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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 18:53:44 UTC

Update Date

2023-02-21 17:30:11 UTC

HMDB ID

HMDB0060703

Secondary Accession Numbers

HMDB60703

Metabolite Identification

Common Name

1-Amino-3-hydroxymethyl-5-methyl-adamantane

Description

1-Amino-3-hydroxymethyl-5-methyl-adamantane is a metabolite of memantine. Memantine is the first in a novel class of Alzheimer's disease medications acting on the glutamatergic system by blocking NMDA glutamate receptors. It was first synthesized by Eli Lilly and Company in 1968. Memantine is marketed under the brands Axura and Akatinol by Merz, Namenda by Forest, Ebixa and Abixa by Lundbeck and Memox by Unipharm. Despite years of research, there is little evidence of effect in mild to moderate Alzheimer's disease. (Wikipedia)

Structure

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

HMDB0060703
     RDKit          3D
1-Amino-3-hydroxymethyl-5-methyl-adamantane
 35 37  0  0  0  0  0  0  0  0999 V2000
   -2.6387   -1.1088   -0.7690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3680   -0.4738   -0.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3127   -0.7224    1.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0641   -0.1207    1.8051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0959    1.3577    1.4952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296    1.5590    0.0014 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1528    2.9571   -0.2520 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2654    0.9850   -0.6083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1692    0.8302   -0.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1105   -0.6390   -0.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2458   -1.3394   -0.9732 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4995   -0.8824   -0.6096 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1459   -0.8037    1.2166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1765   -1.1739   -0.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9936   -0.6991   -1.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4152   -1.0656    0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4337   -2.1948   -0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2525   -1.8186    1.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126   -0.2831    1.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0832   -0.2554    2.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1184    1.7152    1.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6204    1.9491    2.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8975    3.1698   -0.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7216    3.4836   -0.3981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1280    1.0305   -1.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1860    1.5465   -0.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1048    1.2350   -0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0819    0.9373   -1.7076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0978   -1.1684   -2.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1995   -2.4427   -0.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4352   -0.2660    0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1088   -1.8617    1.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0319   -0.2994    1.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2425   -2.2709   -0.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1636   -0.8662   -1.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 10 14  1  0
  8  2  1  0
 14  2  1  0
 13  4  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
M  END

  Mrv0541 07041311532D          

 14 16  0  0  0  0            999 V2000
    0.8517   -2.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8517   -0.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5657   -0.4945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0368   -0.4945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1163   -2.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5873   -2.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3012   -1.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2319   -1.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3012   -0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8517   -1.6585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5657   -1.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0368   -1.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8344   -1.4529    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8133   -1.6163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  2  1  0  0  0  0
  9  3  1  0  0  0  0
  9  4  1  0  0  0  0
 10  1  1  0  0  0  0
 12  7  1  0  0  0  0
 10  5  1  0  0  0  0
 10  6  1  0  0  0  0
 12  6  1  0  0  0  0
 11  5  1  0  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  4  1  0  0  0  0
 11  3  1  0  0  0  0
 10  2  1  0  0  0  0
 13 12  1  0  0  0  0
 14  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060703

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CC3CC(N)(C1)CC(CO)(C3)C2

> <INCHI_IDENTIFIER>
InChI=1S/C12H21NO/c1-10-2-9-3-11(5-10,8-14)7-12(13,4-9)6-10/h9,14H,2-8,13H2,1H3

> <INCHI_KEY>
YANGLOGEEOBUMT-UHFFFAOYSA-N

> <FORMULA>
C12H21NO

> <MOLECULAR_WEIGHT>
195.3012

> <EXACT_MASS>
195.162314299

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
22.76391234013325

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3-amino-5-methyladamantan-1-yl)methanol

> <ALOGPS_LOGP>
1.46

> <JCHEM_LOGP>
0.7852706316666658

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.105587458860764

> <JCHEM_PKA_STRONGEST_BASIC>
10.393199321398416

> <JCHEM_POLAR_SURFACE_AREA>
46.25

> <JCHEM_REFRACTIVITY>
56.26049999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3-amino-5-methyladamantan-1-yl)methanol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060703
     RDKit          3D
1-Amino-3-hydroxymethyl-5-methyl-adamantane
 35 37  0  0  0  0  0  0  0  0999 V2000
   -2.6387   -1.1088   -0.7690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3680   -0.4738   -0.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3127   -0.7224    1.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0641   -0.1207    1.8051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0959    1.3577    1.4952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296    1.5590    0.0014 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1528    2.9571   -0.2520 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2654    0.9850   -0.6083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1692    0.8302   -0.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1105   -0.6390   -0.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2458   -1.3394   -0.9732 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4995   -0.8824   -0.6096 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1459   -0.8037    1.2166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1765   -1.1739   -0.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9936   -0.6991   -1.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4152   -1.0656    0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4337   -2.1948   -0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2525   -1.8186    1.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126   -0.2831    1.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0832   -0.2554    2.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1184    1.7152    1.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6204    1.9491    2.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8975    3.1698   -0.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7216    3.4836   -0.3981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1280    1.0305   -1.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1860    1.5465   -0.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1048    1.2350   -0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0819    0.9373   -1.7076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0978   -1.1684   -2.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1995   -2.4427   -0.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4352   -0.2660    0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1088   -1.8617    1.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0319   -0.2994    1.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2425   -2.2709   -0.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1636   -0.8662   -1.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 10 14  1  0
  8  2  1  0
 14  2  1  0
 13  4  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
M  END

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  C   UNK     0       1.590  -4.636   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.590  -1.701   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.056  -0.923   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.802  -0.923   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.217  -3.793   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.963  -3.793   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.429  -3.016   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.433  -1.925   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.429  -0.225   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.590  -3.096   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.056  -2.318   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.802  -2.318   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       5.291  -2.712   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0      -1.518  -3.017   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2    9   10                                                       
CONECT    3    9   11                                                       
CONECT    4    9   12                                                       
CONECT    5   10   11                                                       
CONECT    6   10   12                                                       
CONECT    7   12   11                                                       
CONECT    8   11   14                                                       
CONECT    9    2    3    4                                                  
CONECT   10    1    5    6    2                                             
CONECT   11    5    7    8    3                                             
CONECT   12    7    6    4   13                                             
CONECT   13   12                                                            
CONECT   14    8                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   32    0
END

COMPND    HMDB0060703
HETATM    1  C1  UNL     1      -2.639  -1.109  -0.769  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.368  -0.474  -0.261  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.313  -0.722   1.227  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.064  -0.121   1.805  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.096   1.358   1.495  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.030   1.559   0.001  1.00  0.00           C  
HETATM    7  N1  UNL     1       0.153   2.957  -0.252  1.00  0.00           N  
HETATM    8  C7  UNL     1      -1.265   0.985  -0.608  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.169   0.830  -0.600  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.110  -0.639  -0.273  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.246  -1.339  -0.973  1.00  0.00           C  
HETATM   12  O1  UNL     1       3.499  -0.882  -0.610  1.00  0.00           O  
HETATM   13  C11 UNL     1       1.146  -0.804   1.217  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.176  -1.174  -0.875  1.00  0.00           C  
HETATM   15  H1  UNL     1      -2.994  -0.699  -1.712  1.00  0.00           H  
HETATM   16  H2  UNL     1      -3.415  -1.066   0.046  1.00  0.00           H  
HETATM   17  H3  UNL     1      -2.434  -2.195  -0.906  1.00  0.00           H  
HETATM   18  H4  UNL     1      -1.252  -1.819   1.380  1.00  0.00           H  
HETATM   19  H5  UNL     1      -2.213  -0.283   1.689  1.00  0.00           H  
HETATM   20  H6  UNL     1      -0.083  -0.255   2.902  1.00  0.00           H  
HETATM   21  H7  UNL     1      -1.118   1.715   1.810  1.00  0.00           H  
HETATM   22  H8  UNL     1       0.620   1.949   2.060  1.00  0.00           H  
HETATM   23  H9  UNL     1       0.898   3.170  -0.942  1.00  0.00           H  
HETATM   24  H10 UNL     1      -0.722   3.484  -0.398  1.00  0.00           H  
HETATM   25  H11 UNL     1      -1.128   1.031  -1.727  1.00  0.00           H  
HETATM   26  H12 UNL     1      -2.186   1.546  -0.398  1.00  0.00           H  
HETATM   27  H13 UNL     1       2.105   1.235  -0.220  1.00  0.00           H  
HETATM   28  H14 UNL     1       1.082   0.937  -1.708  1.00  0.00           H  
HETATM   29  H15 UNL     1       2.098  -1.168  -2.071  1.00  0.00           H  
HETATM   30  H16 UNL     1       2.200  -2.443  -0.844  1.00  0.00           H  
HETATM   31  H17 UNL     1       3.435  -0.266   0.141  1.00  0.00           H  
HETATM   32  H18 UNL     1       1.109  -1.862   1.539  1.00  0.00           H  
HETATM   33  H19 UNL     1       2.032  -0.299   1.616  1.00  0.00           H  
HETATM   34  H20 UNL     1      -0.242  -2.271  -0.826  1.00  0.00           H  
HETATM   35  H21 UNL     1      -0.164  -0.866  -1.956  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    8   14
CONECT    3    4   18   19
CONECT    4    5   13   20
CONECT    5    6   21   22
CONECT    6    7    8    9
CONECT    7   23   24
CONECT    8   25   26
CONECT    9   10   27   28
CONECT   10   11   13   14
CONECT   11   12   29   30
CONECT   12   31
CONECT   13   32   33
CONECT   14   34   35
END

HMDB0060703
     RDKit          3D
1-Amino-3-hydroxymethyl-5-methyl-adamantane
 35 37  0  0  0  0  0  0  0  0999 V2000
   -2.6387   -1.1088   -0.7690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3680   -0.4738   -0.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3127   -0.7224    1.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0641   -0.1207    1.8051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0959    1.3577    1.4952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296    1.5590    0.0014 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1528    2.9571   -0.2520 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2654    0.9850   -0.6083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1692    0.8302   -0.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1105   -0.6390   -0.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2458   -1.3394   -0.9732 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4995   -0.8824   -0.6096 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1459   -0.8037    1.2166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1765   -1.1739   -0.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9936   -0.6991   -1.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4152   -1.0656    0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4337   -2.1948   -0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2525   -1.8186    1.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126   -0.2831    1.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0832   -0.2554    2.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1184    1.7152    1.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6204    1.9491    2.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8975    3.1698   -0.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7216    3.4836   -0.3981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1280    1.0305   -1.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1860    1.5465   -0.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1048    1.2350   -0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0819    0.9373   -1.7076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0978   -1.1684   -2.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1995   -2.4427   -0.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4352   -0.2660    0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1088   -1.8617    1.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0319   -0.2994    1.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2425   -2.2709   -0.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1636   -0.8662   -1.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 10 14  1  0
  8  2  1  0
 14  2  1  0
 13  4  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₂H₂₁NO

Average Molecular Weight

195.3012

Monoisotopic Molecular Weight

195.162314299

IUPAC Name

(3-amino-5-methyladamantan-1-yl)methanol

Traditional Name

(3-amino-5-methyladamantan-1-yl)methanol

CAS Registry Number

Not Available

SMILES

CC12CC3CC(N)(C1)CC(CO)(C3)C2

InChI Identifier

InChI=1S/C12H21NO/c1-10-2-9-3-11(5-10,8-14)7-12(13,4-9)6-10/h9,14H,2-8,13H2,1H3

InChI Key

YANGLOGEEOBUMT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Primary alcohols

Alternative Parents

Substituents

Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Primary alcohol
Organonitrogen compound
Primary aliphatic amine
Amine
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060703)

Organ

Kidney (HMDB: HMDB0060703)
Liver (HMDB: HMDB0060703)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060703)

Cellular substructure

Cytoplasm (HMDB: HMDB0060703)

Source

Endogenous

Endogenous (HMDB: HMDB0060703)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.92 g/L	ALOGPS
logP	1.46	ALOGPS
logP	0.79	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	15.11	ChemAxon
pKa (Strongest Basic)	10.39	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	46.25 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	56.26 m³·mol⁻¹	ChemAxon
Polarizability	22.76 Å³	ChemAxon
Number of Rings	3	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]+	142.524	31661259
DarkChem	[M-H]-	139.284	31661259
DeepCCS	[M-2H]-	191.255	30932474
DeepCCS	[M+Na]+	166.733	30932474
AllCCS	[M+H]+	145.6	32859911
AllCCS	[M+H-H2O]+	141.8	32859911
AllCCS	[M+NH4]+	149.1	32859911
AllCCS	[M+Na]+	150.2	32859911
AllCCS	[M-H]-	149.2	32859911
AllCCS	[M+Na-2H]-	149.6	32859911
AllCCS	[M+HCOO]-	150.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-Amino-3-hydroxymethyl-5-methyl-adamantane	CC12CC3CC(N)(C1)CC(CO)(C3)C2	2383.5	Standard polar	33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane	CC12CC3CC(N)(C1)CC(CO)(C3)C2	1630.4	Standard non polar	33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane	CC12CC3CC(N)(C1)CC(CO)(C3)C2	1601.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-Amino-3-hydroxymethyl-5-methyl-adamantane,1TMS,isomer #1	CC12CC3CC(N)(C1)CC(CO[Si](C)(C)C)(C3)C2	1654.4	Semi standard non polar	33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,1TMS,isomer #2	CC12CC3CC(CO)(C1)CC(N[Si](C)(C)C)(C3)C2	1872.5	Semi standard non polar	33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,2TMS,isomer #1	CC12CC3CC(CO[Si](C)(C)C)(C1)CC(N[Si](C)(C)C)(C3)C2	1823.5	Semi standard non polar	33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,2TMS,isomer #1	CC12CC3CC(CO[Si](C)(C)C)(C1)CC(N[Si](C)(C)C)(C3)C2	1888.7	Standard non polar	33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,2TMS,isomer #1	CC12CC3CC(CO[Si](C)(C)C)(C1)CC(N[Si](C)(C)C)(C3)C2	2239.1	Standard polar	33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,2TMS,isomer #2	CC12CC3CC(CO)(C1)CC(N([Si](C)(C)C)[Si](C)(C)C)(C3)C2	1966.6	Semi standard non polar	33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,2TMS,isomer #2	CC12CC3CC(CO)(C1)CC(N([Si](C)(C)C)[Si](C)(C)C)(C3)C2	2004.5	Standard non polar	33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,2TMS,isomer #2	CC12CC3CC(CO)(C1)CC(N([Si](C)(C)C)[Si](C)(C)C)(C3)C2	2278.2	Standard polar	33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,3TMS,isomer #1	CC12CC3CC(CO[Si](C)(C)C)(C1)CC(N([Si](C)(C)C)[Si](C)(C)C)(C3)C2	1975.4	Semi standard non polar	33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,3TMS,isomer #1	CC12CC3CC(CO[Si](C)(C)C)(C1)CC(N([Si](C)(C)C)[Si](C)(C)C)(C3)C2	2061.8	Standard non polar	33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,3TMS,isomer #1	CC12CC3CC(CO[Si](C)(C)C)(C1)CC(N([Si](C)(C)C)[Si](C)(C)C)(C3)C2	2146.3	Standard polar	33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,1TBDMS,isomer #1	CC12CC3CC(N)(C1)CC(CO[Si](C)(C)C(C)(C)C)(C3)C2	1943.1	Semi standard non polar	33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,1TBDMS,isomer #2	CC12CC3CC(CO)(C1)CC(N[Si](C)(C)C(C)(C)C)(C3)C2	2121.3	Semi standard non polar	33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,2TBDMS,isomer #1	CC12CC3CC(CO[Si](C)(C)C(C)(C)C)(C1)CC(N[Si](C)(C)C(C)(C)C)(C3)C2	2289.6	Semi standard non polar	33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,2TBDMS,isomer #1	CC12CC3CC(CO[Si](C)(C)C(C)(C)C)(C1)CC(N[Si](C)(C)C(C)(C)C)(C3)C2	2297.7	Standard non polar	33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,2TBDMS,isomer #1	CC12CC3CC(CO[Si](C)(C)C(C)(C)C)(C1)CC(N[Si](C)(C)C(C)(C)C)(C3)C2	2500.3	Standard polar	33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,2TBDMS,isomer #2	CC12CC3CC(CO)(C1)CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C3)C2	2390.6	Semi standard non polar	33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,2TBDMS,isomer #2	CC12CC3CC(CO)(C1)CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C3)C2	2427.4	Standard non polar	33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,2TBDMS,isomer #2	CC12CC3CC(CO)(C1)CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C3)C2	2481.8	Standard polar	33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,3TBDMS,isomer #1	CC12CC3CC(CO[Si](C)(C)C(C)(C)C)(C1)CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C3)C2	2611.0	Semi standard non polar	33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,3TBDMS,isomer #1	CC12CC3CC(CO[Si](C)(C)C(C)(C)C)(C1)CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C3)C2	2674.4	Standard non polar	33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,3TBDMS,isomer #1	CC12CC3CC(CO[Si](C)(C)C(C)(C)C)(C1)CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C3)C2	2441.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-adamantane GC-MS (Non-derivatized) - 70eV, Positive	splash10-03gj-0900000000-239a470b7a7f717f372a	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-adamantane GC-MS (1 TMS) - 70eV, Positive	splash10-0umi-9640000000-6c1f4b68b351929b109e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-adamantane 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 - 1-Amino-3-hydroxymethyl-5-methyl-adamantane 10V, Positive-QTOF	splash10-004j-0900000000-7c3f69c532e70bc65644	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-adamantane 20V, Positive-QTOF	splash10-01t9-0900000000-c02fade9e295b01b6064	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-adamantane 40V, Positive-QTOF	splash10-03di-0900000000-565d74909c0bf810f697	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-adamantane 10V, Negative-QTOF	splash10-0006-0900000000-ffc3c256cf08fdf0c59a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-adamantane 20V, Negative-QTOF	splash10-01r6-0900000000-fd832ea7f1d7b2f28ace	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-adamantane 40V, Negative-QTOF	splash10-03dj-0900000000-adae6857a9872ccb9da2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-adamantane 10V, Positive-QTOF	splash10-0002-0900000000-0e0b6e8e50016270ad14	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-adamantane 20V, Positive-QTOF	splash10-002b-0900000000-7a75a3560ff1e26fd625	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-adamantane 40V, Positive-QTOF	splash10-004j-0900000000-e5f85a05e8d59e580be7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-adamantane 10V, Negative-QTOF	splash10-0006-0900000000-7656e1a7f93372378cd4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-adamantane 20V, Negative-QTOF	splash10-0006-0900000000-7656e1a7f93372378cd4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-adamantane 40V, Negative-QTOF	splash10-0006-0900000000-7656e1a7f93372378cd4	2021-10-12	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

2850520

PDB ID

Not Available

ChEBI ID

Not Available

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 1-Amino-3-hydroxymethyl-5-methyl-adamantane (HMDB0060703)

MOL for HMDB0060703 (1-Amino-3-hydroxymethyl-5-methyl-adamantane)

3D MOL for HMDB0060703 (1-Amino-3-hydroxymethyl-5-methyl-adamantane)

3D SDF for HMDB0060703 (1-Amino-3-hydroxymethyl-5-methyl-adamantane)

3D-SDF for HMDB0060703 (1-Amino-3-hydroxymethyl-5-methyl-adamantane)

PDB for HMDB0060703 (1-Amino-3-hydroxymethyl-5-methyl-adamantane)

3D PDB for HMDB0060703 (1-Amino-3-hydroxymethyl-5-methyl-adamantane)

SMILES for HMDB0060703 (1-Amino-3-hydroxymethyl-5-methyl-adamantane)

INCHI for HMDB0060703 (1-Amino-3-hydroxymethyl-5-methyl-adamantane)

Structure for HMDB0060703 (1-Amino-3-hydroxymethyl-5-methyl-adamantane)

3D Structure for HMDB0060703 (1-Amino-3-hydroxymethyl-5-methyl-adamantane)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra