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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

enzymes (6) Show 6 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2020-02-26 21:40:18 UTC

HMDB ID

HMDB0014763

Secondary Accession Numbers

HMDB14763

Metabolite Identification

Common Name

Efavirenz

Description

Efavirenz, also known as sustiva or EFV, 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). Efavirenz is also used in combination with other antiretroviral agents as part of an expanded postexposure prophylaxis regimen to prevent HIV transmission for those exposed to materials associated with a high risk for HIV transmission. Efavirenz is a drug which is used for use in combination treatment of hiv infection (aids). Efavirenz is an extremely weak basic (essentially neutral) compound (based on its pKa). The rate of efavirenz phosphorylation varies, depending on cell type. Efavirenz (brand names Efavirenz and Stocrin) is a non-nucleoside reverse transcriptase inhibitor (NNRTI) and is used as part of highly active antiretroviral therapy (HAART) for the treatment of a human immunodeficiency virus (HIV) type 1. In humans, efavirenz is involved in efavirenz action pathway. Similar to zidovudine, efavirenz inhibits the activity of viral RNA-directed DNA polymerase (i.e., reverse transcriptase). Efavirenz (dideoxyinosine, ddI) is an oral non-nucleoside reverse transcriptase inhibitor (NNRTI). Intracellular enzymes subsequently eliminate the HIV particle that previously had been uncoated, and left unprotected, during entry into the host cell. Currently, the CDC recommends that Efavirenz be given as part of a three-drug regimen that includes another nucleoside reverse transcriptase inhibitor (e.g., lamivudine, stavudine, zidovudine) and a protease inhibitor or efavirenz when treating HIV infection. Efavirenz is principally metabolized by the cytochrome P450 system to hydroxylated metabolites with subsequent glucuronidation of these hydroxylated metabolites.

Structure

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

HMDB0014763
     RDKit          3D
Efavirenz
 30 32  0  0  0  0  0  0  0  0999 V2000
    1.2850   -1.9583    3.4560 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2881   -1.3895    2.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2911   -0.4250    2.0560 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.2379    0.8043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3425    1.1941    0.5701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4173    1.8559   -0.6351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4780    1.5382   -1.5898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5614    2.3711   -3.1243 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.5011    0.5976   -1.3546 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4063   -0.0828   -0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539   -1.0936    0.0937 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9440   -0.4549   -0.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0148    0.0748   -0.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2997    0.7121   -0.5922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0778    1.1117    0.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5664   -0.0470   -0.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4464   -2.2386   -0.9128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5999   -3.1054   -0.5629 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.2081   -1.8457   -2.1929 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6088   -2.9450   -0.7577 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.3646   -1.6912    1.3480 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0222   -0.1700    2.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0815    1.4449    1.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1904    2.5935   -0.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7759    0.3721   -2.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3718    1.3471   -1.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6024    0.9305    1.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6619    2.0327    0.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4309    0.1050   -0.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3993   -1.0724    0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  6
 12 13  3  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 11 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 11 21  1  0
 21  2  1  0
 10  4  1  0
 16 14  1  0
  3 22  1  0
  5 23  1  0
  6 24  1  0
  9 25  1  0
 14 26  1  0
 15 27  1  0
 15 28  1  0
 16 29  1  0
 16 30  1  0
M  END

625
  Mrv0541 02231214492D          

 21 23  0  0  1  0            999 V2000
    5.9914    0.3836    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.0255    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.2540   -1.0255    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.1015    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.8159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.0535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.0535    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3166   -1.7400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0310   -2.1525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3166   -2.5650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.4034    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9041   -1.0255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.8159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916   -0.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665   -0.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5310    0.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5310    2.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2785    0.7988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2785    1.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  2 16  1  0  0  0  0
  3 16  1  0  0  0  0
  4 16  1  0  0  0  0
  5 11  1  0  0  0  0
  5 19  1  0  0  0  0
  6 19  2  0  0  0  0
  7 15  1  0  0  0  0
  7 19  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 11 16  1  1  0  0  0
 12 14  3  0  0  0  0
 13 15  2  0  0  0  0
 13 17  1  0  0  0  0
 15 18  1  0  0  0  0
 17 20  2  0  0  0  0
 18 21  2  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014763

> <DATABASE_NAME>
hmdb

> <SMILES>
FC(F)(F)[C@]1(OC(=O)NC2=C1C=C(Cl)C=C2)C#CC1CC1

> <INCHI_IDENTIFIER>
InChI=1S/C14H9ClF3NO2/c15-9-3-4-11-10(7-9)13(14(16,17)18,21-12(20)19-11)6-5-8-1-2-8/h3-4,7-8H,1-2H2,(H,19,20)/t13-/m0/s1

> <INCHI_KEY>
XPOQHMRABVBWPR-ZDUSSCGKSA-N

> <FORMULA>
C14H9ClF3NO2

> <MOLECULAR_WEIGHT>
315.675

> <EXACT_MASS>
315.027390859

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.811455689844223

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one

> <ALOGPS_LOGP>
3.89

> <JCHEM_LOGP>
4.456526315666666

> <ALOGPS_LOGS>
-4.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.523443377040433

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4900395586410093

> <JCHEM_POLAR_SURFACE_AREA>
38.33

> <JCHEM_REFRACTIVITY>
71.34230000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.55e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
efavirenz

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014763
     RDKit          3D
Efavirenz
 30 32  0  0  0  0  0  0  0  0999 V2000
    1.2850   -1.9583    3.4560 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2881   -1.3895    2.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2911   -0.4250    2.0560 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.2379    0.8043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3425    1.1941    0.5701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4173    1.8559   -0.6351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4780    1.5382   -1.5898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5614    2.3711   -3.1243 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.5011    0.5976   -1.3546 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4063   -0.0828   -0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539   -1.0936    0.0937 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9440   -0.4549   -0.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0148    0.0748   -0.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2997    0.7121   -0.5922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0778    1.1117    0.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5664   -0.0470   -0.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4464   -2.2386   -0.9128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5999   -3.1054   -0.5629 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.2081   -1.8457   -2.1929 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6088   -2.9450   -0.7577 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.3646   -1.6912    1.3480 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0222   -0.1700    2.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0815    1.4449    1.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1904    2.5935   -0.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7759    0.3721   -2.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3718    1.3471   -1.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6024    0.9305    1.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6619    2.0327    0.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4309    0.1050   -0.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3993   -1.0724    0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  6
 12 13  3  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 11 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 11 21  1  0
 21  2  1  0
 10  4  1  0
 16 14  1  0
  3 22  1  0
  5 23  1  0
  6 24  1  0
  9 25  1  0
 14 26  1  0
 15 27  1  0
 15 28  1  0
 16 29  1  0
 16 30  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 625                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      11.184   0.716   0.000  0.00  0.00          Cl+0
HETATM    2  F   UNK     0       5.748  -1.914   0.000  0.00  0.00           F+0
HETATM    3  F   UNK     0       4.207  -1.914   0.000  0.00  0.00           F+0
HETATM    4  F   UNK     0       3.644   0.189   0.000  0.00  0.00           F+0
HETATM    5  O   UNK     0       4.414   1.523   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.080   3.833   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       5.748   3.833   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       8.058  -3.248   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.391  -4.018   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.058  -4.788   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748   0.753   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.288  -1.914   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081   1.523   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.518  -0.581   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081   3.063   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.977  -0.581   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.458   0.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.458   3.887   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414   3.063   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.853   1.491   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.853   3.095   0.000  0.00  0.00           C+0
CONECT    1   20                                                            
CONECT    2   16                                                            
CONECT    3   16                                                            
CONECT    4   16                                                            
CONECT    5   11   19                                                       
CONECT    6   19                                                            
CONECT    7   15   19                                                       
CONECT    8    9   10   12                                                  
CONECT    9    8   10                                                       
CONECT   10    8    9                                                       
CONECT   11    5   13   14   16                                             
CONECT   12    8   14                                                       
CONECT   13   11   15   17                                                  
CONECT   14   11   12                                                       
CONECT   15    7   13   18                                                  
CONECT   16    2    3    4   11                                             
CONECT   17   13   20                                                       
CONECT   18   15   21                                                       
CONECT   19    5    6    7                                                  
CONECT   20    1   17   21                                                  
CONECT   21   18   20                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0014763
HETATM    1  O1  UNL     1       1.285  -1.958   3.456  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.288  -1.390   2.307  1.00  0.00           C  
HETATM    3  N1  UNL     1       2.291  -0.425   2.056  1.00  0.00           N  
HETATM    4  C2  UNL     1       2.346   0.238   0.804  1.00  0.00           C  
HETATM    5  C3  UNL     1       3.342   1.194   0.570  1.00  0.00           C  
HETATM    6  C4  UNL     1       3.417   1.856  -0.635  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.478   1.538  -1.590  1.00  0.00           C  
HETATM    8 CL1  UNL     1       2.561   2.371  -3.124  1.00  0.00          CL  
HETATM    9  C6  UNL     1       1.501   0.598  -1.355  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.406  -0.083  -0.146  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.354  -1.094   0.094  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.944  -0.455  -0.176  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.015   0.075  -0.377  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.300   0.712  -0.592  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.078   1.112   0.655  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.566  -0.047  -0.150  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.446  -2.239  -0.913  1.00  0.00           C  
HETATM   18  F1  UNL     1      -0.600  -3.105  -0.563  1.00  0.00           F  
HETATM   19  F2  UNL     1       0.208  -1.846  -2.193  1.00  0.00           F  
HETATM   20  F3  UNL     1       1.609  -2.945  -0.758  1.00  0.00           F  
HETATM   21  O2  UNL     1       0.365  -1.691   1.348  1.00  0.00           O  
HETATM   22  H1  UNL     1       3.022  -0.170   2.783  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.081   1.445   1.320  1.00  0.00           H  
HETATM   24  H3  UNL     1       4.190   2.593  -0.808  1.00  0.00           H  
HETATM   25  H4  UNL     1       0.776   0.372  -2.130  1.00  0.00           H  
HETATM   26  H5  UNL     1      -3.372   1.347  -1.487  1.00  0.00           H  
HETATM   27  H6  UNL     1      -3.602   0.931   1.641  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.662   2.033   0.598  1.00  0.00           H  
HETATM   29  H8  UNL     1      -5.431   0.105  -0.823  1.00  0.00           H  
HETATM   30  H9  UNL     1      -4.399  -1.072   0.187  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   21
CONECT    3    4   22
CONECT    4    5    5   10
CONECT    5    6   23
CONECT    6    7    7   24
CONECT    7    8    9
CONECT    9   10   10   25
CONECT   10   11
CONECT   11   12   17   21
CONECT   12   13   13   13
CONECT   13   14
CONECT   14   15   16   26
CONECT   15   16   27   28
CONECT   16   29   30
CONECT   17   18   19   20
END

HMDB0014763
     RDKit          3D
Efavirenz
 30 32  0  0  0  0  0  0  0  0999 V2000
    1.2850   -1.9583    3.4560 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2881   -1.3895    2.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2911   -0.4250    2.0560 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.2379    0.8043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3425    1.1941    0.5701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4173    1.8559   -0.6351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4780    1.5382   -1.5898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5614    2.3711   -3.1243 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.5011    0.5976   -1.3546 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4063   -0.0828   -0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539   -1.0936    0.0937 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9440   -0.4549   -0.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0148    0.0748   -0.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2997    0.7121   -0.5922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0778    1.1117    0.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5664   -0.0470   -0.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4464   -2.2386   -0.9128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5999   -3.1054   -0.5629 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.2081   -1.8457   -2.1929 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6088   -2.9450   -0.7577 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.3646   -1.6912    1.3480 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0222   -0.1700    2.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0815    1.4449    1.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1904    2.5935   -0.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7759    0.3721   -2.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3718    1.3471   -1.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6024    0.9305    1.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6619    2.0327    0.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4309    0.1050   -0.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3993   -1.0724    0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  6
 12 13  3  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 11 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 11 21  1  0
 21  2  1  0
 10  4  1  0
 16 14  1  0
  3 22  1  0
  5 23  1  0
  6 24  1  0
  9 25  1  0
 14 26  1  0
 15 27  1  0
 15 28  1  0
 16 29  1  0
 16 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-6-CHLORO-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one	ChEBI
(S)-6-Chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one	ChEBI
(S)-6-Chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-benzo[D][1,3]oxazin-2-one	ChEBI
6-Chloro-4-(2-cyclopropyl-1-ethynyl)-4-trifluoromethyl-(4S)-1,4-dihydro-2H-benzo[D][1,3]oxazin-2-one	ChEBI
Sustiva	Kegg
EFV	HMDB
(S)-6-Chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one	HMDB
DMP-266	HMDB
Du pont brand OF efavirenz	HMDB
Merck sharp and dohme brand OF efavirenz	HMDB
Efavirenz, (R)-isomer	HMDB
Efavirenz, (S)-isomer	HMDB
Stocrin	HMDB
United drug brand OF efavirenz	HMDB
DMP 266	HMDB
Bristol-myers squibb brand OF efavirenz	HMDB

Chemical Formula

C₁₄H₉ClF₃NO₂

Average Molecular Weight

315.675

Monoisotopic Molecular Weight

315.027390859

IUPAC Name

(4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one

Traditional Name

efavirenz

CAS Registry Number

154598-52-4

SMILES

FC(F)(F)[C@]1(OC(=O)NC2=C1C=C(Cl)C=C2)C#CC1CC1

InChI Identifier

InChI=1S/C14H9ClF3NO2/c15-9-3-4-11-10(7-9)13(14(16,17)18,21-12(20)19-11)6-5-8-1-2-8/h3-4,7-8H,1-2H2,(H,19,20)/t13-/m0/s1

InChI Key

XPOQHMRABVBWPR-ZDUSSCGKSA-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
Aryl chloride
Aryl halide
Ynone
Benzenoid
Oxacycle
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organofluoride
Organochloride
Organohalogen compound
Organopnictogen compound
Organic oxygen compound
Alkyl fluoride
Alkyl halide
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organofluorine compound (CHEBI:119486 )
organochlorine compound (CHEBI:119486 )
cyclopropanes (CHEBI:119486 )
acetylenic compound (CHEBI:119486 )
benzoxazine (CHEBI:119486 )

Ontology

Disposition

Biological location

Excreta

Urine

Cellular substructure

Macromolecular complex

Blood

Ingestion

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Efavirenz action pathway

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	139 - 141 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0086 g/L	Not Available
LogP	4.6	Not Available

Experimental Spectral Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0086 g/L	ALOGPS
logP	10^(3.89) g/L	ALOGPS
logP	10^(4.46) g/L	ChemAxon
logS	10^(-4.6) g/L	ALOGPS
pKa (Strongest Acidic)	12.52	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.33 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	71.34 m³·mol⁻¹	ChemAxon
Polarizability	26.81 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Spectral Properties

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Efavirenz GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-5290000000-0868877bc452f2c49eca	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Efavirenz GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Efavirenz 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Efavirenz LC-ESI-QFT , negative-QTOF	splash10-03di-1059000000-f599b397bafd1974176e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Efavirenz LC-ESI-QFT , negative-QTOF	splash10-014l-5090000000-b807e6fcee57f8b27cb6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Efavirenz LC-ESI-QFT , negative-QTOF	splash10-014i-9040000000-260d9ba8c55987cd2b0e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Efavirenz LC-ESI-QFT , negative-QTOF	splash10-014i-9010000000-459e48522e8275e941f8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Efavirenz LC-ESI-QFT , negative-QTOF	splash10-014i-9000000000-531ef8f962aff7837863	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Efavirenz LC-ESI-QFT , negative-QTOF	splash10-014i-9000000000-9574533b450f3724a645	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Efavirenz LC-ESI-QFT , negative-QTOF	splash10-03dl-0098000000-f0d050ef36094b37e62d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Efavirenz 35V, Negative-QTOF	splash10-0006-0091000000-cbe97f1cb442fbe79f63	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Efavirenz 75V, Negative-QTOF	splash10-014i-9000000000-b423df8149eadd941fea	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Efavirenz 90V, Negative-QTOF	splash10-014i-9000000000-4cf0f020e0bbdd0773bf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Efavirenz 15V, Negative-QTOF	splash10-03di-1059000000-91fd5749a85c9f63da83	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Efavirenz 35V, Negative-QTOF	splash10-03dl-0098000000-2fab581d3e853468fd1a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Efavirenz 60V, Negative-QTOF	splash10-014i-9000000000-a97b9e54b0d95065c416	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Efavirenz 30V, Negative-QTOF	splash10-014l-6090000000-bc5270450628f5a4704a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Efavirenz 45V, Negative-QTOF	splash10-014i-9030000000-61a28f676930a76edf5f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Efavirenz LC-ESI-qTof , Positive-QTOF	splash10-016r-1900000000-f04127a0f39b9e0b001f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Efavirenz LC-ESI-QFT , positive-QTOF	splash10-0fxx-0091000000-8ab690a60877e8476640	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Efavirenz LC-ESI-QFT , positive-QTOF	splash10-0frx-0190000000-deeefb25f97b767955b2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Efavirenz LC-ESI-QFT , positive-QTOF	splash10-0giu-0390000000-7a682b484377bc11de1b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Efavirenz LC-ESI-QFT , positive-QTOF	splash10-01b9-0790000000-a789e578dcf6568d7eb9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Efavirenz LC-ESI-QFT , positive-QTOF	splash10-014i-0930000000-a1dae29a53e6be48d87f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Efavirenz LC-ESI-QFT , positive-QTOF	splash10-014r-0910000000-70a86e64f2e50ce28b18	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Efavirenz , positive-QTOF	splash10-00xu-0390000000-d7561e61b30a86d9a480	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Efavirenz LC-ESI-QFT , positive-QTOF	splash10-0giu-1290000000-c402be3d2864520be5fb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Efavirenz 35V, Positive-QTOF	splash10-0gbi-0490000000-0dccaf0bee7073b1ebb9	2021-09-20	HMDB team, MONA	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Efavirenz 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	Taking drug identified by DrugBank entry DB00625	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00625	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00625

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

57715

KEGG Compound ID

C08088

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Efavirenz

METLIN ID

Not Available

PubChem Compound

64139

PDB ID

EFZ

ChEBI ID

119486

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

Ren J, Bird LE, Chamberlain PP, Stewart-Jones GB, Stuart DI, Stammers DK: Structure of HIV-2 reverse transcriptase at 2.35-A resolution and the mechanism of resistance to non-nucleoside inhibitors. Proc Natl Acad Sci U S A. 2002 Oct 29;99(22):14410-5. Epub 2002 Oct 17. [PubMed:12386343 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Cytochrome P450 2B6

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Hesse LM, von Moltke LL, Shader RI, Greenblatt DJ: Ritonavir, efavirenz, and nelfinavir inhibit CYP2B6 activity in vitro: potential drug interactions with bupropion. Drug Metab Dispos. 2001 Feb;29(2):100-2. [PubMed:11159797 ]
Walsky RL, Astuccio AV, Obach RS: Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J Clin Pharmacol. 2006 Dec;46(12):1426-38. [PubMed:17101742 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

6. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Showing metabocard for Efavirenz (HMDB0014763)

MOL for HMDB0014763 (Efavirenz)

3D MOL for HMDB0014763 (Efavirenz)

3D SDF for HMDB0014763 (Efavirenz)

3D-SDF for HMDB0014763 (Efavirenz)

PDB for HMDB0014763 (Efavirenz)

3D PDB for HMDB0014763 (Efavirenz)

SMILES for HMDB0014763 (Efavirenz)

INCHI for HMDB0014763 (Efavirenz)

Structure for HMDB0014763 (Efavirenz)

3D Structure for HMDB0014763 (Efavirenz)

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References