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enzymes (2) Show 2 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:53 UTC

HMDB ID

HMDB0015182

Secondary Accession Numbers

HMDB15182

Metabolite Identification

Common Name

Abacavir

Description

Abacavir is only found in individuals that have used or taken this drug. It is a powerful nucleoside analog reverse transcriptase inhibitor (NRTI) used to treat HIV and AIDS. [Wikipedia ]Abacavir is a carbocyclic synthetic nucleoside analogue. Intracellularly, abacavir is converted by cellular enzymes to the active metabolite carbovir triphosphate, an analogue of deoxyguanosine-5'-triphosphate (dGTP). Carbovir triphosphate inhibits the activity of HIV-1 reverse transcriptase (RT) both by competing with the natural substrate dGTP and by its incorporation into viral DNA.

Structure

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

HMDB0015182
     RDKit          3D
Abacavir
 39 42  0  0  0  0  0  0  0  0999 V2000
    2.1995   -3.1734   -1.3424 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7943   -1.8948   -0.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6604   -0.8670   -0.8209 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2943    0.3386   -0.3333 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2376    1.3997   -0.3525 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5661    1.1892   -0.8856 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3887    0.1511   -0.2183 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7430    1.6050   -0.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0211    0.5345    0.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3701    1.5714    0.7145 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8887    1.1731    1.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0430   -0.1164    0.7140 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2478   -0.8827    0.9133 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0832   -0.3404    2.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2910   -0.0789    1.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4226   -0.4057    0.1481 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8138    0.8181   -0.6749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8825    1.8231   -0.5757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1158   -0.9762   -0.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1219   -0.5264    0.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5664   -1.6946   -0.3247 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7736   -4.0714   -0.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9093   -3.2651   -2.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9634    2.3342    0.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6200    1.3410   -1.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0867   -0.4329   -0.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9943   -0.4167    0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5713    2.0579    0.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6272    1.9980   -0.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6230    1.8342    1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9934   -1.9406    1.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7061   -0.1985    3.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0804    0.3240    2.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2570   -1.1406    0.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9878    0.5577   -1.7218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7706    1.1769   -0.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3168    2.6848   -0.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2998   -2.0331   -0.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6859   -0.4570   -1.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  4  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 12 20  1  0
 20 21  2  0
 21  2  1  0
  8  6  1  0
 20  9  1  0
 19 13  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 11 30  1  0
 13 31  1  1
 14 32  1  0
 15 33  1  0
 16 34  1  1
 17 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
M  END

 
  Mrv0541 02231215122D          
 
 21 24  0  0  1  0            999 V2000
   14.1297   -8.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1080   -9.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8416   -8.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4201   -8.4477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3761   -9.8557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8241  -10.0751    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8162   -7.5107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5984   -8.7882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8916   -9.1264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6909  -10.4135    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.6221   -9.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5879   -7.1102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0001   -9.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4593  -11.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2892  -10.1017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4135   -7.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0079   -6.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3617  -10.4173    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.6374  -11.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5813  -10.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9369  -10.7120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  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  2  0  0  0  0
 10  5  1  1  0  0  0
  6 11  2  0  0  0  0
  7 12  1  0  0  0  0
 10 13  1  0  0  0  0
 10 14  1  0  0  0  0
 11 15  1  0  0  0  0
 12 16  1  0  0  0  0
 12 17  1  0  0  0  0
 13 18  1  0  0  0  0
 14 19  2  0  0  0  0
 18 20  1  1  0  0  0
 20 21  1  0  0  0  0
  5  9  1  0  0  0  0
  8 11  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015182

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=NC2=C(N=CN2[C@@H]2C[C@H](CO)C=C2)C(NC2CC2)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C14H18N6O/c15-14-18-12(17-9-2-3-9)11-13(19-14)20(7-16-11)10-4-1-8(5-10)6-21/h1,4,7-10,21H,2-3,5-6H2,(H3,15,17,18,19)/t8-,10+/m1/s1

> <INCHI_KEY>
MCGSCOLBFJQGHM-SCZZXKLOSA-N

> <FORMULA>
C14H18N6O

> <MOLECULAR_WEIGHT>
286.3323

> <EXACT_MASS>
286.154209228

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
30.432443470405758

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl]methanol

> <ALOGPS_LOGP>
0.61

> <JCHEM_LOGP>
0.38677390133333256

> <ALOGPS_LOGS>
-2.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.707791090804818

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.406517692242982

> <JCHEM_PKA_STRONGEST_BASIC>
5.773719585775946

> <JCHEM_POLAR_SURFACE_AREA>
101.88000000000001

> <JCHEM_REFRACTIVITY>
82.62310000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
abacavir

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015182
     RDKit          3D
Abacavir
 39 42  0  0  0  0  0  0  0  0999 V2000
    2.1995   -3.1734   -1.3424 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7943   -1.8948   -0.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6604   -0.8670   -0.8209 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2943    0.3386   -0.3333 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2376    1.3997   -0.3525 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5661    1.1892   -0.8856 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3887    0.1511   -0.2183 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7430    1.6050   -0.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0211    0.5345    0.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3701    1.5714    0.7145 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8887    1.1731    1.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0430   -0.1164    0.7140 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2478   -0.8827    0.9133 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0832   -0.3404    2.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2910   -0.0789    1.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4226   -0.4057    0.1481 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8138    0.8181   -0.6749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8825    1.8231   -0.5757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1158   -0.9762   -0.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1219   -0.5264    0.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5664   -1.6946   -0.3247 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7736   -4.0714   -0.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9093   -3.2651   -2.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9634    2.3342    0.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6200    1.3410   -1.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0867   -0.4329   -0.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9943   -0.4167    0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5713    2.0579    0.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6272    1.9980   -0.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6230    1.8342    1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9934   -1.9406    1.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7061   -0.1985    3.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0804    0.3240    2.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2570   -1.1406    0.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9878    0.5577   -1.7218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7706    1.1769   -0.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3168    2.6848   -0.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2998   -2.0331   -0.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6859   -0.4570   -1.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  4  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 12 20  1  0
 20 21  2  0
 21  2  1  0
  8  6  1  0
 20  9  1  0
 19 13  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 11 30  1  0
 13 31  1  1
 14 32  1  0
 15 33  1  0
 16 34  1  1
 17 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  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      26.375 -16.268   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.335 -17.963   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      27.704 -15.543   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      25.051 -15.769   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      24.969 -18.397   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      27.672 -18.807   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      27.657 -14.020   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      29.117 -16.405   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      24.064 -17.036   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.690 -19.439   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      29.161 -18.048   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      29.097 -13.272   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.400 -18.537   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.257 -20.837   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      30.407 -18.857   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      30.639 -13.300   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.881 -11.939   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.209 -19.446   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.723 -20.882   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      19.752 -19.034   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      18.549 -19.996   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10    9                                                  
CONECT    6    2   11                                                       
CONECT    7    3   12                                                       
CONECT    8    3   11                                                       
CONECT    9    4    5                                                       
CONECT   10    5   13   14                                                  
CONECT   11    6   15    8                                                  
CONECT   12    7   16   17                                                  
CONECT   13   10   18                                                       
CONECT   14   10   19                                                       
CONECT   15   11                                                            
CONECT   16   12   17                                                       
CONECT   17   12   16                                                       
CONECT   18   13   20   19                                                  
CONECT   19   14   18                                                       
CONECT   20   18   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0015182
HETATM    1  N1  UNL     1       2.199  -3.173  -1.342  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.794  -1.895  -0.819  1.00  0.00           C  
HETATM    3  N2  UNL     1       2.660  -0.867  -0.821  1.00  0.00           N  
HETATM    4  C2  UNL     1       2.294   0.339  -0.333  1.00  0.00           C  
HETATM    5  N3  UNL     1       3.238   1.400  -0.352  1.00  0.00           N  
HETATM    6  C3  UNL     1       4.566   1.189  -0.886  1.00  0.00           C  
HETATM    7  C4  UNL     1       5.389   0.151  -0.218  1.00  0.00           C  
HETATM    8  C5  UNL     1       5.743   1.605  -0.083  1.00  0.00           C  
HETATM    9  C6  UNL     1       1.021   0.535   0.176  1.00  0.00           C  
HETATM   10  N4  UNL     1       0.370   1.571   0.714  1.00  0.00           N  
HETATM   11  C7  UNL     1      -0.889   1.173   1.042  1.00  0.00           C  
HETATM   12  N5  UNL     1      -1.043  -0.116   0.714  1.00  0.00           N  
HETATM   13  C8  UNL     1      -2.248  -0.883   0.913  1.00  0.00           C  
HETATM   14  C9  UNL     1      -3.083  -0.340   2.015  1.00  0.00           C  
HETATM   15  C10 UNL     1      -4.291  -0.079   1.577  1.00  0.00           C  
HETATM   16  C11 UNL     1      -4.423  -0.406   0.148  1.00  0.00           C  
HETATM   17  C12 UNL     1      -4.814   0.818  -0.675  1.00  0.00           C  
HETATM   18  O1  UNL     1      -3.882   1.823  -0.576  1.00  0.00           O  
HETATM   19  C13 UNL     1      -3.116  -0.976  -0.293  1.00  0.00           C  
HETATM   20  C14 UNL     1       0.122  -0.526   0.180  1.00  0.00           C  
HETATM   21  N6  UNL     1       0.566  -1.695  -0.325  1.00  0.00           N  
HETATM   22  H1  UNL     1       1.774  -4.071  -0.981  1.00  0.00           H  
HETATM   23  H2  UNL     1       2.909  -3.265  -2.078  1.00  0.00           H  
HETATM   24  H3  UNL     1       2.963   2.334   0.022  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.620   1.341  -1.991  1.00  0.00           H  
HETATM   26  H5  UNL     1       6.087  -0.433  -0.880  1.00  0.00           H  
HETATM   27  H6  UNL     1       4.994  -0.417   0.640  1.00  0.00           H  
HETATM   28  H7  UNL     1       5.571   2.058   0.904  1.00  0.00           H  
HETATM   29  H8  UNL     1       6.627   1.998  -0.632  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.623   1.834   1.499  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.993  -1.941   1.218  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.706  -0.199   3.021  1.00  0.00           H  
HETATM   33  H12 UNL     1      -5.080   0.324   2.193  1.00  0.00           H  
HETATM   34  H13 UNL     1      -5.257  -1.141   0.048  1.00  0.00           H  
HETATM   35  H14 UNL     1      -4.988   0.558  -1.722  1.00  0.00           H  
HETATM   36  H15 UNL     1      -5.771   1.177  -0.241  1.00  0.00           H  
HETATM   37  H16 UNL     1      -4.317   2.685  -0.355  1.00  0.00           H  
HETATM   38  H17 UNL     1      -3.300  -2.033  -0.632  1.00  0.00           H  
HETATM   39  H18 UNL     1      -2.686  -0.457  -1.175  1.00  0.00           H  
CONECT    1    2   22   23
CONECT    2    3    3   21
CONECT    3    4
CONECT    4    5    9    9
CONECT    5    6   24
CONECT    6    7    8   25
CONECT    7    8   26   27
CONECT    8   28   29
CONECT    9   10   20
CONECT   10   11   11
CONECT   11   12   30
CONECT   12   13   20
CONECT   13   14   19   31
CONECT   14   15   15   32
CONECT   15   16   33
CONECT   16   17   19   34
CONECT   17   18   35   36
CONECT   18   37
CONECT   19   38   39
CONECT   20   21   21
END

HMDB0015182
     RDKit          3D
Abacavir
 39 42  0  0  0  0  0  0  0  0999 V2000
    2.1995   -3.1734   -1.3424 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7943   -1.8948   -0.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6604   -0.8670   -0.8209 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2943    0.3386   -0.3333 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2376    1.3997   -0.3525 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5661    1.1892   -0.8856 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3887    0.1511   -0.2183 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7430    1.6050   -0.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0211    0.5345    0.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3701    1.5714    0.7145 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8887    1.1731    1.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0430   -0.1164    0.7140 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2478   -0.8827    0.9133 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0832   -0.3404    2.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2910   -0.0789    1.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4226   -0.4057    0.1481 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8138    0.8181   -0.6749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8825    1.8231   -0.5757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1158   -0.9762   -0.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1219   -0.5264    0.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5664   -1.6946   -0.3247 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7736   -4.0714   -0.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9093   -3.2651   -2.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9634    2.3342    0.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6200    1.3410   -1.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0867   -0.4329   -0.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9943   -0.4167    0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5713    2.0579    0.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6272    1.9980   -0.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6230    1.8342    1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9934   -1.9406    1.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7061   -0.1985    3.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0804    0.3240    2.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2570   -1.1406    0.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9878    0.5577   -1.7218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7706    1.1769   -0.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3168    2.6848   -0.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2998   -2.0331   -0.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6859   -0.4570   -1.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  4  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 12 20  1  0
 20 21  2  0
 21  2  1  0
  8  6  1  0
 20  9  1  0
 19 13  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 11 30  1  0
 13 31  1  1
 14 32  1  0
 15 33  1  0
 16 34  1  1
 17 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
ABC	ChEBI
{(1S-cis)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol	ChEBI
(1S,4R)-4-(2-Amino-6-(cyclopropylamino)-9H-purin-9-yl)-2-cyclopentene-1-methanol	HMDB
Abacavir succinate	HMDB
Ziagen	HMDB
Abacavir sulfate	HMDB

Chemical Formula

C₁₄H₁₈N₆O

Average Molecular Weight

286.3323

Monoisotopic Molecular Weight

286.154209228

IUPAC Name

[(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl]methanol

Traditional Name

abacavir

CAS Registry Number

136470-78-5

SMILES

NC1=NC2=C(N=CN2[C@@H]2C[C@H](CO)C=C2)C(NC2CC2)=N1

InChI Identifier

InChI=1S/C14H18N6O/c15-14-18-12(17-9-2-3-9)11-13(19-14)20(7-16-11)10-4-1-8(5-10)6-21/h1,4,7-10,21H,2-3,5-6H2,(H3,15,17,18,19)/t8-,10+/m1/s1

InChI Key

MCGSCOLBFJQGHM-SCZZXKLOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,3-substituted cyclopentyl purine nucleosides. These are nucleoside analogues with a structure that consists of a cyclobutane that is substituted a the 1-position with a hydroxyl group and at the 3-position with either a purine base.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Nucleoside and nucleotide analogues

Sub Class

Cyclopentyl nucleosides

Direct Parent

1,3-substituted cyclopentyl purine nucleosides

Alternative Parents

Substituents

1,3-substituted cyclopentyl purine nucleoside
6-alkylaminopurine
6-aminopurine
Imidazopyrimidine
Purine
Aminopyrimidine
Secondary aliphatic/aromatic amine
N-substituted imidazole
Pyrimidine
Imidolactam
Heteroaromatic compound
Azole
Imidazole
Secondary amine
Organoheterocyclic compound
Azacycle
Amine
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Primary alcohol
Primary amine
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

2,6-diaminopurine (CHEBI:421707 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0015182)
Membrane (HMDB: HMDB0015182)

Biofluid or Excreta

Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Abacavir Action Pathway (PathBank: SMP0000737)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	165 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.21 g/L	Not Available
LogP	1.1	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.21 g/L	ALOGPS
logP	0.61	ALOGPS
logP	0.39	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	15.41	ChemAxon
pKa (Strongest Basic)	5.77	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	101.88 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	82.62 m³·mol⁻¹	ChemAxon
Polarizability	30.43 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
DarkChem	[M+H]+	168.624	31661259
DarkChem	[M-H]-	165.961	31661259
DeepCCS	[M+H]+	165.141	30932474
DeepCCS	[M-H]-	162.783	30932474
DeepCCS	[M-2H]-	196.67	30932474
DeepCCS	[M+Na]+	171.898	30932474
AllCCS	[M+H]+	169.9	32859911
AllCCS	[M+H-H2O]+	166.7	32859911
AllCCS	[M+NH4]+	172.9	32859911
AllCCS	[M+Na]+	173.8	32859911
AllCCS	[M-H]-	169.1	32859911
AllCCS	[M+Na-2H]-	168.6	32859911
AllCCS	[M+HCOO]-	168.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Abacavir	NC1=NC2=C(N=CN2[C@@H]2C[C@H](CO)C=C2)C(NC2CC2)=N1	3516.5	Standard polar	33892256
Abacavir	NC1=NC2=C(N=CN2[C@@H]2C[C@H](CO)C=C2)C(NC2CC2)=N1	2845.9	Standard non polar	33892256
Abacavir	NC1=NC2=C(N=CN2[C@@H]2C[C@H](CO)C=C2)C(NC2CC2)=N1	2955.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Abacavir,1TMS,isomer #1	C[Si](C)(C)OC[C@@H]1C=C[C@H](N2C=NC3=C(NC4CC4)N=C(N)N=C32)C1	2972.2	Semi standard non polar	33892256
Abacavir,1TMS,isomer #2	C[Si](C)(C)NC1=NC(NC2CC2)=C2N=CN([C@H]3C=C[C@@H](CO)C3)C2=N1	3025.3	Semi standard non polar	33892256
Abacavir,1TMS,isomer #3	C[Si](C)(C)N(C1=NC(N)=NC2=C1N=CN2[C@H]1C=C[C@@H](CO)C1)C1CC1	2861.3	Semi standard non polar	33892256
Abacavir,2TMS,isomer #1	C[Si](C)(C)NC1=NC(NC2CC2)=C2N=CN([C@H]3C=C[C@@H](CO[Si](C)(C)C)C3)C2=N1	2933.3	Semi standard non polar	33892256
Abacavir,2TMS,isomer #1	C[Si](C)(C)NC1=NC(NC2CC2)=C2N=CN([C@H]3C=C[C@@H](CO[Si](C)(C)C)C3)C2=N1	2821.1	Standard non polar	33892256
Abacavir,2TMS,isomer #1	C[Si](C)(C)NC1=NC(NC2CC2)=C2N=CN([C@H]3C=C[C@@H](CO[Si](C)(C)C)C3)C2=N1	4197.6	Standard polar	33892256
Abacavir,2TMS,isomer #2	C[Si](C)(C)OC[C@@H]1C=C[C@H](N2C=NC3=C(N(C4CC4)[Si](C)(C)C)N=C(N)N=C32)C1	2833.1	Semi standard non polar	33892256
Abacavir,2TMS,isomer #2	C[Si](C)(C)OC[C@@H]1C=C[C@H](N2C=NC3=C(N(C4CC4)[Si](C)(C)C)N=C(N)N=C32)C1	2820.4	Standard non polar	33892256
Abacavir,2TMS,isomer #2	C[Si](C)(C)OC[C@@H]1C=C[C@H](N2C=NC3=C(N(C4CC4)[Si](C)(C)C)N=C(N)N=C32)C1	4034.4	Standard polar	33892256
Abacavir,2TMS,isomer #3	C[Si](C)(C)N(C1=NC(NC2CC2)=C2N=CN([C@H]3C=C[C@@H](CO)C3)C2=N1)[Si](C)(C)C	2921.6	Semi standard non polar	33892256
Abacavir,2TMS,isomer #3	C[Si](C)(C)N(C1=NC(NC2CC2)=C2N=CN([C@H]3C=C[C@@H](CO)C3)C2=N1)[Si](C)(C)C	3046.9	Standard non polar	33892256
Abacavir,2TMS,isomer #3	C[Si](C)(C)N(C1=NC(NC2CC2)=C2N=CN([C@H]3C=C[C@@H](CO)C3)C2=N1)[Si](C)(C)C	4451.0	Standard polar	33892256
Abacavir,2TMS,isomer #4	C[Si](C)(C)NC1=NC(N(C2CC2)[Si](C)(C)C)=C2N=CN([C@H]3C=C[C@@H](CO)C3)C2=N1	2910.4	Semi standard non polar	33892256
Abacavir,2TMS,isomer #4	C[Si](C)(C)NC1=NC(N(C2CC2)[Si](C)(C)C)=C2N=CN([C@H]3C=C[C@@H](CO)C3)C2=N1	2980.7	Standard non polar	33892256
Abacavir,2TMS,isomer #4	C[Si](C)(C)NC1=NC(N(C2CC2)[Si](C)(C)C)=C2N=CN([C@H]3C=C[C@@H](CO)C3)C2=N1	4332.8	Standard polar	33892256
Abacavir,3TMS,isomer #1	C[Si](C)(C)OC[C@@H]1C=C[C@H](N2C=NC3=C(NC4CC4)N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C32)C1	2898.0	Semi standard non polar	33892256
Abacavir,3TMS,isomer #1	C[Si](C)(C)OC[C@@H]1C=C[C@H](N2C=NC3=C(NC4CC4)N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C32)C1	2998.3	Standard non polar	33892256
Abacavir,3TMS,isomer #1	C[Si](C)(C)OC[C@@H]1C=C[C@H](N2C=NC3=C(NC4CC4)N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C32)C1	3937.1	Standard polar	33892256
Abacavir,3TMS,isomer #2	C[Si](C)(C)NC1=NC(N(C2CC2)[Si](C)(C)C)=C2N=CN([C@H]3C=C[C@@H](CO[Si](C)(C)C)C3)C2=N1	2883.2	Semi standard non polar	33892256
Abacavir,3TMS,isomer #2	C[Si](C)(C)NC1=NC(N(C2CC2)[Si](C)(C)C)=C2N=CN([C@H]3C=C[C@@H](CO[Si](C)(C)C)C3)C2=N1	2939.7	Standard non polar	33892256
Abacavir,3TMS,isomer #2	C[Si](C)(C)NC1=NC(N(C2CC2)[Si](C)(C)C)=C2N=CN([C@H]3C=C[C@@H](CO[Si](C)(C)C)C3)C2=N1	3808.0	Standard polar	33892256
Abacavir,3TMS,isomer #3	C[Si](C)(C)N(C1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=C1N=CN2[C@H]1C=C[C@@H](CO)C1)C1CC1	2887.2	Semi standard non polar	33892256
Abacavir,3TMS,isomer #3	C[Si](C)(C)N(C1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=C1N=CN2[C@H]1C=C[C@@H](CO)C1)C1CC1	3143.0	Standard non polar	33892256
Abacavir,3TMS,isomer #3	C[Si](C)(C)N(C1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=C1N=CN2[C@H]1C=C[C@@H](CO)C1)C1CC1	4032.2	Standard polar	33892256
Abacavir,4TMS,isomer #1	C[Si](C)(C)OC[C@@H]1C=C[C@H](N2C=NC3=C(N(C4CC4)[Si](C)(C)C)N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C32)C1	2907.4	Semi standard non polar	33892256
Abacavir,4TMS,isomer #1	C[Si](C)(C)OC[C@@H]1C=C[C@H](N2C=NC3=C(N(C4CC4)[Si](C)(C)C)N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C32)C1	3091.1	Standard non polar	33892256
Abacavir,4TMS,isomer #1	C[Si](C)(C)OC[C@@H]1C=C[C@H](N2C=NC3=C(N(C4CC4)[Si](C)(C)C)N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C32)C1	3554.0	Standard polar	33892256
Abacavir,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H]1C=C[C@H](N2C=NC3=C(NC4CC4)N=C(N)N=C32)C1	3190.6	Semi standard non polar	33892256
Abacavir,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(NC2CC2)=C2N=CN([C@H]3C=C[C@@H](CO)C3)C2=N1	3214.0	Semi standard non polar	33892256
Abacavir,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC(N)=NC2=C1N=CN2[C@H]1C=C[C@@H](CO)C1)C1CC1	3063.0	Semi standard non polar	33892256
Abacavir,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(NC2CC2)=C2N=CN([C@H]3C=C[C@@H](CO[Si](C)(C)C(C)(C)C)C3)C2=N1	3297.0	Semi standard non polar	33892256
Abacavir,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(NC2CC2)=C2N=CN([C@H]3C=C[C@@H](CO[Si](C)(C)C(C)(C)C)C3)C2=N1	3306.0	Standard non polar	33892256
Abacavir,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(NC2CC2)=C2N=CN([C@H]3C=C[C@@H](CO[Si](C)(C)C(C)(C)C)C3)C2=N1	4240.0	Standard polar	33892256
Abacavir,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@@H]1C=C[C@H](N2C=NC3=C(N(C4CC4)[Si](C)(C)C(C)(C)C)N=C(N)N=C32)C1	3195.9	Semi standard non polar	33892256
Abacavir,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@@H]1C=C[C@H](N2C=NC3=C(N(C4CC4)[Si](C)(C)C(C)(C)C)N=C(N)N=C32)C1	3308.0	Standard non polar	33892256
Abacavir,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@@H]1C=C[C@H](N2C=NC3=C(N(C4CC4)[Si](C)(C)C(C)(C)C)N=C(N)N=C32)C1	4088.9	Standard polar	33892256
Abacavir,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC(NC2CC2)=C2N=CN([C@H]3C=C[C@@H](CO)C3)C2=N1)[Si](C)(C)C(C)(C)C	3335.9	Semi standard non polar	33892256
Abacavir,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC(NC2CC2)=C2N=CN([C@H]3C=C[C@@H](CO)C3)C2=N1)[Si](C)(C)C(C)(C)C	3516.9	Standard non polar	33892256
Abacavir,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC(NC2CC2)=C2N=CN([C@H]3C=C[C@@H](CO)C3)C2=N1)[Si](C)(C)C(C)(C)C	4431.7	Standard polar	33892256
Abacavir,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC(N(C2CC2)[Si](C)(C)C(C)(C)C)=C2N=CN([C@H]3C=C[C@@H](CO)C3)C2=N1	3275.1	Semi standard non polar	33892256
Abacavir,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC(N(C2CC2)[Si](C)(C)C(C)(C)C)=C2N=CN([C@H]3C=C[C@@H](CO)C3)C2=N1	3499.3	Standard non polar	33892256
Abacavir,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC(N(C2CC2)[Si](C)(C)C(C)(C)C)=C2N=CN([C@H]3C=C[C@@H](CO)C3)C2=N1	4315.8	Standard polar	33892256
Abacavir,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H]1C=C[C@H](N2C=NC3=C(NC4CC4)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C32)C1	3455.4	Semi standard non polar	33892256
Abacavir,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H]1C=C[C@H](N2C=NC3=C(NC4CC4)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C32)C1	3688.8	Standard non polar	33892256
Abacavir,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H]1C=C[C@H](N2C=NC3=C(NC4CC4)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C32)C1	4035.1	Standard polar	33892256
Abacavir,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(N(C2CC2)[Si](C)(C)C(C)(C)C)=C2N=CN([C@H]3C=C[C@@H](CO[Si](C)(C)C(C)(C)C)C3)C2=N1	3398.5	Semi standard non polar	33892256
Abacavir,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(N(C2CC2)[Si](C)(C)C(C)(C)C)=C2N=CN([C@H]3C=C[C@@H](CO[Si](C)(C)C(C)(C)C)C3)C2=N1	3648.6	Standard non polar	33892256
Abacavir,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(N(C2CC2)[Si](C)(C)C(C)(C)C)=C2N=CN([C@H]3C=C[C@@H](CO[Si](C)(C)C(C)(C)C)C3)C2=N1	3927.7	Standard polar	33892256
Abacavir,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=C1N=CN2[C@H]1C=C[C@@H](CO)C1)C1CC1	3442.0	Semi standard non polar	33892256
Abacavir,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=C1N=CN2[C@H]1C=C[C@@H](CO)C1)C1CC1	3833.7	Standard non polar	33892256
Abacavir,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=C1N=CN2[C@H]1C=C[C@@H](CO)C1)C1CC1	4056.9	Standard polar	33892256
Abacavir,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H]1C=C[C@H](N2C=NC3=C(N(C4CC4)[Si](C)(C)C(C)(C)C)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C32)C1	3585.5	Semi standard non polar	33892256
Abacavir,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H]1C=C[C@H](N2C=NC3=C(N(C4CC4)[Si](C)(C)C(C)(C)C)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C32)C1	3924.1	Standard non polar	33892256
Abacavir,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H]1C=C[C@H](N2C=NC3=C(N(C4CC4)[Si](C)(C)C(C)(C)C)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C32)C1	3760.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Abacavir GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-4290000000-ff09f3896a50abd46e5c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Abacavir GC-MS (1 TMS) - 70eV, Positive	splash10-0005-9257000000-21b4bbc1ab23c07507d6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Abacavir 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 - Abacavir 10V, Positive-QTOF	splash10-00kr-0090000000-0946b359f044edc1eaa7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Abacavir 20V, Positive-QTOF	splash10-014i-2190000000-64675b2273332e37f39a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Abacavir 40V, Positive-QTOF	splash10-0006-9410000000-d05153b2e67c168956b2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Abacavir 10V, Negative-QTOF	splash10-000i-0090000000-2944c593361dbd76b614	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Abacavir 20V, Negative-QTOF	splash10-052r-2390000000-06a2fd880fff3ed2e268	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Abacavir 40V, Negative-QTOF	splash10-0a4i-9630000000-7c461fd855fa0cc2d7b1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Abacavir 10V, Positive-QTOF	splash10-000l-0790000000-368d898ea37a7e409e6e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Abacavir 20V, Positive-QTOF	splash10-0006-0900000000-fcb41525305a5be74f3a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Abacavir 40V, Positive-QTOF	splash10-0udi-0920000000-ce3e8f7641b332656356	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Abacavir 10V, Negative-QTOF	splash10-000i-0090000000-e97d53ff96d49e16f45a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Abacavir 20V, Negative-QTOF	splash10-000i-0190000000-992655fbf9c97b5fcce1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Abacavir 40V, Negative-QTOF	splash10-0002-0930000000-f24bb2b6a90e0a5559a1	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
Abacavir Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01048	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01048	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01048

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

390063

KEGG Compound ID

C07624

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Abacavir

METLIN ID

Not Available

PubChem Compound

441300

PDB ID

Not Available

ChEBI ID

421707

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

Zucman D, Truchis Pd, Majerholc C, Stegman S, Caillat-Zucman S: Prospective screening for human leukocyte antigen-B*5701 avoids abacavir hypersensitivity reaction in the ethnically mixed French HIV population. J Acquir Immune Defic Syndr. 2007 May 1;45(1):1-3. [PubMed:17356469 ]
(). FDA label . .
PharmGKB [Link]

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

References

Yuen GJ, Weller S, Pakes GE: A review of the pharmacokinetics of abacavir. Clin Pharmacokinet. 2008;47(6):351-71. [PubMed:18479171 ]

Enzyme Details

2. Alcohol dehydrogenase 6

General function:: Involved in zinc ion binding
Specific function:: Not Available
Gene Name:: ADH6
Uniprot ID:: P28332
Molecular weight:: 39072.275

References

Yuen GJ, Weller S, Pakes GE: A review of the pharmacokinetics of abacavir. Clin Pharmacokinet. 2008;47(6):351-71. [PubMed:18479171 ]

Showing metabocard for Abacavir (HMDB0015182)

MOL for HMDB0015182 (Abacavir)

3D MOL for HMDB0015182 (Abacavir)

3D SDF for HMDB0015182 (Abacavir)

3D-SDF for HMDB0015182 (Abacavir)

PDB for HMDB0015182 (Abacavir)

3D PDB for HMDB0015182 (Abacavir)

SMILES for HMDB0015182 (Abacavir)

INCHI for HMDB0015182 (Abacavir)

Structure for HMDB0015182 (Abacavir)

3D Structure for HMDB0015182 (Abacavir)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References