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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-18 18:42:46 UTC

Update Date

2019-07-23 07:14:50 UTC

HMDB ID

HMDB0060678

Secondary Accession Numbers

HMDB60678

Metabolite Identification

Common Name

3-Hydroxymonoethylglycinexylidide

Description

3-Hydroxymonoethylglycinexylidide, also known as 3-OH-megx, belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids. Lidocaine is used topically to relieve itching, burning and pain from skin inflammations, injected as a dental anesthetic or as a local anesthetic for minor surgery. 3-Hydroxymonoethylglycinexylidide is a very strong basic compound (based on its pKa). 3-Hydroxymonoethylglycinexylidide is a metabolite of lidocaine. In humans, 3-hydroxymonoethylglycinexylidide is involved in lidocaine (local anaesthetic) metabolism pathway. Lidocaine, Xylocaine, or lignocaine is a common local anesthetic and antiarrhythmic drug.

Structure

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

HMDB0060678
     RDKit          3D
3-Hydroxymonoethylglycinexylidide
 34 34  0  0  0  0  0  0  0  0999 V2000
    5.0524    0.4492    0.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7110   -0.0648   -0.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1603   -1.0339    0.4281 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9194   -1.6047    0.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7599   -0.6644    0.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9468    0.5333    0.4570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5519   -1.0808   -0.2341 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6148   -0.1713   -0.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9408    0.5524   -1.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1813    0.3753   -2.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9835    1.4541   -1.2737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6882    1.6107   -0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3529    0.8809    1.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0899    1.0763    2.2075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3108   -0.0211    1.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9250   -0.8242    2.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5920    1.0307   -0.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6250   -0.4501    0.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8797    1.1524    0.9359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0307    0.8124   -0.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -0.4515   -1.4759 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3680   -0.9308    1.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7141   -2.4564    0.7573 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0041   -2.0433   -0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6938   -2.0769   -0.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9090    0.4122   -3.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7366   -0.6502   -2.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4500    1.1784   -2.7664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2251    2.0131   -2.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5144    2.3162   -0.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8578    1.7335    2.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1641   -0.2914    2.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6352   -1.8568    1.9592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8676   -0.9091    2.8191 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
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  7 25  1  0
 10 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
M  END

 
  Mrv0541 06181311422D          
 
 16 16  0  0  0  0            999 V2000
   13.4247  -10.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1408  -10.9890    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7117  -10.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4247   -9.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8538  -10.5714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9988  -10.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7151  -11.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7117   -9.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1341   -9.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5667  -10.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8884   -9.8262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9988   -9.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2831  -10.5714    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9994  -10.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7055  -10.5714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7118   -8.4957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  2  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  2  0  0  0  0
  6 12  2  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 12  1  0  0  0  0
  8 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060678

> <DATABASE_NAME>
hmdb

> <SMILES>
CCNCC(=O)NC1=C(C)C=CC(O)=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C12H18N2O2/c1-4-13-7-11(16)14-12-8(2)5-6-10(15)9(12)3/h5-6,13,15H,4,7H2,1-3H3,(H,14,16)

> <INCHI_KEY>
YITCMQBVWIHTTA-UHFFFAOYSA-N

> <FORMULA>
C12H18N2O2

> <MOLECULAR_WEIGHT>
222.2835

> <EXACT_MASS>
222.13682783

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.65559747968331

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(ethylamino)-N-(3-hydroxy-2,6-dimethylphenyl)acetamide

> <ALOGPS_LOGP>
1.04

> <JCHEM_LOGP>
1.6254328063496934

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.938800087728104

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.052576091221404

> <JCHEM_PKA_STRONGEST_BASIC>
8.553741605785236

> <JCHEM_POLAR_SURFACE_AREA>
61.36

> <JCHEM_REFRACTIVITY>
65.8672

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(ethylamino)-N-(3-hydroxy-2,6-dimethylphenyl)acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060678
     RDKit          3D
3-Hydroxymonoethylglycinexylidide
 34 34  0  0  0  0  0  0  0  0999 V2000
    5.0524    0.4492    0.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7110   -0.0648   -0.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1603   -1.0339    0.4281 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9194   -1.6047    0.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7599   -0.6644    0.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9468    0.5333    0.4570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5519   -1.0808   -0.2341 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6148   -0.1713   -0.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9408    0.5524   -1.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1813    0.3753   -2.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9835    1.4541   -1.2737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6882    1.6107   -0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3529    0.8809    1.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0899    1.0763    2.2075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3108   -0.0211    1.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9250   -0.8242    2.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5920    1.0307   -0.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6250   -0.4501    0.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8797    1.1524    0.9359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0307    0.8124   -0.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -0.4515   -1.4759 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3680   -0.9308    1.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7141   -2.4564    0.7573 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0041   -2.0433   -0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6938   -2.0769   -0.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9090    0.4122   -3.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7366   -0.6502   -2.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4500    1.1784   -2.7664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2251    2.0131   -2.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5144    2.3162   -0.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8578    1.7335    2.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1641   -0.2914    2.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6352   -1.8568    1.9592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8676   -0.9091    2.8191 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
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  7 25  1  0
 10 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
M  END

HEADER    PROTEIN                                 18-JUN-13   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-JUN-13         0                                  
HETATM    1  C   UNK     0      25.059 -19.740   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      26.396 -20.513   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      23.728 -20.519   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.059 -18.200   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      27.727 -19.733   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.398 -19.740   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.735 -22.053   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.728 -17.433   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      26.384 -17.433   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.058 -20.513   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      27.792 -18.342   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      22.398 -18.200   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      30.395 -19.733   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      31.732 -20.513   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      33.050 -19.733   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      23.729 -15.859   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6    7                                                  
CONECT    4    1    8    9                                                  
CONECT    5    2   10   11                                                  
CONECT    6    3   12                                                       
CONECT    7    3                                                            
CONECT    8    4   12   16                                                  
CONECT    9    4                                                            
CONECT   10    5   13                                                       
CONECT   11    5                                                            
CONECT   12    6    8                                                       
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16    8                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0060678
HETATM    1  C1  UNL     1       5.052   0.449   0.077  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.711  -0.065  -0.457  1.00  0.00           C  
HETATM    3  N1  UNL     1       3.160  -1.034   0.428  1.00  0.00           N  
HETATM    4  C3  UNL     1       1.919  -1.605   0.058  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.760  -0.664   0.105  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.947   0.533   0.457  1.00  0.00           O  
HETATM    7  N2  UNL     1      -0.552  -1.081  -0.234  1.00  0.00           N  
HETATM    8  C5  UNL     1      -1.615  -0.171  -0.180  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.941   0.552  -1.309  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.181   0.375  -2.575  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.983   1.454  -1.274  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.688   1.611  -0.084  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.353   0.881   1.041  1.00  0.00           C  
HETATM   14  O2  UNL     1      -4.090   1.076   2.207  1.00  0.00           O  
HETATM   15  C11 UNL     1      -2.311  -0.021   1.008  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.925  -0.824   2.201  1.00  0.00           C  
HETATM   17  H1  UNL     1       5.592   1.031  -0.699  1.00  0.00           H  
HETATM   18  H2  UNL     1       5.625  -0.450   0.415  1.00  0.00           H  
HETATM   19  H3  UNL     1       4.880   1.152   0.936  1.00  0.00           H  
HETATM   20  H4  UNL     1       3.031   0.812  -0.526  1.00  0.00           H  
HETATM   21  H5  UNL     1       3.929  -0.451  -1.476  1.00  0.00           H  
HETATM   22  H6  UNL     1       3.368  -0.931   1.422  1.00  0.00           H  
HETATM   23  H7  UNL     1       1.714  -2.456   0.757  1.00  0.00           H  
HETATM   24  H8  UNL     1       2.004  -2.043  -0.952  1.00  0.00           H  
HETATM   25  H9  UNL     1      -0.694  -2.077  -0.520  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.909   0.412  -3.435  1.00  0.00           H  
HETATM   27  H11 UNL     1      -0.737  -0.650  -2.637  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.450   1.178  -2.766  1.00  0.00           H  
HETATM   29  H13 UNL     1      -3.225   2.013  -2.170  1.00  0.00           H  
HETATM   30  H14 UNL     1      -4.514   2.316  -0.040  1.00  0.00           H  
HETATM   31  H15 UNL     1      -4.858   1.734   2.232  1.00  0.00           H  
HETATM   32  H16 UNL     1      -1.164  -0.291   2.824  1.00  0.00           H  
HETATM   33  H17 UNL     1      -1.635  -1.857   1.959  1.00  0.00           H  
HETATM   34  H18 UNL     1      -2.868  -0.909   2.819  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4   22
CONECT    4    5   23   24
CONECT    5    6    6    7
CONECT    7    8   25
CONECT    8    9    9   15
CONECT    9   10   11
CONECT   10   26   27   28
CONECT   11   12   12   29
CONECT   12   13   30
CONECT   13   14   15   15
CONECT   14   31
CONECT   15   16
CONECT   16   32   33   34
END

HMDB0060678
     RDKit          3D
3-Hydroxymonoethylglycinexylidide
 34 34  0  0  0  0  0  0  0  0999 V2000
    5.0524    0.4492    0.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7110   -0.0648   -0.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1603   -1.0339    0.4281 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9194   -1.6047    0.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7599   -0.6644    0.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9468    0.5333    0.4570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5519   -1.0808   -0.2341 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6148   -0.1713   -0.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9408    0.5524   -1.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1813    0.3753   -2.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9835    1.4541   -1.2737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6882    1.6107   -0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3529    0.8809    1.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0899    1.0763    2.2075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3108   -0.0211    1.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9250   -0.8242    2.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5920    1.0307   -0.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6250   -0.4501    0.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8797    1.1524    0.9359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0307    0.8124   -0.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -0.4515   -1.4759 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3680   -0.9308    1.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7141   -2.4564    0.7573 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0041   -2.0433   -0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6938   -2.0769   -0.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9090    0.4122   -3.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7366   -0.6502   -2.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4500    1.1784   -2.7664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2251    2.0131   -2.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5144    2.3162   -0.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8578    1.7335    2.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1641   -0.2914    2.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6352   -1.8568    1.9592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8676   -0.9091    2.8191 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
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  7 25  1  0
 10 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-OH-MEGX	HMDB
3-Hydroxy-monoethylglycinexylidide	HMDB
N-(3-Hydroxy-2,6-dimethylphenyl)-2-ethylaminoacetamide	HMDB

Chemical Formula

C₁₂H₁₈N₂O₂

Average Molecular Weight

222.2835

Monoisotopic Molecular Weight

222.13682783

IUPAC Name

2-(ethylamino)-N-(3-hydroxy-2,6-dimethylphenyl)acetamide

Traditional Name

2-(ethylamino)-N-(3-hydroxy-2,6-dimethylphenyl)acetamide

CAS Registry Number

Not Available

SMILES

CCNCC(=O)NC1=C(C)C=CC(O)=C1C

InChI Identifier

InChI=1S/C12H18N2O2/c1-4-13-7-11(16)14-12-8(2)5-6-10(15)9(12)3/h5-6,13,15H,4,7H2,1-3H3,(H,14,16)

InChI Key

YITCMQBVWIHTTA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid amides

Alternative Parents

Substituents

Alpha-amino acid amide
Xylenol
Anilide
O-cresol
P-cresol
M-xylene
Xylene
N-arylamide
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Secondary aliphatic amine
Secondary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

amino acid amide (CHEBI:80575 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060678)

Organ

Liver (HMDB: HMDB0060678)
Kidney (HMDB: HMDB0060678)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060678)

Source

Endogenous

Endogenous (HMDB: HMDB0060678)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Lidocaine (Antiarrhythmic) Action Pathway (PathBank: SMP0000328)
Lidocaine (Local Anaesthetic) Action Pathway (PathBank: SMP0000398)

Metabolic pathway

Lidocaine (Local Anaesthetic) Metabolism Pathway (PathBank: SMP0000620)

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
Water Solubility	0.41 g/L	ALOGPS
logP	1.04	ALOGPS
logP	1.63	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	10.05	ChemAxon
pKa (Strongest Basic)	8.55	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	61.36 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	65.87 m³·mol⁻¹	ChemAxon
Polarizability	24.66 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	154.756	31661259
DarkChem	[M-H]-	153.434	31661259
DeepCCS	[M+H]+	154.515	30932474
DeepCCS	[M-H]-	152.157	30932474
DeepCCS	[M-2H]-	185.941	30932474
DeepCCS	[M+Na]+	161.214	30932474
AllCCS	[M+H]+	150.9	32859911
AllCCS	[M+H-H2O]+	147.1	32859911
AllCCS	[M+NH4]+	154.4	32859911
AllCCS	[M+Na]+	155.4	32859911
AllCCS	[M-H]-	154.4	32859911
AllCCS	[M+Na-2H]-	155.1	32859911
AllCCS	[M+HCOO]-	155.9	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.	2.29 minutes	32390414
Predicted by Siyang on May 30, 2022	9.2423 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.35 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	682.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	209.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	105.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	152.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	45.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	276.7 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	301.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	533.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	619.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	151.0 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	700.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	170.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	213.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	399.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	421.7 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	215.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxymonoethylglycinexylidide	CCNCC(=O)NC1=C(C)C=CC(O)=C1C	2950.1	Standard polar	33892256
3-Hydroxymonoethylglycinexylidide	CCNCC(=O)NC1=C(C)C=CC(O)=C1C	2062.8	Standard non polar	33892256
3-Hydroxymonoethylglycinexylidide	CCNCC(=O)NC1=C(C)C=CC(O)=C1C	2155.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxymonoethylglycinexylidide,1TMS,isomer #1	CCNCC(=O)NC1=C(C)C=CC(O[Si](C)(C)C)=C1C	2073.8	Semi standard non polar	33892256
3-Hydroxymonoethylglycinexylidide,1TMS,isomer #2	CCN(CC(=O)NC1=C(C)C=CC(O)=C1C)[Si](C)(C)C	2181.9	Semi standard non polar	33892256
3-Hydroxymonoethylglycinexylidide,1TMS,isomer #3	CCNCC(=O)N(C1=C(C)C=CC(O)=C1C)[Si](C)(C)C	1907.1	Semi standard non polar	33892256
3-Hydroxymonoethylglycinexylidide,2TMS,isomer #1	CCN(CC(=O)NC1=C(C)C=CC(O[Si](C)(C)C)=C1C)[Si](C)(C)C	2198.4	Semi standard non polar	33892256
3-Hydroxymonoethylglycinexylidide,2TMS,isomer #1	CCN(CC(=O)NC1=C(C)C=CC(O[Si](C)(C)C)=C1C)[Si](C)(C)C	2116.6	Standard non polar	33892256
3-Hydroxymonoethylglycinexylidide,2TMS,isomer #1	CCN(CC(=O)NC1=C(C)C=CC(O[Si](C)(C)C)=C1C)[Si](C)(C)C	2580.6	Standard polar	33892256
3-Hydroxymonoethylglycinexylidide,2TMS,isomer #2	CCNCC(=O)N(C1=C(C)C=CC(O[Si](C)(C)C)=C1C)[Si](C)(C)C	1941.7	Semi standard non polar	33892256
3-Hydroxymonoethylglycinexylidide,2TMS,isomer #2	CCNCC(=O)N(C1=C(C)C=CC(O[Si](C)(C)C)=C1C)[Si](C)(C)C	2014.6	Standard non polar	33892256
3-Hydroxymonoethylglycinexylidide,2TMS,isomer #2	CCNCC(=O)N(C1=C(C)C=CC(O[Si](C)(C)C)=C1C)[Si](C)(C)C	2291.8	Standard polar	33892256
3-Hydroxymonoethylglycinexylidide,2TMS,isomer #3	CCN(CC(=O)N(C1=C(C)C=CC(O)=C1C)[Si](C)(C)C)[Si](C)(C)C	2014.5	Semi standard non polar	33892256
3-Hydroxymonoethylglycinexylidide,2TMS,isomer #3	CCN(CC(=O)N(C1=C(C)C=CC(O)=C1C)[Si](C)(C)C)[Si](C)(C)C	2205.2	Standard non polar	33892256
3-Hydroxymonoethylglycinexylidide,2TMS,isomer #3	CCN(CC(=O)N(C1=C(C)C=CC(O)=C1C)[Si](C)(C)C)[Si](C)(C)C	2445.5	Standard polar	33892256
3-Hydroxymonoethylglycinexylidide,3TMS,isomer #1	CCN(CC(=O)N(C1=C(C)C=CC(O[Si](C)(C)C)=C1C)[Si](C)(C)C)[Si](C)(C)C	2069.5	Semi standard non polar	33892256
3-Hydroxymonoethylglycinexylidide,3TMS,isomer #1	CCN(CC(=O)N(C1=C(C)C=CC(O[Si](C)(C)C)=C1C)[Si](C)(C)C)[Si](C)(C)C	2148.6	Standard non polar	33892256
3-Hydroxymonoethylglycinexylidide,3TMS,isomer #1	CCN(CC(=O)N(C1=C(C)C=CC(O[Si](C)(C)C)=C1C)[Si](C)(C)C)[Si](C)(C)C	2249.3	Standard polar	33892256
3-Hydroxymonoethylglycinexylidide,1TBDMS,isomer #1	CCNCC(=O)NC1=C(C)C=CC(O[Si](C)(C)C(C)(C)C)=C1C	2348.7	Semi standard non polar	33892256
3-Hydroxymonoethylglycinexylidide,1TBDMS,isomer #2	CCN(CC(=O)NC1=C(C)C=CC(O)=C1C)[Si](C)(C)C(C)(C)C	2409.4	Semi standard non polar	33892256
3-Hydroxymonoethylglycinexylidide,1TBDMS,isomer #3	CCNCC(=O)N(C1=C(C)C=CC(O)=C1C)[Si](C)(C)C(C)(C)C	2164.7	Semi standard non polar	33892256
3-Hydroxymonoethylglycinexylidide,2TBDMS,isomer #1	CCN(CC(=O)NC1=C(C)C=CC(O[Si](C)(C)C(C)(C)C)=C1C)[Si](C)(C)C(C)(C)C	2673.9	Semi standard non polar	33892256
3-Hydroxymonoethylglycinexylidide,2TBDMS,isomer #1	CCN(CC(=O)NC1=C(C)C=CC(O[Si](C)(C)C(C)(C)C)=C1C)[Si](C)(C)C(C)(C)C	2528.1	Standard non polar	33892256
3-Hydroxymonoethylglycinexylidide,2TBDMS,isomer #1	CCN(CC(=O)NC1=C(C)C=CC(O[Si](C)(C)C(C)(C)C)=C1C)[Si](C)(C)C(C)(C)C	2751.4	Standard polar	33892256
3-Hydroxymonoethylglycinexylidide,2TBDMS,isomer #2	CCNCC(=O)N(C1=C(C)C=CC(O[Si](C)(C)C(C)(C)C)=C1C)[Si](C)(C)C(C)(C)C	2491.4	Semi standard non polar	33892256
3-Hydroxymonoethylglycinexylidide,2TBDMS,isomer #2	CCNCC(=O)N(C1=C(C)C=CC(O[Si](C)(C)C(C)(C)C)=C1C)[Si](C)(C)C(C)(C)C	2418.9	Standard non polar	33892256
3-Hydroxymonoethylglycinexylidide,2TBDMS,isomer #2	CCNCC(=O)N(C1=C(C)C=CC(O[Si](C)(C)C(C)(C)C)=C1C)[Si](C)(C)C(C)(C)C	2545.1	Standard polar	33892256
3-Hydroxymonoethylglycinexylidide,2TBDMS,isomer #3	CCN(CC(=O)N(C1=C(C)C=CC(O)=C1C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2538.2	Semi standard non polar	33892256
3-Hydroxymonoethylglycinexylidide,2TBDMS,isomer #3	CCN(CC(=O)N(C1=C(C)C=CC(O)=C1C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2589.1	Standard non polar	33892256
3-Hydroxymonoethylglycinexylidide,2TBDMS,isomer #3	CCN(CC(=O)N(C1=C(C)C=CC(O)=C1C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2640.4	Standard polar	33892256
3-Hydroxymonoethylglycinexylidide,3TBDMS,isomer #1	CCN(CC(=O)N(C1=C(C)C=CC(O[Si](C)(C)C(C)(C)C)=C1C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2819.8	Semi standard non polar	33892256
3-Hydroxymonoethylglycinexylidide,3TBDMS,isomer #1	CCN(CC(=O)N(C1=C(C)C=CC(O[Si](C)(C)C(C)(C)C)=C1C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2677.4	Standard non polar	33892256
3-Hydroxymonoethylglycinexylidide,3TBDMS,isomer #1	CCN(CC(=O)N(C1=C(C)C=CC(O[Si](C)(C)C(C)(C)C)=C1C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2624.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxymonoethylglycinexylidide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4r-9600000000-5f020072a97c73daae81	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxymonoethylglycinexylidide GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-9250000000-7456b076121b4fef0dd9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxymonoethylglycinexylidide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxymonoethylglycinexylidide 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 - 3-Hydroxymonoethylglycinexylidide 10V, Positive-QTOF	splash10-0a4i-9020000000-2b9c10fde02d305c23e7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymonoethylglycinexylidide 20V, Positive-QTOF	splash10-0a4i-9100000000-6cbb699e2f4e53b0bd3d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymonoethylglycinexylidide 40V, Positive-QTOF	splash10-056r-9000000000-fde7f5554300c141691e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymonoethylglycinexylidide 10V, Negative-QTOF	splash10-00di-0290000000-be80b1566ce55291a2bc	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymonoethylglycinexylidide 20V, Negative-QTOF	splash10-00du-3950000000-727d3f372178fd4f618f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymonoethylglycinexylidide 40V, Negative-QTOF	splash10-052f-8900000000-ede2452452b422be3133	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymonoethylglycinexylidide 10V, Positive-QTOF	splash10-00di-3090000000-b873de0ee455c3fd9eb5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymonoethylglycinexylidide 20V, Positive-QTOF	splash10-0a6r-9410000000-81b1a289e4c0601a9cf0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymonoethylglycinexylidide 40V, Positive-QTOF	splash10-0a4l-9400000000-7c6332a66389c422a345	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymonoethylglycinexylidide 10V, Negative-QTOF	splash10-00dr-0690000000-c7a1b5009806a7f5edd9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymonoethylglycinexylidide 20V, Negative-QTOF	splash10-0079-2920000000-eeeb9f1b532ae94c10d0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymonoethylglycinexylidide 40V, Negative-QTOF	splash10-0076-8900000000-870ceeac1545371316fb	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Lidocaine (Local Anaesthetic) Action Pathway		Not Available
Lidocaine (Local Anaesthetic) Metabolism Pathway		Not Available
Lidocaine (Antiarrhythmic) 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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

C16572

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3015693

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

Not Available

Showing metabocard for 3-Hydroxymonoethylglycinexylidide (HMDB0060678)

MOL for HMDB0060678 (3-Hydroxymonoethylglycinexylidide)

3D MOL for HMDB0060678 (3-Hydroxymonoethylglycinexylidide)

3D SDF for HMDB0060678 (3-Hydroxymonoethylglycinexylidide)

3D-SDF for HMDB0060678 (3-Hydroxymonoethylglycinexylidide)

PDB for HMDB0060678 (3-Hydroxymonoethylglycinexylidide)

3D PDB for HMDB0060678 (3-Hydroxymonoethylglycinexylidide)

SMILES for HMDB0060678 (3-Hydroxymonoethylglycinexylidide)

INCHI for HMDB0060678 (3-Hydroxymonoethylglycinexylidide)

Structure for HMDB0060678 (3-Hydroxymonoethylglycinexylidide)

3D Structure for HMDB0060678 (3-Hydroxymonoethylglycinexylidide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra