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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References transporters (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:46 UTC

HMDB ID

HMDB0014856

Secondary Accession Numbers

HMDB14856

Metabolite Identification

Common Name

Adefovir Dipivoxil

Description

Adefovir Dipivoxil is only found in individuals that have used or taken this drug.Adefovir dipivoxil, previously called bis-POM PMEA, with trade names Preveon and Hepsera, is an orally-administered nucleotide analog reverse transcriptase inhibitor (ntRTI) used for treatment of hepatitis B. It is a failed treatment for HIV. [Wikipedia ]Adefovir dipivoxil is a prodrug of adefovir. Adefovir is an acyclic nucleotide analog of adenosine monophosphate which is phosphorylated to the active metabolite adefovir diphosphate by cellular kinases. Adefovir diphosphate inhibits HBV DNA polymerase (reverse transcriptase) by competing with the natural substrate deoxyadenosine triphosphate and by causing DNA chain termination after its incorporation into viral DNA. The inhibition constant (Ki) for adefovir diphosphate for HBV DNA polymerase was 0.1 μM. Adefovir diphosphate is a weak inhibitor of human DNA polymerases alpha and gamma with Ki values of 1.18 μM and 0.97μM, respectively.

Structure

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

718
  Mrv0541 02231214572D          

 34 35  0  0  0  0            999 V2000
    6.2431   -0.8927    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.1795    0.0615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9816    0.4271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5630   -2.6313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0273   -0.6364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4994   -1.6769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5376    1.7854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9212   -2.1874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4589   -1.1491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597    1.8001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597    3.1280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.6390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.8765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    4.1140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9360    1.4907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6266   -3.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1922    0.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6796    2.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7201    1.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8423   -3.8419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4108   -3.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8828   -4.3698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1517    1.2344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3703   -2.8014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159    1.0159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9232    0.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9868   -0.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    2.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1974    0.1709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3066   -1.8470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    2.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3411    2.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.2890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  6  1  0  0  0  0
  1  9  2  0  0  0  0
  1 27  1  0  0  0  0
  2 26  1  0  0  0  0
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  3 23  1  0  0  0  0
  3 29  1  0  0  0  0
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  6 30  1  0  0  0  0
  7 23  2  0  0  0  0
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 10 32  1  0  0  0  0
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 16 22  1  0  0  0  0
 16 24  1  0  0  0  0
 25 26  1  0  0  0  0
 28 31  1  0  0  0  0
 31 33  2  0  0  0  0
M  END

HMDB0014856
     RDKit          3D
Adefovir Dipivoxil
 66 67  0  0  0  0  0  0  0  0999 V2000
   -3.2075   -5.7877    1.5063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5452   -4.9426    0.2963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0080   -4.5418    0.3752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3054   -5.8147   -0.9263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6840   -3.7576    0.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8271   -3.5711    1.1805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7505   -2.7844   -0.7116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8894   -1.6583   -0.6763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1322   -0.9814    0.4993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1579    0.3908    0.6562 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.2322    1.2494   -0.5901 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5919   -0.1491    0.7885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4212    0.9435    0.7338 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7606    0.6693    0.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2270   -0.2238   -0.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6660   -0.4776   -0.1232 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -1.4691    0.5597 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6061   -1.3635    0.4642 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8884   -0.3041   -0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0843    0.2475   -0.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3608   -0.2704   -0.3443 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0213    1.3475   -1.4529 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8354    1.8883   -1.8115 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6670    1.3530   -1.4185 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6703    0.2486   -0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6321    1.2164    2.0359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0672    2.4648    2.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3958    3.3240    1.0605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    3.6700    0.7501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6090    3.2027    1.4636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0497    4.5612   -0.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5358    4.7437   -0.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4092    5.9311   -0.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5861    3.9840   -1.7088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5498   -5.3577    2.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1206   -6.0059    1.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3438   -4.2265   -0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0661   -3.6647    1.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6013   -5.3743    0.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7248   -5.3571   -1.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1949   -5.8616   -1.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7026   -6.8186   -0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8469   -2.0530   -0.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9987   -1.0184   -1.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7438   -0.7865   -0.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6577   -0.7309    1.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0273    0.2721    1.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3033    1.6408    0.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0140    0.2818   -1.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7261   -1.1981   -0.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6951   -2.2367    1.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6812   -0.4257    0.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0717   -0.5326   -1.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8361    2.7907   -2.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4061    2.8988    3.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0412    2.4387    2.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0193    3.8113   -0.8374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7983    5.6280   -1.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9261    4.8994    0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2119    6.1217    0.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4720    4.0318   -1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9847    4.6737   -2.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
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 13 14  1  0
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 31 33  1  0
 31 34  1  0
 25 16  1  0
 25 19  1  0
  1 35  1  0
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  1 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
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  8 44  1  0
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 34 64  1  0
 34 65  1  0
 34 66  1  0
M  END

718
  Mrv0541 02231214572D          

 34 35  0  0  0  0            999 V2000
    6.2431   -0.8927    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.1795    0.0615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9816    0.4271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5630   -2.6313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0273   -0.6364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4994   -1.6769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5376    1.7854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9212   -2.1874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4589   -1.1491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597    1.8001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597    3.1280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.6390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.8765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    4.1140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9360    1.4907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6266   -3.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1922    0.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6796    2.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7201    1.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8423   -3.8419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4108   -3.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8828   -4.3698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1517    1.2344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3703   -2.8014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159    1.0159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9232    0.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9868   -0.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    2.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1974    0.1709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3066   -1.8470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    2.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3411    2.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.2890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 16 22  1  0  0  0  0
 16 24  1  0  0  0  0
 25 26  1  0  0  0  0
 28 31  1  0  0  0  0
 31 33  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014856

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N)N=CN=C12)OCOC(=O)C(C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C20H32N5O8P/c1-19(2,3)17(26)30-11-32-34(28,33-12-31-18(27)20(4,5)6)13-29-8-7-25-10-24-14-15(21)22-9-23-16(14)25/h9-10H,7-8,11-13H2,1-6H3,(H2,21,22,23)

> <INCHI_KEY>
WOZSCQDILHKSGG-UHFFFAOYSA-N

> <FORMULA>
C20H32N5O8P

> <MOLECULAR_WEIGHT>
501.4705

> <EXACT_MASS>
501.198849537

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
49.001878806882644

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[({[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}({[(2,2-dimethylpropanoyl)oxy]methoxy})phosphoryl)oxy]methyl 2,2-dimethylpropanoate

> <ALOGPS_LOGP>
1.49

> <JCHEM_LOGP>
3.058480914000002

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.588059554251494

> <JCHEM_PKA_STRONGEST_BASIC>
5.125871848290399

> <JCHEM_POLAR_SURFACE_AREA>
166.98000000000005

> <JCHEM_REFRACTIVITY>
119.9922

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
adefovir dipivoxil

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014856
     RDKit          3D
Adefovir Dipivoxil
 66 67  0  0  0  0  0  0  0  0999 V2000
   -3.2075   -5.7877    1.5063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5452   -4.9426    0.2963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0080   -4.5418    0.3752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3054   -5.8147   -0.9263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6840   -3.7576    0.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8271   -3.5711    1.1805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7505   -2.7844   -0.7116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8894   -1.6583   -0.6763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1322   -0.9814    0.4993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1579    0.3908    0.6562 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.2322    1.2494   -0.5901 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5919   -0.1491    0.7885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4212    0.9435    0.7338 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7606    0.6693    0.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2270   -0.2238   -0.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6660   -0.4776   -0.1232 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -1.4691    0.5597 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6061   -1.3635    0.4642 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8884   -0.3041   -0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0843    0.2475   -0.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3608   -0.2704   -0.3443 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0213    1.3475   -1.4529 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8354    1.8883   -1.8115 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6670    1.3530   -1.4185 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6703    0.2486   -0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6321    1.2164    2.0359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0672    2.4648    2.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3958    3.3240    1.0605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    3.6700    0.7501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6090    3.2027    1.4636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0497    4.5612   -0.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5358    4.7437   -0.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4092    5.9311   -0.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5861    3.9840   -1.7088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5498   -5.3577    2.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7055   -6.7821    1.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1206   -6.0059    1.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3438   -4.2265   -0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0661   -3.6647    1.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6013   -5.3743    0.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7248   -5.3571   -1.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1949   -5.8616   -1.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7026   -6.8186   -0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8469   -2.0530   -0.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9987   -1.0184   -1.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7438   -0.7865   -0.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6577   -0.7309    1.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0273    0.2721    1.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3033    1.6408    0.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0140    0.2818   -1.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7261   -1.1981   -0.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6951   -2.2367    1.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6812   -0.4257    0.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0717   -0.5326   -1.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8361    2.7907   -2.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4061    2.8988    3.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0412    2.4387    2.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0193    3.8113   -0.8374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7983    5.6280   -1.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9261    4.8994    0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2119    6.1217    0.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0831    6.6634   -0.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4295    5.9675   -0.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9621    2.9724   -1.8718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4720    4.0318   -1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9847    4.6737   -2.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 10 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
 25 16  1  0
 25 19  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  4 43  1  0
  8 44  1  0
  8 45  1  0
 12 46  1  0
 12 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  0
 15 51  1  0
 17 52  1  0
 21 53  1  0
 21 54  1  0
 23 55  1  0
 27 56  1  0
 27 57  1  0
 32 58  1  0
 32 59  1  0
 32 60  1  0
 33 61  1  0
 33 62  1  0
 33 63  1  0
 34 64  1  0
 34 65  1  0
 34 66  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 718                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  P   UNK     0      11.654  -1.666   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0       9.668   0.115   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      14.899   0.797   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      14.118  -4.912   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      13.118  -1.188   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      12.132  -3.130   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      14.070   3.333   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      16.653  -4.083   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      10.190  -2.145   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       7.205   3.360   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       7.205   5.839   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       4.414   3.059   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       3.080   5.369   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       4.414   7.679   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      16.681   2.783   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.103  -6.693   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.159   1.319   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.202   4.246   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.144   3.261   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.639  -7.172   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.567  -6.215   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.581  -8.157   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.217   2.304   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.625  -5.229   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.683   1.896   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.190   1.579   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.175  -0.203   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.747   3.829   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.435   0.319   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.639  -3.448   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.747   5.369   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.103   4.599   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.414   6.139   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.080   3.829   0.000  0.00  0.00           C+0
CONECT    1    5    6    9   27                                             
CONECT    2   26   27                                                       
CONECT    3   23   29                                                       
CONECT    4   24   30                                                       
CONECT    5    1   29                                                       
CONECT    6    1   30                                                       
CONECT    7   23                                                            
CONECT    8   24                                                            
CONECT    9    1                                                            
CONECT   10   25   28   32                                                  
CONECT   11   31   32                                                       
CONECT   12   28   34                                                       
CONECT   13   33   34                                                       
CONECT   14   33                                                            
CONECT   15   17   18   19   23                                             
CONECT   16   20   21   22   24                                             
CONECT   17   15                                                            
CONECT   18   15                                                            
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21   16                                                            
CONECT   22   16                                                            
CONECT   23    3    7   15                                                  
CONECT   24    4    8   16                                                  
CONECT   25   10   26                                                       
CONECT   26    2   25                                                       
CONECT   27    1    2                                                       
CONECT   28   10   12   31                                                  
CONECT   29    3    5                                                       
CONECT   30    4    6                                                       
CONECT   31   11   28   33                                                  
CONECT   32   10   11                                                       
CONECT   33   13   14   31                                                  
CONECT   34   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

COMPND    HMDB0014856
HETATM    1  C1  UNL     1      -3.208  -5.788   1.506  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.545  -4.943   0.296  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.008  -4.542   0.375  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.305  -5.815  -0.926  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.684  -3.758   0.277  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.827  -3.571   1.181  1.00  0.00           O  
HETATM    7  O2  UNL     1      -2.751  -2.784  -0.712  1.00  0.00           O  
HETATM    8  C6  UNL     1      -1.889  -1.658  -0.676  1.00  0.00           C  
HETATM    9  O3  UNL     1      -2.132  -0.981   0.499  1.00  0.00           O  
HETATM   10  P1  UNL     1      -1.158   0.391   0.656  1.00  0.00           P  
HETATM   11  O4  UNL     1      -1.232   1.249  -0.590  1.00  0.00           O  
HETATM   12  C7  UNL     1       0.592  -0.149   0.788  1.00  0.00           C  
HETATM   13  O5  UNL     1       1.421   0.943   0.734  1.00  0.00           O  
HETATM   14  C8  UNL     1       2.761   0.669   0.827  1.00  0.00           C  
HETATM   15  C9  UNL     1       3.227  -0.224  -0.277  1.00  0.00           C  
HETATM   16  N1  UNL     1       4.666  -0.478  -0.123  1.00  0.00           N  
HETATM   17  C10 UNL     1       5.266  -1.469   0.560  1.00  0.00           C  
HETATM   18  N2  UNL     1       6.606  -1.364   0.464  1.00  0.00           N  
HETATM   19  C11 UNL     1       6.888  -0.304  -0.281  1.00  0.00           C  
HETATM   20  C12 UNL     1       8.084   0.247  -0.685  1.00  0.00           C  
HETATM   21  N3  UNL     1       9.361  -0.270  -0.344  1.00  0.00           N  
HETATM   22  N4  UNL     1       8.021   1.347  -1.453  1.00  0.00           N  
HETATM   23  C13 UNL     1       6.835   1.888  -1.812  1.00  0.00           C  
HETATM   24  N5  UNL     1       5.667   1.353  -1.419  1.00  0.00           N  
HETATM   25  C14 UNL     1       5.670   0.249  -0.647  1.00  0.00           C  
HETATM   26  O6  UNL     1      -1.632   1.216   2.036  1.00  0.00           O  
HETATM   27  C15 UNL     1      -1.067   2.465   2.150  1.00  0.00           C  
HETATM   28  O7  UNL     1      -1.396   3.324   1.061  1.00  0.00           O  
HETATM   29  C16 UNL     1      -2.691   3.670   0.750  1.00  0.00           C  
HETATM   30  O8  UNL     1      -3.609   3.203   1.464  1.00  0.00           O  
HETATM   31  C17 UNL     1      -3.050   4.561  -0.378  1.00  0.00           C  
HETATM   32  C18 UNL     1      -4.536   4.744  -0.453  1.00  0.00           C  
HETATM   33  C19 UNL     1      -2.409   5.931  -0.234  1.00  0.00           C  
HETATM   34  C20 UNL     1      -2.586   3.984  -1.709  1.00  0.00           C  
HETATM   35  H1  UNL     1      -3.550  -5.358   2.447  1.00  0.00           H  
HETATM   36  H2  UNL     1      -3.705  -6.782   1.332  1.00  0.00           H  
HETATM   37  H3  UNL     1      -2.121  -6.006   1.502  1.00  0.00           H  
HETATM   38  H4  UNL     1      -5.344  -4.226  -0.633  1.00  0.00           H  
HETATM   39  H5  UNL     1      -5.066  -3.665   1.051  1.00  0.00           H  
HETATM   40  H6  UNL     1      -5.601  -5.374   0.782  1.00  0.00           H  
HETATM   41  H7  UNL     1      -3.725  -5.357  -1.842  1.00  0.00           H  
HETATM   42  H8  UNL     1      -2.195  -5.862  -1.056  1.00  0.00           H  
HETATM   43  H9  UNL     1      -3.703  -6.819  -0.733  1.00  0.00           H  
HETATM   44  H10 UNL     1      -0.847  -2.053  -0.646  1.00  0.00           H  
HETATM   45  H11 UNL     1      -1.999  -1.018  -1.559  1.00  0.00           H  
HETATM   46  H12 UNL     1       0.744  -0.786  -0.132  1.00  0.00           H  
HETATM   47  H13 UNL     1       0.658  -0.731   1.711  1.00  0.00           H  
HETATM   48  H14 UNL     1       3.027   0.272   1.842  1.00  0.00           H  
HETATM   49  H15 UNL     1       3.303   1.641   0.754  1.00  0.00           H  
HETATM   50  H16 UNL     1       3.014   0.282  -1.235  1.00  0.00           H  
HETATM   51  H17 UNL     1       2.726  -1.198  -0.305  1.00  0.00           H  
HETATM   52  H18 UNL     1       4.695  -2.237   1.105  1.00  0.00           H  
HETATM   53  H19 UNL     1       9.681  -0.426   0.643  1.00  0.00           H  
HETATM   54  H20 UNL     1      10.072  -0.533  -1.086  1.00  0.00           H  
HETATM   55  H21 UNL     1       6.836   2.791  -2.442  1.00  0.00           H  
HETATM   56  H22 UNL     1      -1.406   2.899   3.114  1.00  0.00           H  
HETATM   57  H23 UNL     1       0.041   2.439   2.189  1.00  0.00           H  
HETATM   58  H24 UNL     1      -5.019   3.811  -0.837  1.00  0.00           H  
HETATM   59  H25 UNL     1      -4.798   5.628  -1.056  1.00  0.00           H  
HETATM   60  H26 UNL     1      -4.926   4.899   0.591  1.00  0.00           H  
HETATM   61  H27 UNL     1      -2.212   6.122   0.840  1.00  0.00           H  
HETATM   62  H28 UNL     1      -3.083   6.663  -0.699  1.00  0.00           H  
HETATM   63  H29 UNL     1      -1.429   5.968  -0.769  1.00  0.00           H  
HETATM   64  H30 UNL     1      -2.962   2.972  -1.872  1.00  0.00           H  
HETATM   65  H31 UNL     1      -1.472   4.032  -1.765  1.00  0.00           H  
HETATM   66  H32 UNL     1      -2.985   4.674  -2.498  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3    4    5
CONECT    3   38   39   40
CONECT    4   41   42   43
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   44   45
CONECT    9   10
CONECT   10   11   11   12   26
CONECT   12   13   46   47
CONECT   13   14
CONECT   14   15   48   49
CONECT   15   16   50   51
CONECT   16   17   25
CONECT   17   18   18   52
CONECT   18   19
CONECT   19   20   20   25
CONECT   20   21   22
CONECT   21   53   54
CONECT   22   23   23
CONECT   23   24   55
CONECT   24   25   25
CONECT   26   27
CONECT   27   28   56   57
CONECT   28   29
CONECT   29   30   30   31
CONECT   31   32   33   34
CONECT   32   58   59   60
CONECT   33   61   62   63
CONECT   34   64   65   66
END

HMDB0014856
     RDKit          3D
Adefovir Dipivoxil
 66 67  0  0  0  0  0  0  0  0999 V2000
   -3.2075   -5.7877    1.5063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5452   -4.9426    0.2963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0080   -4.5418    0.3752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3054   -5.8147   -0.9263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6840   -3.7576    0.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8271   -3.5711    1.1805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7505   -2.7844   -0.7116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8894   -1.6583   -0.6763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1322   -0.9814    0.4993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1579    0.3908    0.6562 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.2322    1.2494   -0.5901 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5919   -0.1491    0.7885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4212    0.9435    0.7338 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7606    0.6693    0.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2270   -0.2238   -0.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6660   -0.4776   -0.1232 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -1.4691    0.5597 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6061   -1.3635    0.4642 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8884   -0.3041   -0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0843    0.2475   -0.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3608   -0.2704   -0.3443 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0213    1.3475   -1.4529 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8354    1.8883   -1.8115 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6670    1.3530   -1.4185 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6703    0.2486   -0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6321    1.2164    2.0359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0672    2.4648    2.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3958    3.3240    1.0605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    3.6700    0.7501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6090    3.2027    1.4636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0497    4.5612   -0.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5358    4.7437   -0.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4092    5.9311   -0.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5861    3.9840   -1.7088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5498   -5.3577    2.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7055   -6.7821    1.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1206   -6.0059    1.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3438   -4.2265   -0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0661   -3.6647    1.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6013   -5.3743    0.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7248   -5.3571   -1.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1949   -5.8616   -1.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7026   -6.8186   -0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8469   -2.0530   -0.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9987   -1.0184   -1.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7438   -0.7865   -0.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6577   -0.7309    1.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0273    0.2721    1.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3033    1.6408    0.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0140    0.2818   -1.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7261   -1.1981   -0.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6951   -2.2367    1.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6812   -0.4257    0.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0717   -0.5326   -1.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8361    2.7907   -2.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4061    2.8988    3.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0412    2.4387    2.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0193    3.8113   -0.8374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7983    5.6280   -1.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9261    4.8994    0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2119    6.1217    0.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0831    6.6634   -0.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4295    5.9675   -0.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9621    2.9724   -1.8718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4720    4.0318   -1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9847    4.6737   -2.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 10 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
 25 16  1  0
 25 19  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  4 43  1  0
  8 44  1  0
  8 45  1  0
 12 46  1  0
 12 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  0
 15 51  1  0
 17 52  1  0
 21 53  1  0
 21 54  1  0
 23 55  1  0
 27 56  1  0
 27 57  1  0
 32 58  1  0
 32 59  1  0
 32 60  1  0
 33 61  1  0
 33 62  1  0
 33 63  1  0
 34 64  1  0
 34 65  1  0
 34 66  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Adefovir pivoxil	Kegg
Hepsera	Kegg
Adefovir	HMDB
Adefovirdipivoxl	HMDB
ADV	HMDB
Bis-pom pmea	HMDB
GS-840	HMDB
PMEA	HMDB
Adefovir depivoxil	HMDB
9-(2-((-Bis((pivaloyloxy)methoxy)phosphinyl)methoxy)ethyl)adenine	HMDB
Preveon	HMDB

Chemical Formula

C₂₀H₃₂N₅O₈P

Average Molecular Weight

501.4705

Monoisotopic Molecular Weight

501.198849537

IUPAC Name

[({[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}({[(2,2-dimethylpropanoyl)oxy]methoxy})phosphoryl)oxy]methyl 2,2-dimethylpropanoate

Traditional Name

adefovir dipivoxil

CAS Registry Number

142340-99-6

SMILES

CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N)N=CN=C12)OCOC(=O)C(C)(C)C

InChI Identifier

InChI=1S/C20H32N5O8P/c1-19(2,3)17(26)30-11-32-34(28,33-12-31-18(27)20(4,5)6)13-29-8-7-25-10-24-14-15(21)22-9-23-16(14)25/h9-10H,7-8,11-13H2,1-6H3,(H2,21,22,23)

InChI Key

WOZSCQDILHKSGG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

6-aminopurines

Alternative Parents

Substituents

6-aminopurine
Aminopyrimidine
Dialkyl alkylphosphonate
Phosphonic acid diester
Dicarboxylic acid or derivatives
Imidolactam
Pyrimidine
Phosphonic acid ester
N-substituted imidazole
Azole
Heteroaromatic compound
Imidazole
Organophosphonic acid derivative
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Azacycle
Organophosphorus compound
Primary amine
Amine
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014856)
Membrane (HMDB: HMDB0014856)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Adefovir Dipivoxil Metabolism Pathway (PathBank: SMP0000629)

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	0.63 g/L	Not Available
LogP	0.8	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.63 g/L	ALOGPS
logP	1.49	ALOGPS
logP	3.06	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	18.59	ChemAxon
pKa (Strongest Basic)	5.13	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	166.98 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	119.99 m³·mol⁻¹	ChemAxon
Polarizability	49 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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
DarkChem	[M+H]+	213.389	31661259
DarkChem	[M-H]-	204.656	31661259
DeepCCS	[M-2H]-	242.385	30932474
DeepCCS	[M+Na]+	217.81	30932474
AllCCS	[M+H]+	210.9	32859911
AllCCS	[M+H-H2O]+	209.5	32859911
AllCCS	[M+NH4]+	212.3	32859911
AllCCS	[M+Na]+	212.7	32859911
AllCCS	[M-H]-	210.5	32859911
AllCCS	[M+Na-2H]-	212.0	32859911
AllCCS	[M+HCOO]-	213.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Adefovir Dipivoxil	CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N)N=CN=C12)OCOC(=O)C(C)(C)C	3756.4	Standard polar	33892256
Adefovir Dipivoxil	CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N)N=CN=C12)OCOC(=O)C(C)(C)C	3041.9	Standard non polar	33892256
Adefovir Dipivoxil	CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N)N=CN=C12)OCOC(=O)C(C)(C)C	3346.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Adefovir Dipivoxil,1TMS,isomer #1	CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N[Si](C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C	3311.3	Semi standard non polar	33892256
Adefovir Dipivoxil,1TMS,isomer #1	CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N[Si](C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C	3239.4	Standard non polar	33892256
Adefovir Dipivoxil,1TMS,isomer #1	CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N[Si](C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C	5496.1	Standard polar	33892256
Adefovir Dipivoxil,2TMS,isomer #1	CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C	3275.4	Semi standard non polar	33892256
Adefovir Dipivoxil,2TMS,isomer #1	CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C	3301.7	Standard non polar	33892256
Adefovir Dipivoxil,2TMS,isomer #1	CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C	4718.8	Standard polar	33892256
Adefovir Dipivoxil,1TBDMS,isomer #1	CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N[Si](C)(C)C(C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C	3457.5	Semi standard non polar	33892256
Adefovir Dipivoxil,1TBDMS,isomer #1	CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N[Si](C)(C)C(C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C	3411.3	Standard non polar	33892256
Adefovir Dipivoxil,1TBDMS,isomer #1	CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N[Si](C)(C)C(C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C	5392.0	Standard polar	33892256
Adefovir Dipivoxil,2TBDMS,isomer #1	CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C	3610.2	Semi standard non polar	33892256
Adefovir Dipivoxil,2TBDMS,isomer #1	CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C	3625.3	Standard non polar	33892256
Adefovir Dipivoxil,2TBDMS,isomer #1	CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C	4661.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Adefovir Dipivoxil GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4j-9715200000-be4793aa3b5324f2d049	2017-09-01	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adefovir Dipivoxil LC-ESI-qTof , Positive-QTOF	splash10-00b9-0291650000-bfacc10ec3119e8320f0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adefovir Dipivoxil , positive-QTOF	splash10-0kfx-1372940000-7cb1aa4d35fd2d90d7b4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adefovir Dipivoxil , positive-QTOF	splash10-00b9-0291650000-bfacc10ec3119e8320f0	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adefovir Dipivoxil 10V, Positive-QTOF	splash10-0udi-1902120000-70d9218f4799e4b06e06	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adefovir Dipivoxil 20V, Positive-QTOF	splash10-0r09-4902210000-8477053656f9d74eeb50	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adefovir Dipivoxil 40V, Positive-QTOF	splash10-0a4r-6910000000-ff29d5990721f46c8df5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adefovir Dipivoxil 10V, Negative-QTOF	splash10-0f6t-0309020000-13dd87f577f6eae4df2c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adefovir Dipivoxil 20V, Negative-QTOF	splash10-0udi-0903000000-3c822353c37c29284a8f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adefovir Dipivoxil 40V, Negative-QTOF	splash10-001i-1922000000-607d6864a8d2801ab89f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adefovir Dipivoxil 10V, Positive-QTOF	splash10-0udr-5239180000-444adb50df8e9dcc8e3c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adefovir Dipivoxil 20V, Positive-QTOF	splash10-0fk9-0096000000-592e65840a6c7d4fec2b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adefovir Dipivoxil 40V, Positive-QTOF	splash10-000i-4972000000-f60e4d26bcfe1943e60c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adefovir Dipivoxil 10V, Negative-QTOF	splash10-0udi-0429260000-3e0596d28028aed80ce0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adefovir Dipivoxil 20V, Negative-QTOF	splash10-0udi-1389000000-87f1f9b00d5ac0c19e44	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adefovir Dipivoxil 40V, Negative-QTOF	splash10-00di-0090000000-6582070f7152c5e52322	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Adefovir Dipivoxil Action Pathway		Not Available
Adefovir Dipivoxil Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00718	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00718	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00718

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

54855

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Adefovir

METLIN ID

Not Available

PubChem Compound

60871

PDB ID

Not Available

ChEBI ID

183515

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

Vazquez E: New drug in expanded access. Posit Aware. 1998 Jan-Feb;9(1):16. [PubMed:11364994 ]
(). FDA label . .

Transporters

Enzyme Details

1. Multidrug resistance-associated protein 4

General function:: Involved in ATP binding
Specific function:: May be an organic anion pump relevant to cellular detoxification
Gene Name:: ABCC4
Uniprot ID:: O15439
Molecular weight:: 149525.3

References

Schuetz JD, Connelly MC, Sun D, Paibir SG, Flynn PM, Srinivas RV, Kumar A, Fridland A: MRP4: A previously unidentified factor in resistance to nucleoside-based antiviral drugs. Nat Med. 1999 Sep;5(9):1048-51. [PubMed:10470083 ]

Enzyme Details

2. Multidrug resistance-associated protein 5

General function:: Involved in ATP binding
Specific function:: Acts as a multispecific organic anion pump which can transport nucleotide analogs
Gene Name:: ABCC5
Uniprot ID:: O15440
Molecular weight:: 160658.8

References

Wijnholds J, Mol CA, van Deemter L, de Haas M, Scheffer GL, Baas F, Beijnen JH, Scheper RJ, Hatse S, De Clercq E, Balzarini J, Borst P: Multidrug-resistance protein 5 is a multispecific organic anion transporter able to transport nucleotide analogs. Proc Natl Acad Sci U S A. 2000 Jun 20;97(13):7476-81. [PubMed:10840050 ]

Enzyme Details

3. Solute carrier family 22 member 3

General function:: Involved in transmembrane transport
Specific function:: Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain
Gene Name:: SLC22A3
Uniprot ID:: O75751
Molecular weight:: 61279.5

References

Grundemann D, Schechinger B, Rappold GA, Schomig E: Molecular identification of the corticosterone-sensitive extraneuronal catecholamine transporter. Nat Neurosci. 1998 Sep;1(5):349-51. [PubMed:10196521 ]

Enzyme Details

4. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Cihlar T, Ho ES: Fluorescence-based assay for the interaction of small molecules with the human renal organic anion transporter 1. Anal Biochem. 2000 Jul 15;283(1):49-55. [PubMed:10929807 ]
Cihlar T, Lin DC, Pritchard JB, Fuller MD, Mendel DB, Sweet DH: The antiviral nucleotide analogs cidofovir and adefovir are novel substrates for human and rat renal organic anion transporter 1. Mol Pharmacol. 1999 Sep;56(3):570-80. [PubMed:10462545 ]
Ho ES, Lin DC, Mendel DB, Cihlar T: Cytotoxicity of antiviral nucleotides adefovir and cidofovir is induced by the expression of human renal organic anion transporter 1. J Am Soc Nephrol. 2000 Mar;11(3):383-93. [PubMed:10703662 ]

Showing metabocard for Adefovir Dipivoxil (HMDB0014856)

MOL for HMDB0014856 (Adefovir Dipivoxil)

3D MOL for HMDB0014856 (Adefovir Dipivoxil)

3D SDF for HMDB0014856 (Adefovir Dipivoxil)

3D-SDF for HMDB0014856 (Adefovir Dipivoxil)

PDB for HMDB0014856 (Adefovir Dipivoxil)

3D PDB for HMDB0014856 (Adefovir Dipivoxil)

SMILES for HMDB0014856 (Adefovir Dipivoxil)

INCHI for HMDB0014856 (Adefovir Dipivoxil)

Structure for HMDB0014856 (Adefovir Dipivoxil)

3D Structure for HMDB0014856 (Adefovir Dipivoxil)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Transporters

References

References

References

References