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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 19:03:32 UTC

Update Date

2019-07-23 07:15:13 UTC

HMDB ID

HMDB0060853

Secondary Accession Numbers

HMDB60853

Metabolite Identification

Common Name

N1-(2-Hydroxyethyl)flurazepam

Description

N1-(2-Hydroxyethyl)flurazepam is a metabolite of flurazepam. Flurazepam (marketed under the brand names Dalmane and Dalmadorm) is a drug which is a benzodiazepine derivative. It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. It produces a metabolite with a very long half-life (40–250 hours), which may stay in the bloodstream for up to four days. http://www. non-benzodiazepines. org. uk/equivalents. html Flurazepam is therefore unsuitable as a sleeping medication for some individuals due to next day sedation. (Wikipedia)

Structure

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

HMDB0060853
     RDKit          3D
N1-(2-Hydroxyethyl)flurazepam
 40 42  0  0  0  0  0  0  0  0999 V2000
    5.5940   -1.0044   -0.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0801   -0.3458    0.7124 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9178    0.3713    0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7926   -0.5064   -0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5664    0.1500   -0.2998 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3147    0.7505   -1.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0230    0.3186   -2.5203 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3027    1.8308   -1.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0411    1.2907   -1.7197 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5052    0.6986   -0.6386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8667    0.2471   -0.6771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4885   -0.5143    0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8333   -0.8170    0.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5788   -0.3417   -0.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9875    0.4390   -1.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6553    0.7241   -1.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0788    1.4922   -2.7019 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7880    0.5612    0.6170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5828    0.7229    1.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0373    0.5314    2.9587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0365    0.7217    4.3912 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.3052    0.1802    3.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0774    0.0326    1.9639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5630    0.2187    0.7252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9603   -1.7532   -0.8399 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0099   -0.3002   -1.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5056   -1.5557    0.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6940    1.0757    1.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2469    1.0670   -0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1495   -0.8788   -1.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7068   -1.4555    0.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4784    2.7498   -1.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4171    2.0471   -3.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9463   -0.9957    1.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3098   -1.4347    0.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6455   -0.5634   -0.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5614    0.8324   -2.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5970    1.0530    1.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7423    0.0255    4.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0922   -0.2566    2.0398 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  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 10 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 24  5  1  0
 16 11  1  0
 24 18  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  8 32  1  0
  8 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 19 38  1  0
 22 39  1  0
 23 40  1  0
M  END


  Mrv0541 07041312032D          

 24 26  0  0  0  0            999 V2000
    1.4874   -3.2453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8826   -2.6842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0662   -1.8798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4614   -1.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6450   -0.5144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6450    1.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4493    1.1558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8073    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4493   -0.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9637   -0.9758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4614    2.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3269    2.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5105    3.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0943    3.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8826    3.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0662    2.7048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8545    2.4617    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060853

> <DATABASE_NAME>
hmdb

> <SMILES>
COCCN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1F

> <INCHI_IDENTIFIER>
InChI=1S/C18H16ClFN2O2/c1-24-9-8-22-16-7-6-12(19)10-14(16)18(21-11-17(22)23)13-4-2-3-5-15(13)20/h2-7,10H,8-9,11H2,1H3

> <INCHI_KEY>
UBKVMFUMOAWHGB-UHFFFAOYSA-N

> <FORMULA>
C18H16ClFN2O2

> <MOLECULAR_WEIGHT>
346.783

> <EXACT_MASS>
346.088433678

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
34.76480158378315

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-chloro-5-(2-fluorophenyl)-1-(2-methoxyethyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one

> <ALOGPS_LOGP>
2.97

> <JCHEM_LOGP>
3.1718129953333336

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.034348291897965

> <JCHEM_POLAR_SURFACE_AREA>
41.9

> <JCHEM_REFRACTIVITY>
91.07180000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.13e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-chloro-5-(2-fluorophenyl)-1-(2-methoxyethyl)-3H-1,4-benzodiazepin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060853
     RDKit          3D
N1-(2-Hydroxyethyl)flurazepam
 40 42  0  0  0  0  0  0  0  0999 V2000
    5.5940   -1.0044   -0.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0801   -0.3458    0.7124 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9178    0.3713    0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7926   -0.5064   -0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5664    0.1500   -0.2998 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3147    0.7505   -1.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0230    0.3186   -2.5203 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3027    1.8308   -1.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0411    1.2907   -1.7197 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5052    0.6986   -0.6386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8667    0.2471   -0.6771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4885   -0.5143    0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8333   -0.8170    0.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5788   -0.3417   -0.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9875    0.4390   -1.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6553    0.7241   -1.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0788    1.4922   -2.7019 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7880    0.5612    0.6170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5828    0.7229    1.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0373    0.5314    2.9587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0365    0.7217    4.3912 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.3052    0.1802    3.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0774    0.0326    1.9639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5630    0.2187    0.7252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9603   -1.7532   -0.8399 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0099   -0.3002   -1.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5056   -1.5557    0.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6940    1.0757    1.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2469    1.0670   -0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1495   -0.8788   -1.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7068   -1.4555    0.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4784    2.7498   -1.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4171    2.0471   -3.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9463   -0.9957    1.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3098   -1.4347    0.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6455   -0.5634   -0.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5614    0.8324   -2.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5970    1.0530    1.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7423    0.0255    4.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0922   -0.2566    2.0398 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  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 10 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 24  5  1  0
 16 11  1  0
 24 18  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  8 32  1  0
  8 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 19 38  1  0
 22 39  1  0
 23 40  1  0
M  END

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  C   UNK     0       2.776  -6.058   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.648  -5.011   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.990  -3.509   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.861  -2.462   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.204  -0.960   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10 Cl   UNK     0      -4.001   2.310   0.000  0.00  0.00          Cl+0
HETATM   11  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.204   2.500   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.705   2.157   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       3.374   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.705  -0.617   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.666  -1.821   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.861   4.002   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.610   4.456   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.953   5.957   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.176   7.004   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.648   6.551   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.990   5.049   0.000  0.00  0.00           C+0
HETATM   24  F   UNK     0       3.462   4.595   0.000  0.00  0.00           F+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    6                                                       
CONECT   13    7   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    5   17                                                  
CONECT   17   16                                                            
CONECT   18   13   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0060853
HETATM    1  C1  UNL     1       5.594  -1.004  -0.371  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.080  -0.346   0.712  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.918   0.371   0.453  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.793  -0.506  -0.041  1.00  0.00           C  
HETATM    5  N1  UNL     1       1.566   0.150  -0.300  1.00  0.00           N  
HETATM    6  C4  UNL     1       1.315   0.751  -1.595  1.00  0.00           C  
HETATM    7  O2  UNL     1       2.023   0.319  -2.520  1.00  0.00           O  
HETATM    8  C5  UNL     1       0.303   1.831  -1.949  1.00  0.00           C  
HETATM    9  N2  UNL     1      -1.041   1.291  -1.720  1.00  0.00           N  
HETATM   10  C6  UNL     1      -1.505   0.699  -0.639  1.00  0.00           C  
HETATM   11  C7  UNL     1      -2.867   0.247  -0.677  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.488  -0.514   0.241  1.00  0.00           C  
HETATM   13  C9  UNL     1      -4.833  -0.817   0.153  1.00  0.00           C  
HETATM   14  C10 UNL     1      -5.579  -0.342  -0.894  1.00  0.00           C  
HETATM   15  C11 UNL     1      -4.987   0.439  -1.861  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.655   0.724  -1.748  1.00  0.00           C  
HETATM   17  F1  UNL     1      -3.079   1.492  -2.702  1.00  0.00           F  
HETATM   18  C13 UNL     1      -0.788   0.561   0.617  1.00  0.00           C  
HETATM   19  C14 UNL     1      -1.583   0.723   1.717  1.00  0.00           C  
HETATM   20  C15 UNL     1      -1.037   0.531   2.959  1.00  0.00           C  
HETATM   21 CL1  UNL     1      -2.037   0.722   4.391  1.00  0.00          CL  
HETATM   22  C16 UNL     1       0.305   0.180   3.111  1.00  0.00           C  
HETATM   23  C17 UNL     1       1.077   0.033   1.964  1.00  0.00           C  
HETATM   24  C18 UNL     1       0.563   0.219   0.725  1.00  0.00           C  
HETATM   25  H1  UNL     1       4.960  -1.753  -0.840  1.00  0.00           H  
HETATM   26  H2  UNL     1       6.010  -0.300  -1.149  1.00  0.00           H  
HETATM   27  H3  UNL     1       6.506  -1.556   0.000  1.00  0.00           H  
HETATM   28  H4  UNL     1       3.694   1.076   1.244  1.00  0.00           H  
HETATM   29  H5  UNL     1       4.247   1.067  -0.406  1.00  0.00           H  
HETATM   30  H6  UNL     1       3.150  -0.879  -1.032  1.00  0.00           H  
HETATM   31  H7  UNL     1       2.707  -1.455   0.535  1.00  0.00           H  
HETATM   32  H8  UNL     1       0.478   2.750  -1.364  1.00  0.00           H  
HETATM   33  H9  UNL     1       0.417   2.047  -3.005  1.00  0.00           H  
HETATM   34  H10 UNL     1      -2.946  -0.996   1.073  1.00  0.00           H  
HETATM   35  H11 UNL     1      -5.310  -1.435   0.915  1.00  0.00           H  
HETATM   36  H12 UNL     1      -6.646  -0.563  -0.992  1.00  0.00           H  
HETATM   37  H13 UNL     1      -5.561   0.832  -2.713  1.00  0.00           H  
HETATM   38  H14 UNL     1      -2.597   1.053   1.590  1.00  0.00           H  
HETATM   39  H15 UNL     1       0.742   0.026   4.078  1.00  0.00           H  
HETATM   40  H16 UNL     1       2.092  -0.257   2.040  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4   28   29
CONECT    4    5   30   31
CONECT    5    6   24
CONECT    6    7    7    8
CONECT    8    9   32   33
CONECT    9   10   10
CONECT   10   11   18
CONECT   11   12   12   16
CONECT   12   13   34
CONECT   13   14   14   35
CONECT   14   15   36
CONECT   15   16   16   37
CONECT   16   17
CONECT   18   19   19   24
CONECT   19   20   38
CONECT   20   21   22   22
CONECT   22   23   39
CONECT   23   24   24   40
END

HMDB0060853
     RDKit          3D
N1-(2-Hydroxyethyl)flurazepam
 40 42  0  0  0  0  0  0  0  0999 V2000
    5.5940   -1.0044   -0.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0801   -0.3458    0.7124 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9178    0.3713    0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7926   -0.5064   -0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5664    0.1500   -0.2998 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3147    0.7505   -1.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0230    0.3186   -2.5203 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3027    1.8308   -1.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0411    1.2907   -1.7197 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5052    0.6986   -0.6386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8667    0.2471   -0.6771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4885   -0.5143    0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8333   -0.8170    0.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5788   -0.3417   -0.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9875    0.4390   -1.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6553    0.7241   -1.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0788    1.4922   -2.7019 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7880    0.5612    0.6170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5828    0.7229    1.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0373    0.5314    2.9587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0365    0.7217    4.3912 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.3052    0.1802    3.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0774    0.0326    1.9639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5630    0.2187    0.7252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9603   -1.7532   -0.8399 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0099   -0.3002   -1.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5056   -1.5557    0.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6940    1.0757    1.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2469    1.0670   -0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1495   -0.8788   -1.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7068   -1.4555    0.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4784    2.7498   -1.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4171    2.0471   -3.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9463   -0.9957    1.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3098   -1.4347    0.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6455   -0.5634   -0.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5614    0.8324   -2.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5970    1.0530    1.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7423    0.0255    4.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0922   -0.2566    2.0398 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  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 10 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 24  5  1  0
 16 11  1  0
 24 18  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  8 32  1  0
  8 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 19 38  1  0
 22 39  1  0
 23 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₈H₁₆ClFN₂O₂

Average Molecular Weight

346.783

Monoisotopic Molecular Weight

346.088433678

IUPAC Name

7-chloro-5-(2-fluorophenyl)-1-(2-methoxyethyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one

Traditional Name

7-chloro-5-(2-fluorophenyl)-1-(2-methoxyethyl)-3H-1,4-benzodiazepin-2-one

CAS Registry Number

Not Available

SMILES

COCCN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1F

InChI Identifier

InChI=1S/C18H16ClFN2O2/c1-24-9-8-22-16-7-6-12(19)10-14(16)18(21-11-17(22)23)13-4-2-3-5-15(13)20/h2-7,10H,8-9,11H2,1H3

InChI Key

UBKVMFUMOAWHGB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

1,4-benzodiazepines

Alternative Parents

Substituents

1,4-benzodiazepine
Alpha-amino acid or derivatives
Fluorobenzene
Halobenzene
Aryl chloride
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Ketimine
Lactam
Azacycle
Carboxylic acid derivative
Dialkyl ether
Ether
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Imine
Organooxygen compound
Organonitrogen compound
Organohalogen compound
Organochloride
Organofluoride
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 (HMDB: HMDB0060853)

Organ

Kidney (HMDB: HMDB0060853)
Liver (HMDB: HMDB0060853)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060853)

Cellular substructure

Cytoplasm (HMDB: HMDB0060853)
Membrane (HMDB: HMDB0060853)

Source

Endogenous

Endogenous (HMDB: HMDB0060853)

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
Water Solubility	0.011 g/L	ALOGPS
logP	2.97	ALOGPS
logP	3.17	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	2.03	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	41.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	91.07 m³·mol⁻¹	ChemAxon
Polarizability	34.76 Å³	ChemAxon
Number of Rings	3	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]+	181.383	30932474
DeepCCS	[M-H]-	179.025	30932474
DeepCCS	[M-2H]-	213.215	30932474
DeepCCS	[M+Na]+	188.441	30932474
AllCCS	[M+H]+	178.0	32859911
AllCCS	[M+H-H2O]+	174.8	32859911
AllCCS	[M+NH4]+	180.9	32859911
AllCCS	[M+Na]+	181.8	32859911
AllCCS	[M-H]-	180.1	32859911
AllCCS	[M+Na-2H]-	179.7	32859911
AllCCS	[M+HCOO]-	179.4	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.	5.72 minutes	32390414
Predicted by Siyang on May 30, 2022	14.7129 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.28 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2312.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	402.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	192.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	216.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	165.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	608.2 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	598.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	69.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1369.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	512.7 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	1503.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	385.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	396.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	290.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	180.9 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	7.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N1-(2-Hydroxyethyl)flurazepam	COCCN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1F	3839.8	Standard polar	33892256
N1-(2-Hydroxyethyl)flurazepam	COCCN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1F	2609.8	Standard non polar	33892256
N1-(2-Hydroxyethyl)flurazepam	COCCN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1F	2565.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N1-(2-Hydroxyethyl)flurazepam GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-4169000000-3fff84a5d465e87f2d31	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N1-(2-Hydroxyethyl)flurazepam 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 - N1-(2-Hydroxyethyl)flurazepam 10V, Positive-QTOF	splash10-0002-0019000000-a1a3b37e77ef936d7ba4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N1-(2-Hydroxyethyl)flurazepam 20V, Positive-QTOF	splash10-014j-1019000000-82f6b5937ad0907e6f3a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N1-(2-Hydroxyethyl)flurazepam 40V, Positive-QTOF	splash10-0aor-3950000000-b5e3af279f5337542b3d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N1-(2-Hydroxyethyl)flurazepam 10V, Negative-QTOF	splash10-0002-0009000000-a3b6ce437f5b95923d14	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N1-(2-Hydroxyethyl)flurazepam 20V, Negative-QTOF	splash10-0002-0019000000-456bc1246ffc39c95fde	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N1-(2-Hydroxyethyl)flurazepam 40V, Negative-QTOF	splash10-0a4l-6291000000-9333facf68fbb7f2aba3	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N1-(2-Hydroxyethyl)flurazepam 10V, Positive-QTOF	splash10-0002-0009000000-d21824eed85f58e55e74	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N1-(2-Hydroxyethyl)flurazepam 20V, Positive-QTOF	splash10-0udi-0019000000-628b436e9f8d8a628047	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N1-(2-Hydroxyethyl)flurazepam 40V, Positive-QTOF	splash10-0frj-0193000000-2d11847b118d1cea3338	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N1-(2-Hydroxyethyl)flurazepam 10V, Negative-QTOF	splash10-0f6t-0029000000-a0a4c76282c7be799e77	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N1-(2-Hydroxyethyl)flurazepam 20V, Negative-QTOF	splash10-0udi-1059000000-5a8eaceaad18a924647c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N1-(2-Hydroxyethyl)flurazepam 40V, Negative-QTOF	splash10-00lj-2090000000-8dfe2e9dddc05551de51	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21498643

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 N1-(2-Hydroxyethyl)flurazepam (HMDB0060853)

MOL for HMDB0060853 (N1-(2-Hydroxyethyl)flurazepam)

3D MOL for HMDB0060853 (N1-(2-Hydroxyethyl)flurazepam)

3D SDF for HMDB0060853 (N1-(2-Hydroxyethyl)flurazepam)

3D-SDF for HMDB0060853 (N1-(2-Hydroxyethyl)flurazepam)

PDB for HMDB0060853 (N1-(2-Hydroxyethyl)flurazepam)

3D PDB for HMDB0060853 (N1-(2-Hydroxyethyl)flurazepam)

SMILES for HMDB0060853 (N1-(2-Hydroxyethyl)flurazepam)

INCHI for HMDB0060853 (N1-(2-Hydroxyethyl)flurazepam)

Structure for HMDB0060853 (N1-(2-Hydroxyethyl)flurazepam)

3D Structure for HMDB0060853 (N1-(2-Hydroxyethyl)flurazepam)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra