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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 09:23:24 UTC

Update Date

2021-09-26 23:04:00 UTC

HMDB ID

HMDB0251775

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Emivirine

Description

Emivirine, also known as coactinon or MKC-442, belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Emivirine is an extremely weak basic (essentially neutral) compound (based on its pKa). A pyrimidone that is uracil which is substituted at positions 1, 5 and 6 by ethoxymethyl, isopropyl, and benzyl groups, respectively. This compound has been identified in human blood as reported by (PMID: 31557052 ). Emivirine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Emivirine 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

HMDB0251775
     RDKit          3D
Emivirine
 44 45  0  0  0  0  0  0  0  0999 V2000
    4.3786    0.8230    0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3605   -0.0054   -0.8055 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1486   -0.6199   -1.0864 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1854    0.3740   -1.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9281   -0.2660   -1.5508 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0164   -0.6425   -0.6058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3658   -0.3961    0.7873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2669    0.7537    1.4552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8711    0.5544    2.6783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4712    1.5976    3.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4785    2.8625    2.7637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8779    3.0523    1.5530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2691    2.0267    0.8803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1663   -1.2668   -0.9737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2081   -1.6595   -0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1370   -2.7514   -0.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0636   -0.4584    0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3266   -1.4657   -2.3402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3835   -2.0340   -2.7934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4260   -1.0938   -3.2666 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6795   -0.5027   -2.8481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5132   -0.1627   -3.7556 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7317    0.4273    1.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0152    1.8408    0.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4225    0.9056    0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6843    0.6432   -1.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1231   -0.8137   -0.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5534    0.9548   -2.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2197    1.0268   -0.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760   -0.2605    0.8847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1902   -1.2957    1.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8817   -0.4198    3.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9378    1.4075    4.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9460    3.6795    3.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8953    4.0579    1.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1942    2.1835   -0.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7418   -2.0434    0.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9292   -2.3408   -1.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6198   -3.5454   -1.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5916   -3.3089    0.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1118   -0.5820   -0.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2475   -0.4403    1.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7074    0.4897   -0.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6304   -1.2855   -4.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 14 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 21  5  1  0
 13  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  4 28  1  0
  4 29  1  0
  7 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 13 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 20 44  1  0
M  END

MKC
  Mrv0541 02241213552D          

 22 23  0  0  0  0            999 V2000
    1.0554   -0.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7699   -1.1832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7699   -2.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0554   -2.4207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3409   -2.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3409   -1.1832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3409    0.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3735    0.0543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0880    0.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8025    0.0543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0880    1.2918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3735    1.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3735    2.5293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3409    1.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0554    0.0543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0554    1.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0554    2.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7699    1.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3735   -0.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0880   -1.1832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8025   -0.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5170   -1.1832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1 15  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  8  1  0  0  0  0
  7 14  2  0  0  0  0
  7 15  1  0  0  0  0
  8  9  1  0  0  0  0
  8 19  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0251775

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOCN1C(=O)NC(=O)C(C(C)C)=C1CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H22N2O3/c1-4-22-11-19-14(10-13-8-6-5-7-9-13)15(12(2)3)16(20)18-17(19)21/h5-9,12H,4,10-11H2,1-3H3,(H,18,20,21)

> <INCHI_KEY>
MLILORUFDVLTSP-UHFFFAOYSA-N

> <FORMULA>
C17H22N2O3

> <MOLECULAR_WEIGHT>
302.3682

> <EXACT_MASS>
302.16304258

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.87282496006705

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-benzyl-1-(ethoxymethyl)-5-(propan-2-yl)-1,2,3,4-tetrahydropyrimidine-2,4-dione

> <ALOGPS_LOGP>
2.57

> <JCHEM_LOGP>
2.7738557826666668

> <ALOGPS_LOGS>
-3.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.232539986512974

> <JCHEM_PKA_STRONGEST_BASIC>
-3.858978754776905

> <JCHEM_POLAR_SURFACE_AREA>
58.64

> <JCHEM_REFRACTIVITY>
85.41240000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
emivirine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0251775
     RDKit          3D
Emivirine
 44 45  0  0  0  0  0  0  0  0999 V2000
    4.3786    0.8230    0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3605   -0.0054   -0.8055 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1486   -0.6199   -1.0864 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1854    0.3740   -1.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9281   -0.2660   -1.5508 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0164   -0.6425   -0.6058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3658   -0.3961    0.7873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2669    0.7537    1.4552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8711    0.5544    2.6783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4712    1.5976    3.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4785    2.8625    2.7637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8779    3.0523    1.5530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2691    2.0267    0.8803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1663   -1.2668   -0.9737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2081   -1.6595   -0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1370   -2.7514   -0.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0636   -0.4584    0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3266   -1.4657   -2.3402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3835   -2.0340   -2.7934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4260   -1.0938   -3.2666 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6795   -0.5027   -2.8481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5132   -0.1627   -3.7556 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7317    0.4273    1.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0152    1.8408    0.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4225    0.9056    0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6843    0.6432   -1.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1231   -0.8137   -0.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5534    0.9548   -2.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2197    1.0268   -0.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760   -0.2605    0.8847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1902   -1.2957    1.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8817   -0.4198    3.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9378    1.4075    4.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9460    3.6795    3.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8953    4.0579    1.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1942    2.1835   -0.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7418   -2.0434    0.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9292   -2.3408   -1.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6198   -3.5454   -1.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5916   -3.3089    0.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1118   -0.5820   -0.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2475   -0.4403    1.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7074    0.4897   -0.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6304   -1.2855   -4.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 14 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 21  5  1  0
 13  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  4 28  1  0
  4 29  1  0
  7 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 13 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 20 44  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: MKC                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       1.970  -1.439   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.304  -2.209   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.304  -3.749   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.970  -4.519   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.636  -3.749   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.636  -2.209   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.636   0.871   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -0.697   0.101   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -2.031   0.871   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.365   0.101   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      -2.031   2.411   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -0.697   3.181   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.697   4.721   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.636   2.411   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.970   0.101   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.970   3.181   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.970   4.721   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.304   2.411   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.697  -1.439   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.031  -2.209   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.365  -1.439   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.698  -2.209   0.000  0.00  0.00           C+0
CONECT    1    2    6   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    8   14   15                                                  
CONECT    8    7    9   19                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14    7   12   16                                                  
CONECT   15    1    7                                                       
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    8   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0251775
HETATM    1  C1  UNL     1       4.379   0.823   0.433  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.360  -0.005  -0.805  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.149  -0.620  -1.086  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.185   0.374  -1.260  1.00  0.00           C  
HETATM    5  N1  UNL     1       0.928  -0.266  -1.551  1.00  0.00           N  
HETATM    6  C4  UNL     1       0.016  -0.642  -0.606  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.366  -0.396   0.787  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.267   0.754   1.455  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.871   0.554   2.678  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.471   1.598   3.327  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.479   2.862   2.764  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.878   3.052   1.553  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.269   2.027   0.880  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.166  -1.267  -0.974  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.208  -1.659  -0.017  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.137  -2.751  -0.524  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.064  -0.458   0.401  1.00  0.00           C  
HETATM   18  C16 UNL     1      -1.327  -1.466  -2.340  1.00  0.00           C  
HETATM   19  O2  UNL     1      -2.384  -2.034  -2.793  1.00  0.00           O  
HETATM   20  N2  UNL     1      -0.426  -1.094  -3.267  1.00  0.00           N  
HETATM   21  C17 UNL     1       0.679  -0.503  -2.848  1.00  0.00           C  
HETATM   22  O3  UNL     1       1.513  -0.163  -3.756  1.00  0.00           O  
HETATM   23  H1  UNL     1       3.732   0.427   1.244  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.015   1.841   0.189  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.422   0.906   0.803  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.684   0.643  -1.650  1.00  0.00           H  
HETATM   27  H5  UNL     1       5.123  -0.814  -0.676  1.00  0.00           H  
HETATM   28  H6  UNL     1       2.553   0.955  -2.165  1.00  0.00           H  
HETATM   29  H7  UNL     1       2.220   1.027  -0.400  1.00  0.00           H  
HETATM   30  H8  UNL     1       1.476  -0.261   0.885  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.190  -1.296   1.438  1.00  0.00           H  
HETATM   32  H10 UNL     1      -0.882  -0.420   3.136  1.00  0.00           H  
HETATM   33  H11 UNL     1      -1.938   1.408   4.288  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.946   3.680   3.269  1.00  0.00           H  
HETATM   35  H13 UNL     1      -0.895   4.058   1.128  1.00  0.00           H  
HETATM   36  H14 UNL     1       0.194   2.183  -0.068  1.00  0.00           H  
HETATM   37  H15 UNL     1      -1.742  -2.043   0.892  1.00  0.00           H  
HETATM   38  H16 UNL     1      -3.929  -2.341  -1.170  1.00  0.00           H  
HETATM   39  H17 UNL     1      -2.620  -3.545  -1.086  1.00  0.00           H  
HETATM   40  H18 UNL     1      -3.592  -3.309   0.355  1.00  0.00           H  
HETATM   41  H19 UNL     1      -4.112  -0.582  -0.025  1.00  0.00           H  
HETATM   42  H20 UNL     1      -3.248  -0.440   1.492  1.00  0.00           H  
HETATM   43  H21 UNL     1      -2.707   0.490  -0.037  1.00  0.00           H  
HETATM   44  H22 UNL     1      -0.630  -1.286  -4.292  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4
CONECT    4    5   28   29
CONECT    5    6   21
CONECT    6    7   14   14
CONECT    7    8   30   31
CONECT    8    9    9   13
CONECT    9   10   32
CONECT   10   11   11   33
CONECT   11   12   34
CONECT   12   13   13   35
CONECT   13   36
CONECT   14   15   18
CONECT   15   16   17   37
CONECT   16   38   39   40
CONECT   17   41   42   43
CONECT   18   19   19   20
CONECT   20   21   44
CONECT   21   22   22
END

HMDB0251775
     RDKit          3D
Emivirine
 44 45  0  0  0  0  0  0  0  0999 V2000
    4.3786    0.8230    0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3605   -0.0054   -0.8055 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1486   -0.6199   -1.0864 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1854    0.3740   -1.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9281   -0.2660   -1.5508 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0164   -0.6425   -0.6058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3658   -0.3961    0.7873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2669    0.7537    1.4552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8711    0.5544    2.6783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4712    1.5976    3.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4785    2.8625    2.7637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8779    3.0523    1.5530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2691    2.0267    0.8803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1663   -1.2668   -0.9737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2081   -1.6595   -0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1370   -2.7514   -0.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0636   -0.4584    0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3266   -1.4657   -2.3402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3835   -2.0340   -2.7934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4260   -1.0938   -3.2666 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6795   -0.5027   -2.8481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5132   -0.1627   -3.7556 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7317    0.4273    1.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0152    1.8408    0.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4225    0.9056    0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6843    0.6432   -1.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1231   -0.8137   -0.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5534    0.9548   -2.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2197    1.0268   -0.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760   -0.2605    0.8847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1902   -1.2957    1.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8817   -0.4198    3.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9378    1.4075    4.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9460    3.6795    3.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8953    4.0579    1.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1942    2.1835   -0.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7418   -2.0434    0.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9292   -2.3408   -1.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6198   -3.5454   -1.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5916   -3.3089    0.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1118   -0.5820   -0.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2475   -0.4403    1.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7074    0.4897   -0.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6304   -1.2855   -4.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 14 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 21  5  1  0
 13  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  4 28  1  0
  4 29  1  0
  7 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 13 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 20 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(Ethoxymethyl)-5-(1-methylethyl)-6-(phenylmethyl)pyrimidine-2,4(1H,3H)-dione	ChEBI
6-Benzyl-1-(ethoxymethyl)-5-(1-methylethyl)uracil	ChEBI
6-BENZYL-1-ethoxymethyl-5-isopropyl uracil	ChEBI
Coactinon	ChEBI
MKC-442	ChEBI
MKC 442	MeSH
6-Benzyl-1-(ethoxymethyl)-5-isopropyluracil	MeSH
6-Benzyl-1-ethoxymethyl-5-isopropyluracil	MeSH

Chemical Formula

C₁₇H₂₂N₂O₃

Average Molecular Weight

302.3682

Monoisotopic Molecular Weight

302.16304258

IUPAC Name

6-benzyl-1-(ethoxymethyl)-5-(propan-2-yl)-1,2,3,4-tetrahydropyrimidine-2,4-dione

Traditional Name

emivirine

CAS Registry Number

Not Available

SMILES

CCOCN1C(=O)NC(=O)C(C(C)C)=C1CC1=CC=CC=C1

InChI Identifier

InChI=1S/C17H22N2O3/c1-4-22-11-19-14(10-13-8-6-5-7-9-13)15(12(2)3)16(20)18-17(19)21/h5-9,12H,4,10-11H2,1-3H3,(H,18,20,21)

InChI Key

MLILORUFDVLTSP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Pyrimidones

Alternative Parents

Substituents

Pyrimidone
Monocyclic benzene moiety
Hydropyrimidine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Lactam
Urea
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrimidone (CHEBI:44143 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0251775)

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	2.57	ALOGPS
logP	2.77	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	10.23	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	58.64 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	85.41 m³·mol⁻¹	ChemAxon
Polarizability	32.87 Å³	ChemAxon
Number of Rings	2	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]+	173.517	30932474
DeepCCS	[M-H]-	171.159	30932474
DeepCCS	[M-2H]-	204.045	30932474
DeepCCS	[M+Na]+	179.61	30932474
AllCCS	[M+H]+	169.9	32859911
AllCCS	[M+H-H2O]+	166.4	32859911
AllCCS	[M+NH4]+	173.2	32859911
AllCCS	[M+Na]+	174.1	32859911
AllCCS	[M-H]-	177.4	32859911
AllCCS	[M+Na-2H]-	177.3	32859911
AllCCS	[M+HCOO]-	177.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Emivirine	CCOCN1C(=O)NC(=O)C(C(C)C)=C1CC1=CC=CC=C1	3647.2	Standard polar	33892256
Emivirine	CCOCN1C(=O)NC(=O)C(C(C)C)=C1CC1=CC=CC=C1	2386.9	Standard non polar	33892256
Emivirine	CCOCN1C(=O)NC(=O)C(C(C)C)=C1CC1=CC=CC=C1	2380.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Emivirine,1TMS,isomer #1	CCOCN1C(CC2=CC=CC=C2)=C(C(C)C)C(=O)N([Si](C)(C)C)C1=O	2346.1	Semi standard non polar	33892256
Emivirine,1TMS,isomer #1	CCOCN1C(CC2=CC=CC=C2)=C(C(C)C)C(=O)N([Si](C)(C)C)C1=O	2353.8	Standard non polar	33892256
Emivirine,1TMS,isomer #1	CCOCN1C(CC2=CC=CC=C2)=C(C(C)C)C(=O)N([Si](C)(C)C)C1=O	2871.5	Standard polar	33892256
Emivirine,1TBDMS,isomer #1	CCOCN1C(CC2=CC=CC=C2)=C(C(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2556.8	Semi standard non polar	33892256
Emivirine,1TBDMS,isomer #1	CCOCN1C(CC2=CC=CC=C2)=C(C(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2543.6	Standard non polar	33892256
Emivirine,1TBDMS,isomer #1	CCOCN1C(CC2=CC=CC=C2)=C(C(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2963.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Emivirine GC-MS (Non-derivatized) - 70eV, Positive	splash10-054o-5090000000-1eb45caf8bf6be7eafdc	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Emivirine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emivirine 10V, Positive-QTOF	splash10-0002-0091000000-65eecd36e0ecbe7f8e51	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emivirine 20V, Positive-QTOF	splash10-0f6w-3190000000-94dad63eeb1f7482e29e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emivirine 40V, Positive-QTOF	splash10-0006-9540000000-939eab7255005fbc45e1	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emivirine 10V, Negative-QTOF	splash10-0pbc-3192000000-b7181f65ae696e0c35ab	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emivirine 20V, Negative-QTOF	splash10-0f6x-0190000000-43aa8d9b1953a10a6d95	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emivirine 40V, Negative-QTOF	splash10-0udi-4690000000-ab9369b3198f3fe0e069	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emivirine 10V, Positive-QTOF	splash10-0pb9-0096000000-c9bdfbe5013a7f59efd9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emivirine 20V, Positive-QTOF	splash10-0a4i-1490000000-ea115245a23cbc152e0c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emivirine 40V, Positive-QTOF	splash10-015c-6980000000-1765efff05be2744bb20	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emivirine 10V, Negative-QTOF	splash10-0pb9-0097000000-65f3543e29201c15fd4b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emivirine 20V, Negative-QTOF	splash10-0a4m-0190000000-e03919a70c8408eca735	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emivirine 40V, Negative-QTOF	splash10-0f6x-7950000000-54f65e36a152f4530d19	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

DB08188

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

Emivirine

METLIN ID

Not Available

PubChem Compound

65013

PDB ID

Not Available

ChEBI ID

44143

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 Emivirine (HMDB0251775)

MOL for HMDB0251775 (Emivirine)

3D MOL for HMDB0251775 (Emivirine)

3D SDF for HMDB0251775 (Emivirine)

3D-SDF for HMDB0251775 (Emivirine)

PDB for HMDB0251775 (Emivirine)

3D PDB for HMDB0251775 (Emivirine)

SMILES for HMDB0251775 (Emivirine)

INCHI for HMDB0251775 (Emivirine)

Structure for HMDB0251775 (Emivirine)

3D Structure for HMDB0251775 (Emivirine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra