NP-MRD: Showing NP-Card for Clenbuterol (NP0334591)

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Record Information

Version

2.0

Created at

2024-09-10 19:02:55 UTC

Updated at

2024-09-10 19:02:56 UTC

NP-MRD ID

NP0334591

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Clenbuterol

Description

Clenbuterol, also known as (+-)-clenbuterol or contraspasmin, belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it. Clenbuterol is a drug which is used as a bronchodilator in the treatment of asthma patients. . A substituted aniline that is 2,6-dichloroaniline in which the hydrogen at position 4 has been replaced by a 2-(tert-butylamino)-1-hydroxyethyl group. Clenbuterol is a very strong basic compound (based on its pKa). Clenbuterol was first documented in 2012 (PMID: 22071161). Clenbuterol is a potentially toxic compound (PMID: 22241580) (PMID: 22341861) (PMID: 22447758) (PMID: 22505058).

Structure

MOL SDF PDB SMILES InChI

1407
  Mrv0541 02231215282D          

 17 17  0  0  1  0            999 V2000
    5.2224    1.8794    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8794    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.0082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.8332    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.7044    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0  0  0  0
  2 16  1  0  0  0  0
  3  8  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5 17  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 13 16  1  0  0  0  0
 14 15  2  0  0  0  0
 15 17  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0334591

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(Cl)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H18Cl2N2O/c1-12(2,3)16-6-10(17)7-4-8(13)11(15)9(14)5-7/h4-5,10,16-17H,6,15H2,1-3H3

> <INCHI_KEY>
STJMRWALKKWQGH-UHFFFAOYSA-N

> <FORMULA>
C12H18Cl2N2O

> <MOLECULAR_WEIGHT>
277.19

> <EXACT_MASS>
276.079618622

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.806207507816204

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(4-amino-3,5-dichlorophenyl)-2-(tert-butylamino)ethan-1-ol

> <ALOGPS_LOGP>
2.94

> <JCHEM_LOGP>
2.3343827499999996

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.838522049375044

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.06230490983889

> <JCHEM_PKA_STRONGEST_BASIC>
9.628065086799161

> <JCHEM_POLAR_SURFACE_AREA>
58.28

> <JCHEM_REFRACTIVITY>
73.38409999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
clenbuterol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1407                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       9.748   3.508   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0       4.414   3.508   0.000  0.00  0.00          Cl+0
HETATM    3  O   UNK     0       8.415  -1.882   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       5.748  -3.422   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       7.081   5.048   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       4.414  -4.192   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.748  -1.882   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081  -1.112   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.080  -4.962   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184  -5.526   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.644  -2.858   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081   0.428   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748   1.198   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.415   1.198   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.415   2.738   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748   2.738   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.081   3.508   0.000  0.00  0.00           C+0
CONECT    1   15                                                            
CONECT    2   16                                                            
CONECT    3    8                                                            
CONECT    4    6    7                                                       
CONECT    5   17                                                            
CONECT    6    4    9   10   11                                             
CONECT    7    4    8                                                       
CONECT    8    3    7   12                                                  
CONECT    9    6                                                            
CONECT   10    6                                                            
CONECT   11    6                                                            
CONECT   12    8   13   14                                                  
CONECT   13   12   16                                                       
CONECT   14   12   15                                                       
CONECT   15    1   14   17                                                  
CONECT   16    2   13   17                                                  
CONECT   17    5   15   16                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Value	Source
(+-)-Clenbuterol	ChEBI
1-(4-Amino-3,5-dichloro-phenyl)-2-tert-butylamino-ethanol	ChEBI
4-Amino-3,5-dichloro-alpha-(((1,1-dimethylethyl)amino)methyl)benzenemethanol	ChEBI
4-Amino-alpha-((tert-butylamino)methyl)-3,5-dichlorobenzyl alcohol	ChEBI
Clenbuterolum	ChEBI
Contraspasmin	Kegg
Planipart	Kegg
4-Amino-3,5-dichloro-a-(((1,1-dimethylethyl)amino)methyl)benzenemethanol	Generator
4-Amino-3,5-dichloro-α-(((1,1-dimethylethyl)amino)methyl)benzenemethanol	Generator
4-Amino-a-((tert-butylamino)methyl)-3,5-dichlorobenzyl alcohol	Generator
4-Amino-α-((tert-butylamino)methyl)-3,5-dichlorobenzyl alcohol	Generator
NAB 365	HMDB
NAB-365	HMDB

Chemical Formula

C₁₂H₁₈Cl₂N₂O

Average Mass

277.1900 Da

Monoisotopic Mass

276.07962 Da

IUPAC Name

1-(4-amino-3,5-dichlorophenyl)-2-(tert-butylamino)ethan-1-ol

Traditional Name

clenbuterol

CAS Registry Number

Not Available

SMILES

CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(Cl)=C1

InChI Identifier

InChI=1S/C12H18Cl2N2O/c1-12(2,3)16-6-10(17)7-4-8(13)11(15)9(14)5-7/h4-5,10,16-17H,6,15H2,1-3H3

InChI Key

STJMRWALKKWQGH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Dichlorobenzenes

Alternative Parents

Substituents

1,3-dichlorobenzene
Aniline or substituted anilines
Aralkylamine
Aryl chloride
Aryl halide
1,2-aminoalcohol
Secondary alcohol
Secondary aliphatic amine
Secondary amine
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic nitrogen compound
Aromatic alcohol
Alcohol
Organic oxygen compound
Amine
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

substituted aniline (CHEBI:174690 )
secondary amino compound (CHEBI:174690 )
dichlorobenzene (CHEBI:174690 )
primary arylamine (CHEBI:174690 )
ethanolamines (CHEBI:174690 )
amino alcohol (CHEBI:174690 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	2.94	ALOGPS
logP	2.33	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	14.06	ChemAxon
pKa (Strongest Basic)	9.63	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	58.28 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	73.38 m³·mol⁻¹	ChemAxon
Polarizability	28.81 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0015477

DrugBank ID

DB01407

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008487

KNApSAcK ID

Not Available

Chemspider ID

2681

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Clenbuterol

METLIN ID

Not Available

PubChem Compound

2783

PDB ID

Not Available

ChEBI ID

174690

Good Scents ID

Not Available

References

General References

Hoshino D, Yoshida Y, Holloway GP, Lally J, Hatta H, Bonen A: Clenbuterol, a beta2-adrenergic agonist, reciprocally alters PGC-1 alpha and RIP140 and reduces fatty acid and pyruvate oxidation in rat skeletal muscle. Am J Physiol Regul Integr Comp Physiol. 2012 Feb 1;302(3):R373-84. doi: 10.1152/ajpregu.00183.2011. Epub 2011 Nov 9. [PubMed:22071161 ]
Gonzalez-Antuna A, Rodriguez-Gonzalez P, Lavandera I, Centineo G, Gotor V, Garcia Alonso JI: Development of a routine method for the simultaneous confirmation and determination of clenbuterol in urine by minimal labeling isotope pattern deconvolution and GC-EI-MS. Anal Bioanal Chem. 2012 Feb;402(5):1879-88. doi: 10.1007/s00216-011-5611-1. Epub 2012 Jan 13. [PubMed:22241580 ]
Zhang X, Zhao H, Xue Y, Wu Z, Zhang Y, He Y, Li X, Yuan Z: Colorimetric sensing of clenbuterol using gold nanoparticles in the presence of melamine. Biosens Bioelectron. 2012 Apr 15;34(1):112-7. doi: 10.1016/j.bios.2012.01.026. Epub 2012 Jan 28. [PubMed:22341861 ]
Guddat S, Fussholler G, Geyer H, Thomas A, Braun H, Haenelt N, Schwenke A, Klose C, Thevis M, Schanzer W: Clenbuterol - regional food contamination a possible source for inadvertent doping in sports. Drug Test Anal. 2012 Jun;4(6):534-8. doi: 10.1002/dta.1330. Epub 2012 Mar 22. [PubMed:22447758 ]
Mokhtari B, Pourabdollah K: Chromatographic separation of clenbuterol by bonded phases bearing nano-baskets of p-tert-calix[4]-1,2-crown-3, -crown-4, -crown-5 and -crown-6. J Sci Food Agric. 2012 Oct;92(13):2679-88. doi: 10.1002/jsfa.5688. Epub 2012 Apr 16. [PubMed:22505058 ]

Showing NP-Card for Clenbuterol (NP0334591)

MOL for NP0334591 (Clenbuterol)

3D MOL for NP0334591 (Clenbuterol)

3D SDF for NP0334591 (Clenbuterol)

3D-SDF for NP0334591 (Clenbuterol)

PDB for NP0334591 (Clenbuterol)

3D PDB for NP0334591 (Clenbuterol)

SMILES for NP0334591 (Clenbuterol)

INCHI for NP0334591 (Clenbuterol)

Structure for NP0334591 (Clenbuterol)

3D Structure for NP0334591 (Clenbuterol)