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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:11:08 UTC

Update Date

2019-07-23 07:15:31 UTC

HMDB ID

HMDB0060987

Secondary Accession Numbers

HMDB60987

Metabolite Identification

Common Name

2-hydroxymethylolanzapine

Description

2-hydroxymethylolanzapine is a metabolite of olanzapine. Olanzapine (trade name Zyprexa or in combination with fluoxetine Symbyax) is an atypical antipsychotic, approved by the FDA for the treatment of schizophrenia and bipolar disorder. Olanzapine is structurally similar to clozapine, but is classified as a thienobenzodiazepine. The olanzapine formulations are manufactured and marketed by the pharmaceutical company Eli Lilly and Company; the drug went generic in 2011. Sales of Zyprexa in 2008 were $2.2B in the US alone, and $4.7B in total. (Wikipedia)

Structure

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

HMDB0060987
     RDKit          3D
2-hydroxymethylolanzapine
 43 46  0  0  0  0  0  0  0  0999 V2000
    4.6258   -1.2380   -0.2965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8487   -0.0200   -0.1797 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0729    0.2646   -1.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185   -0.4134   -1.2539 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0490    0.0942   -0.0738 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3380   -0.1685    0.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6427   -1.3670    0.4882 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8590   -2.0079    0.7776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7480   -3.3879    0.9250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8355   -4.1769    1.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0683   -3.5766    1.3677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1740   -2.1890    1.2183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0902   -1.4170    0.9283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3907   -0.0424    0.8070 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5754    0.9872    0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1140    2.5363   -0.2831 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6522    3.1575   -0.8870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3829    4.5051   -1.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0565    4.5669   -1.8392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7731    2.1297   -0.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2432    0.9996   -0.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8736    0.8540    0.8404 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1482    0.0701    1.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1072   -1.8720   -1.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9246    1.3461   -1.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6048   -0.2059   -2.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1360   -0.3159   -2.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9420   -1.5133   -1.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7948   -3.8756    0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7240   -5.2599    1.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9310   -4.1918    1.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1143   -1.7000    1.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2901    0.3162    1.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0773    4.7201   -2.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5725    5.2698   -0.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5040    5.0811   -1.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2912    2.2575   -1.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3988    1.0092    1.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2005    1.8340    0.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9569   -0.9094    1.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7660    0.6893    1.7850 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
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  5 22  1  0
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 13  8  1  0
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M  END


  Mrv0541 07091309112D          

 23 26  0  0  0  0            999 V2000
   -1.0698   -3.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1383    0.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9637    0.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5273   -0.3938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1781    1.2188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1198   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1606   -2.3028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4860   -2.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7944   -1.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9344   -0.1859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0524    0.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2502    0.5763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1120   -0.1211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5671    0.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3952   -0.7718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0806    0.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2201   -0.7811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8279    1.0307    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7035   -2.9896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0289   -1.5111    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2867    1.5599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6228    1.1121    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
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 12 10  2  0  0  0  0
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 21 16  1  0  0  0  0
 22 11  1  0  0  0  0
 23 12  1  0  0  0  0
 23 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060987

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCN(CC1)C1=NC2=CC=CC=C2NC2=C1C=C(CO)S2

> <INCHI_IDENTIFIER>
InChI=1S/C17H20N4OS/c1-20-6-8-21(9-7-20)16-13-10-12(11-22)23-17(13)19-15-5-3-2-4-14(15)18-16/h2-5,10,19,22H,6-9,11H2,1H3

> <INCHI_KEY>
FPDIERBPQFAFSI-UHFFFAOYSA-N

> <FORMULA>
C17H20N4OS

> <MOLECULAR_WEIGHT>
328.432

> <EXACT_MASS>
328.135781972

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
36.0628309996738

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[8-(4-methylpiperazin-1-yl)-4-thia-2,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(14),3(7),5,8,10,12-hexaen-5-yl]methanol

> <ALOGPS_LOGP>
2.35

> <JCHEM_LOGP>
2.1077239253333326

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.916410797702301

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.420765589554382

> <JCHEM_PKA_STRONGEST_BASIC>
7.1968846943435425

> <JCHEM_POLAR_SURFACE_AREA>
51.10000000000001

> <JCHEM_REFRACTIVITY>
95.4174

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[8-(4-methylpiperazin-1-yl)-4-thia-2,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(14),3(7),5,8,10,12-hexaen-5-yl]methanol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060987
     RDKit          3D
2-hydroxymethylolanzapine
 43 46  0  0  0  0  0  0  0  0999 V2000
    4.6258   -1.2380   -0.2965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8487   -0.0200   -0.1797 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0729    0.2646   -1.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185   -0.4134   -1.2539 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0490    0.0942   -0.0738 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3380   -0.1685    0.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6427   -1.3670    0.4882 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8590   -2.0079    0.7776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7480   -3.3879    0.9250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8355   -4.1769    1.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0683   -3.5766    1.3677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1740   -2.1890    1.2183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0902   -1.4170    0.9283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3907   -0.0424    0.8070 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5754    0.9872    0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1140    2.5363   -0.2831 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6522    3.1575   -0.8870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3829    4.5051   -1.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0565    4.5669   -1.8392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7731    2.1297   -0.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2432    0.9996   -0.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8736    0.8540    0.8404 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1482    0.0701    1.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1072   -1.8720   -1.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6362   -1.0299   -0.6869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6431   -1.8100    0.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9246    1.3461   -1.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6048   -0.2059   -2.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1360   -0.3159   -2.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9420   -1.5133   -1.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7948   -3.8756    0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7240   -5.2599    1.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9310   -4.1918    1.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1143   -1.7000    1.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2901    0.3162    1.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0773    4.7201   -2.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5725    5.2698   -0.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5040    5.0811   -1.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2912    2.2575   -1.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3988    1.0092    1.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2005    1.8340    0.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9569   -0.9094    1.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7660    0.6893    1.7850 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  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  2  0
 20 21  1  0
  5 22  1  0
 22 23  1  0
 23  2  1  0
 21  6  1  0
 13  8  1  0
 21 15  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 14 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 22 40  1  0
 22 41  1  0
 23 42  1  0
 23 43  1  0
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0      -1.997  -6.961   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.858   0.300   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.532   1.805   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.718  -0.735   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.066   2.275   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.224  -5.483   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.166  -4.299   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.907  -4.103   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.483  -2.919   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.744  -0.347   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.831   1.435   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.334   1.076   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.209  -0.226   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.251  -0.265   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.925   1.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.738  -1.441   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.150   1.271   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       2.278  -1.458   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       1.545   1.924   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0      -1.313  -5.581   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0       0.054  -2.821   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0      -4.269   2.912   0.000  0.00  0.00           O+0
HETATM   23  S   UNK     0      -1.163   2.076   0.000  0.00  0.00           S+0
CONECT    1   20                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   14                                                       
CONECT    5    3   15                                                       
CONECT    6    8   20                                                       
CONECT    7    9   20                                                       
CONECT    8    6   21                                                       
CONECT    9    7   21                                                       
CONECT   10   12   13                                                       
CONECT   11   12   22                                                       
CONECT   12   10   11   23                                                  
CONECT   13   10   16   17                                                  
CONECT   14    4   15   18                                                  
CONECT   15    5   14   19                                                  
CONECT   16   13   18   21                                                  
CONECT   17   13   19   23                                                  
CONECT   18   14   16                                                       
CONECT   19   15   17                                                       
CONECT   20    1    6    7                                                  
CONECT   21    8    9   16                                                  
CONECT   22   11                                                            
CONECT   23   12   17                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0060987
HETATM    1  C1  UNL     1       4.626  -1.238  -0.296  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.849  -0.020  -0.180  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.073   0.265  -1.344  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.719  -0.413  -1.254  1.00  0.00           C  
HETATM    5  N2  UNL     1       1.049   0.094  -0.074  1.00  0.00           N  
HETATM    6  C4  UNL     1      -0.338  -0.168   0.124  1.00  0.00           C  
HETATM    7  N3  UNL     1      -0.643  -1.367   0.488  1.00  0.00           N  
HETATM    8  C5  UNL     1      -1.859  -2.008   0.778  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.748  -3.388   0.925  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.836  -4.177   1.217  1.00  0.00           C  
HETATM   11  C8  UNL     1      -4.068  -3.577   1.368  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.174  -2.189   1.218  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.090  -1.417   0.928  1.00  0.00           C  
HETATM   14  N4  UNL     1      -3.391  -0.042   0.807  1.00  0.00           N  
HETATM   15  C11 UNL     1      -2.575   0.987   0.204  1.00  0.00           C  
HETATM   16  S1  UNL     1      -3.114   2.536  -0.283  1.00  0.00           S  
HETATM   17  C12 UNL     1      -1.652   3.158  -0.887  1.00  0.00           C  
HETATM   18  C13 UNL     1      -1.383   4.505  -1.492  1.00  0.00           C  
HETATM   19  O1  UNL     1      -0.057   4.567  -1.839  1.00  0.00           O  
HETATM   20  C14 UNL     1      -0.773   2.130  -0.690  1.00  0.00           C  
HETATM   21  C15 UNL     1      -1.243   1.000  -0.125  1.00  0.00           C  
HETATM   22  C16 UNL     1       1.874   0.854   0.840  1.00  0.00           C  
HETATM   23  C17 UNL     1       3.148   0.070   1.070  1.00  0.00           C  
HETATM   24  H1  UNL     1       4.107  -1.872  -1.042  1.00  0.00           H  
HETATM   25  H2  UNL     1       5.636  -1.030  -0.687  1.00  0.00           H  
HETATM   26  H3  UNL     1       4.643  -1.810   0.647  1.00  0.00           H  
HETATM   27  H4  UNL     1       2.925   1.346  -1.482  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.605  -0.206  -2.219  1.00  0.00           H  
HETATM   29  H6  UNL     1       1.136  -0.316  -2.170  1.00  0.00           H  
HETATM   30  H7  UNL     1       1.942  -1.513  -1.131  1.00  0.00           H  
HETATM   31  H8  UNL     1      -0.795  -3.876   0.812  1.00  0.00           H  
HETATM   32  H9  UNL     1      -2.724  -5.260   1.328  1.00  0.00           H  
HETATM   33  H10 UNL     1      -4.931  -4.192   1.599  1.00  0.00           H  
HETATM   34  H11 UNL     1      -5.114  -1.700   1.330  1.00  0.00           H  
HETATM   35  H12 UNL     1      -4.290   0.316   1.174  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.077   4.720  -2.327  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.572   5.270  -0.693  1.00  0.00           H  
HETATM   38  H15 UNL     1       0.504   5.081  -1.191  1.00  0.00           H  
HETATM   39  H16 UNL     1       0.291   2.257  -1.001  1.00  0.00           H  
HETATM   40  H17 UNL     1       1.399   1.009   1.828  1.00  0.00           H  
HETATM   41  H18 UNL     1       2.201   1.834   0.389  1.00  0.00           H  
HETATM   42  H19 UNL     1       2.957  -0.909   1.549  1.00  0.00           H  
HETATM   43  H20 UNL     1       3.766   0.689   1.785  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   23
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6   22
CONECT    6    7    7   21
CONECT    7    8
CONECT    8    9    9   13
CONECT    9   10   31
CONECT   10   11   11   32
CONECT   11   12   33
CONECT   12   13   13   34
CONECT   13   14
CONECT   14   15   35
CONECT   15   16   21   21
CONECT   16   17
CONECT   17   18   20   20
CONECT   18   19   36   37
CONECT   19   38
CONECT   20   21   39
CONECT   22   23   40   41
CONECT   23   42   43
END

HMDB0060987
     RDKit          3D
2-hydroxymethylolanzapine
 43 46  0  0  0  0  0  0  0  0999 V2000
    4.6258   -1.2380   -0.2965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8487   -0.0200   -0.1797 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0729    0.2646   -1.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185   -0.4134   -1.2539 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0490    0.0942   -0.0738 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3380   -0.1685    0.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6427   -1.3670    0.4882 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8590   -2.0079    0.7776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7480   -3.3879    0.9250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8355   -4.1769    1.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0683   -3.5766    1.3677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1740   -2.1890    1.2183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0902   -1.4170    0.9283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3907   -0.0424    0.8070 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5754    0.9872    0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1140    2.5363   -0.2831 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6522    3.1575   -0.8870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3829    4.5051   -1.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0565    4.5669   -1.8392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7731    2.1297   -0.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2432    0.9996   -0.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8736    0.8540    0.8404 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1482    0.0701    1.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1072   -1.8720   -1.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6362   -1.0299   -0.6869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6431   -1.8100    0.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9246    1.3461   -1.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6048   -0.2059   -2.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1360   -0.3159   -2.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9420   -1.5133   -1.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7948   -3.8756    0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7240   -5.2599    1.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9310   -4.1918    1.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1143   -1.7000    1.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2901    0.3162    1.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0773    4.7201   -2.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5725    5.2698   -0.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5040    5.0811   -1.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2912    2.2575   -1.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3988    1.0092    1.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2005    1.8340    0.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9569   -0.9094    1.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7660    0.6893    1.7850 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  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  2  0
 20 21  1  0
  5 22  1  0
 22 23  1  0
 23  2  1  0
 21  6  1  0
 13  8  1  0
 21 15  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 14 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 22 40  1  0
 22 41  1  0
 23 42  1  0
 23 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Hydroxy-methylolanzapine	HMDB

Chemical Formula

C₁₇H₂₀N₄OS

Average Molecular Weight

328.432

Monoisotopic Molecular Weight

328.135781972

IUPAC Name

[8-(4-methylpiperazin-1-yl)-4-thia-2,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(14),3(7),5,8,10,12-hexaen-5-yl]methanol

Traditional Name

[8-(4-methylpiperazin-1-yl)-4-thia-2,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(14),3(7),5,8,10,12-hexaen-5-yl]methanol

CAS Registry Number

Not Available

SMILES

CN1CCN(CC1)C1=NC2=CC=CC=C2NC2=C1C=C(CO)S2

InChI Identifier

InChI=1S/C17H20N4OS/c1-20-6-8-21(9-7-20)16-13-10-12(11-22)23-17(13)19-15-5-3-2-4-14(15)18-16/h2-5,10,19,22H,6-9,11H2,1H3

InChI Key

FPDIERBPQFAFSI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzodiazepines. These are organic compounds containing a benzene ring fused to either isomers of diazepine(unsaturated seven-member heterocycle with two nitrogen atoms replacing two carbon atoms).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

Not Available

Direct Parent

Benzodiazepines

Alternative Parents

Substituents

Benzodiazepine
Thieno-para-diazepine
2,3,5-trisubstituted thiophene
Para-diazepine
N-arylated-2-aminothiophene
N-methylpiperazine
N-alkylpiperazine
1,4-diazinane
Piperazine
2-aminothiophene
Imidolactam
Benzenoid
Heteroaromatic compound
Thiophene
Tertiary amine
Tertiary aliphatic amine
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Amidine
Secondary amine
Carboxylic acid amidine
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Primary alcohol
Organic oxygen compound
Amine
Organic nitrogen compound
Aromatic alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060987)
Liver (HMDB: HMDB0060987)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060987)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060987)

Cellular substructure

Cytoplasm (HMDB: HMDB0060987)
Membrane (HMDB: HMDB0060987)

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	0.14 g/L	ALOGPS
logP	2.35	ALOGPS
logP	2.11	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	13.42	ChemAxon
pKa (Strongest Basic)	7.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	51.1 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	95.42 m³·mol⁻¹	ChemAxon
Polarizability	36.06 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	175.13	31661259
DarkChem	[M-H]-	175.383	31661259
DeepCCS	[M+H]+	172.652	30932474
DeepCCS	[M-H]-	170.294	30932474
DeepCCS	[M-2H]-	203.179	30932474
DeepCCS	[M+Na]+	178.745	30932474
AllCCS	[M+H]+	175.8	32859911
AllCCS	[M+H-H2O]+	172.8	32859911
AllCCS	[M+NH4]+	178.7	32859911
AllCCS	[M+Na]+	179.5	32859911
AllCCS	[M-H]-	177.9	32859911
AllCCS	[M+Na-2H]-	177.5	32859911
AllCCS	[M+HCOO]-	177.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-hydroxymethylolanzapine	CN1CCN(CC1)C1=NC2=CC=CC=C2NC2=C1C=C(CO)S2	4277.5	Standard polar	33892256
2-hydroxymethylolanzapine	CN1CCN(CC1)C1=NC2=CC=CC=C2NC2=C1C=C(CO)S2	2851.8	Standard non polar	33892256
2-hydroxymethylolanzapine	CN1CCN(CC1)C1=NC2=CC=CC=C2NC2=C1C=C(CO)S2	3117.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-hydroxymethylolanzapine,1TMS,isomer #1	CN1CCN(C2=NC3=CC=CC=C3NC3=C2C=C(CO[Si](C)(C)C)S3)CC1	3072.4	Semi standard non polar	33892256
2-hydroxymethylolanzapine,1TMS,isomer #2	CN1CCN(C2=NC3=CC=CC=C3N([Si](C)(C)C)C3=C2C=C(CO)S3)CC1	2968.3	Semi standard non polar	33892256
2-hydroxymethylolanzapine,2TMS,isomer #1	CN1CCN(C2=NC3=CC=CC=C3N([Si](C)(C)C)C3=C2C=C(CO[Si](C)(C)C)S3)CC1	2937.5	Semi standard non polar	33892256
2-hydroxymethylolanzapine,2TMS,isomer #1	CN1CCN(C2=NC3=CC=CC=C3N([Si](C)(C)C)C3=C2C=C(CO[Si](C)(C)C)S3)CC1	2871.2	Standard non polar	33892256
2-hydroxymethylolanzapine,2TMS,isomer #1	CN1CCN(C2=NC3=CC=CC=C3N([Si](C)(C)C)C3=C2C=C(CO[Si](C)(C)C)S3)CC1	4147.3	Standard polar	33892256
2-hydroxymethylolanzapine,1TBDMS,isomer #1	CN1CCN(C2=NC3=CC=CC=C3NC3=C2C=C(CO[Si](C)(C)C(C)(C)C)S3)CC1	3241.1	Semi standard non polar	33892256
2-hydroxymethylolanzapine,1TBDMS,isomer #2	CN1CCN(C2=NC3=CC=CC=C3N([Si](C)(C)C(C)(C)C)C3=C2C=C(CO)S3)CC1	3132.5	Semi standard non polar	33892256
2-hydroxymethylolanzapine,2TBDMS,isomer #1	CN1CCN(C2=NC3=CC=CC=C3N([Si](C)(C)C(C)(C)C)C3=C2C=C(CO[Si](C)(C)C(C)(C)C)S3)CC1	3264.8	Semi standard non polar	33892256
2-hydroxymethylolanzapine,2TBDMS,isomer #1	CN1CCN(C2=NC3=CC=CC=C3N([Si](C)(C)C(C)(C)C)C3=C2C=C(CO[Si](C)(C)C(C)(C)C)S3)CC1	3300.5	Standard non polar	33892256
2-hydroxymethylolanzapine,2TBDMS,isomer #1	CN1CCN(C2=NC3=CC=CC=C3N([Si](C)(C)C(C)(C)C)C3=C2C=C(CO[Si](C)(C)C(C)(C)C)S3)CC1	4226.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-hydroxymethylolanzapine GC-MS (Non-derivatized) - 70eV, Positive	splash10-05bb-9184000000-4e40bc5dc4de68575720	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-hydroxymethylolanzapine GC-MS (1 TMS) - 70eV, Positive	splash10-01w0-6009000000-1917a64f05414b677383	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-hydroxymethylolanzapine 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 - 2-hydroxymethylolanzapine 10V, Positive-QTOF	splash10-01t9-0009000000-409ab686ec434dc26b8b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxymethylolanzapine 20V, Positive-QTOF	splash10-03fr-0059000000-7200e8a1e99e03d06870	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxymethylolanzapine 40V, Positive-QTOF	splash10-0ika-7930000000-30786d93dd19d0d11a55	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxymethylolanzapine 10V, Negative-QTOF	splash10-004i-0089000000-e8ae2cb9b2de1d4576a6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxymethylolanzapine 20V, Negative-QTOF	splash10-00dr-0090000000-28b4fe20849240908023	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxymethylolanzapine 40V, Negative-QTOF	splash10-00kf-3690000000-078cec935aaa1a7b11fb	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxymethylolanzapine 10V, Negative-QTOF	splash10-004i-0009000000-93e1684d98a6abe38638	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxymethylolanzapine 20V, Negative-QTOF	splash10-004i-0049000000-8e2c30477cc5ccf57851	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxymethylolanzapine 40V, Negative-QTOF	splash10-0bt9-1191000000-a7e2620c0ab55095cb76	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxymethylolanzapine 10V, Positive-QTOF	splash10-004i-0009000000-8d4c85c4dfeb69b50908	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxymethylolanzapine 20V, Positive-QTOF	splash10-004i-0019000000-05cb4ca54f1204bf0d2c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxymethylolanzapine 40V, Positive-QTOF	splash10-00di-0191000000-13fde00567dbf8250ac8	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

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

18940859

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71549171

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 2-hydroxymethylolanzapine (HMDB0060987)

MOL for HMDB0060987 (2-hydroxymethylolanzapine)

3D MOL for HMDB0060987 (2-hydroxymethylolanzapine)

3D SDF for HMDB0060987 (2-hydroxymethylolanzapine)

3D-SDF for HMDB0060987 (2-hydroxymethylolanzapine)

PDB for HMDB0060987 (2-hydroxymethylolanzapine)

3D PDB for HMDB0060987 (2-hydroxymethylolanzapine)

SMILES for HMDB0060987 (2-hydroxymethylolanzapine)

INCHI for HMDB0060987 (2-hydroxymethylolanzapine)

Structure for HMDB0060987 (2-hydroxymethylolanzapine)

3D Structure for HMDB0060987 (2-hydroxymethylolanzapine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra