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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:40 UTC

HMDB ID

HMDB0014585

Secondary Accession Numbers

HMDB14585

Metabolite Identification

Common Name

Entecavir

Description

Entecavir is an oral antiviral drug used in the treatment of hepatitis B infection. It is marketed under the trade name Baraclude (BMS). Entecavir is a guanine analogue that inhibits all three steps in the viral replication process, and the manufacturer claims that it is more efficacious than previous agents used to treat hepatitis B (lamivudine and adefovir). It was approved by the U.S. Food and Drug Administration (FDA) in March 2005.

Structure

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

HMDB0014585
     RDKit          3D
Entecavir
 35 37  0  0  0  0  0  0  0  0999 V2000
   -0.5836    0.5787    2.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1518    0.4776    0.8211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7486    1.1167   -0.4704 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5650    1.6482   -0.4503 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9098    2.9237   -0.7080 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2627    3.0632   -0.5928 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7793    1.8690   -0.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0573    1.4178   -0.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0604    2.2078   -0.0899 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2244    0.1243    0.3013 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1677   -0.7139    0.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3136   -2.0827    0.7128 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9175   -0.2835    0.1442 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115    1.0013   -0.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9616    0.0107   -1.4647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9194   -0.9741   -0.8242 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9825   -1.2826   -1.6488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3617   -0.3172    0.4712 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6914   -1.3382    1.5304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8262   -2.0624    1.1720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0166    0.0399    2.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2920    1.1721    2.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5126    1.8945   -0.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2274    3.7309   -0.9692 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9900   -2.6572    0.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7479   -2.4885    1.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0966   -0.9532    0.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0458   -0.4485   -1.8394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4999    0.4110   -2.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4050   -1.9172   -0.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0702   -2.2689   -1.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2377    0.3455    0.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8108   -1.9945    1.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9089   -0.8138    2.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5886   -1.4367    1.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  3 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 18  2  1  0
 14  4  1  0
 14  7  2  0
  1 21  1  0
  1 22  1  0
  3 23  1  6
  5 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  1
 17 31  1  0
 18 32  1  6
 19 33  1  0
 19 34  1  0
 20 35  1  0
M  END

442
  Mrv0541 02231214412D          

 20 22  0  0  1  0            999 V2000
    5.0221    2.3275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6433    2.5906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.8905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0170   -0.5766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.4155    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0170   -1.9044    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.6530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.4155    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2734    0.2076    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0598    1.2862    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2757    1.5425    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7896    0.8759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0584    0.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7281    1.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -0.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7250   -0.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4985   -1.2405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -1.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11  1  1  6  0  0  0
  2 14  1  0  0  0  0
  3 19  2  0  0  0  0
  9  4  1  1  0  0  0
  4 15  1  0  0  0  0
  4 17  1  0  0  0  0
  5 15  1  0  0  0  0
  5 20  1  0  0  0  0
  6 17  2  0  0  0  0
  6 18  1  0  0  0  0
  7 19  1  0  0  0  0
  7 20  2  0  0  0  0
  8 20  1  0  0  0  0
  9 12  1  0  0  0  0
  9 13  1  0  0  0  0
 10 11  1  0  0  0  0
 10 13  1  0  0  0  0
 10 14  1  1  0  0  0
 11 12  1  0  0  0  0
 13 16  2  0  0  0  0
 15 18  2  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014585

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=NC(=O)C2=C(N1)N(C=N2)[C@H]1C[C@H](O)[C@@H](CO)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C12H15N5O3/c1-5-6(3-18)8(19)2-7(5)17-4-14-9-10(17)15-12(13)16-11(9)20/h4,6-8,18-19H,1-3H2,(H3,13,15,16,20)/t6-,7-,8-/m0/s1

> <INCHI_KEY>
QDGZDCVAUDNJFG-FXQIFTODSA-N

> <FORMULA>
C12H15N5O3

> <MOLECULAR_WEIGHT>
277.2792

> <EXACT_MASS>
277.117489371

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
27.308722207267255

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-6,9-dihydro-3H-purin-6-one

> <ALOGPS_LOGP>
-0.81

> <JCHEM_LOGP>
-1.4446591723333337

> <ALOGPS_LOGS>
-1.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.64255089215305

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.003302101181076

> <JCHEM_PKA_STRONGEST_BASIC>
2.7731139288504045

> <JCHEM_POLAR_SURFACE_AREA>
125.75999999999999

> <JCHEM_REFRACTIVITY>
71.0008

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.59e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
entecavir

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014585
     RDKit          3D
Entecavir
 35 37  0  0  0  0  0  0  0  0999 V2000
   -0.5836    0.5787    2.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1518    0.4776    0.8211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7486    1.1167   -0.4704 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5650    1.6482   -0.4503 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9098    2.9237   -0.7080 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2627    3.0632   -0.5928 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7793    1.8690   -0.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0573    1.4178   -0.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0604    2.2078   -0.0899 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2244    0.1243    0.3013 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1677   -0.7139    0.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3136   -2.0827    0.7128 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9175   -0.2835    0.1442 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115    1.0013   -0.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9616    0.0107   -1.4647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9194   -0.9741   -0.8242 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9825   -1.2826   -1.6488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3617   -0.3172    0.4712 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6914   -1.3382    1.5304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8262   -2.0624    1.1720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0166    0.0399    2.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2920    1.1721    2.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5126    1.8945   -0.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2274    3.7309   -0.9692 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9900   -2.6572    0.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7479   -2.4885    1.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0966   -0.9532    0.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0458   -0.4485   -1.8394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4999    0.4110   -2.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4050   -1.9172   -0.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0702   -2.2689   -1.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2377    0.3455    0.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8108   -1.9945    1.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9089   -0.8138    2.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5886   -1.4367    1.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  3 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 18  2  1  0
 14  4  1  0
 14  7  2  0
  1 21  1  0
  1 22  1  0
  3 23  1  6
  5 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  1
 17 31  1  0
 18 32  1  6
 19 33  1  0
 19 34  1  0
 20 35  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 442                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       9.375   4.345   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      12.401   4.836   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       6.574  -5.396   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       9.365  -1.076   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       6.574  -0.776   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       9.365  -3.555   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       5.241  -3.086   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       3.907  -0.776   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       9.844   0.388   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.312   2.401   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.848   2.879   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.941   1.635   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.309   0.861   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.559   3.304   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.908  -1.546   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.553  -0.046   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.264  -2.316   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.908  -3.086   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.574  -3.856   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.241  -1.546   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   14                                                            
CONECT    3   19                                                            
CONECT    4    9   15   17                                                  
CONECT    5   15   20                                                       
CONECT    6   17   18                                                       
CONECT    7   19   20                                                       
CONECT    8   20                                                            
CONECT    9    4   12   13                                                  
CONECT   10   11   13   14                                                  
CONECT   11    1   10   12                                                  
CONECT   12    9   11                                                       
CONECT   13    9   10   16                                                  
CONECT   14    2   10                                                       
CONECT   15    4    5   18                                                  
CONECT   16   13                                                            
CONECT   17    4    6                                                       
CONECT   18    6   15   19                                                  
CONECT   19    3    7   18                                                  
CONECT   20    5    7    8                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0014585
HETATM    1  C1  UNL     1      -0.584   0.579   2.009  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.152   0.478   0.821  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.749   1.117  -0.470  1.00  0.00           C  
HETATM    4  N1  UNL     1       0.565   1.648  -0.450  1.00  0.00           N  
HETATM    5  C4  UNL     1       0.910   2.924  -0.708  1.00  0.00           C  
HETATM    6  N2  UNL     1       2.263   3.063  -0.593  1.00  0.00           N  
HETATM    7  C5  UNL     1       2.779   1.869  -0.260  1.00  0.00           C  
HETATM    8  C6  UNL     1       4.057   1.418  -0.016  1.00  0.00           C  
HETATM    9  O1  UNL     1       5.060   2.208  -0.090  1.00  0.00           O  
HETATM   10  N3  UNL     1       4.224   0.124   0.301  1.00  0.00           N  
HETATM   11  C7  UNL     1       3.168  -0.714   0.380  1.00  0.00           C  
HETATM   12  N4  UNL     1       3.314  -2.083   0.713  1.00  0.00           N  
HETATM   13  N5  UNL     1       1.918  -0.283   0.144  1.00  0.00           N  
HETATM   14  C8  UNL     1       1.711   1.001  -0.176  1.00  0.00           C  
HETATM   15  C9  UNL     1      -0.962   0.011  -1.465  1.00  0.00           C  
HETATM   16  C10 UNL     1      -1.919  -0.974  -0.824  1.00  0.00           C  
HETATM   17  O2  UNL     1      -2.983  -1.283  -1.649  1.00  0.00           O  
HETATM   18  C11 UNL     1      -2.362  -0.317   0.471  1.00  0.00           C  
HETATM   19  C12 UNL     1      -2.691  -1.338   1.530  1.00  0.00           C  
HETATM   20  O3  UNL     1      -3.826  -2.062   1.172  1.00  0.00           O  
HETATM   21  H1  UNL     1      -1.017   0.040   2.841  1.00  0.00           H  
HETATM   22  H2  UNL     1       0.292   1.172   2.194  1.00  0.00           H  
HETATM   23  H3  UNL     1      -1.513   1.895  -0.676  1.00  0.00           H  
HETATM   24  H4  UNL     1       0.227   3.731  -0.969  1.00  0.00           H  
HETATM   25  H5  UNL     1       3.990  -2.657   0.190  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.748  -2.489   1.467  1.00  0.00           H  
HETATM   27  H7  UNL     1       1.097  -0.953   0.210  1.00  0.00           H  
HETATM   28  H8  UNL     1      -0.046  -0.449  -1.839  1.00  0.00           H  
HETATM   29  H9  UNL     1      -1.500   0.411  -2.374  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.405  -1.917  -0.527  1.00  0.00           H  
HETATM   31  H11 UNL     1      -3.070  -2.269  -1.754  1.00  0.00           H  
HETATM   32  H12 UNL     1      -3.238   0.346   0.324  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.811  -1.994   1.663  1.00  0.00           H  
HETATM   34  H14 UNL     1      -2.909  -0.814   2.465  1.00  0.00           H  
HETATM   35  H15 UNL     1      -4.589  -1.437   1.136  1.00  0.00           H  
CONECT    1    2    2   21   22
CONECT    2    3   18
CONECT    3    4   15   23
CONECT    4    5   14
CONECT    5    6    6   24
CONECT    6    7
CONECT    7    8   14   14
CONECT    8    9    9   10
CONECT   10   11   11
CONECT   11   12   13
CONECT   12   25   26
CONECT   13   14   27
CONECT   15   16   28   29
CONECT   16   17   18   30
CONECT   17   31
CONECT   18   19   32
CONECT   19   20   33   34
CONECT   20   35
END

HMDB0014585
     RDKit          3D
Entecavir
 35 37  0  0  0  0  0  0  0  0999 V2000
   -0.5836    0.5787    2.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1518    0.4776    0.8211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7486    1.1167   -0.4704 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5650    1.6482   -0.4503 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9098    2.9237   -0.7080 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2627    3.0632   -0.5928 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7793    1.8690   -0.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0573    1.4178   -0.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0604    2.2078   -0.0899 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2244    0.1243    0.3013 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1677   -0.7139    0.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3136   -2.0827    0.7128 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9175   -0.2835    0.1442 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115    1.0013   -0.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9616    0.0107   -1.4647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9194   -0.9741   -0.8242 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9825   -1.2826   -1.6488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3617   -0.3172    0.4712 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6914   -1.3382    1.5304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8262   -2.0624    1.1720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0166    0.0399    2.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2920    1.1721    2.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5126    1.8945   -0.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2274    3.7309   -0.9692 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9900   -2.6572    0.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7479   -2.4885    1.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0966   -0.9532    0.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0458   -0.4485   -1.8394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4999    0.4110   -2.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4050   -1.9172   -0.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0702   -2.2689   -1.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2377    0.3455    0.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8108   -1.9945    1.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9089   -0.8138    2.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5886   -1.4367    1.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  3 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 18  2  1  0
 14  4  1  0
 14  7  2  0
  1 21  1  0
  1 22  1  0
  3 23  1  6
  5 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  1
 17 31  1  0
 18 32  1  6
 19 33  1  0
 19 34  1  0
 20 35  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Baraclude	HMDB
Entecavir	ChEBI

Chemical Formula

C₁₂H₁₅N₅O₃

Average Molecular Weight

277.2792

Monoisotopic Molecular Weight

277.117489371

IUPAC Name

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-6,9-dihydro-3H-purin-6-one

Traditional Name

entecavir

CAS Registry Number

142217-69-4

SMILES

NC1=NC(=O)C2=C(N1)N(C=N2)[C@H]1C[C@H](O)[C@@H](CO)C1=C

InChI Identifier

InChI=1S/C12H15N5O3/c1-5-6(3-18)8(19)2-7(5)17-4-14-9-10(17)15-12(13)16-11(9)20/h4,6-8,18-19H,1-3H2,(H3,13,15,16,20)/t6-,7-,8-/m0/s1

InChI Key

QDGZDCVAUDNJFG-FXQIFTODSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nucleoside and nucleotide analogues. These are analogues of nucleosides and nucleotides. These include phosphonated nucleosides, C-glycosylated nucleoside bases, analogues where the sugar unit is a pyranose, and carbocyclic nucleosides, among others.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Nucleoside and nucleotide analogues

Sub Class

Not Available

Direct Parent

Nucleoside and nucleotide analogues

Alternative Parents

Substituents

6-oxopurine
Hypoxanthine
Purinone
Purine
Imidazopyrimidine
Aminopyrimidine
Pyrimidone
Cyclopentanol
Pyrimidine
N-substituted imidazole
Azole
Cyclic alcohol
Heteroaromatic compound
Imidazole
Vinylogous amide
Secondary alcohol
Azacycle
Organoheterocyclic compound
Primary alcohol
Primary amine
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

secondary alcohol (CHEBI:473990 )
oxopurine (CHEBI:473990 )
primary alcohol (CHEBI:473990 )
2-aminopurines (CHEBI:473990 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014585)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	6.59 g/L	Not Available
LogP	-0.8	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.59 g/L	ALOGPS
logP	-0.81	ALOGPS
logP	-1.4	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	8	ChemAxon
pKa (Strongest Basic)	2.77	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	71 m³·mol⁻¹	ChemAxon
Polarizability	27.31 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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]+	164.335	31661259
DarkChem	[M-H]-	161.376	31661259
DeepCCS	[M+H]+	165.794	30932474
DeepCCS	[M-H]-	163.436	30932474
DeepCCS	[M-2H]-	197.793	30932474
DeepCCS	[M+Na]+	172.978	30932474
AllCCS	[M+H]+	163.6	32859911
AllCCS	[M+H-H2O]+	160.1	32859911
AllCCS	[M+NH4]+	166.8	32859911
AllCCS	[M+Na]+	167.7	32859911
AllCCS	[M-H]-	163.3	32859911
AllCCS	[M+Na-2H]-	162.8	32859911
AllCCS	[M+HCOO]-	162.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Entecavir	NC1=NC(=O)C2=C(N1)N(C=N2)[C@H]1C[C@H](O)[C@@H](CO)C1=C	3464.6	Standard polar	33892256
Entecavir	NC1=NC(=O)C2=C(N1)N(C=N2)[C@H]1C[C@H](O)[C@@H](CO)C1=C	2086.0	Standard non polar	33892256
Entecavir	NC1=NC(=O)C2=C(N1)N(C=N2)[C@H]1C[C@H](O)[C@@H](CO)C1=C	3103.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Entecavir,1TMS,isomer #1	C=C1[C@@H](N2C=NC3=C2[NH]C(N)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO	2656.7	Semi standard non polar	33892256
Entecavir,1TMS,isomer #2	C=C1[C@@H](N2C=NC3=C2[NH]C(N)=NC3=O)C[C@H](O)[C@H]1CO[Si](C)(C)C	2634.8	Semi standard non polar	33892256
Entecavir,1TMS,isomer #3	C=C1[C@@H](N2C=NC3=C2[NH]C(N[Si](C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO	2668.5	Semi standard non polar	33892256
Entecavir,1TMS,isomer #4	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N)=NC3=O)C[C@H](O)[C@H]1CO	2734.2	Semi standard non polar	33892256
Entecavir,2TMS,isomer #1	C=C1[C@@H](N2C=NC3=C2[NH]C(N)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO[Si](C)(C)C	2585.8	Semi standard non polar	33892256
Entecavir,2TMS,isomer #2	C=C1[C@@H](N2C=NC3=C2[NH]C(N[Si](C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO	2592.0	Semi standard non polar	33892256
Entecavir,2TMS,isomer #3	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO	2659.6	Semi standard non polar	33892256
Entecavir,2TMS,isomer #4	C=C1[C@@H](N2C=NC3=C2[NH]C(N[Si](C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO[Si](C)(C)C	2566.1	Semi standard non polar	33892256
Entecavir,2TMS,isomer #5	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N)=NC3=O)C[C@H](O)[C@H]1CO[Si](C)(C)C	2633.3	Semi standard non polar	33892256
Entecavir,2TMS,isomer #6	C=C1[C@@H](N2C=NC3=C2[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO	2596.5	Semi standard non polar	33892256
Entecavir,2TMS,isomer #7	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N[Si](C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO	2666.7	Semi standard non polar	33892256
Entecavir,3TMS,isomer #1	C=C1[C@@H](N2C=NC3=C2[NH]C(N[Si](C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO[Si](C)(C)C	2592.1	Semi standard non polar	33892256
Entecavir,3TMS,isomer #1	C=C1[C@@H](N2C=NC3=C2[NH]C(N[Si](C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO[Si](C)(C)C	2779.8	Standard non polar	33892256
Entecavir,3TMS,isomer #1	C=C1[C@@H](N2C=NC3=C2[NH]C(N[Si](C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO[Si](C)(C)C	3846.3	Standard polar	33892256
Entecavir,3TMS,isomer #2	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO[Si](C)(C)C	2642.0	Semi standard non polar	33892256
Entecavir,3TMS,isomer #2	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO[Si](C)(C)C	2738.9	Standard non polar	33892256
Entecavir,3TMS,isomer #2	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO[Si](C)(C)C	3997.6	Standard polar	33892256
Entecavir,3TMS,isomer #3	C=C1[C@@H](N2C=NC3=C2[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO	2619.7	Semi standard non polar	33892256
Entecavir,3TMS,isomer #3	C=C1[C@@H](N2C=NC3=C2[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO	2861.1	Standard non polar	33892256
Entecavir,3TMS,isomer #3	C=C1[C@@H](N2C=NC3=C2[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO	3682.5	Standard polar	33892256
Entecavir,3TMS,isomer #4	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N[Si](C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO	2655.2	Semi standard non polar	33892256
Entecavir,3TMS,isomer #4	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N[Si](C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO	2772.0	Standard non polar	33892256
Entecavir,3TMS,isomer #4	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N[Si](C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO	3741.7	Standard polar	33892256
Entecavir,3TMS,isomer #5	C=C1[C@@H](N2C=NC3=C2[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO[Si](C)(C)C	2599.1	Semi standard non polar	33892256
Entecavir,3TMS,isomer #5	C=C1[C@@H](N2C=NC3=C2[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO[Si](C)(C)C	2920.3	Standard non polar	33892256
Entecavir,3TMS,isomer #5	C=C1[C@@H](N2C=NC3=C2[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO[Si](C)(C)C	3691.0	Standard polar	33892256
Entecavir,3TMS,isomer #6	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N[Si](C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO[Si](C)(C)C	2636.1	Semi standard non polar	33892256
Entecavir,3TMS,isomer #6	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N[Si](C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO[Si](C)(C)C	2825.1	Standard non polar	33892256
Entecavir,3TMS,isomer #6	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N[Si](C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO[Si](C)(C)C	3753.0	Standard polar	33892256
Entecavir,3TMS,isomer #7	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO	2699.1	Semi standard non polar	33892256
Entecavir,3TMS,isomer #7	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO	2921.4	Standard non polar	33892256
Entecavir,3TMS,isomer #7	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO	3637.9	Standard polar	33892256
Entecavir,4TMS,isomer #1	C=C1[C@@H](N2C=NC3=C2[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO[Si](C)(C)C	2664.7	Semi standard non polar	33892256
Entecavir,4TMS,isomer #1	C=C1[C@@H](N2C=NC3=C2[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO[Si](C)(C)C	2882.9	Standard non polar	33892256
Entecavir,4TMS,isomer #1	C=C1[C@@H](N2C=NC3=C2[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO[Si](C)(C)C	3455.1	Standard polar	33892256
Entecavir,4TMS,isomer #2	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N[Si](C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO[Si](C)(C)C	2684.9	Semi standard non polar	33892256
Entecavir,4TMS,isomer #2	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N[Si](C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO[Si](C)(C)C	2809.2	Standard non polar	33892256
Entecavir,4TMS,isomer #2	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N[Si](C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO[Si](C)(C)C	3509.8	Standard polar	33892256
Entecavir,4TMS,isomer #3	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO	2727.3	Semi standard non polar	33892256
Entecavir,4TMS,isomer #3	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO	2895.5	Standard non polar	33892256
Entecavir,4TMS,isomer #3	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO	3378.7	Standard polar	33892256
Entecavir,4TMS,isomer #4	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO[Si](C)(C)C	2708.0	Semi standard non polar	33892256
Entecavir,4TMS,isomer #4	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO[Si](C)(C)C	2946.4	Standard non polar	33892256
Entecavir,4TMS,isomer #4	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO[Si](C)(C)C	3393.4	Standard polar	33892256
Entecavir,5TMS,isomer #1	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO[Si](C)(C)C	2767.3	Semi standard non polar	33892256
Entecavir,5TMS,isomer #1	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO[Si](C)(C)C	2922.9	Standard non polar	33892256
Entecavir,5TMS,isomer #1	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C)[C@H]1CO[Si](C)(C)C	3188.6	Standard polar	33892256
Entecavir,1TBDMS,isomer #1	C=C1[C@@H](N2C=NC3=C2[NH]C(N)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO	2841.5	Semi standard non polar	33892256
Entecavir,1TBDMS,isomer #2	C=C1[C@@H](N2C=NC3=C2[NH]C(N)=NC3=O)C[C@H](O)[C@H]1CO[Si](C)(C)C(C)(C)C	2841.4	Semi standard non polar	33892256
Entecavir,1TBDMS,isomer #3	C=C1[C@@H](N2C=NC3=C2[NH]C(N[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO	2874.5	Semi standard non polar	33892256
Entecavir,1TBDMS,isomer #4	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N)=NC3=O)C[C@H](O)[C@H]1CO	2906.3	Semi standard non polar	33892256
Entecavir,2TBDMS,isomer #1	C=C1[C@@H](N2C=NC3=C2[NH]C(N)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO[Si](C)(C)C(C)(C)C	2969.0	Semi standard non polar	33892256
Entecavir,2TBDMS,isomer #2	C=C1[C@@H](N2C=NC3=C2[NH]C(N[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO	2938.3	Semi standard non polar	33892256
Entecavir,2TBDMS,isomer #3	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO	3004.8	Semi standard non polar	33892256
Entecavir,2TBDMS,isomer #4	C=C1[C@@H](N2C=NC3=C2[NH]C(N[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO[Si](C)(C)C(C)(C)C	2952.4	Semi standard non polar	33892256
Entecavir,2TBDMS,isomer #5	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N)=NC3=O)C[C@H](O)[C@H]1CO[Si](C)(C)C(C)(C)C	3008.6	Semi standard non polar	33892256
Entecavir,2TBDMS,isomer #6	C=C1[C@@H](N2C=NC3=C2[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO	3013.5	Semi standard non polar	33892256
Entecavir,2TBDMS,isomer #7	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO	3050.8	Semi standard non polar	33892256
Entecavir,3TBDMS,isomer #1	C=C1[C@@H](N2C=NC3=C2[NH]C(N[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO[Si](C)(C)C(C)(C)C	3138.6	Semi standard non polar	33892256
Entecavir,3TBDMS,isomer #1	C=C1[C@@H](N2C=NC3=C2[NH]C(N[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO[Si](C)(C)C(C)(C)C	3453.2	Standard non polar	33892256
Entecavir,3TBDMS,isomer #1	C=C1[C@@H](N2C=NC3=C2[NH]C(N[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO[Si](C)(C)C(C)(C)C	3904.0	Standard polar	33892256
Entecavir,3TBDMS,isomer #2	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO[Si](C)(C)C(C)(C)C	3191.0	Semi standard non polar	33892256
Entecavir,3TBDMS,isomer #2	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO[Si](C)(C)C(C)(C)C	3377.7	Standard non polar	33892256
Entecavir,3TBDMS,isomer #2	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO[Si](C)(C)C(C)(C)C	4009.7	Standard polar	33892256
Entecavir,3TBDMS,isomer #3	C=C1[C@@H](N2C=NC3=C2[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO	3153.4	Semi standard non polar	33892256
Entecavir,3TBDMS,isomer #3	C=C1[C@@H](N2C=NC3=C2[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO	3521.1	Standard non polar	33892256
Entecavir,3TBDMS,isomer #3	C=C1[C@@H](N2C=NC3=C2[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO	3747.8	Standard polar	33892256
Entecavir,3TBDMS,isomer #4	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO	3169.9	Semi standard non polar	33892256
Entecavir,3TBDMS,isomer #4	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO	3457.0	Standard non polar	33892256
Entecavir,3TBDMS,isomer #4	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO	3785.0	Standard polar	33892256
Entecavir,3TBDMS,isomer #5	C=C1[C@@H](N2C=NC3=C2[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO[Si](C)(C)C(C)(C)C	3168.3	Semi standard non polar	33892256
Entecavir,3TBDMS,isomer #5	C=C1[C@@H](N2C=NC3=C2[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO[Si](C)(C)C(C)(C)C	3562.0	Standard non polar	33892256
Entecavir,3TBDMS,isomer #5	C=C1[C@@H](N2C=NC3=C2[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO[Si](C)(C)C(C)(C)C	3771.4	Standard polar	33892256
Entecavir,3TBDMS,isomer #6	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO[Si](C)(C)C(C)(C)C	3202.5	Semi standard non polar	33892256
Entecavir,3TBDMS,isomer #6	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO[Si](C)(C)C(C)(C)C	3496.9	Standard non polar	33892256
Entecavir,3TBDMS,isomer #6	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO[Si](C)(C)C(C)(C)C	3808.7	Standard polar	33892256
Entecavir,3TBDMS,isomer #7	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO	3226.1	Semi standard non polar	33892256
Entecavir,3TBDMS,isomer #7	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO	3582.5	Standard non polar	33892256
Entecavir,3TBDMS,isomer #7	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO	3704.8	Standard polar	33892256
Entecavir,4TBDMS,isomer #1	C=C1[C@@H](N2C=NC3=C2[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO[Si](C)(C)C(C)(C)C	3336.7	Semi standard non polar	33892256
Entecavir,4TBDMS,isomer #1	C=C1[C@@H](N2C=NC3=C2[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO[Si](C)(C)C(C)(C)C	3706.6	Standard non polar	33892256
Entecavir,4TBDMS,isomer #1	C=C1[C@@H](N2C=NC3=C2[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO[Si](C)(C)C(C)(C)C	3675.9	Standard polar	33892256
Entecavir,4TBDMS,isomer #2	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO[Si](C)(C)C(C)(C)C	3370.4	Semi standard non polar	33892256
Entecavir,4TBDMS,isomer #2	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO[Si](C)(C)C(C)(C)C	3652.6	Standard non polar	33892256
Entecavir,4TBDMS,isomer #2	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO[Si](C)(C)C(C)(C)C	3720.1	Standard polar	33892256
Entecavir,4TBDMS,isomer #3	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO	3388.4	Semi standard non polar	33892256
Entecavir,4TBDMS,isomer #3	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO	3711.9	Standard non polar	33892256
Entecavir,4TBDMS,isomer #3	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO	3590.4	Standard polar	33892256
Entecavir,4TBDMS,isomer #4	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO[Si](C)(C)C(C)(C)C	3411.7	Semi standard non polar	33892256
Entecavir,4TBDMS,isomer #4	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO[Si](C)(C)C(C)(C)C	3752.8	Standard non polar	33892256
Entecavir,4TBDMS,isomer #4	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O)[C@H]1CO[Si](C)(C)C(C)(C)C	3615.9	Standard polar	33892256
Entecavir,5TBDMS,isomer #1	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO[Si](C)(C)C(C)(C)C	3570.2	Semi standard non polar	33892256
Entecavir,5TBDMS,isomer #1	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO[Si](C)(C)C(C)(C)C	3869.2	Standard non polar	33892256
Entecavir,5TBDMS,isomer #1	C=C1[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC3=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO[Si](C)(C)C(C)(C)C	3543.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Entecavir GC-MS (Non-derivatized) - 70eV, Positive	splash10-001j-3190000000-4c1e30013236fcf851e8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Entecavir GC-MS (2 TMS) - 70eV, Positive	splash10-0a4l-4009600000-59f2f642d2b55baa6f98	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Entecavir 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 - Entecavir 10V, Positive-QTOF	splash10-03fr-0090000000-fece17372f19f5c56b9b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Entecavir 20V, Positive-QTOF	splash10-03dl-4190000000-2224afe131c0d7ffddeb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Entecavir 40V, Positive-QTOF	splash10-0udi-2940000000-a8c2e92ba3db7d5cb611	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Entecavir 10V, Negative-QTOF	splash10-004i-0090000000-f7f436db2922d84e90de	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Entecavir 20V, Negative-QTOF	splash10-0kdi-0290000000-c1ee67566ff6950ae6f0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Entecavir 40V, Negative-QTOF	splash10-0zfu-5930000000-de30bdfb529397180104	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Entecavir 10V, Negative-QTOF	splash10-004i-0190000000-7ffc04d8ffba36aeed92	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Entecavir 20V, Negative-QTOF	splash10-0fb9-0590000000-1b65c7578c809b708633	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Entecavir 40V, Negative-QTOF	splash10-0a4l-3910000000-a8e292ae929a7d25bd82	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Entecavir 10V, Positive-QTOF	splash10-0fb9-0890000000-debf13b5f5c060081554	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Entecavir 20V, Positive-QTOF	splash10-0fb9-0490000000-e8b9bbbb389fdfb1560f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Entecavir 40V, Positive-QTOF	splash10-0udi-1920000000-f30d5851e10d4f2b16c5	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00442	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00442	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00442

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

135679

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Entecavir

METLIN ID

Not Available

PubChem Compound

153941

PDB ID

Not Available

ChEBI ID

473990

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Entecavir (HMDB0014585)

MOL for HMDB0014585 (Entecavir)

3D MOL for HMDB0014585 (Entecavir)

3D SDF for HMDB0014585 (Entecavir)

3D-SDF for HMDB0014585 (Entecavir)

PDB for HMDB0014585 (Entecavir)

3D PDB for HMDB0014585 (Entecavir)

SMILES for HMDB0014585 (Entecavir)

INCHI for HMDB0014585 (Entecavir)

Structure for HMDB0014585 (Entecavir)

3D Structure for HMDB0014585 (Entecavir)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra