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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:55 UTC

HMDB ID

HMDB0015249

Secondary Accession Numbers

HMDB15249

Metabolite Identification

Common Name

Atovaquone

Description

Atovaquone is only found in individuals that have used or taken this drug. It is a hydroxynaphthoquinone that has antimicrobial activity and is being used in antimalarial protocols. [PubChem]Atovaquone is a hydroxy- 1, 4- naphthoquinone, an analog of ubiquinone, with antipneumocystis activity. The mechanism of action against Pneumocystis carinii has not been fully elucidated. In Plasmodium species, the site of action appears to be the cytochrome bc1 complex (Complex III). Several metabolic enzymes are linked to the mitochondrial electron transport chain via ubiquinone. Inhibition of electron transport by atovaquone will result in indirect inhibition of these enzymes. The ultimate metabolic effects of such blockade may include inhibition of nucleic acid and ATP synthesis. Atovaquone also has been shown to have good in vitro activity against Toxoplasma gondii.

Structure

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

 
  Mrv0541 02231215152D          
 
 26 29  0  0  1  0            999 V2000
   17.5799   -9.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2899  -10.2670    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.8630  -10.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5832   -9.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2899  -11.0936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0068   -9.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1495   -9.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8595  -11.0867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8699   -8.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2968   -8.6171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0068  -11.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7169  -10.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1530   -9.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4429  -10.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8732   -7.7871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7169  -11.0936    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.4429   -8.6102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7260   -9.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4338  -11.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7260   -9.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4338  -12.3285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1506  -11.0936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1506  -12.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8606  -11.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8606  -12.3285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5774  -12.7401    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  4  9  1  0  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7 13  1  0  0  0  0
  7 14  2  0  0  0  0
  9 15  2  0  0  0  0
 11 16  1  0  0  0  0
 13 17  2  0  0  0  0
 14 18  1  0  0  0  0
 16 19  1  6  0  0  0
 17 20  1  0  0  0  0
 19 21  2  0  0  0  0
 19 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  2  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
  9 13  1  0  0  0  0
 12 16  1  0  0  0  0
 18 20  2  0  0  0  0
 24 25  1  0  0  0  0
M  END

HMDB0015249
     RDKit          3D
Atovaquone
 45 48  0  0  0  0  0  0  0  0999 V2000
   -4.2979   -2.5543   -1.9913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6924   -1.6663   -1.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2433   -1.5251   -1.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4726   -2.4151   -2.1038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6142   -0.5717   -0.6417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1515   -0.4404   -0.6533 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3559    0.7650   -1.3991 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8806    0.6780   -1.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2975    1.0449    0.0534 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7114    0.6201    0.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1017   -0.6994    0.3289 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4122   -1.0772    0.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3620   -0.1087    0.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0365   -0.5190    1.1709 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.9920    1.2199    0.8439 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6763    1.5652    0.5869 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3544    0.5536    1.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4935   -0.5844    0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4242    0.3331    0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8697    1.2401    0.8040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8889    0.2487    0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6063    1.1441    0.9435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9771    1.0384    0.9680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6370    0.0450    0.2380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8737   -0.8360   -0.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5053   -0.7496   -0.5547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5659   -3.4128   -1.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2314   -1.3172   -1.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1033    0.7328   -2.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0655    1.7221   -0.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1339   -0.3662   -1.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3154    1.4170   -2.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2564    2.1710    0.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3803   -1.4576    0.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7288   -2.1092    0.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6999    2.0043    1.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4202    2.6111    0.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7577    1.3727    1.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0036    0.1799    1.9556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3379   -0.6880    1.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0840   -1.5290    0.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0814    1.8994    1.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5791    1.7127    1.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7049   -0.0619    0.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3311   -1.6302   -1.1043 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
  3  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26  2  1  0
 18  6  1  0
 26 21  1  0
 16 10  1  0
  4 27  1  0
  6 28  1  6
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  6
 11 34  1  0
 12 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
 18 41  1  0
 22 42  1  0
 23 43  1  0
 24 44  1  0
 25 45  1  0
M  END

 
  Mrv0541 02231215152D          
 
 26 29  0  0  1  0            999 V2000
   17.5799   -9.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2899  -10.2670    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.8630  -10.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5832   -9.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2899  -11.0936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0068   -9.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1495   -9.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8595  -11.0867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8699   -8.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2968   -8.6171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0068  -11.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7169  -10.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1530   -9.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4429  -10.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8732   -7.7871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7169  -11.0936    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.4429   -8.6102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7260   -9.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4338  -11.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7260   -9.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4338  -12.3285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1506  -11.0936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1506  -12.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8606  -11.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8606  -12.3285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5774  -12.7401    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  4  9  1  0  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7 13  1  0  0  0  0
  7 14  2  0  0  0  0
  9 15  2  0  0  0  0
 11 16  1  0  0  0  0
 13 17  2  0  0  0  0
 14 18  1  0  0  0  0
 16 19  1  6  0  0  0
 17 20  1  0  0  0  0
 19 21  2  0  0  0  0
 19 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  2  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
  9 13  1  0  0  0  0
 12 16  1  0  0  0  0
 18 20  2  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015249

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=C([C@H]2CC[C@@H](CC2)C2=CC=C(Cl)C=C2)C(=O)C2=CC=CC=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H19ClO3/c23-16-11-9-14(10-12-16)13-5-7-15(8-6-13)19-20(24)17-3-1-2-4-18(17)21(25)22(19)26/h1-4,9-13,15,26H,5-8H2/t13-,15-

> <INCHI_KEY>
KUCQYCKVKVOKAY-CTYIDZIISA-N

> <FORMULA>
C22H19ClO3

> <MOLECULAR_WEIGHT>
366.837

> <EXACT_MASS>
366.102272181

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
39.55113071275029

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-3-[(1r,4r)-4-(4-chlorophenyl)cyclohexyl]-1,4-dihydronaphthalene-1,4-dione

> <ALOGPS_LOGP>
4.74

> <JCHEM_LOGP>
4.997646357666667

> <ALOGPS_LOGS>
-5.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.23386811185948

> <JCHEM_PKA_STRONGEST_BASIC>
-4.126766087872874

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
103.10650000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.96e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
atovaquone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015249
     RDKit          3D
Atovaquone
 45 48  0  0  0  0  0  0  0  0999 V2000
   -4.2979   -2.5543   -1.9913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6924   -1.6663   -1.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2433   -1.5251   -1.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4726   -2.4151   -2.1038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6142   -0.5717   -0.6417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1515   -0.4404   -0.6533 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3559    0.7650   -1.3991 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8806    0.6780   -1.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2975    1.0449    0.0534 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7114    0.6201    0.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1017   -0.6994    0.3289 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4122   -1.0772    0.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3620   -0.1087    0.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0365   -0.5190    1.1709 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.9920    1.2199    0.8439 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6763    1.5652    0.5869 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3544    0.5536    1.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4935   -0.5844    0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4242    0.3331    0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8697    1.2401    0.8040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8889    0.2487    0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6063    1.1441    0.9435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9771    1.0384    0.9680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6370    0.0450    0.2380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8737   -0.8360   -0.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5053   -0.7496   -0.5547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5659   -3.4128   -1.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2314   -1.3172   -1.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1033    0.7328   -2.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0655    1.7221   -0.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1339   -0.3662   -1.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3154    1.4170   -2.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2564    2.1710    0.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3803   -1.4576    0.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7288   -2.1092    0.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6999    2.0043    1.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4202    2.6111    0.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7577    1.3727    1.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0036    0.1799    1.9556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3379   -0.6880    1.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0840   -1.5290    0.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0814    1.8994    1.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5791    1.7127    1.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7049   -0.0619    0.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3311   -1.6302   -1.1043 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
  3  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26  2  1  0
 18  6  1  0
 26 21  1  0
 16 10  1  0
  4 27  1  0
  6 28  1  6
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  6
 11 34  1  0
 12 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
 18 41  1  0
 22 42  1  0
 23 43  1  0
 24 44  1  0
 25 45  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      32.816 -18.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      34.141 -19.165   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      31.478 -19.159   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      32.822 -16.847   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      34.141 -20.708   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      35.479 -18.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      30.146 -18.378   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      31.471 -20.695   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      31.490 -16.079   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      34.154 -16.085   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      35.479 -21.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      36.805 -19.165   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      30.152 -16.834   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      28.827 -19.152   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      31.497 -14.536   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      36.805 -20.708   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.827 -16.072   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      27.489 -18.378   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      38.143 -21.470   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      27.489 -16.834   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      38.143 -23.013   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      39.481 -20.708   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      39.481 -23.788   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      40.806 -21.470   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      40.806 -23.013   0.000  0.00  0.00           C+0
HETATM   26 Cl   UNK     0      42.144 -23.782   0.000  0.00  0.00          Cl+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9   10                                                  
CONECT    5    2   11                                                       
CONECT    6    2   12                                                       
CONECT    7    3   13   14                                                  
CONECT    8    3                                                            
CONECT    9    4   15   13                                                  
CONECT   10    4                                                            
CONECT   11    5   16                                                       
CONECT   12    6   16                                                       
CONECT   13    7   17    9                                                  
CONECT   14    7   18                                                       
CONECT   15    9                                                            
CONECT   16   11   19   12                                                  
CONECT   17   13   20                                                       
CONECT   18   14   20                                                       
CONECT   19   16   21   22                                                  
CONECT   20   17   18                                                       
CONECT   21   19   23                                                       
CONECT   22   19   24                                                       
CONECT   23   21   25                                                       
CONECT   24   22   25                                                       
CONECT   25   23   26   24                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0015249
HETATM    1  O1  UNL     1      -4.298  -2.554  -1.991  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.692  -1.666  -1.340  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.243  -1.525  -1.343  1.00  0.00           C  
HETATM    4  O2  UNL     1      -1.473  -2.415  -2.104  1.00  0.00           O  
HETATM    5  C3  UNL     1      -1.614  -0.572  -0.642  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.152  -0.440  -0.653  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.356   0.765  -1.399  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.881   0.678  -1.335  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.297   1.045   0.053  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.711   0.620   0.326  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.102  -0.699   0.329  1.00  0.00           C  
HETATM   12  C10 UNL     1       5.412  -1.077   0.583  1.00  0.00           C  
HETATM   13  C11 UNL     1       6.362  -0.109   0.842  1.00  0.00           C  
HETATM   14 CL1  UNL     1       8.036  -0.519   1.171  1.00  0.00          CL  
HETATM   15  C12 UNL     1       5.992   1.220   0.844  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.676   1.565   0.587  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.354   0.554   1.106  1.00  0.00           C  
HETATM   18  C15 UNL     1       0.494  -0.584   0.703  1.00  0.00           C  
HETATM   19  C16 UNL     1      -2.424   0.333   0.134  1.00  0.00           C  
HETATM   20  O3  UNL     1      -1.870   1.240   0.804  1.00  0.00           O  
HETATM   21  C17 UNL     1      -3.889   0.249   0.182  1.00  0.00           C  
HETATM   22  C18 UNL     1      -4.606   1.144   0.943  1.00  0.00           C  
HETATM   23  C19 UNL     1      -5.977   1.038   0.968  1.00  0.00           C  
HETATM   24  C20 UNL     1      -6.637   0.045   0.238  1.00  0.00           C  
HETATM   25  C21 UNL     1      -5.874  -0.836  -0.515  1.00  0.00           C  
HETATM   26  C22 UNL     1      -4.505  -0.750  -0.555  1.00  0.00           C  
HETATM   27  H1  UNL     1      -1.566  -3.413  -1.948  1.00  0.00           H  
HETATM   28  H2  UNL     1       0.231  -1.317  -1.245  1.00  0.00           H  
HETATM   29  H3  UNL     1       0.103   0.733  -2.478  1.00  0.00           H  
HETATM   30  H4  UNL     1       0.066   1.722  -0.995  1.00  0.00           H  
HETATM   31  H5  UNL     1       2.134  -0.366  -1.614  1.00  0.00           H  
HETATM   32  H6  UNL     1       2.315   1.417  -2.032  1.00  0.00           H  
HETATM   33  H7  UNL     1       2.256   2.171   0.100  1.00  0.00           H  
HETATM   34  H8  UNL     1       3.380  -1.458   0.130  1.00  0.00           H  
HETATM   35  H9  UNL     1       5.729  -2.109   0.588  1.00  0.00           H  
HETATM   36  H10 UNL     1       6.700   2.004   1.041  1.00  0.00           H  
HETATM   37  H11 UNL     1       4.420   2.611   0.596  1.00  0.00           H  
HETATM   38  H12 UNL     1       0.758   1.373   1.571  1.00  0.00           H  
HETATM   39  H13 UNL     1       2.004   0.180   1.956  1.00  0.00           H  
HETATM   40  H14 UNL     1      -0.338  -0.688   1.431  1.00  0.00           H  
HETATM   41  H15 UNL     1       1.084  -1.529   0.814  1.00  0.00           H  
HETATM   42  H16 UNL     1      -4.081   1.899   1.497  1.00  0.00           H  
HETATM   43  H17 UNL     1      -6.579   1.713   1.546  1.00  0.00           H  
HETATM   44  H18 UNL     1      -7.705  -0.062   0.238  1.00  0.00           H  
HETATM   45  H19 UNL     1      -6.331  -1.630  -1.104  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   26
CONECT    3    4    5    5
CONECT    4   27
CONECT    5    6   19
CONECT    6    7   18   28
CONECT    7    8   29   30
CONECT    8    9   31   32
CONECT    9   10   17   33
CONECT   10   11   11   16
CONECT   11   12   34
CONECT   12   13   13   35
CONECT   13   14   15
CONECT   15   16   16   36
CONECT   16   37
CONECT   17   18   38   39
CONECT   18   40   41
CONECT   19   20   20   21
CONECT   21   22   22   26
CONECT   22   23   42
CONECT   23   24   24   43
CONECT   24   25   44
CONECT   25   26   26   45
END

HMDB0015249
     RDKit          3D
Atovaquone
 45 48  0  0  0  0  0  0  0  0999 V2000
   -4.2979   -2.5543   -1.9913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6924   -1.6663   -1.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2433   -1.5251   -1.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4726   -2.4151   -2.1038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6142   -0.5717   -0.6417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1515   -0.4404   -0.6533 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3559    0.7650   -1.3991 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8806    0.6780   -1.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2975    1.0449    0.0534 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7114    0.6201    0.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1017   -0.6994    0.3289 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4122   -1.0772    0.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3620   -0.1087    0.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0365   -0.5190    1.1709 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.9920    1.2199    0.8439 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6763    1.5652    0.5869 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3544    0.5536    1.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4935   -0.5844    0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4242    0.3331    0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8697    1.2401    0.8040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8889    0.2487    0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6063    1.1441    0.9435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9771    1.0384    0.9680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6370    0.0450    0.2380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8737   -0.8360   -0.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5053   -0.7496   -0.5547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5659   -3.4128   -1.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2314   -1.3172   -1.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1033    0.7328   -2.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0655    1.7221   -0.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1339   -0.3662   -1.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3154    1.4170   -2.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2564    2.1710    0.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3803   -1.4576    0.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7288   -2.1092    0.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6999    2.0043    1.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4202    2.6111    0.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7577    1.3727    1.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0036    0.1799    1.9556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3379   -0.6880    1.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0840   -1.5290    0.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0814    1.8994    1.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5791    1.7127    1.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7049   -0.0619    0.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3311   -1.6302   -1.1043 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
  3  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26  2  1  0
 18  6  1  0
 26 21  1  0
 16 10  1  0
  4 27  1  0
  6 28  1  6
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  6
 11 34  1  0
 12 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
 18 41  1  0
 22 42  1  0
 23 43  1  0
 24 44  1  0
 25 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(trans-4-(p-Chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone	ChEBI
Acuvel	ChEBI
Mepron	ChEBI
Wellvone	ChEBI

Chemical Formula

C₂₂H₁₉ClO₃

Average Molecular Weight

366.837

Monoisotopic Molecular Weight

366.102272181

IUPAC Name

2-hydroxy-3-[(1r,4r)-4-(4-chlorophenyl)cyclohexyl]-1,4-dihydronaphthalene-1,4-dione

Traditional Name

atovaquone

CAS Registry Number

95233-18-4

SMILES

OC1=C([C@H]2CC[C@@H](CC2)C2=CC=C(Cl)C=C2)C(=O)C2=CC=CC=C2C1=O

InChI Identifier

InChI=1S/C22H19ClO3/c23-16-11-9-14(10-12-16)13-5-7-15(8-6-13)19-20(24)17-3-1-2-4-18(17)21(25)22(19)26/h1-4,9-13,15,26H,5-8H2/t13-,15-

InChI Key

KUCQYCKVKVOKAY-CTYIDZIISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Naphthoquinone
Quinone
Aryl ketone
Chlorobenzene
Halobenzene
Aryl chloride
Monocyclic benzene moiety
Aryl halide
Vinylogous acid
Ketone
Enol
Organic oxide
Organooxygen compound
Organochloride
Organohalogen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

naphthoquinone (CHEBI:575568 )
monochlorobenzenes (CHEBI:575568 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015249)
Membrane (HMDB: HMDB0015249)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0008 g/L	Not Available
LogP	5.8	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0008 g/L	ALOGPS
logP	4.74	ALOGPS
logP	5	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	8.23	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	103.11 m³·mol⁻¹	ChemAxon
Polarizability	39.55 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	181.159	30932474
DeepCCS	[M-H]-	178.801	30932474
DeepCCS	[M-2H]-	212.414	30932474
DeepCCS	[M+Na]+	187.528	30932474
AllCCS	[M+H]+	189.9	32859911
AllCCS	[M+H-H2O]+	186.9	32859911
AllCCS	[M+NH4]+	192.7	32859911
AllCCS	[M+Na]+	193.5	32859911
AllCCS	[M-H]-	189.7	32859911
AllCCS	[M+Na-2H]-	189.5	32859911
AllCCS	[M+HCOO]-	189.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Atovaquone	OC1=C([C@H]2CC[C@@H](CC2)C2=CC=C(Cl)C=C2)C(=O)C2=CC=CC=C2C1=O	4429.1	Standard polar	33892256
Atovaquone	OC1=C([C@H]2CC[C@@H](CC2)C2=CC=C(Cl)C=C2)C(=O)C2=CC=CC=C2C1=O	2673.7	Standard non polar	33892256
Atovaquone	OC1=C([C@H]2CC[C@@H](CC2)C2=CC=C(Cl)C=C2)C(=O)C2=CC=CC=C2C1=O	3306.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Atovaquone,1TMS,isomer #1	C[Si](C)(C)OC1=C([C@H]2CC[C@H](C3=CC=C(Cl)C=C3)CC2)C(=O)C2=CC=CC=C2C1=O	3316.7	Semi standard non polar	33892256
Atovaquone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C([C@H]2CC[C@H](C3=CC=C(Cl)C=C3)CC2)C(=O)C2=CC=CC=C2C1=O	3572.8	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 - Atovaquone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f79-0829000000-4b88673ebb0412947f94	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Atovaquone GC-MS (1 TMS) - 70eV, Positive	splash10-0fe0-4923400000-57e2c568b6623d698ca6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Atovaquone 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 - Atovaquone LC-ESI-qTof , Positive-QTOF	splash10-0udj-0910000000-f7b2a59bcc1e1195bf1f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Atovaquone , positive-QTOF	splash10-066r-0968000000-4d83793ef10d849ce35e	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atovaquone 10V, Positive-QTOF	splash10-014i-0119000000-5f209ebb20fbf0259351	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atovaquone 20V, Positive-QTOF	splash10-066s-0897000000-79bdad72004b4a42d8c7	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atovaquone 40V, Positive-QTOF	splash10-0zi0-6931000000-6ac22d2b522d431d04c1	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atovaquone 10V, Negative-QTOF	splash10-014i-0009000000-d52277af59ec8f79fa22	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atovaquone 20V, Negative-QTOF	splash10-014i-0419000000-87e2b6ffb344b5930d26	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atovaquone 40V, Negative-QTOF	splash10-0kor-2913000000-40a03b8ec8ba93c6c3e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atovaquone 10V, Positive-QTOF	splash10-014i-0009000000-8e8c322593e61a1fcd3a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atovaquone 20V, Positive-QTOF	splash10-014j-0009000000-887d32008948c60e375f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atovaquone 40V, Positive-QTOF	splash10-052u-1927000000-b03db76b9884df28bfe8	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atovaquone 10V, Negative-QTOF	splash10-014i-0009000000-811d88e8ea937d34fe7b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atovaquone 20V, Negative-QTOF	splash10-014i-0009000000-05e44597e6bf573643ee	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atovaquone 40V, Negative-QTOF	splash10-001i-9222000000-b6a748454bc56651ddf0	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01117	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01117	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01117

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10482034

KEGG Compound ID

C06835

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Atovaquone

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

575568

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Dihydroorotate dehydrogenase (quinone), mitochondrial

General function:: Involved in catalytic activity
Specific function:: Catalyzes the conversion of dihydroorotate to orotate with quinone as electron acceptor.
Gene Name:: DHODH
Uniprot ID:: Q02127
Molecular weight:: 42866.93

References

Knecht W, Henseling J, Loffler M: Kinetics of inhibition of human and rat dihydroorotate dehydrogenase by atovaquone, lawsone derivatives, brequinar sodium and polyporic acid. Chem Biol Interact. 2000 Jan 3;124(1):61-76. [PubMed:10658902 ]
Hansen M, Le Nours J, Johansson E, Antal T, Ullrich A, Loffler M, Larsen S: Inhibitor binding in a class 2 dihydroorotate dehydrogenase causes variations in the membrane-associated N-terminal domain. Protein Sci. 2004 Apr;13(4):1031-42. [PubMed:15044733 ]
Ittarat I, Asawamahasakda W, Bartlett MS, Smith JW, Meshnick SR: Effects of atovaquone and other inhibitors on Pneumocystis carinii dihydroorotate dehydrogenase. Antimicrob Agents Chemother. 1995 Feb;39(2):325-8. [PubMed:7726490 ]
Seymour KK, Lyons SD, Phillips L, Rieckmann KH, Christopherson RI: Cytotoxic effects of inhibitors of de novo pyrimidine biosynthesis upon Plasmodium falciparum. Biochemistry. 1994 May 3;33(17):5268-74. [PubMed:7909690 ]
Seymour KK, Yeo AE, Rieckmann KH, Christopherson RI: dCTP levels are maintained in Plasmodium falciparum subjected to pyrimidine deficiency or excess. Ann Trop Med Parasitol. 1997 Sep;91(6):603-9. [PubMed:9425362 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

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 ]

Showing metabocard for Atovaquone (HMDB0015249)

MOL for HMDB0015249 (Atovaquone)

3D MOL for HMDB0015249 (Atovaquone)

3D SDF for HMDB0015249 (Atovaquone)

3D-SDF for HMDB0015249 (Atovaquone)

PDB for HMDB0015249 (Atovaquone)

3D PDB for HMDB0015249 (Atovaquone)

SMILES for HMDB0015249 (Atovaquone)

INCHI for HMDB0015249 (Atovaquone)

Structure for HMDB0015249 (Atovaquone)

3D Structure for HMDB0015249 (Atovaquone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References