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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 09:17:12 UTC

Update Date

2021-10-01 21:23:45 UTC

HMDB ID

HMDB0251712

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Efaroxan

Description

2-(2-ethyl-2,3-dihydro-1-benzofuran-2-yl)-4,5-dihydro-1H-imidazole belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring. 2-(2-ethyl-2,3-dihydro-1-benzofuran-2-yl)-4,5-dihydro-1H-imidazole is a very strong basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Efaroxan is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Efaroxan is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0251712
     RDKit          3D
Efaroxan
 32 34  0  0  0  0  0  0  0  0999 V2000
   -1.9546    2.3843   -1.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0009    1.5191   -1.9174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2323    0.6773   -0.9553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1252   -0.1775   -0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4061   -0.2087   -0.2873 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0077   -1.1401    0.6109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8752   -1.9584    1.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7334   -1.1034    0.8354 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6876    1.5083   -0.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7204    0.5096    0.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6125    0.4309    1.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4769   -0.6286    1.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4309   -1.6287    0.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5435   -1.5706   -0.5903 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6919   -0.4922   -0.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6997   -0.1820   -1.6158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9760    2.2680   -1.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6390    3.4370   -1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9543    2.1162   -0.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5906    0.8190   -2.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3476    2.1538   -2.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7611   -1.7781    0.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5050   -0.6057    1.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9345   -2.1461    2.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8106   -2.9226    0.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1917   -1.1664    1.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1644    1.9239    0.7977 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1017    2.3264   -0.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6776    1.1877    2.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1888   -0.7197    2.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1152   -2.4643    0.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5512   -2.3685   -1.3081 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  3  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16  3  1  0
  8  4  1  0
 15 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
M  END

  Mrv1572004221604382D          

 16 18  0  0  0  0            999 V2000
    0.2122    2.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0407    2.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1788    0.4280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6267   -0.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0407    0.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7663    1.1424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1269    0.1504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
 10  5  2  0  0  0  0
 10  9  1  0  0  0  0
 11  6  2  0  0  0  0
 11 10  1  0  0  0  0
 13  2  1  0  0  0  0
 13  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14  7  1  0  0  0  0
 14 12  2  0  0  0  0
 15  8  1  0  0  0  0
 15 12  1  0  0  0  0
 16 11  1  0  0  0  0
 16 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0251712

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1(CC2=CC=CC=C2O1)C1=NCCN1

> <INCHI_IDENTIFIER>
InChI=1S/C13H16N2O/c1-2-13(12-14-7-8-15-12)9-10-5-3-4-6-11(10)16-13/h3-6H,2,7-9H2,1H3,(H,14,15)

> <INCHI_KEY>
RATZLMXRALDSJW-UHFFFAOYSA-N

> <FORMULA>
C13H16N2O

> <MOLECULAR_WEIGHT>
216.284

> <EXACT_MASS>
216.126263143

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
24.17042594079689

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2-ethyl-2,3-dihydro-1-benzofuran-2-yl)-4,5-dihydro-1H-imidazole

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
2.0933370213333338

> <ALOGPS_LOGS>
-2.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.058610955510742

> <JCHEM_POLAR_SURFACE_AREA>
33.620000000000005

> <JCHEM_REFRACTIVITY>
62.601700000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.81e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
efaroxan

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0251712
     RDKit          3D
Efaroxan
 32 34  0  0  0  0  0  0  0  0999 V2000
   -1.9546    2.3843   -1.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0009    1.5191   -1.9174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2323    0.6773   -0.9553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1252   -0.1775   -0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4061   -0.2087   -0.2873 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0077   -1.1401    0.6109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8752   -1.9584    1.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7334   -1.1034    0.8354 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6876    1.5083   -0.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7204    0.5096    0.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6125    0.4309    1.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4769   -0.6286    1.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4309   -1.6287    0.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5435   -1.5706   -0.5903 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6919   -0.4922   -0.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6997   -0.1820   -1.6158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9760    2.2680   -1.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6390    3.4370   -1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9543    2.1162   -0.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5906    0.8190   -2.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3476    2.1538   -2.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7611   -1.7781    0.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5050   -0.6057    1.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9345   -2.1461    2.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8106   -2.9226    0.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1917   -1.1664    1.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1644    1.9239    0.7977 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1017    2.3264   -0.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6776    1.1877    2.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1888   -0.7197    2.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1152   -2.4643    0.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5512   -2.3685   -1.3081 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  3  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16  3  1  0
  8  4  1  0
 15 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
M  END

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       0.396   5.380   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.076   3.873   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.200   0.799   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.170  -0.346   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.076   1.812   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -1.430   2.133   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       0.237   0.281   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   13                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3   10                                                       
CONECT    6    4   11                                                       
CONECT    7    8   14                                                       
CONECT    8    7   15                                                       
CONECT    9   10   13                                                       
CONECT   10    5    9   11                                                  
CONECT   11    6   10   16                                                  
CONECT   12   13   14   15                                                  
CONECT   13    2    9   12   16                                             
CONECT   14    7   12                                                       
CONECT   15    8   12                                                       
CONECT   16   11   13                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

COMPND    HMDB0251712
HETATM    1  C1  UNL     1      -1.955   2.384  -1.125  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.001   1.519  -1.917  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.232   0.677  -0.955  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.125  -0.178  -0.171  1.00  0.00           C  
HETATM    5  N1  UNL     1      -2.406  -0.209  -0.287  1.00  0.00           N  
HETATM    6  C5  UNL     1      -3.008  -1.140   0.611  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.875  -1.958   1.138  1.00  0.00           C  
HETATM    8  N2  UNL     1      -0.733  -1.103   0.835  1.00  0.00           N  
HETATM    9  C7  UNL     1       0.688   1.508  -0.089  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.720   0.510   0.283  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.612   0.431   1.320  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.477  -0.629   1.429  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.431  -1.629   0.460  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.543  -1.571  -0.590  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.692  -0.492  -0.665  1.00  0.00           C  
HETATM   16  O1  UNL     1       0.700  -0.182  -1.616  1.00  0.00           O  
HETATM   17  H1  UNL     1      -2.976   2.268  -1.537  1.00  0.00           H  
HETATM   18  H2  UNL     1      -1.639   3.437  -1.219  1.00  0.00           H  
HETATM   19  H3  UNL     1      -1.954   2.116  -0.053  1.00  0.00           H  
HETATM   20  H4  UNL     1      -1.591   0.819  -2.569  1.00  0.00           H  
HETATM   21  H5  UNL     1      -0.348   2.154  -2.545  1.00  0.00           H  
HETATM   22  H6  UNL     1      -3.761  -1.778   0.080  1.00  0.00           H  
HETATM   23  H7  UNL     1      -3.505  -0.606   1.447  1.00  0.00           H  
HETATM   24  H8  UNL     1      -1.935  -2.146   2.232  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.811  -2.923   0.584  1.00  0.00           H  
HETATM   26  H10 UNL     1       0.192  -1.166   1.278  1.00  0.00           H  
HETATM   27  H11 UNL     1       0.164   1.924   0.798  1.00  0.00           H  
HETATM   28  H12 UNL     1       1.102   2.326  -0.717  1.00  0.00           H  
HETATM   29  H13 UNL     1       2.678   1.188   2.091  1.00  0.00           H  
HETATM   30  H14 UNL     1       4.189  -0.720   2.230  1.00  0.00           H  
HETATM   31  H15 UNL     1       4.115  -2.464   0.548  1.00  0.00           H  
HETATM   32  H16 UNL     1       2.551  -2.369  -1.308  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4    9   16
CONECT    4    5    5    8
CONECT    5    6
CONECT    6    7   22   23
CONECT    7    8   24   25
CONECT    8   26
CONECT    9   10   27   28
CONECT   10   11   11   15
CONECT   11   12   29
CONECT   12   13   13   30
CONECT   13   14   31
CONECT   14   15   15   32
CONECT   15   16
END

