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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:26:49 UTC

Update Date

2021-09-26 22:57:08 UTC

HMDB ID

HMDB0247440

Secondary Accession Numbers

None

Metabolite Identification

Common Name

8-Hydroxyefavirenz

Description

8-Hydroxyefavirenz belongs to the class of organic compounds known as benzoxazines. These are organic compounds containing a benzene fused to an oxazine ring (a six-membered aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom). Based on a literature review very few articles have been published on 8-Hydroxyefavirenz. This compound has been identified in human blood as reported by (PMID: 31557052 ). 8-hydroxyefavirenz is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 8-Hydroxyefavirenz 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

HMDB0247440
     RDKit          3D
8-Hydroxyefavirenz
 31 33  0  0  0  0  0  0  0  0999 V2000
   -1.2572   -2.2361   -3.7006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2329   -1.4375   -2.5182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2151   -1.5213   -1.6903 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2476   -0.7484   -0.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3294   -0.8936    0.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3737   -1.7573    0.0986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3341   -0.1557    1.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3060    0.7066    1.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3295    1.6484    3.3358 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2727    0.8159    0.9548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2032    0.0982   -0.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0939    0.2467   -1.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2130    0.0508   -0.4607 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2559   -0.1276    0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5277   -0.3618    0.8002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5308   -0.0600    2.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2924    0.8233    1.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0243    1.6909   -1.6852 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184    1.6630   -2.5612 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.4290    2.4663   -0.6259 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0927    2.1196   -2.3219 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1943   -0.5997   -2.2595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4073   -2.7382   -3.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1457   -1.8494    0.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1475   -0.2372    2.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4789    1.5000    1.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1855   -1.1848    0.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1529   -0.7553    2.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6074    0.2563    2.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4087    0.7756    1.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9159    1.8021    1.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  3  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 12 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 12 22  1  0
 22  2  1  0
 11  4  1  0
 17 15  1  0
  1 23  1  0
  6 24  1  0
  7 25  1  0
 10 26  1  0
 15 27  1  0
 16 28  1  0
 16 29  1  0
 17 30  1  0
 17 31  1  0
M  END

  Mrv1652306031609372D          

 22 24  0  0  0  0            999 V2000
   -0.3052    2.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9372    2.1781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3683    1.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986    0.6320    0.0000 C   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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1620    1.8960    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    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
    2.1434   -1.2375    0.0000 C   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
    1.9592    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4895    1.2640    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.3273    1.1623    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.5912    0.1017    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  3  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  9  2  0  0  0  0
 11 10  1  0  0  0  0
 13  4  1  0  0  0  0
 13  9  1  0  0  0  0
 14 13  1  0  0  0  0
 15  8  1  0  0  0  0
 16 14  1  0  0  0  0
 17 14  1  0  0  0  0
 18 14  1  0  0  0  0
 19 11  1  0  0  0  0
 19 12  2  0  0  0  0
 20 10  1  0  0  0  0
 21 12  1  0  0  0  0
 22 12  1  0  0  0  0
 22 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247440

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=NC2=C(C=C(Cl)C=C2O)C(O1)(C#CC1CC1)C(F)(F)F

> <INCHI_IDENTIFIER>
InChI=1S/C14H9ClF3NO3/c15-8-5-9-11(10(20)6-8)19-12(21)22-13(9,14(16,17)18)4-3-7-1-2-7/h5-7,20H,1-2H2,(H,19,21)

> <INCHI_KEY>
OOVOMPCQLMFEDT-UHFFFAOYSA-N

> <FORMULA>
C14H9ClF3NO3

> <MOLECULAR_WEIGHT>
331.68

> <EXACT_MASS>
331.0223053

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
27.8695028999599

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-4H-3,1-benzoxazine-2,8-diol

> <ALOGPS_LOGP>
3.54

> <JCHEM_LOGP>
5.497350997666667

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.258590350639682

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.2838001084042383

> <JCHEM_PKA_STRONGEST_BASIC>
-4.520222320721021

> <JCHEM_POLAR_SURFACE_AREA>
62.05000000000001

> <JCHEM_REFRACTIVITY>
74.3472

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-3,1-benzoxazine-2,8-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0247440
     RDKit          3D
8-Hydroxyefavirenz
 31 33  0  0  0  0  0  0  0  0999 V2000
   -1.2572   -2.2361   -3.7006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2329   -1.4375   -2.5182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2151   -1.5213   -1.6903 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2476   -0.7484   -0.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3294   -0.8936    0.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3737   -1.7573    0.0986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3341   -0.1557    1.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3060    0.7066    1.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3295    1.6484    3.3358 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2727    0.8159    0.9548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2032    0.0982   -0.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0939    0.2467   -1.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2130    0.0508   -0.4607 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2559   -0.1276    0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5277   -0.3618    0.8002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5308   -0.0600    2.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2924    0.8233    1.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0243    1.6909   -1.6852 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184    1.6630   -2.5612 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.4290    2.4663   -0.6259 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0927    2.1196   -2.3219 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1943   -0.5997   -2.2595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4073   -2.7382   -3.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1457   -1.8494    0.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1475   -0.2372    2.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4789    1.5000    1.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1855   -1.1848    0.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1529   -0.7553    2.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6074    0.2563    2.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4087    0.7756    1.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9159    1.8021    1.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  3  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 12 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 12 22  1  0
 22  2  1  0
 11  4  1  0
 17 15  1  0
  1 23  1  0
  6 24  1  0
  7 25  1  0
 10 26  1  0
 15 27  1  0
 16 28  1  0
 16 29  1  0
 17 30  1  0
 17 31  1  0
M  END

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0      -0.570   5.056   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.749   4.066   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.688   2.359   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.677   1.180   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.302   3.539   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.657   1.180   0.000  0.00  0.00           C+0
HETATM   15 Cl   UNK     0      -2.667  -0.000   0.000  0.00  0.00          Cl+0
HETATM   16  F   UNK     0       4.647   2.359   0.000  0.00  0.00           F+0
HETATM   17  F   UNK     0       2.478   2.170   0.000  0.00  0.00           F+0
HETATM   18  F   UNK     0       4.837   0.190   0.000  0.00  0.00           F+0
HETATM   19  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    7                                                       
CONECT    3    4    7                                                       
CONECT    4    3   13                                                       
CONECT    5    8    9                                                       
CONECT    6    8   10                                                       
CONECT    7    1    2    3                                                  
CONECT    8    5    6   15                                                  
CONECT    9    5   11   13                                                  
CONECT   10    6   11   20                                                  
CONECT   11    9   10   19                                                  
CONECT   12   19   21   22                                                  
CONECT   13    4    9   14   22                                             
CONECT   14   13   16   17   18                                             
CONECT   15    8                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
CONECT   18   14                                                            
CONECT   19   11   12                                                       
CONECT   20   10                                                            
CONECT   21   12                                                            
CONECT   22   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0247440
HETATM    1  O1  UNL     1      -1.257  -2.236  -3.701  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.233  -1.437  -2.518  1.00  0.00           C  
HETATM    3  N1  UNL     1      -2.215  -1.521  -1.690  1.00  0.00           N  
HETATM    4  C2  UNL     1      -2.248  -0.748  -0.495  1.00  0.00           C  
HETATM    5  C3  UNL     1      -3.329  -0.894   0.383  1.00  0.00           C  
HETATM    6  O2  UNL     1      -4.374  -1.757   0.099  1.00  0.00           O  
HETATM    7  C4  UNL     1      -3.334  -0.156   1.541  1.00  0.00           C  
HETATM    8  C5  UNL     1      -2.306   0.707   1.839  1.00  0.00           C  
HETATM    9 CL1  UNL     1      -2.329   1.648   3.336  1.00  0.00          CL  
HETATM   10  C6  UNL     1      -1.273   0.816   0.955  1.00  0.00           C  
HETATM   11  C7  UNL     1      -1.203   0.098  -0.239  1.00  0.00           C  
HETATM   12  C8  UNL     1      -0.094   0.247  -1.173  1.00  0.00           C  
HETATM   13  C9  UNL     1       1.213   0.051  -0.461  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.256  -0.128   0.117  1.00  0.00           C  
HETATM   15  C11 UNL     1       3.528  -0.362   0.800  1.00  0.00           C  
HETATM   16  C12 UNL     1       3.531  -0.060   2.252  1.00  0.00           C  
HETATM   17  C13 UNL     1       4.292   0.823   1.351  1.00  0.00           C  
HETATM   18  C14 UNL     1       0.024   1.691  -1.685  1.00  0.00           C  
HETATM   19  F1  UNL     1       1.118   1.663  -2.561  1.00  0.00           F  
HETATM   20  F2  UNL     1       0.429   2.466  -0.626  1.00  0.00           F  
HETATM   21  F3  UNL     1      -1.093   2.120  -2.322  1.00  0.00           F  
HETATM   22  O3  UNL     1      -0.194  -0.600  -2.259  1.00  0.00           O  
HETATM   23  H1  UNL     1      -0.407  -2.738  -3.965  1.00  0.00           H  
HETATM   24  H2  UNL     1      -5.146  -1.849   0.743  1.00  0.00           H  
HETATM   25  H3  UNL     1      -4.147  -0.237   2.243  1.00  0.00           H  
HETATM   26  H4  UNL     1      -0.479   1.500   1.219  1.00  0.00           H  
HETATM   27  H5  UNL     1       4.185  -1.185   0.418  1.00  0.00           H  
HETATM   28  H6  UNL     1       4.153  -0.755   2.871  1.00  0.00           H  
HETATM   29  H7  UNL     1       2.607   0.256   2.765  1.00  0.00           H  
HETATM   30  H8  UNL     1       5.409   0.776   1.365  1.00  0.00           H  
HETATM   31  H9  UNL     1       3.916   1.802   1.019  1.00  0.00           H  
CONECT    1    2   23
CONECT    2    3    3   22
CONECT    3    4
CONECT    4    5    5   11
CONECT    5    6    7
CONECT    6   24
CONECT    7    8    8   25
CONECT    8    9   10
CONECT   10   11   11   26
CONECT   11   12
CONECT   12   13   18   22
CONECT   13   14   14   14
CONECT   14   15
CONECT   15   16   17   27
CONECT   16   17   28   29
CONECT   17   30   31
CONECT   18   19   20   21
END

HMDB0247440
     RDKit          3D
8-Hydroxyefavirenz
 31 33  0  0  0  0  0  0  0  0999 V2000
   -1.2572   -2.2361   -3.7006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2329   -1.4375   -2.5182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2151   -1.5213   -1.6903 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2476   -0.7484   -0.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3294   -0.8936    0.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3737   -1.7573    0.0986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3341   -0.1557    1.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3060    0.7066    1.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3295    1.6484    3.3358 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2727    0.8159    0.9548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2032    0.0982   -0.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0939    0.2467   -1.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2130    0.0508   -0.4607 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2559   -0.1276    0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5277   -0.3618    0.8002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5308   -0.0600    2.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2924    0.8233    1.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0243    1.6909   -1.6852 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184    1.6630   -2.5612 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.4290    2.4663   -0.6259 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0927    2.1196   -2.3219 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1943   -0.5997   -2.2595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4073   -2.7382   -3.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1457   -1.8494    0.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1475   -0.2372    2.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4789    1.5000    1.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1855   -1.1848    0.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1529   -0.7553    2.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6074    0.2563    2.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4087    0.7756    1.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9159    1.8021    1.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  3  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 12 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 12 22  1  0
 22  2  1  0
 11  4  1  0
 17 15  1  0
  1 23  1  0
  6 24  1  0
  7 25  1  0
 10 26  1  0
 15 27  1  0
 16 28  1  0
 16 29  1  0
 17 30  1  0
 17 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₄H₉ClF₃NO₃

Average Molecular Weight

331.68

Monoisotopic Molecular Weight

331.0223053

IUPAC Name

6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-4H-3,1-benzoxazine-2,8-diol

Traditional Name

6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-3,1-benzoxazine-2,8-diol

CAS Registry Number

Not Available

SMILES

OC1=NC2=C(C=C(Cl)C=C2O)C(O1)(C#CC1CC1)C(F)(F)F

InChI Identifier

InChI=1S/C14H9ClF3NO3/c15-8-5-9-11(10(20)6-8)19-12(21)22-13(9,14(16,17)18)4-3-7-1-2-7/h5-7,20H,1-2H2,(H,19,21)

InChI Key

OOVOMPCQLMFEDT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoxazines. These are organic compounds containing a benzene fused to an oxazine ring (a six-membered aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxazines

Sub Class

Not Available

Direct Parent

Benzoxazines

Alternative Parents

Substituents

Benzoxazine
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Aryl chloride
Aryl halide
Benzenoid
Ynone
Carbamic acid ester
Carbonic acid derivative
Oxacycle
Azacycle
Alkyl fluoride
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organofluoride
Organochloride
Organohalogen compound
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Alkyl halide
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	3.54	ALOGPS
logP	5.5	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	2.28	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.05 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	74.35 m³·mol⁻¹	ChemAxon
Polarizability	27.87 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]+	167.154	30932474
DeepCCS	[M-H]-	164.796	30932474
DeepCCS	[M-2H]-	198.501	30932474
DeepCCS	[M+Na]+	173.728	30932474
AllCCS	[M+H]+	168.0	32859911
AllCCS	[M+H-H2O]+	164.8	32859911
AllCCS	[M+NH4]+	171.0	32859911
AllCCS	[M+Na]+	171.9	32859911
AllCCS	[M-H]-	163.5	32859911
AllCCS	[M+Na-2H]-	162.6	32859911
AllCCS	[M+HCOO]-	161.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Hydroxyefavirenz	OC1=NC2=C(C=C(Cl)C=C2O)C(O1)(C#CC1CC1)C(F)(F)F	3362.9	Standard polar	33892256
8-Hydroxyefavirenz	OC1=NC2=C(C=C(Cl)C=C2O)C(O1)(C#CC1CC1)C(F)(F)F	2167.9	Standard non polar	33892256
8-Hydroxyefavirenz	OC1=NC2=C(C=C(Cl)C=C2O)C(O1)(C#CC1CC1)C(F)(F)F	2204.9	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 - 8-Hydroxyefavirenz GC-MS (Non-derivatized) - 70eV, Positive	splash10-02dl-9382000000-524528e29867f1693f2c	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxyefavirenz GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxyefavirenz GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxyefavirenz GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxyefavirenz GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxyefavirenz GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxyefavirenz GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxyefavirenz GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	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 - 8-Hydroxyefavirenz 10V, Positive-QTOF	splash10-0019-0094000000-c637bf619194d1344f62	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyefavirenz 20V, Positive-QTOF	splash10-0udi-9067000000-098bcc65042f22817a17	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyefavirenz 40V, Positive-QTOF	splash10-0udl-9670000000-cf986b6e724029d45ae0	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyefavirenz 10V, Negative-QTOF	splash10-001i-3029000000-606be633d62aa63b5f6e	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyefavirenz 20V, Negative-QTOF	splash10-001i-1039000000-0ce3ba01c4d850ab7ef8	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyefavirenz 40V, Negative-QTOF	splash10-0006-9100000000-0ccf0bb5f92b0719ff07	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyefavirenz 10V, Positive-QTOF	splash10-001i-0009000000-c2bc5f2ab4414fd967ea	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyefavirenz 20V, Positive-QTOF	splash10-001i-0009000000-7e7c959fb7ffcd8a4c7e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyefavirenz 40V, Positive-QTOF	splash10-014i-5695000000-fbe524ceb02a431d6359	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyefavirenz 10V, Negative-QTOF	splash10-001i-0029000000-62cefba89648c0416558	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyefavirenz 20V, Negative-QTOF	splash10-01q9-1039000000-46da2ed62508d64a0d84	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyefavirenz 40V, Negative-QTOF	splash10-001r-8791000000-5853b24010c938b02b98	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

8016257

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9840539

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 ]

Showing metabocard for 8-Hydroxyefavirenz (HMDB0247440)

MOL for HMDB0247440 (8-Hydroxyefavirenz)

3D MOL for HMDB0247440 (8-Hydroxyefavirenz)

3D SDF for HMDB0247440 (8-Hydroxyefavirenz)

3D-SDF for HMDB0247440 (8-Hydroxyefavirenz)

PDB for HMDB0247440 (8-Hydroxyefavirenz)

3D PDB for HMDB0247440 (8-Hydroxyefavirenz)

SMILES for HMDB0247440 (8-Hydroxyefavirenz)

INCHI for HMDB0247440 (8-Hydroxyefavirenz)

Structure for HMDB0247440 (8-Hydroxyefavirenz)

3D Structure for HMDB0247440 (8-Hydroxyefavirenz)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra