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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2019-06-27 17:24:11 UTC

Update Date

2022-03-07 03:18:16 UTC

HMDB ID

HMDB0240368

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Ractopamine

Description

Ractopamine (CAS: 97825-25-7) is a beta-agonist livestock feed additive used to increase lean muscle mass. Pharmacologically, ractopamine is a TAAR1 agonist and beta adrenoreceptor agonist that stimulates beta1 and beta2 adrenergic receptors (PMID: 24799633 ). In clinical use, beta-agonists relax the smooth muscles of airways, thereby resulting in bronchodilation (i.e. widened airways) and easier breathing. In livestock feed, these compounds are able to alter the ratio in which dietary energy intake is distributed between lean and fat tissue. Increasing protein synthesis results in increased muscle fibre size. Ractopamine is banned in over 160 countries including the member nations of the European Union, China, and Russia. Countries such as the United States and South Korea still permit ractopamine use (PMID: 26761809 ). Serious side effects, including mortality, have been attributed to beta-agonists (e.g. ractopamine and zilpaterol) in cattle and swine. Cooking is not able to completely degrade ractopamine, therefore human exposure to ractopamine is expected in countries where the feed additive is permitted. In humans, beta-agonists containing phenolic hydroxyl groups, are metabolized in the liver and intestine through glucuronidation and sulfation by UDP-glucuronosyltransferase (UGT) 1A6 and 1A9 and sulfotransferase (SULT1A3). Ractopamine is eliminated in urine mostly as its monoglucuronide and monosulfate conjugates (PMID: 27641640 ). Butopamine, the R,R diastereoisomer, is the most active of ractopamine's four diastereoisomers and is responsible for most of the leanness-enhancing effects.

Structure

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

HMDB0240368
     RDKit          3D
Ractopamine
 45 46  0  0  0  0  0  0  0  0999 V2000
   -0.4046   -0.8201    1.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5774   -0.6156    0.2895 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4002   -1.6572   -0.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8035   -1.7909    0.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5921   -0.5401   -0.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3149   -0.2770   -1.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0578    0.8548   -1.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1038    1.8075   -0.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8461    2.9771   -0.5519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3895    1.5607    0.7508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6370    0.4079    0.9395 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6488   -0.4555   -0.4165 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5387   -1.5681   -0.3913 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8128   -1.2883   -1.1947 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6670   -2.3868   -1.1570 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5428   -0.1255   -0.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4776    1.0839   -1.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1408    2.1875   -0.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8802    2.0842    0.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5721    3.1905    0.8769 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2869   -0.2217    0.5194 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3080   -1.0035   -2.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4055    2.2906    1.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0970    0.2810    1.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4132   -0.2522   -1.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8861   -1.7237    0.6584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1326   -2.5058   -0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5665   -1.0996   -2.2576 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2322   -2.4513   -1.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9009    1.1954   -2.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0685    3.1326   -1.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5067    4.0612    0.3804 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5454    0.8278    1.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3722   -1.1579    1.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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M  END


  Mrv1652306271919282D          

 22 23  0  0  0  0            999 V2000
 9998.233810000.2159    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9481 9999.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.662410000.2159    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.3763 9999.8031    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.091810000.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8053 9999.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.663210001.4532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.3763 9998.9783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.233810001.0408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3767 9998.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.805210000.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0908 9999.8035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0908 9998.9784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8052 9998.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5197 9998.9784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5197 9999.8035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.519710001.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.519710000.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.2343 9999.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.948710000.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.948810001.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.234210001.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  1  0  0  0
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M  END
> <DATABASE_ID>
HMDB0240368

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@H](CCC1=CC=C(O)C=C1)NC[C@H](O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H23NO3/c1-13(2-3-14-4-8-16(20)9-5-14)19-12-18(22)15-6-10-17(21)11-7-15/h4-11,13,18-22H,2-3,12H2,1H3/t13-,18+/m1/s1

> <INCHI_KEY>
YJQZYXCXBBCEAQ-ACJLOTCBSA-N

> <FORMULA>
C18H23NO3

> <MOLECULAR_WEIGHT>
301.386

> <EXACT_MASS>
301.167793605

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
34.41136942233055

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(1R)-1-hydroxy-2-{[(2R)-4-(4-hydroxyphenyl)butan-2-yl]amino}ethyl]phenol

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
2.2040715040809156

> <ALOGPS_LOGS>
-4.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.500351874503771

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.194440468811358

> <JCHEM_PKA_STRONGEST_BASIC>
9.888725546966933

> <JCHEM_POLAR_SURFACE_AREA>
72.72

> <JCHEM_REFRACTIVITY>
87.6177

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(1R)-1-hydroxy-2-{[(2R)-4-(4-hydroxyphenyl)butan-2-yl]amino}ethyl]phenol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0240368
     RDKit          3D
Ractopamine
 45 46  0  0  0  0  0  0  0  0999 V2000
   -0.4046   -0.8201    1.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5774   -0.6156    0.2895 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4002   -1.6572   -0.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8035   -1.7909    0.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5921   -0.5401   -0.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3149   -0.2770   -1.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0578    0.8548   -1.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1038    1.8075   -0.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8461    2.9771   -0.5519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3895    1.5607    0.7508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6370    0.4079    0.9395 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6488   -0.4555   -0.4165 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5387   -1.5681   -0.3913 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8128   -1.2883   -1.1947 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6670   -2.3868   -1.1570 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5428   -0.1255   -0.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4776    1.0839   -1.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1408    2.1875   -0.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8802    2.0842    0.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5721    3.1905    0.8769 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9568    0.8747    1.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2869   -0.2217    0.5194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4787   -1.3856    2.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3058   -1.2656    2.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2959    0.1942    2.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4599   -1.3611   -1.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8585   -2.1798    1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3080   -1.0035   -2.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0970    0.2810    1.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8861   -1.7237    0.6584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1326   -2.5058   -0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5665   -1.0996   -2.2576 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2322   -2.4513   -1.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9009    1.1954   -2.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0685    3.1326   -1.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5067    4.0612    0.3804 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5454    0.8278    1.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3722   -1.1579    1.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
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  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
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 16 17  2  0
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 11  5  1  0
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  4 29  1  0
  4 30  1  0
  6 31  1  0
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 11 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  6
 15 40  1  0
 17 41  1  0
 18 42  1  0
 20 43  1  0
 21 44  1  0
 22 45  1  0
M  END

HEADER    PROTEIN                                 27-JUN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-JUN-19         0                                  
HETATM    1  C   UNK     0    8663.3708667.070   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8664.7038666.299   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    8666.0368667.070   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    8667.3698666.299   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8668.7058667.070   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8670.0378666.299   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8675.3718669.379   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8667.3698664.759   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8663.3708668.609   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8658.0378663.991   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8660.7038667.070   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8659.3698666.300   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8659.3698664.760   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8660.7038663.990   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8662.0378664.760   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8662.0378666.300   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8671.3708668.609   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8671.3708667.069   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8672.7048666.299   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8674.0388667.069   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8674.0388668.609   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8672.7048669.379   0.000  0.00  0.00           C+0
CONECT    1    2    9   16                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5   18                                                       
CONECT    7   21                                                            
CONECT    8    4                                                            
CONECT    9    1                                                            
CONECT   10   13                                                            
CONECT   11   12   16                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   10                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11    1                                                  
CONECT   17   18   22                                                       
CONECT   18   17   19    6                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22    7                                                  
CONECT   22   21   17                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0240368
HETATM    1  C1  UNL     1      -0.405  -0.820   1.747  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.577  -0.616   0.289  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.400  -1.657  -0.402  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.803  -1.791   0.091  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.592  -0.540  -0.061  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.315  -0.277  -1.213  1.00  0.00           C  
HETATM    7  C7  UNL     1      -5.058   0.855  -1.406  1.00  0.00           C  
HETATM    8  C8  UNL     1      -5.104   1.808  -0.403  1.00  0.00           C  
HETATM    9  O1  UNL     1      -5.846   2.977  -0.552  1.00  0.00           O  
HETATM   10  C9  UNL     1      -4.389   1.561   0.751  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.637   0.408   0.939  1.00  0.00           C  
HETATM   12  N1  UNL     1       0.649  -0.456  -0.416  1.00  0.00           N  
HETATM   13  C11 UNL     1       1.539  -1.568  -0.391  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.813  -1.288  -1.195  1.00  0.00           C  
HETATM   15  O2  UNL     1       3.667  -2.387  -1.157  1.00  0.00           O  
HETATM   16  C13 UNL     1       3.543  -0.126  -0.636  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.478   1.084  -1.287  1.00  0.00           C  
HETATM   18  C15 UNL     1       4.141   2.187  -0.802  1.00  0.00           C  
HETATM   19  C16 UNL     1       4.880   2.084   0.350  1.00  0.00           C  
HETATM   20  O3  UNL     1       5.572   3.191   0.877  1.00  0.00           O  
HETATM   21  C17 UNL     1       4.957   0.875   1.018  1.00  0.00           C  
HETATM   22  C18 UNL     1       4.287  -0.222   0.519  1.00  0.00           C  
HETATM   23  H1  UNL     1       0.479  -1.386   2.068  1.00  0.00           H  
HETATM   24  H2  UNL     1      -1.306  -1.266   2.217  1.00  0.00           H  
HETATM   25  H3  UNL     1      -0.296   0.194   2.228  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.141   0.357   0.154  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.460  -1.361  -1.481  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.905  -2.640  -0.373  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.858  -2.180   1.138  1.00  0.00           H  
HETATM   30  H8  UNL     1      -3.299  -2.564  -0.534  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.308  -1.004  -2.035  1.00  0.00           H  
HETATM   32  H10 UNL     1      -5.616   1.036  -2.322  1.00  0.00           H  
HETATM   33  H11 UNL     1      -6.809   2.932  -0.238  1.00  0.00           H  
HETATM   34  H12 UNL     1      -4.406   2.291   1.558  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.097   0.281   1.882  1.00  0.00           H  
HETATM   36  H14 UNL     1       0.413  -0.252  -1.428  1.00  0.00           H  
HETATM   37  H15 UNL     1       1.886  -1.724   0.658  1.00  0.00           H  
HETATM   38  H16 UNL     1       1.133  -2.506  -0.781  1.00  0.00           H  
HETATM   39  H17 UNL     1       2.567  -1.100  -2.258  1.00  0.00           H  
HETATM   40  H18 UNL     1       4.232  -2.451  -1.967  1.00  0.00           H  
HETATM   41  H19 UNL     1       2.901   1.195  -2.200  1.00  0.00           H  
HETATM   42  H20 UNL     1       4.068   3.133  -1.343  1.00  0.00           H  
HETATM   43  H21 UNL     1       5.507   4.061   0.380  1.00  0.00           H  
HETATM   44  H22 UNL     1       5.545   0.828   1.918  1.00  0.00           H  
HETATM   45  H23 UNL     1       4.372  -1.158   1.075  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   12   26
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6    6   11
CONECT    6    7   31
CONECT    7    8    8   32
CONECT    8    9   10
CONECT    9   33
CONECT   10   11   11   34
CONECT   11   35
CONECT   12   13   36
CONECT   13   14   37   38
CONECT   14   15   16   39
CONECT   15   40
CONECT   16   17   17   22
CONECT   17   18   41
CONECT   18   19   19   42
CONECT   19   20   21
CONECT   20   43
CONECT   21   22   22   44
CONECT   22   45
END

HMDB0240368
     RDKit          3D
Ractopamine
 45 46  0  0  0  0  0  0  0  0999 V2000
   -0.4046   -0.8201    1.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5774   -0.6156    0.2895 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4002   -1.6572   -0.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8035   -1.7909    0.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5921   -0.5401   -0.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3149   -0.2770   -1.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0578    0.8548   -1.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1038    1.8075   -0.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8461    2.9771   -0.5519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3895    1.5607    0.7508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6370    0.4079    0.9395 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6488   -0.4555   -0.4165 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5387   -1.5681   -0.3913 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8128   -1.2883   -1.1947 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6670   -2.3868   -1.1570 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5428   -0.1255   -0.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4776    1.0839   -1.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1408    2.1875   -0.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8802    2.0842    0.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5721    3.1905    0.8769 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9568    0.8747    1.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2869   -0.2217    0.5194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4787   -1.3856    2.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3058   -1.2656    2.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2959    0.1942    2.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1408    0.3569    0.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4599   -1.3611   -1.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9055   -2.6395   -0.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8585   -2.1798    1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2988   -2.5639   -0.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3080   -1.0035   -2.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6161    1.0359   -2.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8088    2.9319   -0.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4055    2.2906    1.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0970    0.2810    1.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4132   -0.2522   -1.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8861   -1.7237    0.6584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1326   -2.5058   -0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5665   -1.0996   -2.2576 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2322   -2.4513   -1.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9009    1.1954   -2.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0685    3.1326   -1.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5067    4.0612    0.3804 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5454    0.8278    1.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3722   -1.1579    1.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 11  5  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  1
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  6 31  1  0
  7 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  6
 15 40  1  0
 17 41  1  0
 18 42  1  0
 20 43  1  0
 21 44  1  0
 22 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(R)-p-Hydroxy-alpha-((((R)-3-(p-hydroxyphenyl)-1-methylpropyl)amino)methyl)benzyl alcohol	ChEBI
(R,R)-Ractopamine	ChEBI
Butopamina	ChEBI
Butopaminum	ChEBI
LY 131126	ChEBI
(R)-p-Hydroxy-a-((((R)-3-(p-hydroxyphenyl)-1-methylpropyl)amino)methyl)benzyl alcohol	Generator
(R)-p-Hydroxy-α-((((R)-3-(p-hydroxyphenyl)-1-methylpropyl)amino)methyl)benzyl alcohol	Generator
p-Hydroxy-alpha-(((-3-(p-hydroxyphenyl)-1-methylpropyl)amino)methyl)benzyl alcohol	MeSH
Butopamine	HMDB
Ractopamine	HMDB

Chemical Formula

C₁₈H₂₃NO₃

Average Molecular Weight

301.386

Monoisotopic Molecular Weight

301.167793605

IUPAC Name

4-[(1R)-1-hydroxy-2-{[(2R)-4-(4-hydroxyphenyl)butan-2-yl]amino}ethyl]phenol

Traditional Name

4-[(1R)-1-hydroxy-2-{[(2R)-4-(4-hydroxyphenyl)butan-2-yl]amino}ethyl]phenol

CAS Registry Number

66734-12-1

SMILES

C[C@H](CCC1=CC=C(O)C=C1)NC[C@H](O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C18H23NO3/c1-13(2-3-14-4-8-16(20)9-5-14)19-12-18(22)15-6-10-17(21)11-7-15/h4-11,13,18-22H,2-3,12H2,1H3/t13-,18+/m1/s1

InChI Key

YJQZYXCXBBCEAQ-ACJLOTCBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-2-unsubstituted benzenoids

Direct Parent

1-hydroxy-2-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Monocyclic benzene moiety
1,2-aminoalcohol
Secondary alcohol
Secondary amine
Secondary aliphatic amine
Organic oxygen compound
Aromatic alcohol
Alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

4-(1-hydroxy-2-\{[4-(4-hydroxyphenyl)butan-2-yl]amino\}ethyl)phenol (CHEBI:82648 )

Ontology

Not Available

Urine (PMID: 27641640)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.17	ALOGPS
logP	2.2	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	9.19	ChemAxon
pKa (Strongest Basic)	9.89	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	72.72 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	87.62 m³·mol⁻¹	ChemAxon
Polarizability	34.41 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
DeepCCS	[M+H]+	178.192	30932474
DeepCCS	[M-H]-	175.834	30932474
DeepCCS	[M-2H]-	209.947	30932474
DeepCCS	[M+Na]+	185.269	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ractopamine	C[C@H](CCC1=CC=C(O)C=C1)NC[C@H](O)C1=CC=C(O)C=C1	4176.2	Standard polar	33892256
Ractopamine	C[C@H](CCC1=CC=C(O)C=C1)NC[C@H](O)C1=CC=C(O)C=C1	2723.2	Standard non polar	33892256
Ractopamine	C[C@H](CCC1=CC=C(O)C=C1)NC[C@H](O)C1=CC=C(O)C=C1	2968.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ractopamine,1TMS,isomer #1	C[C@H](CCC1=CC=C(O[Si](C)(C)C)C=C1)NC[C@H](O)C1=CC=C(O)C=C1	2881.7	Semi standard non polar	33892256
Ractopamine,1TMS,isomer #2	C[C@H](CCC1=CC=C(O)C=C1)NC[C@H](O[Si](C)(C)C)C1=CC=C(O)C=C1	2937.1	Semi standard non polar	33892256
Ractopamine,1TMS,isomer #3	C[C@H](CCC1=CC=C(O)C=C1)NC[C@H](O)C1=CC=C(O[Si](C)(C)C)C=C1	2874.1	Semi standard non polar	33892256
Ractopamine,1TMS,isomer #4	C[C@H](CCC1=CC=C(O)C=C1)N(C[C@H](O)C1=CC=C(O)C=C1)[Si](C)(C)C	2991.7	Semi standard non polar	33892256
Ractopamine,2TMS,isomer #1	C[C@H](CCC1=CC=C(O[Si](C)(C)C)C=C1)NC[C@H](O[Si](C)(C)C)C1=CC=C(O)C=C1	2847.6	Semi standard non polar	33892256
Ractopamine,2TMS,isomer #2	C[C@H](CCC1=CC=C(O[Si](C)(C)C)C=C1)NC[C@H](O)C1=CC=C(O[Si](C)(C)C)C=C1	2843.1	Semi standard non polar	33892256
Ractopamine,2TMS,isomer #3	C[C@H](CCC1=CC=C(O[Si](C)(C)C)C=C1)N(C[C@H](O)C1=CC=C(O)C=C1)[Si](C)(C)C	2918.6	Semi standard non polar	33892256
Ractopamine,2TMS,isomer #4	C[C@H](CCC1=CC=C(O)C=C1)NC[C@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1	2837.4	Semi standard non polar	33892256
Ractopamine,2TMS,isomer #5	C[C@H](CCC1=CC=C(O)C=C1)N(C[C@H](O[Si](C)(C)C)C1=CC=C(O)C=C1)[Si](C)(C)C	2997.9	Semi standard non polar	33892256
Ractopamine,2TMS,isomer #6	C[C@H](CCC1=CC=C(O)C=C1)N(C[C@H](O)C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C	2926.7	Semi standard non polar	33892256
Ractopamine,3TMS,isomer #1	C[C@H](CCC1=CC=C(O[Si](C)(C)C)C=C1)NC[C@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1	2827.7	Semi standard non polar	33892256
Ractopamine,3TMS,isomer #2	C[C@H](CCC1=CC=C(O[Si](C)(C)C)C=C1)N(C[C@H](O[Si](C)(C)C)C1=CC=C(O)C=C1)[Si](C)(C)C	2907.6	Semi standard non polar	33892256
Ractopamine,3TMS,isomer #3	C[C@H](CCC1=CC=C(O[Si](C)(C)C)C=C1)N(C[C@H](O)C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C	2923.9	Semi standard non polar	33892256
Ractopamine,3TMS,isomer #4	C[C@H](CCC1=CC=C(O)C=C1)N(C[C@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C	2907.1	Semi standard non polar	33892256
Ractopamine,4TMS,isomer #1	C[C@H](CCC1=CC=C(O[Si](C)(C)C)C=C1)N(C[C@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C	2970.1	Semi standard non polar	33892256
Ractopamine,4TMS,isomer #1	C[C@H](CCC1=CC=C(O[Si](C)(C)C)C=C1)N(C[C@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C	2640.2	Standard non polar	33892256
Ractopamine,4TMS,isomer #1	C[C@H](CCC1=CC=C(O[Si](C)(C)C)C=C1)N(C[C@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C	2906.6	Standard polar	33892256
Ractopamine,1TBDMS,isomer #1	C[C@H](CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)NC[C@H](O)C1=CC=C(O)C=C1	3151.9	Semi standard non polar	33892256
Ractopamine,1TBDMS,isomer #2	C[C@H](CCC1=CC=C(O)C=C1)NC[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C=C1	3181.1	Semi standard non polar	33892256
Ractopamine,1TBDMS,isomer #3	C[C@H](CCC1=CC=C(O)C=C1)NC[C@H](O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3149.3	Semi standard non polar	33892256
Ractopamine,1TBDMS,isomer #4	C[C@H](CCC1=CC=C(O)C=C1)N(C[C@H](O)C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C	3236.8	Semi standard non polar	33892256
Ractopamine,2TBDMS,isomer #1	C[C@H](CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)NC[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C=C1	3340.5	Semi standard non polar	33892256
Ractopamine,2TBDMS,isomer #2	C[C@H](CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)NC[C@H](O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3416.3	Semi standard non polar	33892256
Ractopamine,2TBDMS,isomer #3	C[C@H](CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N(C[C@H](O)C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C	3435.5	Semi standard non polar	33892256
Ractopamine,2TBDMS,isomer #4	C[C@H](CCC1=CC=C(O)C=C1)NC[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3336.3	Semi standard non polar	33892256
Ractopamine,2TBDMS,isomer #5	C[C@H](CCC1=CC=C(O)C=C1)N(C[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C	3494.8	Semi standard non polar	33892256
Ractopamine,2TBDMS,isomer #6	C[C@H](CCC1=CC=C(O)C=C1)N(C[C@H](O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3449.9	Semi standard non polar	33892256
Ractopamine,3TBDMS,isomer #1	C[C@H](CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)NC[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3543.3	Semi standard non polar	33892256
Ractopamine,3TBDMS,isomer #2	C[C@H](CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N(C[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C	3675.9	Semi standard non polar	33892256
Ractopamine,3TBDMS,isomer #3	C[C@H](CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N(C[C@H](O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3714.1	Semi standard non polar	33892256
Ractopamine,3TBDMS,isomer #4	C[C@H](CCC1=CC=C(O)C=C1)N(C[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3655.7	Semi standard non polar	33892256
Ractopamine,4TBDMS,isomer #1	C[C@H](CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N(C[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3909.5	Semi standard non polar	33892256
Ractopamine,4TBDMS,isomer #1	C[C@H](CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N(C[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3376.5	Standard non polar	33892256
Ractopamine,4TBDMS,isomer #1	C[C@H](CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N(C[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3231.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ractopamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ractopamine 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 - Ractopamine 10V, Positive-QTOF	splash10-001i-0193000000-878c254fd540fd0dd8ba	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ractopamine 20V, Positive-QTOF	splash10-01q9-0930000000-a514bfa3ab2c531b3885	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ractopamine 40V, Positive-QTOF	splash10-0c2d-4910000000-26e3c7a51192de4a018b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ractopamine 10V, Negative-QTOF	splash10-0udi-0009000000-d8889aea2cbe8e49784e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ractopamine 20V, Negative-QTOF	splash10-0zmi-1914000000-9c64653b9780bcd31f59	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ractopamine 40V, Negative-QTOF	splash10-014l-5920000000-0b6babcfaa6d55de2535	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Expected but not Quantified	Not Quantified	Not Specified	Not Available	Normal	27641640	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

61830

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

68556

PDB ID

Not Available

ChEBI ID

82648

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

Cheng TD, Shelver WL, Hong CC, McCann SE, Davis W, Zhang Y, Ambrosone CB, Smith DJ: Urinary Excretion of the beta-Adrenergic Feed Additives Ractopamine and Zilpaterol in Breast and Lung Cancer Patients. J Agric Food Chem. 2016 Oct 12;64(40):7632-7639. doi: 10.1021/acs.jafc.6b02723. Epub 2016 Sep 27. [PubMed:27641640 ]
Liu X, Grandy DK, Janowsky A: Ractopamine, a livestock feed additive, is a full agonist at trace amine-associated receptor 1. J Pharmacol Exp Ther. 2014 Jul;350(1):124-9. doi: 10.1124/jpet.114.213116. Epub 2014 May 5. [PubMed:24799633 ]
Sung IK, Park SJ, Kang K, Kim MY, Cho S: Development and Application of a Method for Rapid and Simultaneous Determination of Three beta-agonists (Clenbuterol, Ractopamine, and Zilpaterol) using Liquid Chromatography-tandem Mass Spectrometry. Korean J Food Sci Anim Resour. 2015;35(1):121-9. doi: 10.5851/kosfa.2015.35.1.121. Epub 2015 Feb 28. [PubMed:26761809 ]

Showing metabocard for Ractopamine (HMDB0240368)

MOL for HMDB0240368 (Ractopamine)

3D MOL for HMDB0240368 (Ractopamine)

3D SDF for HMDB0240368 (Ractopamine)

3D-SDF for HMDB0240368 (Ractopamine)

PDB for HMDB0240368 (Ractopamine)

3D PDB for HMDB0240368 (Ractopamine)

SMILES for HMDB0240368 (Ractopamine)

INCHI for HMDB0240368 (Ractopamine)

Structure for HMDB0240368 (Ractopamine)

3D Structure for HMDB0240368 (Ractopamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra