O)CNCCCCC2=CC=C(O)C=C2)=CC=C1O	3084.7	Semi standard non polar	33892256
Arbutamine,1TMS,isomer #4	C[Si](C)(C)OC1=CC=C([C@@H](O)CNCCCCC2=CC=C(O)C=C2)C=C1O	3113.6	Semi standard non polar	33892256
Arbutamine,1TMS,isomer #5	C[Si](C)(C)N(CCCCC1=CC=C(O)C=C1)C[C@H](O)C1=CC=C(O)C(O)=C1	3228.6	Semi standard non polar	33892256
Arbutamine,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CCCCNC[C@H](O[Si](C)(C)C)C2=CC=C(O)C(O)=C2)C=C1	3056.0	Semi standard non polar	33892256
Arbutamine,2TMS,isomer #10	C[Si](C)(C)OC1=CC=C([C@@H](O)CN(CCCCC2=CC=C(O)C=C2)[Si](C)(C)C)C=C1O	3147.4	Semi standard non polar	33892256
Arbutamine,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C([C@H](CNCCCCC2=CC=C(O)C=C2)O[Si](C)(C)C)C=C1O	3077.5	Semi standard non polar	33892256
Arbutamine,2TMS,isomer #3	C[Si](C)(C)OC1=CC([C@H](CNCCCCC2=CC=C(O)C=C2)O[Si](C)(C)C)=CC=C1O	3058.4	Semi standard non polar	33892256
Arbutamine,2TMS,isomer #4	C[Si](C)(C)O[C@@H](CN(CCCCC1=CC=C(O)C=C1)[Si](C)(C)C)C1=CC=C(O)C(O)=C1	3213.3	Semi standard non polar	33892256
Arbutamine,2TMS,isomer #5	C[Si](C)(C)OC1=CC=C(CCCCNC[C@H](O)C2=CC=C(O[Si](C)(C)C)C(O)=C2)C=C1	3065.1	Semi standard non polar	33892256
Arbutamine,2TMS,isomer #6	C[Si](C)(C)OC1=CC=C(CCCCNC[C@H](O)C2=CC=C(O)C(O[Si](C)(C)C)=C2)C=C1	3044.4	Semi standard non polar	33892256
Arbutamine,2TMS,isomer #7	C[Si](C)(C)OC1=CC=C(CCCCN(C[C@H](O)C2=CC=C(O)C(O)=C2)[Si](C)(C)C)C=C1	3146.3	Semi standard non polar	33892256
Arbutamine,2TMS,isomer #8	C[Si](C)(C)OC1=CC=C([C@@H](O)CNCCCCC2=CC=C(O)C=C2)C=C1O[Si](C)(C)C	3078.3	Semi standard non polar	33892256
Arbutamine,2TMS,isomer #9	C[Si](C)(C)OC1=CC([C@@H](O)CN(CCCCC2=CC=C(O)C=C2)[Si](C)(C)C)=CC=C1O	3129.7	Semi standard non polar	33892256
Arbutamine,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CCCCNC[C@H](O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C(O)=C2)C=C1	3003.7	Semi standard non polar	33892256
Arbutamine,3TMS,isomer #10	C[Si](C)(C)OC1=CC=C([C@@H](O)CN(CCCCC2=CC=C(O)C=C2)[Si](C)(C)C)C=C1O[Si](C)(C)C	3131.5	Semi standard non polar	33892256
Arbutamine,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(CCCCNC[C@H](O[Si](C)(C)C)C2=CC=C(O)C(O[Si](C)(C)C)=C2)C=C1	2987.7	Semi standard non polar	33892256
Arbutamine,3TMS,isomer #3	C[Si](C)(C)OC1=CC=C(CCCCN(C[C@H](O[Si](C)(C)C)C2=CC=C(O)C(O)=C2)[Si](C)(C)C)C=C1	3097.0	Semi standard non polar	33892256
Arbutamine,3TMS,isomer #4	C[Si](C)(C)OC1=CC=C([C@H](CNCCCCC2=CC=C(O)C=C2)O[Si](C)(C)C)C=C1O[Si](C)(C)C	3036.0	Semi standard non polar	33892256
Arbutamine,3TMS,isomer #5	C[Si](C)(C)OC1=CC=C([C@H](CN(CCCCC2=CC=C(O)C=C2)[Si](C)(C)C)O[Si](C)(C)C)C=C1O	3107.1	Semi standard non polar	33892256
Arbutamine,3TMS,isomer #6	C[Si](C)(C)OC1=CC([C@H](CN(CCCCC2=CC=C(O)C=C2)[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O	3095.3	Semi standard non polar	33892256
Arbutamine,3TMS,isomer #7	C[Si](C)(C)OC1=CC=C(CCCCNC[C@H](O)C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C=C1	3082.4	Semi standard non polar	33892256
Arbutamine,3TMS,isomer #8	C[Si](C)(C)OC1=CC=C(CCCCN(C[C@H](O)C2=CC=C(O[Si](C)(C)C)C(O)=C2)[Si](C)(C)C)C=C1	3091.7	Semi standard non polar	33892256
Arbutamine,3TMS,isomer #9	C[Si](C)(C)OC1=CC=C(CCCCN(C[C@H](O)C2=CC=C(O)C(O[Si](C)(C)C)=C2)[Si](C)(C)C)C=C1	3071.4	Semi standard non polar	33892256
Arbutamine,4TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CCCCNC[C@H](O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C=C1	3045.9	Semi standard non polar	33892256
Arbutamine,4TMS,isomer #2	C[Si](C)(C)OC1=CC=C(CCCCN(C[C@H](O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C(O)=C2)[Si](C)(C)C)C=C1	3090.1	Semi standard non polar	33892256
Arbutamine,4TMS,isomer #3	C[Si](C)(C)OC1=CC=C(CCCCN(C[C@H](O[Si](C)(C)C)C2=CC=C(O)C(O[Si](C)(C)C)=C2)[Si](C)(C)C)C=C1	3073.7	Semi standard non polar	33892256
Arbutamine,4TMS,isomer #4	C[Si](C)(C)OC1=CC=C([C@H](CN(CCCCC2=CC=C(O)C=C2)[Si](C)(C)C)O[Si](C)(C)C)C=C1O[Si](C)(C)C	3085.7	Semi standard non polar	33892256
Arbutamine,4TMS,isomer #5	C[Si](C)(C)OC1=CC=C(CCCCN(C[C@H](O)C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)[Si](C)(C)C)C=C1	3115.2	Semi standard non polar	33892256
Arbutamine,5TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CCCCN(C[C@H](O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)[Si](C)(C)C)C=C1	3135.2	Semi standard non polar	33892256
Arbutamine,5TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CCCCN(C[C@H](O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)[Si](C)(C)C)C=C1	2826.9	Standard non polar	33892256
Arbutamine,5TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CCCCN(C[C@H](O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)[Si](C)(C)C)C=C1	3038.3	Standard polar	33892256
Arbutamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H](CNCCCCC1=CC=C(O)C=C1)C1=CC=C(O)C(O)=C1	3441.7	Semi standard non polar	33892256
Arbutamine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(CCCCNC[C@H](O)C2=CC=C(O)C(O)=C2)C=C1	3399.3	Semi standard non polar	33892256
Arbutamine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC([C@@H](O)CNCCCCC2=CC=C(O)C=C2)=CC=C1O	3387.9	Semi standard non polar	33892256
Arbutamine,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H](O)CNCCCCC2=CC=C(O)C=C2)C=C1O	3413.5	Semi standard non polar	33892256
Arbutamine,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(CCCCC1=CC=C(O)C=C1)C[C@H](O)C1=CC=C(O)C(O)=C1	3498.2	Semi standard non polar	33892256
Arbutamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CCCCNC[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=C(O)C(O)=C2)C=C1	3606.7	Semi standard non polar	33892256
Arbutamine,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H](O)CN(CCCCC2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)C=C1O	3681.3	Semi standard non polar	33892256
Arbutamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C([C@H](CNCCCCC2=CC=C(O)C=C2)O[Si](C)(C)C(C)(C)C)C=C1O	3604.6	Semi standard non polar	33892256
Arbutamine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC([C@H](CNCCCCC2=CC=C(O)C=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O	3582.8	Semi standard non polar	33892256
Arbutamine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H](CN(CCCCC1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O)=C1	3717.8	Semi standard non polar	33892256
Arbutamine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C(CCCCNC[C@H](O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)C=C1	3647.9	Semi standard non polar	33892256
Arbutamine,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC=C(CCCCNC[C@H](O)C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C=C1	3615.6	Semi standard non polar	33892256
Arbutamine,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC=C(CCCCN(C[C@H](O)C2=CC=C(O)C(O)=C2)[Si](C)(C)C(C)(C)C)C=C1	3662.9	Semi standard non polar	33892256
Arbutamine,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H](O)CNCCCCC2=CC=C(O)C=C2)C=C1O[Si](C)(C)C(C)(C)C	3640.3	Semi standard non polar	33892256
Arbutamine,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC([C@@H](O)CN(CCCCC2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)=CC=C1O	3652.8	Semi standard non polar	33892256
Arbutamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CCCCNC[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)C=C1	3765.3	Semi standard non polar	33892256
Arbutamine,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H](O)CN(CCCCC2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	3851.9	Semi standard non polar	33892256
Arbutamine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(CCCCNC[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C=C1	3746.4	Semi standard non polar	33892256
Arbutamine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(CCCCN(C[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=C(O)C(O)=C2)[Si](C)(C)C(C)(C)C)C=C1	3864.6	Semi standard non polar	33892256
Arbutamine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C([C@H](CNCCCCC2=CC=C(O)C=C2)O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	3754.0	Semi standard non polar	33892256
Arbutamine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C([C@H](CN(CCCCC2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1O	3854.1	Semi standard non polar	33892256
Arbutamine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC([C@H](CN(CCCCC2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O	3839.7	Semi standard non polar	33892256
Arbutamine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC=C(CCCCNC[C@H](O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)C=C1	3848.7	Semi standard non polar	33892256
Arbutamine,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=CC=C(CCCCN(C[C@H](O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)[Si](C)(C)C(C)(C)C)C=C1	3872.1	Semi standard non polar	33892256
Arbutamine,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC=C(CCCCN(C[C@H](O)C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)[Si](C)(C)C(C)(C)C)C=C1	3838.7	Semi standard non polar	33892256
Arbutamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CCCCNC[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)C=C1	3957.8	Semi standard non polar	33892256
Arbutamine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(CCCCN(C[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)[Si](C)(C)C(C)(C)C)C=C1	4051.9	Semi standard non polar	33892256
Arbutamine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(CCCCN(C[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)[Si](C)(C)C(C)(C)C)C=C1	4034.9	Semi standard non polar	33892256
Arbutamine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C([C@H](CN(CCCCC2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	4040.4	Semi standard non polar	33892256
Arbutamine,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C(CCCCN(C[C@H](O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)[Si](C)(C)C(C)(C)C)C=C1	4090.6	Semi standard non polar	33892256
Arbutamine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CCCCN(C[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)[Si](C)(C)C(C)(C)C)C=C1	4267.6	Semi standard non polar	33892256
Arbutamine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CCCCN(C[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)[Si](C)(C)C(C)(C)C)C=C1	3678.6	Standard non polar	33892256
Arbutamine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CCCCN(C[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)[Si](C)(C)C(C)(C)C)C=C1	3433.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Arbutamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4r-0900000000-beab4528e7ae0c5e38b5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arbutamine GC-MS (4 TMS) - 70eV, Positive	splash10-001l-1191070000-bc9a7cc5fdaffaee1815	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arbutamine 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 - Arbutamine 10V, Positive-QTOF	splash10-0uxr-0209000000-cb09be2863ef695c2d29	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arbutamine 20V, Positive-QTOF	splash10-0udj-0913000000-0491c75318d1f3342f09	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arbutamine 40V, Positive-QTOF	splash10-0a4j-5900000000-053a6953711858f14790	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arbutamine 10V, Negative-QTOF	splash10-014i-0229000000-c34a09d0f43937c79954	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arbutamine 20V, Negative-QTOF	splash10-03xs-0933000000-11bf8026af6aaad0368d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arbutamine 40V, Negative-QTOF	splash10-0bt9-1900000000-1c392070d0270adc6ce8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arbutamine 10V, Positive-QTOF	splash10-0uxr-0109000000-38c3340b26375b90d1bb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arbutamine 20V, Positive-QTOF	splash10-0udi-0947000000-265ff6fc9fb91b44eb44	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arbutamine 40V, Positive-QTOF	splash10-0a4j-3910000000-475756670ba2db15f4f4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arbutamine 10V, Negative-QTOF	splash10-014i-0009000000-3fe3b20def364ac29f1a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arbutamine 20V, Negative-QTOF	splash10-00ri-0944000000-82eb66b772a067f48e57	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arbutamine 40V, Negative-QTOF	splash10-0acc-3980000000-a6c3b823ca6dc07e05fb	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Arbutamine Action Pathway		Not Available

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 DB01102	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01102	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01102

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

54785

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Arbutamine

METLIN ID

Not Available

PubChem Compound

60789

PDB ID

Not Available

ChEBI ID

50580

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

Not Available

Enzymes

Enzyme Details

1. Beta-1 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. This receptor binds epinephrine and norepinephrine with approximately equal affinity
Gene Name:: ADRB1
Uniprot ID:: P08588
Molecular weight:: 51322.1

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Abou-Mohamed G, Nagarajan R, Ibrahim TM, Caldwell RW: Characterization of the adrenergic activity of arbutamine, a novel agent for pharmacological stress testing. Cardiovasc Drugs Ther. 1996 Mar;10(1):39-47. [PubMed:8723169 ]

Enzyme Details

2. 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

Abou-Mohamed G, Nagarajan R, Ibrahim TM, Caldwell RW: Characterization of the adrenergic activity of arbutamine, a novel agent for pharmacological stress testing. Cardiovasc Drugs Ther. 1996 Mar;10(1):39-47. [PubMed:8723169 ]

Enzyme Details

3. Beta-3 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. Beta-3 is involved in the regulation of lipolysis and thermogenesis
Gene Name:: ADRB3
Uniprot ID:: P13945
Molecular weight:: 43518.6

References

Abou-Mohamed G, Nagarajan R, Ibrahim TM, Caldwell RW: Characterization of the adrenergic activity of arbutamine, a novel agent for pharmacological stress testing. Cardiovasc Drugs Ther. 1996 Mar;10(1):39-47. [PubMed:8723169 ]

Showing metabocard for Arbutamine (HMDB0015234)

MOL for HMDB0015234 (Arbutamine)

3D MOL for HMDB0015234 (Arbutamine)

3D SDF for HMDB0015234 (Arbutamine)

3D-SDF for HMDB0015234 (Arbutamine)

PDB for HMDB0015234 (Arbutamine)

3D PDB for HMDB0015234 (Arbutamine)

SMILES for HMDB0015234 (Arbutamine)

INCHI for HMDB0015234 (Arbutamine)

Structure for HMDB0015234 (Arbutamine)

3D Structure for HMDB0015234 (Arbutamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References