HMDB0251712
     RDKit          3D
Efaroxan
 32 34  0  0  0  0  0  0  0  0999 V2000
   -1.9546    2.3843   -1.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0009    1.5191   -1.9174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2323    0.6773   -0.9553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1252   -0.1775   -0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4061   -0.2087   -0.2873 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0077   -1.1401    0.6109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8752   -1.9584    1.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7334   -1.1034    0.8354 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6876    1.5083   -0.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7204    0.5096    0.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6125    0.4309    1.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4769   -0.6286    1.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4309   -1.6287    0.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5435   -1.5706   -0.5903 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6919   -0.4922   -0.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6997   -0.1820   -1.6158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9760    2.2680   -1.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6390    3.4370   -1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9543    2.1162   -0.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5906    0.8190   -2.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3476    2.1538   -2.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7611   -1.7781    0.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5050   -0.6057    1.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9345   -2.1461    2.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8106   -2.9226    0.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1917   -1.1664    1.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1644    1.9239    0.7977 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1017    2.3264   -0.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6776    1.1877    2.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1888   -0.7197    2.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1152   -2.4643    0.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5512   -2.3685   -1.3081 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  3  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16  3  1  0
  8  4  1  0
 15 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Efaroxan	MeSH
2-((2-Ethyl-2,3-dihydrobenzofuran-2-yl))-2-imidazoline	MeSH
Efaroxan hydrochloride	MeSH

Chemical Formula

C₁₃H₁₆N₂O

Average Molecular Weight

216.284

Monoisotopic Molecular Weight

216.126263143

IUPAC Name

2-(2-ethyl-2,3-dihydro-1-benzofuran-2-yl)-4,5-dihydro-1H-imidazole

Traditional Name

efaroxan

CAS Registry Number

Not Available

SMILES

CCC1(CC2=CC=CC=C2O1)C1=NCCN1

InChI Identifier

InChI=1S/C13H16N2O/c1-2-13(12-14-7-8-15-12)9-10-5-3-4-6-11(10)16-13/h3-6H,2,7-9H2,1H3,(H,14,15)

InChI Key

RATZLMXRALDSJW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Coumarans

Sub Class

Not Available

Direct Parent

Coumarans

Alternative Parents

Substituents

Coumaran
Alkyl aryl ether
Benzenoid
Imidolactam
2-imidazoline
Amidine
Carboxylic acid amidine
Ether
Carboximidamide
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Oxacycle
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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	2.98	ALOGPS
logP	2.09	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Basic)	9.06	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	33.62 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	62.6 m³·mol⁻¹	ChemAxon
Polarizability	24.17 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	146.623	30932474
DeepCCS	[M-H]-	144.26	30932474
DeepCCS	[M-2H]-	177.857	30932474
DeepCCS	[M+Na]+	152.713	30932474
AllCCS	[M+H]+	148.2	32859911
AllCCS	[M+H-H2O]+	144.0	32859911
AllCCS	[M+NH4]+	152.1	32859911
AllCCS	[M+Na]+	153.3	32859911
AllCCS	[M-H]-	155.4	32859911
AllCCS	[M+Na-2H]-	155.3	32859911
AllCCS	[M+HCOO]-	155.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Efaroxan	CCC1(CC2=CC=CC=C2O1)C1=NCCN1	2749.6	Standard polar	33892256
Efaroxan	CCC1(CC2=CC=CC=C2O1)C1=NCCN1	1918.9	Standard non polar	33892256
Efaroxan	CCC1(CC2=CC=CC=C2O1)C1=NCCN1	1876.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Efaroxan,1TMS,isomer #1	CCC1(C2=NCCN2[Si](C)(C)C)CC2=CC=CC=C2O1	2055.6	Semi standard non polar	33892256
Efaroxan,1TMS,isomer #1	CCC1(C2=NCCN2[Si](C)(C)C)CC2=CC=CC=C2O1	1863.9	Standard non polar	33892256
Efaroxan,1TMS,isomer #1	CCC1(C2=NCCN2[Si](C)(C)C)CC2=CC=CC=C2O1	2700.5	Standard polar	33892256
Efaroxan,1TBDMS,isomer #1	CCC1(C2=NCCN2[Si](C)(C)C(C)(C)C)CC2=CC=CC=C2O1	2239.2	Semi standard non polar	33892256
Efaroxan,1TBDMS,isomer #1	CCC1(C2=NCCN2[Si](C)(C)C(C)(C)C)CC2=CC=CC=C2O1	2087.4	Standard non polar	33892256
Efaroxan,1TBDMS,isomer #1	CCC1(C2=NCCN2[Si](C)(C)C(C)(C)C)CC2=CC=CC=C2O1	2843.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Efaroxan GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fri-9620000000-0bbc60cd35f13faf57f8	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Efaroxan 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 - Efaroxan 10V, Positive-QTOF	splash10-014i-0090000000-1a79fa2d0b0c50180bf2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Efaroxan 20V, Positive-QTOF	splash10-014i-2790000000-13ab373b7e7864003429	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Efaroxan 40V, Positive-QTOF	splash10-0006-9200000000-89bd612519ca1eaba526	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Efaroxan 10V, Negative-QTOF	splash10-014i-0290000000-bbf5ada407e2e932c4cc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Efaroxan 20V, Negative-QTOF	splash10-014i-1960000000-abbac943e2ab1adc5951	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Efaroxan 40V, Negative-QTOF	splash10-0a4i-4900000000-9915481c191a9b7d05a0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Efaroxan 10V, Positive-QTOF	splash10-014i-0090000000-b3b3217a7e594f652193	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Efaroxan 20V, Positive-QTOF	splash10-014i-0890000000-cc672b7bf8800f1c4636	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Efaroxan 40V, Positive-QTOF	splash10-066u-8900000000-addda3b55459477fece4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Efaroxan 10V, Negative-QTOF	splash10-014i-0090000000-810ec31dac75bb9d724b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Efaroxan 20V, Negative-QTOF	splash10-014i-7980000000-e564d49ac37e88506514	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Efaroxan 40V, Negative-QTOF	splash10-014i-1910000000-c5f0d0db1ea22ac82980	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72016

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Enzymes

Enzyme Details

1. Nischarin

General function:: Not Available
Specific function:: Acts either as the functional imidazoline-1 receptor (I1R) candidate or as a membrane-associated mediator of the I1R signaling. Binds numerous imidazoline ligands that induces initiation of cell-signaling cascades triggering to cell survival, growth and migration. Its activation by the agonist rilmenidine induces an increase in phosphorylation of mitogen-activated protein kinases MAPK1 and MAPK3 in rostral ventrolateral medulla (RVLM) neurons that exhibited rilmenidine-evoked hypotension (By similarity). Blocking its activation with efaroxan abolished rilmenidine-induced mitogen-activated protein kinase phosphorylation in RVLM neurons (By similarity). Acts as a modulator of Rac-regulated signal transduction pathways (By similarity). Suppresses Rac1-stimulated cell migration by interacting with PAK1 and inhibiting its kinase activity (By similarity). Also blocks Pak-independent Rac signaling by interacting with RAC1 and inhibiting Rac1-stimulated NF-kB response element and cyclin D1 promoter activation (By similarity). Inhibits also LIMK1 kinase activity by reducing LIMK1 'Tyr-508' phosphorylation (By similarity). Inhibits Rac-induced cell migration and invasion in breast and colon epithelial cells (By similarity). Inhibits lamellipodia formation, when overexpressed (By similarity). Plays a role in protection against apoptosis. Involved in association with IRS4 in the enhancement of insulin activation of MAPK1 and MAPK3. When overexpressed, induces a redistribution of cell surface ITGA5 integrin to intracellular endosomal structures.
Gene Name:: NISCH
Uniprot ID:: Q9Y2I1
Molecular weight:: 166627.105

Showing metabocard for Efaroxan (HMDB0251712)

MOL for HMDB0251712 (Efaroxan)

3D MOL for HMDB0251712 (Efaroxan)

3D SDF for HMDB0251712 (Efaroxan)

3D-SDF for HMDB0251712 (Efaroxan)

PDB for HMDB0251712 (Efaroxan)

3D PDB for HMDB0251712 (Efaroxan)

SMILES for HMDB0251712 (Efaroxan)

INCHI for HMDB0251712 (Efaroxan)

Structure for HMDB0251712 (Efaroxan)

3D Structure for HMDB0251712 (Efaroxan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes