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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 08:57:22 UTC

Update Date

2021-09-26 23:03:40 UTC

HMDB ID

HMDB0251589

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Doravirine

Description

Doravirine belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups. A) or moderate (Child-Pugh Class. Doravirine is a moderately basic compound (based on its pKa). No dosage adjustment of doravirine is required in patients with mild, moderate, or severe renal impairment. C), or <18 years of age is unknown . Once administered and absorbed into the plasma circulation, unchanged doravirine is the major circulating component, followed by its M9 metabolite - a product of cytochrome P450 3A4/5 mediated oxidative metabolism, resulting in the addition of oxygen to doravirine's triazolone ring - as the most abundant doravirine metabolite present . Doravirine is subsequently available by itself or as a combination product of doravirine (100 mg), lamivudine (300 mg), and tenofovir disoproxil fumarate (300 mg) . The pharmacokinetics of doravirine in patients with end-stage renal disease or undergoing dialysis, severe hepatic impairment (Child-Pugh. This compound has been identified in human blood as reported by (PMID: 31557052 ). Doravirine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Doravirine 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


  Mrv0541 05031421082D          

 29 31  0  0  0  0            999 V2000
    0.7981   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5389   -5.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2033   -4.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1195   -2.9136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8141   -3.4948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9702   -4.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9635   -2.0737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3527   -3.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2991   -2.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4551   -3.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1497   -4.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3594   -5.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8376   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8443   -4.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5087   -4.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6949   -6.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2756   -3.7535    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0305   -7.0045    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.4486   -5.9152    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.9413   -6.5863    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.6279   -1.3200    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6626   -2.5687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9176   -1.7840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5827   -1.7840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6883   -3.9898    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9937   -3.4086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501   -0.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6648   -4.9159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  4  1  0  0  0  0
 10  6  2  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  2  1  0  0  0  0
 13  8  1  0  0  0  0
 14 12  2  0  0  0  0
 15 14  1  0  0  0  0
 17 12  1  0  0  0  0
 18 10  1  0  0  0  0
 19 17  1  0  0  0  0
 20 17  1  0  0  0  0
 21 17  1  0  0  0  0
 22  7  3  0  0  0  0
 23 13  2  0  0  0  0
 24 16  2  0  0  0  0
 24 23  1  0  0  0  0
 25  1  1  0  0  0  0
 25 13  1  0  0  0  0
 25 16  1  0  0  0  0
 26  3  1  0  0  0  0
 26  8  1  0  0  0  0
 26 15  1  0  0  0  0
 27 15  2  0  0  0  0
 28 16  1  0  0  0  0
 29 11  1  0  0  0  0
 29 14  1  0  0  0  0
M  END

HMDB0251589
     RDKit          3D
Doravirine
 40 42  0  0  0  0  0  0  0  0999 V2000
   -4.9998   -0.5315   -0.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3899    0.7184    0.1859 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9595    1.9246   -0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1343    2.1771   -0.7930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1296    2.8298    0.4493 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1105    2.2200    1.0334 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2581    0.8781    0.8767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3376   -0.1903    1.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3444   -0.4193    0.3459 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5315   -1.3332   -0.6220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5986   -1.5676   -1.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5891   -0.8419   -1.6294 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6203   -1.0543   -2.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8689    0.0962   -3.4070 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.1185   -1.9926   -3.5659 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.8068   -1.5295   -2.2147 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.7558    0.0887   -0.6256 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9301    0.8457   -0.5936 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0272    0.4060    0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0453   -0.7587    0.8691 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1603   -1.1425    1.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2137   -2.6255    2.5179 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2931   -0.3675    1.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3116    0.8171    0.8137 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4893    1.6315    0.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4497    2.2800    0.7788 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1777    1.1802    0.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088    0.3051    0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0015    1.1771    1.2682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6798   -1.3014    0.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5547   -0.8555   -1.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0972   -0.4688   -0.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0794    2.4016   -1.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8269    0.2581    2.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8822   -1.1131    1.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4712   -1.8947   -0.5913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7607   -2.3047   -2.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1529   -1.3643    0.8816 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1633   -0.6723    2.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1829    2.0940   -0.4495 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
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 12 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  3  0
 24 27  2  0
 17 28  1  0
 28 29  2  0
  7  2  1  0
 28  9  1  0
 27 19  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  8 34  1  0
  8 35  1  0
 10 36  1  0
 11 37  1  0
 20 38  1  0
 23 39  1  0
 27 40  1  0
M  END


  Mrv0541 05031421082D          

 29 31  0  0  0  0            999 V2000
    0.7981   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5389   -5.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2033   -4.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1195   -2.9136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8141   -3.4948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9702   -4.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9635   -2.0737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3527   -3.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2991   -2.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4551   -3.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1497   -4.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3594   -5.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8376   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8443   -4.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5087   -4.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6949   -6.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2756   -3.7535    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0305   -7.0045    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.4486   -5.9152    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.9413   -6.5863    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.6279   -1.3200    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6626   -2.5687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9176   -1.7840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5827   -1.7840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6883   -3.9898    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9937   -3.4086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501   -0.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6648   -4.9159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  4  1  0  0  0  0
 10  6  2  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  2  1  0  0  0  0
 13  8  1  0  0  0  0
 14 12  2  0  0  0  0
 15 14  1  0  0  0  0
 17 12  1  0  0  0  0
 18 10  1  0  0  0  0
 19 17  1  0  0  0  0
 20 17  1  0  0  0  0
 21 17  1  0  0  0  0
 22  7  3  0  0  0  0
 23 13  2  0  0  0  0
 24 16  2  0  0  0  0
 24 23  1  0  0  0  0
 25  1  1  0  0  0  0
 25 13  1  0  0  0  0
 25 16  1  0  0  0  0
 26  3  1  0  0  0  0
 26  8  1  0  0  0  0
 26 15  1  0  0  0  0
 27 15  2  0  0  0  0
 28 16  1  0  0  0  0
 29 11  1  0  0  0  0
 29 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0251589

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(O)=NN=C1CN1C=CC(=C(OC2=CC(=CC(Cl)=C2)C#N)C1=O)C(F)(F)F

> <INCHI_IDENTIFIER>
InChI=1S/C17H11ClF3N5O3/c1-25-13(23-24-16(25)28)8-26-3-2-12(17(19,20)21)14(15(26)27)29-11-5-9(7-22)4-10(18)6-11/h2-6H,8H2,1H3,(H,24,28)

> <INCHI_KEY>
ZIAOVIPSKUPPQW-UHFFFAOYSA-N

> <FORMULA>
C17H11ClF3N5O3

> <MOLECULAR_WEIGHT>
425.749

> <EXACT_MASS>
425.050251565

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
35.42002741245383

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-chloro-5-({1-[(5-hydroxy-4-methyl-4H-1,2,4-triazol-3-yl)methyl]-2-oxo-4-(trifluoromethyl)-1,2-dihydropyridin-3-yl}oxy)benzonitrile

> <ALOGPS_LOGP>
3.47

> <JCHEM_LOGP>
2.1885739873333336

> <ALOGPS_LOGS>
-4.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.257022401373844

> <JCHEM_PKA_STRONGEST_BASIC>
1.3198112504888515

> <JCHEM_POLAR_SURFACE_AREA>
104.27000000000001

> <JCHEM_REFRACTIVITY>
98.3717

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-chloro-5-({1-[(5-hydroxy-4-methyl-1,2,4-triazol-3-yl)methyl]-2-oxo-4-(trifluoromethyl)pyridin-3-yl}oxy)benzonitrile

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0251589
     RDKit          3D
Doravirine
 40 42  0  0  0  0  0  0  0  0999 V2000
   -4.9998   -0.5315   -0.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3899    0.7184    0.1859 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9595    1.9246   -0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1343    2.1771   -0.7930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1296    2.8298    0.4493 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1105    2.2200    1.0334 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2581    0.8781    0.8767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3376   -0.1903    1.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3444   -0.4193    0.3459 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5315   -1.3332   -0.6220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5986   -1.5676   -1.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5891   -0.8419   -1.6294 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6203   -1.0543   -2.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8689    0.0962   -3.4070 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.1185   -1.9926   -3.5659 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.8068   -1.5295   -2.2147 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.7558    0.0887   -0.6256 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9301    0.8457   -0.5936 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0272    0.4060    0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0453   -0.7587    0.8691 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1603   -1.1425    1.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2137   -2.6255    2.5179 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2931   -0.3675    1.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3116    0.8171    0.8137 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4893    1.6315    0.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4497    2.2800    0.7788 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1777    1.1802    0.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088    0.3051    0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0015    1.1771    1.2682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6798   -1.3014    0.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5547   -0.8555   -1.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0972   -0.4688   -0.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0794    2.4016   -1.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8269    0.2581    2.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8822   -1.1131    1.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4712   -1.8947   -0.5913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7607   -2.3047   -2.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1529   -1.3643    0.8816 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1633   -0.6723    2.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1829    2.0940   -0.4495 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
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 12 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  3  0
 24 27  2  0
 17 28  1  0
 28 29  2  0
  7  2  1  0
 28  9  1  0
 27 19  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  8 34  1  0
  8 35  1  0
 10 36  1  0
 11 37  1  0
 20 38  1  0
 23 39  1  0
 27 40  1  0
M  END

HEADER    PROTEIN                                 03-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
HETATM   19  F   UNK     0       0.000   0.000   0.000  0.00  0.00           F+0
HETATM   20  F   UNK     0       0.000   0.000   0.000  0.00  0.00           F+0
HETATM   21  F   UNK     0       0.000   0.000   0.000  0.00  0.00           F+0
HETATM   22  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   27  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1   25                                                            
CONECT    2    3   12                                                       
CONECT    3    2   26                                                       
CONECT    4    9   10                                                       
CONECT    5    9   11                                                       
CONECT    6   10   11                                                       
CONECT    7    9   22                                                       
CONECT    8   13   26                                                       
CONECT    9    4    5    7                                                  
CONECT   10    4    6   18                                                  
CONECT   11    5    6   29                                                  
CONECT   12    2   14   17                                                  
CONECT   13    8   23   25                                                  
CONECT   14   12   15   29                                                  
CONECT   15   14   26   27                                                  
CONECT   16   24   25   28                                                  
CONECT   17   12   19   20   21                                             
CONECT   18   10                                                            
CONECT   19   17                                                            
CONECT   20   17                                                            
CONECT   21   17                                                            
CONECT   22    7                                                            
CONECT   23   13   24                                                       
CONECT   24   16   23                                                       
CONECT   25    1   13   16                                                  
CONECT   26    3    8   15                                                  
CONECT   27   15                                                            
CONECT   28   16                                                            
CONECT   29   11   14                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

COMPND    HMDB0251589
HETATM    1  C1  UNL     1      -5.000  -0.532  -0.244  1.00  0.00           C  
HETATM    2  N1  UNL     1      -4.390   0.718   0.186  1.00  0.00           N  
HETATM    3  C2  UNL     1      -4.960   1.925  -0.097  1.00  0.00           C  
HETATM    4  O1  UNL     1      -6.134   2.177  -0.793  1.00  0.00           O  
HETATM    5  N2  UNL     1      -4.130   2.830   0.449  1.00  0.00           N  
HETATM    6  N3  UNL     1      -3.110   2.220   1.033  1.00  0.00           N  
HETATM    7  C3  UNL     1      -3.258   0.878   0.877  1.00  0.00           C  
HETATM    8  C4  UNL     1      -2.338  -0.190   1.377  1.00  0.00           C  
HETATM    9  N4  UNL     1      -1.344  -0.419   0.346  1.00  0.00           N  
HETATM   10  C5  UNL     1      -1.531  -1.333  -0.622  1.00  0.00           C  
HETATM   11  C6  UNL     1      -0.599  -1.568  -1.612  1.00  0.00           C  
HETATM   12  C7  UNL     1       0.589  -0.842  -1.629  1.00  0.00           C  
HETATM   13  C8  UNL     1       1.620  -1.054  -2.674  1.00  0.00           C  
HETATM   14  F1  UNL     1       1.869   0.096  -3.407  1.00  0.00           F  
HETATM   15  F2  UNL     1       1.118  -1.993  -3.566  1.00  0.00           F  
HETATM   16  F3  UNL     1       2.807  -1.530  -2.215  1.00  0.00           F  
HETATM   17  C9  UNL     1       0.756   0.089  -0.626  1.00  0.00           C  
HETATM   18  O2  UNL     1       1.930   0.846  -0.594  1.00  0.00           O  
HETATM   19  C10 UNL     1       3.027   0.406   0.132  1.00  0.00           C  
HETATM   20  C11 UNL     1       3.045  -0.759   0.869  1.00  0.00           C  
HETATM   21  C12 UNL     1       4.160  -1.143   1.567  1.00  0.00           C  
HETATM   22 CL1  UNL     1       4.214  -2.626   2.518  1.00  0.00          CL  
HETATM   23  C13 UNL     1       5.293  -0.367   1.548  1.00  0.00           C  
HETATM   24  C14 UNL     1       5.312   0.817   0.814  1.00  0.00           C  
HETATM   25  C15 UNL     1       6.489   1.632   0.788  1.00  0.00           C  
HETATM   26  N5  UNL     1       7.450   2.280   0.779  1.00  0.00           N  
HETATM   27  C16 UNL     1       4.178   1.180   0.120  1.00  0.00           C  
HETATM   28  C17 UNL     1      -0.209   0.305   0.366  1.00  0.00           C  
HETATM   29  O3  UNL     1      -0.001   1.177   1.268  1.00  0.00           O  
HETATM   30  H1  UNL     1      -4.680  -1.301   0.515  1.00  0.00           H  
HETATM   31  H2  UNL     1      -4.555  -0.855  -1.209  1.00  0.00           H  
HETATM   32  H3  UNL     1      -6.097  -0.469  -0.267  1.00  0.00           H  
HETATM   33  H4  UNL     1      -6.079   2.402  -1.791  1.00  0.00           H  
HETATM   34  H5  UNL     1      -1.827   0.258   2.275  1.00  0.00           H  
HETATM   35  H6  UNL     1      -2.882  -1.113   1.647  1.00  0.00           H  
HETATM   36  H7  UNL     1      -2.471  -1.895  -0.591  1.00  0.00           H  
HETATM   37  H8  UNL     1      -0.761  -2.305  -2.384  1.00  0.00           H  
HETATM   38  H9  UNL     1       2.153  -1.364   0.882  1.00  0.00           H  
HETATM   39  H10 UNL     1       6.163  -0.672   2.096  1.00  0.00           H  
HETATM   40  H11 UNL     1       4.183   2.094  -0.449  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    7
CONECT    3    4    5    5
CONECT    4   33
CONECT    5    6
CONECT    6    7    7
CONECT    7    8
CONECT    8    9   34   35
CONECT    9   10   28
CONECT   10   11   11   36
CONECT   11   12   37
CONECT   12   13   17   17
CONECT   13   14   15   16
CONECT   17   18   28
CONECT   18   19
CONECT   19   20   20   27
CONECT   20   21   38
CONECT   21   22   23   23
CONECT   23   24   39
CONECT   24   25   27   27
CONECT   25   26   26   26
CONECT   27   40
CONECT   28   29   29
END

HMDB0251589
     RDKit          3D
Doravirine
 40 42  0  0  0  0  0  0  0  0999 V2000
   -4.9998   -0.5315   -0.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3899    0.7184    0.1859 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9595    1.9246   -0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1343    2.1771   -0.7930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1296    2.8298    0.4493 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1105    2.2200    1.0334 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2581    0.8781    0.8767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3376   -0.1903    1.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3444   -0.4193    0.3459 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5315   -1.3332   -0.6220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5986   -1.5676   -1.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5891   -0.8419   -1.6294 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6203   -1.0543   -2.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8689    0.0962   -3.4070 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.1185   -1.9926   -3.5659 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.8068   -1.5295   -2.2147 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.7558    0.0887   -0.6256 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9301    0.8457   -0.5936 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0272    0.4060    0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0453   -0.7587    0.8691 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1603   -1.1425    1.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2137   -2.6255    2.5179 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2931   -0.3675    1.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3116    0.8171    0.8137 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4893    1.6315    0.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4497    2.2800    0.7788 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1777    1.1802    0.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088    0.3051    0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0015    1.1771    1.2682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6798   -1.3014    0.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5547   -0.8555   -1.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0972   -0.4688   -0.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0794    2.4016   -1.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8269    0.2581    2.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8822   -1.1131    1.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4712   -1.8947   -0.5913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7607   -2.3047   -2.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1529   -1.3643    0.8816 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1633   -0.6723    2.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1829    2.0940   -0.4495 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
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 12 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  3  0
 24 27  2  0
 17 28  1  0
 28 29  2  0
  7  2  1  0
 28  9  1  0
 27 19  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  8 34  1  0
  8 35  1  0
 10 36  1  0
 11 37  1  0
 20 38  1  0
 23 39  1  0
 27 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
MK-1439DORAVIRINE	ChEMBL

Chemical Formula

C₁₇H₁₁ClF₃N₅O₃

Average Molecular Weight

425.749

Monoisotopic Molecular Weight

425.050251565

IUPAC Name

3-chloro-5-({1-[(5-hydroxy-4-methyl-4H-1,2,4-triazol-3-yl)methyl]-2-oxo-4-(trifluoromethyl)-1,2-dihydropyridin-3-yl}oxy)benzonitrile

Traditional Name

3-chloro-5-({1-[(5-hydroxy-4-methyl-1,2,4-triazol-3-yl)methyl]-2-oxo-4-(trifluoromethyl)pyridin-3-yl}oxy)benzonitrile

CAS Registry Number

Not Available

SMILES

CN1C(O)=NN=C1CN1C=CC(=C(OC2=CC(=CC(Cl)=C2)C#N)C1=O)C(F)(F)F

InChI Identifier

InChI=1S/C17H11ClF3N5O3/c1-25-13(23-24-16(25)28)8-26-3-2-12(17(19,20)21)14(15(26)27)29-11-5-9(7-22)4-10(18)6-11/h2-6H,8H2,1H3,(H,24,28)

InChI Key

ZIAOVIPSKUPPQW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Diarylethers

Alternative Parents

Substituents

Diaryl ether
Benzonitrile
Phenoxy compound
Phenol ether
Chlorobenzene
Dihydropyridine
Halobenzene
Pyridinone
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Hydropyridine
Pyridine
Benzenoid
Azole
1,2,4-triazole
Heteroaromatic compound
Lactam
Organoheterocyclic compound
Azacycle
Nitrile
Carbonitrile
Hydrocarbon derivative
Organic oxide
Cyanide
Organic nitrogen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Alkyl fluoride
Organofluoride
Alkyl halide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (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	3.47	ALOGPS
logP	2.19	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	8.26	ChemAxon
pKa (Strongest Basic)	1.32	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	104.27 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	98.37 m³·mol⁻¹	ChemAxon
Polarizability	35.42 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]+	186.217	30932474
DeepCCS	[M-H]-	183.699	30932474
DeepCCS	[M-2H]-	218.266	30932474
DeepCCS	[M+Na]+	193.471	30932474
AllCCS	[M+H]+	188.9	32859911
AllCCS	[M+H-H2O]+	186.4	32859911
AllCCS	[M+NH4]+	191.2	32859911
AllCCS	[M+Na]+	191.9	32859911
AllCCS	[M-H]-	184.4	32859911
AllCCS	[M+Na-2H]-	183.6	32859911
AllCCS	[M+HCOO]-	182.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Doravirine	CN1C(O)=NN=C1CN1C=CC(=C(OC2=CC(=CC(Cl)=C2)C#N)C1=O)C(F)(F)F	3718.0	Standard polar	33892256
Doravirine	CN1C(O)=NN=C1CN1C=CC(=C(OC2=CC(=CC(Cl)=C2)C#N)C1=O)C(F)(F)F	2798.4	Standard non polar	33892256
Doravirine	CN1C(O)=NN=C1CN1C=CC(=C(OC2=CC(=CC(Cl)=C2)C#N)C1=O)C(F)(F)F	3115.3	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 - Doravirine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0wmi-1539200000-bc5dd78c5dc9b16615e9	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Doravirine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Doravirine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Doravirine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	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 - Doravirine 10V, Positive-QTOF	splash10-004i-1102900000-85159263a4e1f67db4fd	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Doravirine 20V, Positive-QTOF	splash10-02ta-0219100000-d6ddc6a4128222a041d1	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Doravirine 40V, Positive-QTOF	splash10-053i-8928000000-39d7c30b07d1de9e85d9	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Doravirine 10V, Negative-QTOF	splash10-014i-2009000000-f1affba5de17dc10816d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Doravirine 20V, Negative-QTOF	splash10-014i-1109100000-d953f236c324da9b5329	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Doravirine 40V, Negative-QTOF	splash10-0zfu-4912000000-7eac1fbcbbae47e7fb50	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Doravirine 10V, Positive-QTOF	splash10-004i-0000900000-c2c10af104f690d1e43c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Doravirine 20V, Positive-QTOF	splash10-004r-0109400000-f42cb9021f31cd5b24ab	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Doravirine 40V, Positive-QTOF	splash10-0f9i-3819000000-209cda74b17fdb5cce5f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Doravirine 10V, Negative-QTOF	splash10-00di-0401900000-17fb69f803a4a3e2aa13	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Doravirine 20V, Negative-QTOF	splash10-0udi-5809000000-c18aeb067425b7980067	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Doravirine 40V, Negative-QTOF	splash10-001i-9001000000-7e76979acba163304f23	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

DB12301

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

Doravirine

METLIN ID

Not Available

PubChem Compound

58460047

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 Doravirine (HMDB0251589)

MOL for HMDB0251589 (Doravirine)

3D MOL for HMDB0251589 (Doravirine)

3D SDF for HMDB0251589 (Doravirine)

3D-SDF for HMDB0251589 (Doravirine)

PDB for HMDB0251589 (Doravirine)

3D PDB for HMDB0251589 (Doravirine)

SMILES for HMDB0251589 (Doravirine)

INCHI for HMDB0251589 (Doravirine)

Structure for HMDB0251589 (Doravirine)

3D Structure for HMDB0251589 (Doravirine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra