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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3)transporters (1) Show 4 proteins XML

enzymes (3)transporters (1) Show 4 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2023-02-21 17:18:12 UTC

HMDB ID

HMDB0014526

Secondary Accession Numbers

HMDB14526

Metabolite Identification

Common Name

Tacrine

Description

Tacrine, also known as tacrinal or THA, belongs to the class of organic compounds known as acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocycle which consists of two benzene rings joined by a pyridine ring. Taste changesUnknown incidence adverse effects includeUrinary tract infectionDeliriumOther optic effects such as glaucoma, cataracts, etc (also not conclusively linked to tacrine treatment)DepressionSuicidal ideation and behaviourHypotensionBradycardiaAs stated above, overdosage of tacrine may give rise to severe side effects such as nausea, vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Tacrine is a drug which is used for the palliative treatment of mild to moderate dementia of the alzheimer's type. InsomniaRhinitisRashFatigueWeight lossConstipationSomnolenceTremorAnxietyUrinary incontinenceHallucinatonsAgitationConjunctivitis (a link to tacrine treatment has not been conclusively proven)Diaphoresis — sweating.Uncommon/rare (<1% incidence) adverse effects includeHepatotoxicity (that is toxic effects on the liver)Ototoxicity (hearing/ear damage; a link to tacrine treatment has not been conclusively proven)SeizuresAgranulocytosis (a link between treatment and this adverse effect has not been proven) — a potentially fatal drop in white blood cells, the body's immune/defensive cells. Atropine is a popular treatment for overdose. It was the first centrally acting cholinesterase inhibitor approved for the treatment of Alzheimer's disease, and was marketed under the trade name Cognex. Tacrine was the prototypical cholinesterase inhibitor for the treatment of Alzheimer's disease. Tacrine was first synthesised by Adrien Albert at the University of Sydney. Tacrine is a centrally acting acetylcholinesterase inhibitor and indirect cholinergic agonist (parasympathomimetic). Tacrine is a very strong basic compound (based on its pKa). Tacrine is a potentially toxic compound. Studies found that it may have a small beneficial effect on cognition and other clinical measures, though study data was limited and the clinical relevance of these findings was unclear. William K. Summers received a patent for this use. Major form of metabolism is in the liver via hydroxylation of benzylic carbon by CYP1A2. This forms the major metabolite 1-hydroxy-tacrine (velnacrine) which is still active. Tacrine has been discontinued in the US in 2013, due to concerns over safety.

Structure

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

HMDB0014526
     RDKit          3D
Tacrine
 29 31  0  0  0  0  0  0  0  0999 V2000
   -1.1984   -2.2087   -0.5496 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7586   -0.8923   -0.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5989   -0.6529   -0.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9789    0.6337    0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0519    1.5970    0.3126 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2745    1.3940    0.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1692    2.4495    0.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5205    2.2068    0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9315    0.9242   -0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0504   -0.1215   -0.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6918    0.1116   -0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3909    1.0656    0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3684   -0.0472    0.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9658   -1.1895   -0.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6093   -1.7292   -0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9836   -2.6799   -0.0654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7154   -2.7516   -1.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8059    3.4243    0.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2613    3.0105    0.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0126    0.7641   -0.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3738   -1.1194   -0.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4364    1.6138    1.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5791    1.8277   -0.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3370    0.3479   -0.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6118   -0.3970    1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7182   -1.9962   -0.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0758   -0.8424   -1.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6995   -2.3073    0.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3257   -2.4355   -1.1134 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 11  2  1  0
 15  3  1  0
 11  6  1  0
  1 16  1  0
  1 17  1  0
  7 18  1  0
  8 19  1  0
  9 20  1  0
 10 21  1  0
 12 22  1  0
 12 23  1  0
 13 24  1  0
 13 25  1  0
 14 26  1  0
 14 27  1  0
 15 28  1  0
 15 29  1  0
M  END

382
  Mrv0541 02231214382D          

 15 17  0  0  0  0            999 V2000
    3.6958   -1.2972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6958    1.0790    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5842   -0.0926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3019    0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5842   -0.9176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0099   -0.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3019   -1.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0099   -0.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6958    0.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3819   -0.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3819   -0.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0899    0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0899   -1.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8076   -0.0926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8076   -0.9176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  2  0  0  0  0
  1 11  1  0  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11 13  2  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014526

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=C2CCCCC2=NC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C13H14N2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1,3,5,7H,2,4,6,8H2,(H2,14,15)

> <INCHI_KEY>
YLJREFDVOIBQDA-UHFFFAOYSA-N

> <FORMULA>
C13H14N2

> <MOLECULAR_WEIGHT>
198.2637

> <EXACT_MASS>
198.115698458

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
22.79015707088682

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,2,3,4-tetrahydroacridin-9-amine

> <ALOGPS_LOGP>
3.13

> <JCHEM_LOGP>
2.628144685

> <ALOGPS_LOGS>
-3.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.953831978668072

> <JCHEM_POLAR_SURFACE_AREA>
38.91

> <JCHEM_REFRACTIVITY>
61.73810000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tacrine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014526
     RDKit          3D
Tacrine
 29 31  0  0  0  0  0  0  0  0999 V2000
   -1.1984   -2.2087   -0.5496 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7586   -0.8923   -0.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5989   -0.6529   -0.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9789    0.6337    0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0519    1.5970    0.3126 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2745    1.3940    0.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1692    2.4495    0.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5205    2.2068    0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9315    0.9242   -0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0504   -0.1215   -0.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6918    0.1116   -0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3909    1.0656    0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3684   -0.0472    0.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9658   -1.1895   -0.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6093   -1.7292   -0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9836   -2.6799   -0.0654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7154   -2.7516   -1.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8059    3.4243    0.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2613    3.0105    0.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0126    0.7641   -0.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3738   -1.1194   -0.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4364    1.6138    1.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5791    1.8277   -0.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3370    0.3479   -0.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6118   -0.3970    1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7182   -1.9962   -0.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0758   -0.8424   -1.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6995   -2.3073    0.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3257   -2.4355   -1.1134 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 11  2  1  0
 15  3  1  0
 11  6  1  0
  1 16  1  0
  1 17  1  0
  7 18  1  0
  8 19  1  0
  9 20  1  0
 10 21  1  0
 12 22  1  0
 12 23  1  0
 13 24  1  0
 13 25  1  0
 14 26  1  0
 14 27  1  0
 15 28  1  0
 15 29  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 382                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       6.899  -2.421   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0       6.899   2.014   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.957  -0.173   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.297   0.587   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.957  -1.713   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.618  -0.204   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.297  -2.473   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.618  -1.682   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.899   0.536   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.180  -0.204   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.180  -1.682   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.501   0.587   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.501  -2.473   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.841  -0.173   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.841  -1.713   0.000  0.00  0.00           C+0
CONECT    1    8   11                                                       
CONECT    2    9                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8    9                                                  
CONECT    7    5    8                                                       
CONECT    8    1    6    7                                                  
CONECT    9    2    6   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11    1   10   13                                                  
CONECT   12   10   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   15                                                       
CONECT   15   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

COMPND    HMDB0014526
HETATM    1  N1  UNL     1      -1.198  -2.209  -0.550  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.759  -0.892  -0.251  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.599  -0.653  -0.135  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.979   0.634   0.154  1.00  0.00           C  
HETATM    5  N2  UNL     1       0.052   1.597   0.313  1.00  0.00           N  
HETATM    6  C4  UNL     1      -1.275   1.394   0.206  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.169   2.449   0.385  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.520   2.207   0.269  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.931   0.924  -0.021  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.050  -0.122  -0.199  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.692   0.112  -0.084  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.391   1.066   0.313  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.368  -0.047   0.283  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.966  -1.190  -0.620  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.609  -1.729  -0.313  1.00  0.00           C  
HETATM   16  H1  UNL     1      -1.984  -2.680  -0.065  1.00  0.00           H  
HETATM   17  H2  UNL     1      -0.715  -2.752  -1.298  1.00  0.00           H  
HETATM   18  H3  UNL     1      -1.806   3.424   0.608  1.00  0.00           H  
HETATM   19  H4  UNL     1      -4.261   3.010   0.403  1.00  0.00           H  
HETATM   20  H5  UNL     1      -5.013   0.764  -0.107  1.00  0.00           H  
HETATM   21  H6  UNL     1      -3.374  -1.119  -0.425  1.00  0.00           H  
HETATM   22  H7  UNL     1       2.436   1.614   1.299  1.00  0.00           H  
HETATM   23  H8  UNL     1       2.579   1.828  -0.476  1.00  0.00           H  
HETATM   24  H9  UNL     1       4.337   0.348  -0.137  1.00  0.00           H  
HETATM   25  H10 UNL     1       3.612  -0.397   1.317  1.00  0.00           H  
HETATM   26  H11 UNL     1       3.718  -1.996  -0.477  1.00  0.00           H  
HETATM   27  H12 UNL     1       3.076  -0.842  -1.674  1.00  0.00           H  
HETATM   28  H13 UNL     1       1.700  -2.307   0.653  1.00  0.00           H  
HETATM   29  H14 UNL     1       1.326  -2.435  -1.113  1.00  0.00           H  
CONECT    1    2   16   17
CONECT    2    3    3   11
CONECT    3    4   15
CONECT    4    5    5   12
CONECT    5    6
CONECT    6    7    7   11
CONECT    7    8   18
CONECT    8    9    9   19
CONECT    9   10   20
CONECT   10   11   11   21
CONECT   12   13   22   23
CONECT   13   14   24   25
CONECT   14   15   26   27
CONECT   15   28   29
END

HMDB0014526
     RDKit          3D
Tacrine
 29 31  0  0  0  0  0  0  0  0999 V2000
   -1.1984   -2.2087   -0.5496 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7586   -0.8923   -0.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5989   -0.6529   -0.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9789    0.6337    0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0519    1.5970    0.3126 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2745    1.3940    0.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1692    2.4495    0.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5205    2.2068    0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9315    0.9242   -0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0504   -0.1215   -0.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6918    0.1116   -0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3909    1.0656    0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3684   -0.0472    0.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9658   -1.1895   -0.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6093   -1.7292   -0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9836   -2.6799   -0.0654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7154   -2.7516   -1.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8059    3.4243    0.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2613    3.0105    0.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0126    0.7641   -0.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3738   -1.1194   -0.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4364    1.6138    1.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5791    1.8277   -0.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3370    0.3479   -0.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6118   -0.3970    1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7182   -1.9962   -0.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0758   -0.8424   -1.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6995   -2.3073    0.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3257   -2.4355   -1.1134 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 11  2  1  0
 15  3  1  0
 11  6  1  0
  1 16  1  0
  1 17  1  0
  7 18  1  0
  8 19  1  0
  9 20  1  0
 10 21  1  0
 12 22  1  0
 12 23  1  0
 13 24  1  0
 13 25  1  0
 14 26  1  0
 14 27  1  0
 15 28  1  0
 15 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2,3,4-Tetrahydro-9-acridinamine	ChEBI
1,2,3,4-Tetrahydro-9-aminoacridine	ChEBI
5-Amino-6,7,8,9-tetrahydroacridine	ChEBI
9-Amino-1,2,3,4-tetrahydroacridine	ChEBI
Tetrahydroaminacrine	ChEBI
Tacrinal	Kegg
Tetrahydroaminoacridine	HMDB
Tetrahydroaminocrin	HMDB
Tetrahydroaminocrine	HMDB
THA	HMDB
1,2,3,4-Tetrahydroaminoacridine	HMDB
Horizon brand OF tacrine hydrochloride	HMDB
OTL pharm brand OF tacrine hydrochloride	HMDB
Parke davis brand OF tacrine hydrochloride	HMDB
Tenakrin	HMDB
Romotal	HMDB
Cognex	HMDB
Tacrine hydrochloride	HMDB
Woods brand OF tacrine hydrochloride	HMDB

Chemical Formula

C₁₃H₁₄N₂

Average Molecular Weight

198.2637

Monoisotopic Molecular Weight

198.115698458

IUPAC Name

1,2,3,4-tetrahydroacridin-9-amine

Traditional Name

tacrine

CAS Registry Number

321-64-2

SMILES

NC1=C2CCCCC2=NC2=CC=CC=C12

InChI Identifier

InChI=1S/C13H14N2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1,3,5,7H,2,4,6,8H2,(H2,14,15)

InChI Key

YLJREFDVOIBQDA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocycle which consists of two benzene rings joined by a pyridine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Acridines

Alternative Parents

Substituents

Acridine
4-aminoquinoline
Aminoquinoline
Aminopyridine
Benzenoid
Pyridine
Heteroaromatic compound
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic amine (CHEBI:45980 )
acridines (CHEBI:45980 )
a small molecule (CPD-10887 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0014526)
Membrane (HMDB: HMDB0014526)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Not Available

EC 3.1.1.7 (acetylcholinesterase) inhibitor (HMDB: HMDB0014526)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	183.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.14 g/L	Not Available
LogP	2.2	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	141.43	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001107

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	3.13	ALOGPS
logP	2.63	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	8.95	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.91 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	61.74 m³·mol⁻¹	ChemAxon
Polarizability	22.79 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	143.174	31661259
DarkChem	[M-H]-	143.993	31661259
DeepCCS	[M-2H]-	177.978	30932474
DeepCCS	[M+Na]+	153.516	30932474
AllCCS	[M+H]+	144.9	32859911
AllCCS	[M+H-H2O]+	140.6	32859911
AllCCS	[M+NH4]+	149.0	32859911
AllCCS	[M+Na]+	150.1	32859911
AllCCS	[M-H]-	150.7	32859911
AllCCS	[M+Na-2H]-	150.5	32859911
AllCCS	[M+HCOO]-	150.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tacrine	NC1=C2CCCCC2=NC2=CC=CC=C12	2983.7	Standard polar	33892256
Tacrine	NC1=C2CCCCC2=NC2=CC=CC=C12	2179.2	Standard non polar	33892256
Tacrine	NC1=C2CCCCC2=NC2=CC=CC=C12	2172.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tacrine,1TMS,isomer #1	C[Si](C)(C)NC1=C2CCCCC2=NC2=CC=CC=C12	2152.8	Semi standard non polar	33892256
Tacrine,1TMS,isomer #1	C[Si](C)(C)NC1=C2CCCCC2=NC2=CC=CC=C12	1952.7	Standard non polar	33892256
Tacrine,1TMS,isomer #1	C[Si](C)(C)NC1=C2CCCCC2=NC2=CC=CC=C12	2768.3	Standard polar	33892256
Tacrine,2TMS,isomer #1	C[Si](C)(C)N(C1=C2CCCCC2=NC2=CC=CC=C12)[Si](C)(C)C	2227.5	Semi standard non polar	33892256
Tacrine,2TMS,isomer #1	C[Si](C)(C)N(C1=C2CCCCC2=NC2=CC=CC=C12)[Si](C)(C)C	2096.8	Standard non polar	33892256
Tacrine,2TMS,isomer #1	C[Si](C)(C)N(C1=C2CCCCC2=NC2=CC=CC=C12)[Si](C)(C)C	2650.2	Standard polar	33892256
Tacrine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=C2CCCCC2=NC2=CC=CC=C12	2396.3	Semi standard non polar	33892256
Tacrine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=C2CCCCC2=NC2=CC=CC=C12	2185.4	Standard non polar	33892256
Tacrine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=C2CCCCC2=NC2=CC=CC=C12	2915.2	Standard polar	33892256
Tacrine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=C2CCCCC2=NC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2632.6	Semi standard non polar	33892256
Tacrine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=C2CCCCC2=NC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2537.4	Standard non polar	33892256
Tacrine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=C2CCCCC2=NC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2824.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tacrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00r2-0900000000-e2921d2cb64d7c502a4b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tacrine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tacrine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tacrine LC-ESI-QQ , positive-QTOF	splash10-0002-0900000000-453e4e963f034e9de4cf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tacrine LC-ESI-QQ , positive-QTOF	splash10-0002-0900000000-256a5702a96325bc74f2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tacrine LC-ESI-QQ , positive-QTOF	splash10-0002-0900000000-af483bfb98e7e2b87b39	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tacrine LC-ESI-QQ , positive-QTOF	splash10-006t-0900000000-3c9902ca237f9c26a2fb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tacrine LC-ESI-QQ , positive-QTOF	splash10-006x-0900000000-dec59115a19fdec78a9f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tacrine , positive-QTOF	splash10-0002-0900000000-c04cbf634e493a774cd5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tacrine 90V, Positive-QTOF	splash10-006t-0900000000-2ea3694383dd21b13356	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tacrine 15V, Positive-QTOF	splash10-0002-0900000000-2ffc3da62f3c0184f7c5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tacrine 35V, Positive-QTOF	splash10-0002-0900000000-676b079fd7de743702db	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tacrine 30V, Positive-QTOF	splash10-0002-0900000000-67a5eac4e8faa4d5cd65	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tacrine 45V, Positive-QTOF	splash10-0002-0900000000-b04e175289861dc518f1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tacrine 90V, Positive-QTOF	splash10-006t-0900000000-9ebb090b4661d7668df3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tacrine 60V, Positive-QTOF	splash10-0002-0900000000-f2347baf04672bb9e5bb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tacrine 75V, Positive-QTOF	splash10-0002-0900000000-9a37bfbb7353bd8bce87	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tacrine 10V, Positive-QTOF	splash10-001j-0900000000-2f420836beda4ff3e6b2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tacrine 20V, Positive-QTOF	splash10-001i-0900000000-2275f7938116d06948a0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tacrine 40V, Positive-QTOF	splash10-001i-2900000000-1f84e054a206191e525d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tacrine 10V, Negative-QTOF	splash10-0002-0900000000-e9e614ab5237139c5988	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tacrine 20V, Negative-QTOF	splash10-0002-0900000000-0903202525aeeeca151c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tacrine 40V, Negative-QTOF	splash10-00l2-0900000000-ba164ed659e5620dad0a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tacrine 10V, Negative-QTOF	splash10-0002-0900000000-d2d648aa4423d0c7a455	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tacrine 20V, Negative-QTOF	splash10-0002-0900000000-d2d648aa4423d0c7a455	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tacrine 40V, Negative-QTOF	splash10-014m-0900000000-28208ede76de2a1de764	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tacrine 10V, Positive-QTOF	splash10-0002-0900000000-d89ea9976ffd35a15c71	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tacrine 20V, Positive-QTOF	splash10-0002-0900000000-d89ea9976ffd35a15c71	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00382	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00382	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00382

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

1859

KEGG Compound ID

C01453

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tacrine

METLIN ID

Not Available

PubChem Compound

1935

PDB ID

Not Available

ChEBI ID

45980

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

Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: [PubMed:20480924 ]
Qizilbash N, Whitehead A, Higgins J, Wilcock G, Schneider L, Farlow M: Cholinesterase inhibition for Alzheimer disease: a meta-analysis of the tacrine trials. Dementia Trialists' Collaboration. JAMA. 1998 Nov 25;280(20):1777-82. [PubMed:9842955 ]

Enzymes

Enzyme Details

1. Acetylcholinesterase

General function:: Involved in carboxylesterase activity
Specific function:: Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:: ACHE
Uniprot ID:: P22303
Molecular weight:: 67795.525

References

Davis KL: Alzheimer's disease: seeking new ways to preserve brain function. Interview by Alice V. Luddington. Geriatrics. 1999 Feb;54(2):42-7; quiz 48. [PubMed:10024872 ]
Wang H, Carlier PR, Ho WL, Wu DC, Lee NT, Li CP, Pang YP, Han YF: Effects of bis(7)-tacrine, a novel anti-Alzheimer's agent, on rat brain AChE. Neuroreport. 1999 Mar 17;10(4):789-93. [PubMed:10208549 ]
Traykov L, Tavitian B, Jobert A, Boller F, Forette F, Crouzel C, Di Giamberardino L, Pappata S: In vivo PET study of cerebral [11C] methyl- tetrahydroaminoacridine distribution and kinetics in healthy human subjects. Eur J Neurol. 1999 May;6(3):273-8. [PubMed:10210906 ]
Wang H, Tang XC: Anticholinesterase effects of huperzine A, E2020, and tacrine in rats. Zhongguo Yao Li Xue Bao. 1998 Jan;19(1):27-30. [PubMed:10375753 ]
Kosasa T, Kuriya Y, Matsui K, Yamanishi Y: Effect of donepezil hydrochloride (E2020) on basal concentration of extracellular acetylcholine in the hippocampus of rats. Eur J Pharmacol. 1999 Sep 10;380(2-3):101-7. [PubMed:10513568 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Takatori Y: [Mechanisms of neuroprotective effects of therapeutic acetylcholinesterase inhibitors used in treatment of Alzheimer's disease]. Yakugaku Zasshi. 2006 Aug;126(8):607-16. [PubMed:16880719 ]
Du DM, Carlier PR: Development of bivalent acetylcholinesterase inhibitors as potential therapeutic drugs for Alzheimer's disease. Curr Pharm Des. 2004;10(25):3141-56. [PubMed:15544504 ]
Krustev AD, Argirova MD, Getova DP, Turiiski VI, Prissadova NA: Calcium-independent tacrine-induced relaxation of rat gastric corpus smooth muscles. Can J Physiol Pharmacol. 2006 Nov;84(11):1133-8. [PubMed:17218977 ]
Villarroya M, Garcia AG, Marco JL: New classes of AChE inhibitors with additional pharmacological effects of interest for the treatment of Alzheimer's disease. Curr Pharm Des. 2004;10(25):3177-84. [PubMed:15544507 ]
Marco JL, Carreiras MC: Recent developments in the synthesis of acetylcholinesterase inhibitors. Mini Rev Med Chem. 2003 Sep;3(6):518-24. [PubMed:12871155 ]
Ahmed M, Rocha JB, Correa M, Mazzanti CM, Zanin RF, Morsch AL, Morsch VM, Schetinger MR: Inhibition of two different cholinesterases by tacrine. Chem Biol Interact. 2006 Aug 25;162(2):165-71. Epub 2006 Jun 17. [PubMed:16860785 ]

Enzyme Details

2. Cholinesterase

General function:: Involved in carboxylesterase activity
Specific function:: Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:: BCHE
Uniprot ID:: P06276
Molecular weight:: 68417.575

References

Wang H, Tang XC: Anticholinesterase effects of huperzine A, E2020, and tacrine in rats. Zhongguo Yao Li Xue Bao. 1998 Jan;19(1):27-30. [PubMed:10375753 ]
Krustev AD, Argirova MD, Getova DP, Turiiski VI, Prissadova NA: Calcium-independent tacrine-induced relaxation of rat gastric corpus smooth muscles. Can J Physiol Pharmacol. 2006 Nov;84(11):1133-8. [PubMed:17218977 ]
Marco JL, Carreiras MC: Recent developments in the synthesis of acetylcholinesterase inhibitors. Mini Rev Med Chem. 2003 Sep;3(6):518-24. [PubMed:12871155 ]
Ahmed M, Rocha JB, Correa M, Mazzanti CM, Zanin RF, Morsch AL, Morsch VM, Schetinger MR: Inhibition of two different cholinesterases by tacrine. Chem Biol Interact. 2006 Aug 25;162(2):165-71. Epub 2006 Jun 17. [PubMed:16860785 ]

Enzyme Details

3. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Wang B, Zhou SF: Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218. [PubMed:19754423 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Obach RS, Reed-Hagen AE: Measurement of Michaelis constants for cytochrome P450-mediated biotransformation reactions using a substrate depletion approach. Drug Metab Dispos. 2002 Jul;30(7):831-7. [PubMed:12065442 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. [PubMed:12438524 ]

Showing metabocard for Tacrine (HMDB0014526)

MOL for HMDB0014526 (Tacrine)

3D MOL for HMDB0014526 (Tacrine)

3D SDF for HMDB0014526 (Tacrine)

3D-SDF for HMDB0014526 (Tacrine)

PDB for HMDB0014526 (Tacrine)

3D PDB for HMDB0014526 (Tacrine)

SMILES for HMDB0014526 (Tacrine)

INCHI for HMDB0014526 (Tacrine)

Structure for HMDB0014526 (Tacrine)

3D Structure for HMDB0014526 (Tacrine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Enzymes

References

References

References

Transporters

References